charter sailboat hawaii

Private Sailing Charters, Honolulu, Oahu, Hawaii

Ocean Yacht Adventures Honolulu Oahu

WELCOME ABOARD SailBlueHawaii.com

Sail your own exclusive private yacht charter .

You’ll sail in the safety of your own private bubble. How perfect is that during this challenging time? Your private sailing charter in Hawaii offers you an incredible opportunity to explore the stunning waters of the Hawaiian Islands in a luxurious and personalized way.

Sign up today for your sailing adventure with Hawaii’s premiere sailing charter company. [email protected]

“DON’T DREAM YOUR LIFE, LIVE YOUR DREAM”

Any occasion is a great one to get out sailing on Hawaiian waters to enjoy some relaxing and refreshing ocean time. Especially true here in Hawaii where the air is balmy and year-round trade winds provide Honolulu with wonderful sailing conditions.

At Sail Blue Hawaii, the possibilities are endless and  THE HORIZON IS NO LIMIT.

Honolulu Sailing, Yacht Charters, Oahu

While sailing off the Oahu coastline, we often see Hawaiian green sea turtles lazing in the sun, dolphins jumping the bow, whales (winter only) spouting off to starboard, and the stunning shine of Venus at sunset. Leave Waikiki and the crowds behind. Step onto your own private yacht and enjoy the ride of your life. The wind is our engine as we sail the beautiful azure blue Pacific waters. The sound of the ocean will thrill. You can choose a magical sunrise cruise, an adventurous tradewind day-sail, a romantic sunset cruise; depending on your preferences and schedules…anything is available for any occasion.

Your private sailing charter in Hawaii is perfect for intimate gatherings, family vacations, or romantic getaways. It comes with an exceptionally experienced captain and crew who are knowledgeable about the islands’ marine life, culture, and history. You will enjoy tradewind sailing as only Hawaii can offer.

The stunning coastal landscapes, crystal-clear waters, and the chance to see marine wildlife up close makes your private sailing charter an unforgettable experience. However, it’s essential to book in advance, especially during peak tourist seasons, to ensure availability and secure your preferred sailing date.

SUNSET SERVED DAILY

“Years from now you will be more disappointed by the things you didn’t do than by the ones you did do. So throw off the bow lines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover.” -Mark Twain

Recent Sailing Charters/ Sail Blue Hawaii BLOG

Your hawaii whale watch.

This has been a busy week for our humpback visitors as the season winds down for a Hawaii whale watch. I prefer to call it a “whale sail”: we set sail with the hope of seeing these gentle leviathans cruising our waters. February and March are the best for Oahu. The females come to the …

Continue reading “Your Hawaii Whale Watch”

Hawaii Ash Scattering

Hawaii has a strong spiritual energy both on and off the ocean so it is no surprise that a farewell at sea is a healing and soothing way to help say goodbye and help you to have strength as you begin this change. Call for your custom ash scattering at sea.  Let us know about …

Continue reading “Hawaii Ash Scattering”

Hawaii Proposal at Sea

Definition of romance: chartering your private yacht to propose to your loved one while in Hawaii. Imagine saying “YES” while sailing into the sunset. Sail Sunset on Valentine’s Day This Valentine’s Day was a highlight for me. I have been running private charters for many years now but this one stands out. The young couple, …

Continue reading “Hawaii Proposal at Sea”

Private Luxury Yacht Charters Based in Waikiki, HI

Choose a sailing charter.

• Most Popular

Enjoy the sun, surf, and spectacular views aboard your own luxury yacht. With a variety of options to customize your day sail, you can experience the day of your dreams aboard the SV Pau Hana.

• Hour Glass 2 Hours , 3 Hours , 4 Hours
• Hour Glass 2.5 Hours

Friday Fireworks Sail

Watch the Friday night fireworks in Waikiki from the SV Pau Hana. Leave the crowds behind and enjoy your own private fireworks show as our crew caters to your every need.

• Hour Glass 2 Hours

Ash Scattering

We would be honored to help you say goodbye to a loved one with a beautiful ash scattering ceremony on the Pacific Ocean.

Why Sail Oahu?

We offer the finest in luxury performance sailing on one of the newest sailing catamarans in Waikiki. Our Captain and crew are here to see to your every need while providing the highest level of comfort possible aboard a yacht of this caliber.

We will present you with the finest selection freshly prepared local food and beverage customized for you. Whether you are a first-time sailor or a seasoned “Shellback,” relax in comfort and pleasure as the Hawaiian trade winds blow us favorably past Diamond Head.

Customize Your Sail!

Have a special day in mind? Tell us about it. We can provide a no-obligation quote tailored to your perfect day in paradise. We also guarantee our quote for 60 days to give you plenty of time to decide.

Set Sail On Your Adventure

We ensure that your day in our blue paradise is spent the way you always dreamed it could be. Experience Hawaii and the Pacific Ocean aboard your private yacht.

All of our charter guests rate us 5 stars on TripAdvisor

Can't say enough good things about Alan and his crew!! So kind. So knowledgeable of the island. We swam up close with turtles and had a freshly made lunch served. We felt like celebrities. Highly recommend!!

What an awesome afternoon with Sail Oahu! Captain Alan, First Mate Wanda, and crew are first class in every way. We had a beautiful day with stunning views of Waikiki and Diamond Head - with wine, beer, and a delicious lunch to top off the trip. The sailboat was impeccable, impressive and well appointed. We felt well cared for and very welcome. We are looking forward to our next visit to the island and another afternoon with Sail Oahu.

Sail Oahu was Soo Much Fun!!! I had the best day celebrating my birthday!! Captain Alan and First Mate Wanda will make your Trip so enjoyable! They are amazing hosts! And their boat is so classy! I felt like a princess! And the views of Diamond Head were breathtaking!! I will definitely Sail with them again!!

Sail Oahu was one of the most exciting, tranquil, humbling experiences of my life. Capt. Alan, his mate Wanda, and the entire crew were so welcoming & warm. They were particularly great with my nieces and nephews (ages 3-10) as well! They always put safety and comfort first! The sailboat itself is beautiful and lavish. The views of the Island from the open water were breathtaking. I will definitely Sail Oahu every trip I make to the island.

A fantastic day out with my friends with breathtaking views, lovely food, and a stunning boat. The crew were amazing people with such interesting stories, they really made us feel like a big happy family. I recommend this for all families, friend groups, young and old. A day I will never forget! Thank you Sail Oahu and hope to see you soon.

HAWAII Yacht Charter & Boat Rentals

Hawaii Yacht Rentals

50′ CORINTHIAN | 49 Guests

74′ STRIKER | 12 Guests

75′ SUNSEEKER | 12 Guests

Private yacht charter getaway – maui.

47′ Catamaran | 38 Guests

47′ Catamaran II | 38 Guests

64′ Catamaran | 38 Guests

Private yacht charter getaway – hawaii.

In the heart of the vast Pacific Ocean lies a paradise unlike any other – Hawaii. The mere mention of its name conjures images of swaying palms, pristine beaches, and a culture deeply rooted in the spirit of aloha. Now, imagine embarking on a voyage of a lifetime, a private charter that allows you to explore Hawaii’s enchanting waters, immerse yourself in its vibrant marine life, and experience the essence of aloha in a way that only the ocean can reveal.

As your private charter sets sail on the turquoise waters of Hawaii, a world of natural marvels unveils itself before you. Majestic cliffs rise from the sea, adorned with lush vegetation that seems to defy gravity. Hidden coves with powdery white sands invite you to step ashore, each beach a pristine canvas waiting to be explored. This is a land of contrasts, where the verdant mountains meet the azure ocean in a breathtaking embrace.

Hawaii’s waters are a playground of marine majesty, a realm where dolphins dance in the wake of your vessel and sea turtles glide gracefully through the sea. Snorkel into an underwater kingdom where corals bloom in a riot of colors and schools of fish move in choreographed harmony. Every moment spent beneath the waves is a reminder of the intricate beauty that thrives beneath the surface, a world that exists in perfect harmony with Hawaii’s terrestrial wonders.

Hawaii’s sunsets are nothing short of celestial masterpieces. From the deck of your private charter, watch as the sun dips below the horizon, painting the sky with hues that range from soft pinks to fiery oranges. It’s a moment of pure magic, when time stands still and the world around you is bathed in a warm, golden glow. As darkness falls, the stars emerge to create a celestial panorama, reminding you of the vastness of the universe.

Sailing on a private charter in Hawaii is a voyage of awe, wonder, and deep connection. It’s an invitation to witness the marriage of land and sea, to embrace the magic of marine life, and to experience the spirit of aloha in its purest form. As you sail into the horizon, with the wind in your hair and the ocean at your feet, you’ll find yourself captivated by the beauty, mystery, and allure of Hawaii’s boundless waters.

Whale Watching in Hawaii | Romantic Getaways

Corporate Events

Plan your party yacht charter with us!

Hawaii Yacht Charter

Luxury Liners offers yacht charters, boat rentals, and private chef services for groups of all sizes. Our Hawaii yachts are well maintained for the perfect yacht charter experience traveling to in and around the islands of Hawaii the perfect destination.

A Hawaii yacht charter is perfect for family vacations , fishing trips , and whale watching , and more!

HAWAII PRIVATE YACHT CHARTER

Our yachts are perfect for birthdays parties, corporate events, and dinner cruises. Luxury Liners offers exciting private yacht charter getaways like no other. Plan your yacht party with us!

Hawaii Yacht Charter Destinations

E Komo Mai to Waikiki Boat Charters. The largest selection of quality and award winning vessels located in Waikiki. No matter the size of your Ohana, we can find the catamaran, sailboat, or yacht that suits your needs.

Our team specializes in Waikiki sunset sailing cruises, Hawaiian Green Sea Turtle snorkeling trips, Oahu fishing charters, whale watching excursions, corporate events, ash scattering services, weddings, and much more…

OUR VESSELS AVAILABLE IN WAIKIKI

Royal hawaiian, 52′ classic rudy choy catamaran | up to 30 passengers.

41′ Trimaran | Up To 45 Passengers

40′ Sailing Catamaran | Up to 12 Passengers

70′ Sunreef Catamaran | Up To 12 Passengers

My Sunshine

43′ Sailing Yacht | Up To 6 Passengers

50′ Motor Catamaran | Up to 49 Passengers

74′ Luxury Sportfisher | Up To 12 Passengers

The vida mia.

61′ Classic Luxury Yacht | Up To 35 Passengers

52′ Classic Rudy Choy Catamaran | Up To 30 Passengers

74′ Luxury Sportfisher | Up to 12 Passengers

BEST VARIETY OF CHARTERS IN WAIKIKI

Waikiki sunset cruise.

Tropical sunsets followed by Honolulu’s city lights celebrated from the sea must be experienced on your Hawaiian vacation.

A unique and romantic way to tie the knot… Couples who desire a unique, romantic and spectacularly beautiful environment that’s stress-free...

Turtle Canyon Snorkeling Adventure

Turtle Canyon Snorkeling is an amazing way to experience Hawaii’s incredible Ocean life on Oahu’s Southshore right in front of the Waikiki Skyline.

Large Group Charters

Our Aloha Kai Power Catamaran can cater to groups up to 49 people. A great space with a fantastic stereo system for company parties, graduations, family reunions, weddings, group snorkel trips...

Customize your own " Fun in the Sun" Charter

Have an idea of what your perfect Hawaiian boat charter should be, let us know and we will work with you to customize the charter on one of our vessels to your liking.

Whale Watching Excursions

Officially, whale season in Hawaii runs from December 15th - May 15th Perfect for visitors and Kama’ainas with a desire for an intimate experience with Hawaii’s...

Memorials- Oahu Ash Scatterings

An Hawaii ash scattering is a beautiful and memorable way to remember your loved ones and deliver them back to the Aina.

Waikiki Friday Night Fireworks

The vantage point from the water is incredible with the fireworks bursts of colorful light reflecting off Waikiki’s beautiful skyline.

(+1) 808-657-2178

[email protected]

Harbor Addresses Ala Wai Harbor: 1651 Ala Moana Blvd, Honolulu, HI 96815 Kewalo Harbor: 1125 Ala Moana Blvd, Honolulu, HI 96814

© 2024 Waikiki Boat Charters.

Hawaii’s Finest Private Yacht Experience

Forget waterfront and ocean views when you can be “ en sea” to experience the best of Hawaii on a private yacht charter with the most luxurious of accommodations aboard our elite fleet. Sometimes, an excursion aboard the largest luxury charter yacht amongst the Hawaiian Islands is all you need for a bit of inspiration in your life.

Live Inspired.

“E KŪLIA I KA NU’U.”

Strive to reach the highest. 

— Hawaiian Proverb

Hawaii’s Largest Luxury Charter Yacht

94′ broward.

• 3 En-Suite Staterooms & 3 Crew Rooms
• Entertainment deck
• Full Kitchen
• Salon & Bar
• Player Grand Piano
• What’s included: Certified Captain & Crew, Fuel, Water/Sodas & Ice, Water Toys

94′ (28.65m)

Engines & Misc.

870hp Engine, Twin Diesel Motors, Dual Stabilizers

Browse Activities

Private charters, per person cruise & private events, your voyage is fully customizable to suit your needs. contact us and we’ll handle the rest..

Snorkel & Swim

Private charter activity.

Discover more of Hawaii on-board and just below the surface. Our snorkel & swim cruise offers both adventure and relaxation for everyone to enjoy. Exquisite snorkeling in remote locations teeming with marine life. 

Waikiki & Sea Life

Soak in the best views of the Waikiki city skyline and Diamond Head on Hawaii’s largest luxury yacht. Be on the lookout for whales* (seasonal) and other sea life– an exclusive experience with only the finest captain that knows the best spots to view these beloved marine animals.

Morning Coffee

Start your day the right way. There is no better way to wake up and enjoy your morning coffee than on-board our elite fleet with breathtaking views of the best that Hawaii has to offer. Coffee bar included.

Honolulu Sunset

Take in unforgettable views and create memories of the moments that matter. Experience the Hawaiian sunset with the sky’s incredible rainbow of colors as the Honolulu skyline comes to life with shimmering lights and the twinkling stars above emerge. 

Evening Fireworks

Private charter activity and per person cruise available.

Kick off your weekend with the the best unobstructed views of the dazzling Waikiki fireworks display from Hawaii’s largest charter yacht with the breathtaking backdrop of the sparkling city skyline. *(Available Friday evenings for an exclusive experience limited to 12 people per tour. Per person booking available!)

On-the-Dock Luxury Private Dining

Enjoy an extraordinary private dining experience like no other on-board our 94” Yacht transformed-to-bistro with incredible views from the dock. Features dining options from renowned chefs and private service to ensure your experience is nothing short of spectacular.

Corporate Events

Choose Inspire for a unique experience and exquisite event space that makes quite a lasting impression. On-board our elite fleet you will find the ultimate escape with all your needs catered to as you celebrate, bond and find that inspiration.

Weddings & Special Events

Looking for a unique event space for your special moments? Create lifelong memories on-board (dock or on sea) with every aspect customizable to fit your needs. Curate a magical experience like no other with our dedicated team of experts and capture breathtaking photos to last you a lifetime.

Give the Gift of Hawaii’s Finest Yacht Experience

The best experiences we have in life create beautiful memories, and those memories are priceless. Give the gift of Inspire with our E-Gift Cards.

Escape the Ordinary.

Escape the ordinary. contact us. we are here to make your adventure a reality..

SPOTS FILLING QUICKLY! BOOK YOUR SUMMER CRUISE & SNORKEL TODAY

Tradewind Charters

Escape on a private charter | honolulu, hi.

• Most Popular!

Cruise & Snorkel

Perfect for visitors with a desire for real sailing in a private setting. Our luxury yachts are limited to private parties ensuring comfort and no crowds!

Fishing Adventures

Create fantastic family memories at sea on your Oahu vacation by combining a few ocean activities together.

Mimosa Sunrise Cruise

Ideal for the romantic couple who’s up at the crack of dawn during their Hawaiian vacation due to time zone changes. Witness the brilliant colors of a sunrise at sea from the deck of the Love Boat.

Sea Spa Cruise

Perfect for couples, families, and groups celebrating life events like birthdays, anniversaries, showers, and bachelor/bachelorette parties.

Aloha to Tradewind Charters

Tradewind Charters Hawaii offers visitors and Kama’ainas private sailing cruises, fishing charters, sunset dinner sails, snorkeling tours, whale watching and dolphins swims, scenic sightseeing tours, weddings at sea, sea burial services, and much more. Whether you are looking to relax for an afternoon or a whole week, host a wedding and reception at sea, entertain family, friends, and business associates for a luncheon cruise, or savor a romantic sunset dinner sail, we do it all for you.

Meet Captain Ken

Capt. Ken at the helm. Over 25 years ago, I sailed over from the West Coast and started up Tradewind Charters to provide the very best in private boat charters for clients from all over the world. Our islands’ perfect weather is ideal for sailing and living in comfort, and coupled with an unsurpassed beauty and allure, incredible marine life year-round, and neighbors full of ALOHA, it truly is Paradise. Come sail with us and let us show you the reasons why we call these islands home.

Raving Reviews

"A group of four of us took a morning sailing cruise out past the shores of Waikiki. Captain Nate was a great source of information and shared some fantastic recommendations of things to see/do. He was very personable and informative and made our trip very enjoyable."

"This was an amazing way to end our vacation in Hawaii. Our family sailed for two hours and enjoyed the sunset while eating and drinking. Best of all it was just us! Our own private cruise. Paul was an incredible captain and host who took care of all of our needs. We just sat back and enjoyed the ride."

"My family thoroughly enjoyed a three-hour sail trip on "My Sunshine." Captain Paul was amazing, as was the boat trip. Beautiful say on Waikiki swimming, sailing and enjoying the sun. Perfect cruise!!!!"

"I had a WONDERFUL experience. Captain Ken was incredibly responsive and easy to coordinate with. He and his crew made sure that we had an enjoyable and safe time out on the water. The boat was incredibly clean, and well-equipped with everything you would need - snorkels, bathrooms, and a full bar! Can't wait to sail again with Tradewind Charters."

• Paradise Sailing Hawaii

Kailua Kona Sailing Catamaran Charters - Big Island Boat Tours

Enjoy a true sailing experience with a small number of passengers during a Kona sailing charter on Hawaii's Big Island! Our beautiful new sailing catamaran features plenty of shade , comfortable cushioned seating with tables, nice clean toilet facilities and the roominess, stability and speed of the newest 36' sailing catamaran offering Big Island boat tours.  We offer a variety of Kona sailing charters including a relaxing Kona Sunset Cruise and private catamaran charters.

Because we are family owned and operated , we provide the kind of personal service only a small business can and the comfort of catamaran sailing without the big boat crowds . Please check out our reviews on GOOGLE and TripAdvisor to find out how much our guests enjoy sailing with us!

Our most popular Kona Sailing tours

4 hour private catamaran charter.

Have our beautiful catamaran all to yourself and spend the morning sailing, snorkeling & looking for wildlife. Snorkel equipment and refreshments are provided. BYOB STARTING AT $1,595 Click here for more details

Private Kona Sunset Cruise

Sail into the sunset aboard Kōlea on our  Sunset Sail and enjoy the beautiful  Big Island Sunset. Refreshments are provided.  BYOB STARTING AT $995 Click here for more details

CUSTOM PRIVATE CATAMARAN CHARTERS

Starting at just $995*.

Google Rating

5.0 159 reviews

Paradise Sailing Hawaii , Honokohau Marina Slip J24, 74-380 Kealakehe Pkwy, , Kailua Kona , HI 96740 , United States (US) - Phone: (808) 883-0399

Hawaii Sailing Adventures, LLC

Private Charters in Maui, Oahu, Lanai, Kauai

Private Catamaran Sailing Charters

1/2 day, one-day, sunset, dinner, multi-day to multi-week inter-island vacation, and trip options are available.

Hawaii Sailing Adventures is proud and committed to offering you a unique, unusual, adventurous experience on the best and only private pleasure sailing catamarans available in all Hawaiian islands. Sail Maui, Oahu, and the rest of Hawaii by our luxurious and private catamaran charters.

All our boats are individually owned and well maintained, giving you the benefits of pride of ownership. Hawaii Sailing Adventures delivers personal attention, years of experience, and a love of sailing Hawaii's islands and waters. We have local insights, a love of Hawaiian culture, and want to share the beauty of land and sea life above and below.

We are all Hawaii locals, lovers of the deep ocean, owners, captains, and sailors. In addition, we have sailed on these boats all around the Pacific Ocean from the Caribbean, Panama, Mexico, Tahiti, and more.

If you want a truly intimate and adventurous vacation, contact Hawaii Sailing adventures today for more information about private charters.

Explore Our Fleet

Fountaine Pajot Bahia 46

Lagoon 440 Fly Bridge

Fountaine Pajot Helia 44

Excess 12 – 39’

Beneteau Oceanis 50

Beneteau Oceanis 48

Nautor Swan 46

Beneteau 42

Beneteau Oceanis 41

Beneteau 393

Beneteau 39

The sunreef 62 - as seen on netflix.

The Sunreef 62 is featured in the Netflix series “The most Amazing Vacation Rentals” “episode titled "Aloha Hawaii” Season 1, Episode 9.

Click here to learn more .

We're proud to offer the "only catamaran sailboats available for private vacation charter in all of the Hawaiian Islands" Just your family and friends

What our customers say...

"We have traveled several times with Capt. Jerry Bryant, in Hawaii, Mexico and in the BVI in 2008. We have always had the best of experiences on and off the ship. I look forward to sailing again with him in the near future and would recommend him to anyone thinking of a Hawaiian or Caribbean experience you won’t forget."

Tim & Janis Londos

Ready to find out more.

Get information on prices, itineraries, private daily or weekly charters & tours in Hawaii.

• (808) 664-1164
• [email protected]
• Ko Olina / Waikiki

PRIVATE & SHARED YACHT CHARTERS

We specialize in providing private and shared yacht charters in hawaii, from ko olina and waikiki. with a passenger limit of six, we cater to families, couples, corporate suites and more.  browse from our three vessels, two oahu locations, and various experiences to find the perfect match for you. trust in our genuine service and aloha from beginning to end..

MANA Cruises + Charters

92-100 Waipahe Place, Kapolei

5.0 211 reviews

Sailing In Hawaii – A Comprehensive Guide

Sailing in Hawaii: A Comprehensive Guide to the Best Adventures     If you’re looking for an unforgettable sailing adventure, Hawaii is the place to be. With its crystal-clear waters, stunning beaches, and incredible wildlife, Hawaii offers an experience like no other. In this comprehensive

Choosing Reef-Safe Sunscreen for Your MANA Adventure

Today we focus on the Sun, Sand & Sustainability!! As the sun dips below the horizon, painting the sky with fiery Hawaiian hues, you’ve just finished another incredible day of exploring the wonders of the islands with MANA Cruises. From snorkeling among beautiful coral reefs

Reducing Waste: Responsible Eco-Tourism

The Key to Sustainable Experiences in Hawaii As the world is shifting towards more sustainable practices, Hawaii has been taking significant steps towards reducing waste and promoting ecotourism. The island state is renowned for its beautiful beaches, clear waters, and vibrant marine life. However, the

Explore Your Options

Ko Olina: Ko Olina Marina 92-100 Waipahe Place, Kapolei, HI 96707 Waikiki: Ala Wai Boat Harbor 5 Holomoana St, Honolulu, HI 96815

Native Hawaiian Owned & Operated

OFFICE HOURS

Daily 8 AM - 5 PM

Experiences Locations Ko Olina Waikiki Gallery FAQ About Fleet Contact Privacy Policy

• © MANA CRUISES AND CHARTERS - 2024
• ALL RIGHTS RESERVED

Twenty years from now, you will be more disappointed by the things you didn’t do, than by the ones you did. So throw off the bowlines. Sail away from the safe harbor. Catch the trade wind in your sails. Explore. Dream. Discover.” – Mark Twain

Whale Watch Sails

Enjoy humpback whales all around during the winter season, and listen to their song. It is a treat to have them here. 

Sail And Snorkel Adventures

Sail along the coast and let yourself be captured by the beauty of the island, or swim or snorkel in our beautiful, turquoise water. 

Sunset or Dinner Sails

Savor a magical evening as you enjoy appetizers on the foredeck and watch the soft, evening light fall on the island as the sun sets. 

Order breakfast, lunch or dinner through our private Chef, or have our Chef prepare a special menu for dinner on board.

[email protected]

808-960-9744

Our Mailing Address

P.o. box 6600 kamuela, hi 96743.

North Shore Sailing Adventures

NORTH SHORE SAILING ADVENTURES | HALEIWA, HAWAII

New Paragraph

SAILING ADVENTURES

We specialize in private charters exclusive to you and yours (up to 6 people)..

We provide the sailboat, captain, crew, and adventure!

Private Charters

We specialize in private charters exclusive to you and yours (up to 6 people).

Public Charters

For public charter availablity, please call . You may be combined with others.

Choose the Adventure that's Right For You!

We offer morning, afternoon and sunset sails. Join our crew for stunning views of the North Shore. View the magnificent wildlife of our waters, including whales (seasonal), dolphins, turtles, seabirds, rays, sharks, and more!

Our Adventures are Seasonal

CURRENT SEASON ADVENTURES:

Winter/Spring 2024:

This is a paragraph. Writing in paragraphs lets visitors find what they are looking for quickly and easily.

Private (just you--up to 6 people).

1.5, 3, Half-Day, and Full-Day

1.5, 3, Half-Day, and Full-Day 

SUMMER ADVENTURES:

Sail to and anchor at the bay.

Swim, snorkel, and more!

PRIVATE CHARTERS

Whales & dolphins, sunset cruises, listen to whales, anchor at waimea bay.

MEET YOUR CAPTAIN

Dr. porter turnbull.

Whale watch with an expert!

Sunset or daytime excursions

Dolphins love Keet!

Sail with dolphins

Sailing in rainbow country

Swim and relax at Waimea Bay

Whale season fun!

Testimonials.

...f you are looking for true Aloha, then this is your boat and crew. They took such good care of us, the boat is meticulous and safe, and the views were amazing. We were even blessed to sail with spooner dolphins swimming all around us. It was truly a magical morning. Thank you again North Shore Sailing Adventures...you guys are the best!!

Sara G., Wailua, Hawaii (Yelp)

Best private sailing trip yet! We saw a ton of dolphins & Turtles! Captain Porter & Will were fantastic hosts, constantly offering drinks & snacks & making sure everyone was having a great time. We have booked private charters all over the world & have to say this was at the top of the list. The tri-hull “Keet” was surprisingly stable cutting thru the chop & had ample room for our family. Over all it was an Amazing Experience and look forward to coming back and spending some time with our new friends!!

--Matt Rogers (Google Business)

**If you are ANYWHERE on the island of Oahu, please take some time to head to the North Shore and hang out with this crew.**

--John H. Charlotte, NC (Yelp)

Captain Porter and Jacob were great hosts on our tranquil sail from Haleiwa to Waimea Bay. We were able to swim and view Hawaii wildlife thanks again !!!!

--TurtleNinja2020 (TripAdvisor)

This sailing experience made our vacation! The captain is highly experienced and engaged us in stories of his adventures sailing around the world. We were so lucky to see turtles and even watch dolphins swim with our boat. Even though I've never sailed before, I got to learn so much about the intricacies of a trimaran. We really feel that we got a much more personalized tour than we would have had with the larger operations that host large tourism groups. If you are looking for a more local and authentic experience, I highly recommend this tour operator.

--Mathias Z (Yelp)

The Sea Calls...

Will you answer, connect .

We are no longer booking charters at his time

North Shore Sailboat Charter

Private Sailboat Tours

[email protected]

Private Sailing Tours

Day sails/Whale Watching

Sail away on S/V Namaste for a day sail or our seasonal Humpback whale watching tour. 

2 hours 

Sunset Cruise

You and your friends finish your day with an incredible 2 hour Hawaiian sunset cruise.  

Full Day Charter

Get your sea legs on our full day (6 hour) charter.  We also offer multi-day charters.  Call for details.

ALL tours are private and same price for 1 or up to 6 people

[email protected].

(808) 429-3344

Pull into Haleiwa Harbor and take a right, keep going till you see the 200 row on your right. Slip 214

We are located in Haleiwa small boat harbor on Oahu's North Shore.  Enjoy sailing with your friends and family on Sailing Vessel Namaste, our 32ft. Gulf Pilothouse.  Namaste has plenty of space for you to move around on deck in the cabin.  These Gulf Pilothouse vessels are built heavy duty with a displacement of 16,000 lbs and the full keel makes for great sailing in Hawaiian waters.   We offer a variety of private sailboat charters from whale watching, day sails or sunset cruises.  Full day (6 hour) and Multi day charters are available.  You are welcome to bring your own food and beverages.  

Sailing Information

What to Bring?

It is always a great idea to bring plenty of water and sunscreen.  Hats are great but can get blown overboard so be careful.  Bring layered clothing as the weather in Hawaii can change in just a few minutes.  If you are prone to motion sickness products like Dramamine can help.  Be sure to use as directed, often times hours before getting on the boat.  You are more than welcome to bring food and alcoholic beverages  

If you forget, we try and always have all the above items on board.

We have a couple sets of binoculars on the boat so you can help the Captain find the whales.

We have life jackets to fit most people.  

2 infant life jackets under 30 lbs

2 Child 30-50 lbs

1 youth 50-90 lbs

7 type III adult life jackets 90+lbs, chest size up to 46"

4 type I adult life jackets

If you have any questions about life jackets feel free to call 

The fine print

$200/hour, minimum of  2 hours.  

Our pricing is the same for 1 or up to 6 people.  Full day sails are from 10am to sunset.  Times can be adjusted if needed, feel free to call with any questions. 

• * 7.16% added to the hourly rate (4.16% HST & 3% Harbor fees)
• Gratuity for your Captain is not included in charter rate .
• Cancellation Policy: If canceled more than 5 days in advance a full refund will be given. If canceled less than 5 days a refund is given if space is resold
• If we cancel your trip due to weather a full refund will be given.

Capital Yachts Gulf Pilothouse 32

Friends around oahu.

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​​​ Kainani Sails

​ makai adventures, choosing to sail with us means you are choosing to support a locally owned and family operated business that employs  full-time maui residents, many of whom have lost their homes. we appreciate you #lahainastrong.

Snorkel with a sea turtle! Private half-day snorkel sails available at an affordable rate. Great option for couples, families, or small groups looking for a unique experience. Maui Sailing Charters

Enjoy Hawaii on a private yacht.

Sail without the crowds. .

Or call us directly at 

Set sail on Maui's newest private yacht. Experience performance sailing, personalized snorkel trips , whale watching , or relaxing sunset cruises aboard a yacht all your own. Departing from world famous Ka'anapali Beach!

Sit back and relax as we discover true hawaii from the sea. , maui snorkeling tours, maui sunset sail and maui private charters.

Snorkel | Sunset | Charter

Come as guests & leave as friends.

RECOMMENDED PLACES TO EAT:

BEST HAPPY HOUR: http://www.dthmaui.com

BEST EATS WITH A VIEW: http://malatavern.com

BEST SHAVE ICE: http://www.breakwallmaui.com

BEST BREWERY: http://www.koholabrewery.com

BEST PIZZA: http://prisonstreetpizza.com

BEST BURGER: http://www.coolcatcafe.com

BEST FRESH POKE:  https://www.tobismaui.com/

BEST VEGETARIAN: https://www.mokuroots.com

What We Offer

3-hr  Intimate Maui Sunset Sails

3-hr Memorials At Sea or Ash Scattering Services

5-hr Maui Snorkeling & Sailing Adventures

6+ hr All Day Fun Under The Sun

We specialize in private sailing charters. Whether you are looking for some time to relax and kick back, or if you want to real in luxury - give us a call and see how we can help you make the most of your time while onboard. 

Real Sailing Aboard a Private Sailboat...

Lana'i is home to a resident pod of spinner dolphins, seen regularly playing off the rugged coastline. See them play at the bow with Kainani Sails of Maui Sailing Charters

*All trips depend on the weather and sea conditions. Destinations are at the Captain's discretion.*

Maui Sailing Blog

• Dec 28, 2022

Where is the best place to whale watch?

• Nov 8, 2022

The Whales are Defrosting

• Oct 27, 2021

We Turtley Love You!

• Sep 15, 2021

Keeping it Classy, not Trashy

• Jan 30, 2021

A true Hawaiian!

• Jan 16, 2021

Featured Destination: The Mala Wharf Experience

• Nov 3, 2019

Our NEW boat!

• Feb 11, 2019

Fish Galore!

• Feb 7, 2019

Cruise Into The Maui Sunset

• Feb 4, 2019

Kainani Sails Snorkel Extravaganza

• Jan 31, 2019

What Will I See?

• Jan 28, 2019

Snorkel with Fish Seen Nowhere Else on Earth

• All Adventures
• Waikiki Sail & Snorkel Adventure

Diamond Head Sunset Cruise

Explore famous turtle canyons, private whale watching cruise.

• Friday Nite Fireworks Cruise

Offshore Fishing

• Private Sunset Dinner Cruise
• Interisland Overnight Adventures
• ASA Sailing School
• Event Planning
• Luxury 43 Ft Sailing Yacht
• Luxury 48 Ft Sailing Yacht
• Luxury 50 Ft Sailing Yacht
• Luxury 50 Ft Sailing Catamaran
• Articles & latest News

Experience the Magic of Hawaii!

Sunset sails, snorkeling adventures, whale watching, friday night fireworks, explore turtle canyons, asa certified sailing school, anniversaries, bachelorette parties, memorials & ash ceremonies, catering photography, waikiki sail & snorkel adventure.

Oahu’s Best Snorkeling Tour features a three hour cruise aboard a private luxury yacht. Enjoy a leisurely sail off the idyllic coast of Oahu’s famous Waikiki Beach with stunning views and  a chance to see dolphins, sea turtles and whales in season.

Escape the crowds and let your captain guide you to a relaxing anchorage where you can snorkel with tropical fish, sea turtles and beautiful coral.  Invite your family and friends and make memories while your Captain and crew take care of the rest.

Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Immerse yourself in a gorgeous Hawaiian sunset. Idyllic sailing awaits you with spectacular views of iconic Diamond Head and Waikiki. Catch a glimpse of dolphins, sea turtles, and whales in season.  Honolulu’s city lights provide an enchanting backdrop for your return to port.

Immerse yourself in a vibrant underwater wonderland as you snorkel through coral reefs teeming with Sea Turtles and tropical fish. The crystal clear waters of Waikiki’s Famous Turtle Canyons reveal a kaleidoscope of colors and marine life. Discover the secrets of this diverse marine ecosystem as you swim among the colorful inhabitants and witness the beauty of Hawaii’s underwater world up close. Our Top Rated Sea Turtle Swim features a three hour private cruise aboard a luxury yacht. Get a chance to see dolphins and whales (in season) while taking in the magnificent views of Oahu’s Famous Waikiki coastline. 

From the comfort of your private luxury yacht, enjoy an amazing experience with Hawaii’s humpback whales.  Departing near Waikiki, enjoy a leisurely sail against the majestic backdrop of Diamond Head as you scan the water for majestic whales. Dolphins, sea turtles, and manta rays are often seen while relaxing aboard with your family and friends.

Sport fishing from a sailboat is a true adventure!  We head offshore where the big fish are and sail fast to catch real gamefish like mahimahi, ono, and tuna. We do not fish the delicate reef ecosystem, those fish should only be caught on camera, and you can do that on our snorkeling tours. Offshore fishing in Hawaiian conditions can be physically challenging so be sure you are ready. We often see dolphins, sea turtles and manta rays while sailing offshore.

We offer beginner to advanced sailing and navigation instruction aboard private yachts in the Hawaiian Islands. Instructors are ASA Certified and dedicated to teaching you the skills required to be your own Captain. We give you the knowledge and experience to be confident and safe on all your sailing adventures- Whether you charter a boat from a local harbor, go on an exotic sailing vacation, or even buy your own boat.

Special Event Planning

Bring the Spirit of Aloha to your next Birthday, Anniversary, Hawaiian Wedding, or Corporate event. Let our preferred Honolulu event specialists assist you in making your event an unforgettable success! If you would like to have a Memorial at Sea or a Hawaii Ash Scattering we can help you create the right ceremony.

Your message

Want your own private sunset tour? This is it! The tour was very professional as well as fun. Michelle made booking the tour very easy. Michelle and Will were very good on the open Ocean and very accommodating. Allowed music if you wanted and can bring whatever drinks you want. Will had just crossed the Pacific Ocean in a boat! Wow!

What to do with a dozen friends all in town at once? Our sunset sail was wonderful! Everyone had a lovely time, enjoying the beautiful skyline and horizon. The highlight of the trip was our close sighting of humpback whales! They were less than 30 yards away at times – it’s hard to say whether the kids or the adults were more excited! The crew was very helpful and the boat Tefiti (for sailing nerds) is beautiful, clean, in perfect condition, and amazingly set up for singlehanding – almost everything is automated to the point she almost sails herself. Not a spot of rust anywhere – she clearly gets a lot of TLC!

Our family of 10 rented the boat originally for two hours to take my husband’s ashes out to Diamond Head and scatter them in the ocean he loved so much and sailed so often. It was a Memory that the entire family will cherish forever. Michele and our captain couldn’t have been more accommodating. After we put his ashes into the water, we asked if it would be possible to stay out an extra hour so that we could all swim in the waters off Waikiki…and the two of them were totally good with that! Such a fun time after such an emotional day for us all. Michele was so good with the two youngsters we had with us…even providing brand-new life jackets for them…ages 6 + 7! It was sunset as we came into the channel…docking was a picture perfect ending to the afternoon. Thank you so much! We loved it and highly recommend this team for a perfect sail aboard the Beneteau 50 Te Fiti!

Had a great day with Honolulu Sailing Company. It was really nice to have a private yacht and avoid the crowds packed on other boats. Our family really appreciated that the captain and crew were fully vaccinated and it made the tour very relaxing. It’s hard these days to find something to do that feels safe. We booked a snorkel cruise and will book a sunset sail before we head home to Arizona.

Pua Ka Ilima

Sailing Charters

Aloha friends... Let's go sailing!

A local seafaring voyage.

Sailing, snorkeling and off-shore exploration of the Big Island of Hawai'i's stunning west coast.

Pristine Water, Stunning Landscape

300+ days of perfect sailing conditions 

78 degree water

80 degree weather

Breathtaking landscape of 5  volcanoes

Marine wildlife sightings 

Cultural Educational Sailing Experience Good, HI Vibes

Tradewind Sails

Sunset Sails

  Six Passengers

High Service Luxury

Sailing Yacht

Call to ask about 

Private Snorkel Sails

808 874-1110

Maui Luxury Sail

Hawaii charter.

Follow S HADOWFAX

Complimentary upscale pupu & soft drinks included.

Privates: $375/hour

2 hour minimum for sails

2 1/2 hour minimum for sunset sails

4 hour minimum for snorkeling

Check Availability

Call (808) 874-1110

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Hawaii's Only Renewable Electric Charter

Experience the Difference

Welcome to Kohala Blue Sail Hawaii, the most eco-friendly c harter in the Hawaiian Islands ! Come enjoy a virtually silent and peaceful ocean adventure while also significantly lowering the impact on our local marine wildlife. We operate the only renewable electric charter vessel in the state of Hawaii, the Dolce Vita,  our newly converted 34' Gemini 105Mc sailing catamaran .   Her twin electric motors charge with solar, wind and propeller regeneration technologies, bringing tranquility both on and in the water.

From Kawaihae South Harbor on the Big Island of Hawaii, we provide fully customized, private and shared  charter experiences for your crew of  family and friends. Let us know if you have anything particular in mind! We love exploring the beautiful Kohala Coast and are here to make sure your time with us is as sweet as life can be. 

Morning Sail

Afternoon Sail

Sunset Sail

“the crew was fabulous. the catamaran sailboat was quiet & peaceful with no motor and only electric propulsion. all we heard was the splashing of whales and dolphins.”.

- Mel C.  Anchorage, AK

Matt Weidert

Sailing in Hawaii: Is a Bareboat Charter Possible?

Where to go sailing in hawaii, what is it like to go sailing in hawaii, how you can take a hawaii yacht charter trip.

Week-long Kauai sailing itinerary:

Day 1: cross kauai channel, anchor at hanalei bay, day 2: hanalei bay.

Day 3: Ha’ena and Tunnels Beach

Day 4: Off to explore Napali Coast

Day 5: Polihale Beach

Day 6: Go visit the forbidden island, Ni’ihau

Day 7: cross back to oahu or disembark.

Hawaii cruising conditions

Pacific trade winds.

Hawaii’s summer season

Hawaii’s winter season, tides and current.

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