annapolis sailboat racing schedule

Naval Academy Athletics

2023-24 offshore sailing schedule.

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Scheduled Games

Annapolis Labor Day Regatta

J/105 Fleet 3 Women's Regatta

Race to Oxford

Hammond Memorial Race

US Offshore Championships

Hospice Cup

Great Lakes Intercollegiate Offshore Regatta

Shields Trophy

Annapolis Yacht Club Fall Series

Storm Trysail Intercollegiate Offshore Regatta

JV Keelboat Invitational Regatta

McMillan Cup

J/105 Chesapeake Bay Championship

Kennedy Cup

Southern Collegiate Offshore Regatta

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ANNAPOLIS, MD PERFORMANCE RACE WEEK +  REGATTA EXPERIENCE ®

Welcome to American Sailing's Performance Race Week powered by North U. This clinic includes two days of on-the-water clinics, plus three days of racing at the Helly Hansen Sailing World Regatta. Seasoned coaches will be onboard your J/80, for both training and racing, guiding you through every facet of regatta success: strategic planning, tactical positioning, starting, boat speed, trim, helming, boat handling, and more!

“Performance Race Week is about getting faster and smarter, and while a sunburn will soon fade, the memories and the lessons will last a lifetime.”

Performance race week + REGATTA EXPERIENCE® ANNAPOLIS

Course overview.

North U has been turning sailors into racers and racers into winners since 1980. Whatever your level, we can raise your game. Sailboat racing is a complex endeavor: Trim, tactics, boat speed, helming, rules, sets, jibes, douses, wind shifts, current, waves, chop, weight placement, downwind angles, rig tuning, wind shadows, starting, heavy air, light air, etc. We will help you build on your strengths and improve in areas of weakness to become a better, more versatile racer.

The clinic teaches refined techniques to transform you from a racer into a winner.  Sailboat racing is a complex endeavor drawing upon a broad mix of skills. Every sailor has strengths and weaknesses in their skill set.  We’ll improve areas of weakness and build on your strengths to send you home a better, more versatile racer.  By having your coach on board we are able to focus on your particular skill set.

The Coaches

North U coaches combine championship racing skills with years of coaching experience. With just four sailors plus a coach aboard each boat you’ll get close personal attention. Just to be clear: The coaches will NOT be sailing the boats. You and your team do all the sailing.

The Boats - J/80

The J/80 is a comfortable, responsive, stable, high performance racing boat that features a large open cockpit with plenty of room for each crew member to do their job. It has a retractable bowsprit, a transom-hung rudder, fin keel, and large fractional rig. The sail plan includes a full-batten main, furling jib, and asymmetric spinnaker. The full range of sail controls and responsive design allow you to learn the impact of changes in trim on speed, balance, and pointing.

The Regatta

The Helly Hansen Sailing World Regatta in Annapolis is one of the premier events on the winter racing calendar. Among the 100s of boats, we will be racing one-design in the J/80 fleet with upwards of 30 boats competing. Your coach will be on board to provide training in real-time. We'll also have our video team on the water compiling footage for each day’s debrief.

Annapolis, Maryland, often referred to as the "Sailing Capital of the United States," boasts a rich maritime history, idyllic sailing conditions, a vibrant sailing culture, and a captivating blend of old-world charm and modern boating amenities. Whether you're an experienced sailor or just setting sail for the first time, Annapolis offers an unparalleled sailing experience.

Sailors are drawn to Annapolis for its picturesque Chesapeake Bay, which provides a perfect setting for sailboat races. The Chesapeake Bay is known for its moderate winds, making it ideal for sailors of all skill levels.

The rich maritime heritage of Annapolis is celebrated through museums, historic tours, and festivals, allowing visitors to connect with Annapolis's seafaring past. Its charming downtown, with its cobblestone streets and 18th-century architecture, provides a captivating backdrop to the sailing adventures on the Chesapeake Bay.

THE SAILING VENUE

The clinic is being run out of JWorld Annapolis in the Eastport neighborhood of Annapolis. The sailing will take place on the waters of Chesapeake Bay.

ACCOMMODATIONS

There are plenty of hotels in close vicinity to Eastport / Annapolis and plenty of good vacation rental options in the area. JWorld Annapolis has an accommodation guide to help get you started.

The Details

May 1st - 2nd: Pre-Regatta Clinic

• Morning Class Session
• Afternoon On-the-Water training
• Video Debrief

May 3rd - 5th: Helly Hansen Sailing World Regatta

• Morning Pre-Brief
• Regatta Sailing
• Post-Race Video Debrief

What's Included

Fully equipped J/80

• A Two Day Clinic Prior to the Regatta
• The Three Day Regatta
• A North U Coach On Board for both the Clinic & Regatta
• Lunch will be provided every day
• Regatta Entry Fee
• Daily Debriefs

What's Not Included

• Travel & Accommodations
• Food (except lunch which is provided)
• Personal Sailing Gear (bring your PFD and Racing Watch)

$2,490 - Individual Sailor ( Book Online )

$9,360 - Full Crew of 4 Sailors ( Book Online )

$7,360 - Bring Your Own Boat + Full Crew ( Book Online )

$QUOTE - Bring Your Own Boat Options ( Contact us to book )

Risk Free Registration Pay a $500/person deposit to reserve your space today and your payment will be fully refundable until February 15th, 2024.

Payment Due Dates All registrations must be paid in full by March 1st, 2024 .

Performance Race Week Regatta - Annapolis

• LOCATION: Annapolis, Maryland
• STARTS: Wednesday May 1st 2024 @ 8:30am
• ENDS: Sunday May 5th 2024 @ 6:00pm
• Crew #1 Price:

Choose a package:

• Hidden Performance Race Week
• Individual Sailor $2,490
• Full Crew of 4 Sailors (SAVE $150/person) $9,360
• Bring Your Own Boat + Full Crew (SAVE $1,750) $8,210
• Crew #2 Price:
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• Crew #4 Price:
• Pay In Full
• Pay $500 deposit/person
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• If you are registering a team of 4 sailors, please enter the contact information for each sailor.
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• Billing Address * Street Address Address Line 2 City State / Province / Region ZIP / Postal Code Afghanistan Albania Algeria American Samoa Andorra Angola Anguilla Antarctica Antigua and Barbuda Argentina Armenia Aruba Australia Austria Azerbaijan Bahamas Bahrain Bangladesh Barbados Belarus Belgium Belize Benin Bermuda Bhutan Bolivia Bonaire, Sint Eustatius and Saba Bosnia and Herzegovina Botswana Bouvet Island Brazil British Indian Ocean Territory Brunei Darussalam Bulgaria Burkina Faso Burundi Cabo Verde Cambodia Cameroon Canada Cayman Islands Central African Republic Chad Chile China Christmas Island Cocos Islands Colombia Comoros Congo Congo, Democratic Republic of the Cook Islands Costa Rica Croatia Cuba Curaçao Cyprus Czechia Côte d'Ivoire Denmark Djibouti Dominica Dominican Republic Ecuador Egypt El Salvador Equatorial Guinea Eritrea Estonia Eswatini Ethiopia Falkland Islands Faroe Islands Fiji Finland France French Guiana French Polynesia French Southern Territories Gabon Gambia Georgia Germany Ghana Gibraltar Greece Greenland Grenada Guadeloupe Guam Guatemala Guernsey Guinea Guinea-Bissau Guyana Haiti Heard Island and McDonald Islands Holy See Honduras Hong Kong Hungary Iceland India Indonesia Iran Iraq Ireland Isle of Man Israel Italy Jamaica Japan Jersey Jordan Kazakhstan Kenya Kiribati Korea, Democratic People's Republic of Korea, Republic of Kuwait Kyrgyzstan Lao People's Democratic Republic Latvia Lebanon Lesotho Liberia Libya Liechtenstein Lithuania Luxembourg Macao Madagascar Malawi Malaysia Maldives Mali Malta Marshall Islands Martinique Mauritania Mauritius Mayotte Mexico Micronesia Moldova Monaco Mongolia Montenegro Montserrat Morocco Mozambique Myanmar Namibia Nauru Nepal Netherlands New Caledonia New Zealand Nicaragua Niger Nigeria Niue Norfolk Island North Macedonia Northern Mariana Islands Norway Oman Pakistan Palau Palestine, State of Panama Papua New Guinea Paraguay Peru Philippines Pitcairn Poland Portugal Puerto Rico Qatar Romania Russian Federation Rwanda Réunion Saint Barthélemy Saint Helena, Ascension and Tristan da Cunha Saint Kitts and Nevis Saint Lucia Saint Martin Saint Pierre and Miquelon Saint Vincent and the Grenadines Samoa San Marino Sao Tome and Principe Saudi Arabia Senegal Serbia Seychelles Sierra Leone Singapore Sint Maarten Slovakia Slovenia Solomon Islands Somalia South Africa South Georgia and the South Sandwich Islands South Sudan Spain Sri Lanka Sudan Suriname Svalbard and Jan Mayen Sweden Switzerland Syria Arab Republic Taiwan Tajikistan Tanzania, the United Republic of Thailand Timor-Leste Togo Tokelau Tonga Trinidad and Tobago Tunisia Turkmenistan Turks and Caicos Islands Tuvalu Türkiye US Minor Outlying Islands Uganda Ukraine United Arab Emirates United Kingdom United States Uruguay Uzbekistan Vanuatu Venezuela Viet Nam Virgin Islands, British Virgin Islands, U.S. Wallis and Futuna Western Sahara Yemen Zambia Zimbabwe Åland Islands Country

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• Annapolis, MD May 1st – 5th, 2024
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Ready, Set Annapolis

• By Dave Reed
• May 2, 2023

Come Friday morning, the Annapolis, Maryland, waterfront will be abuzz with race teams preparing for the opening day of racing at the Helly Hansen Sailing World Regatta , hosted by the Annapolis YC. This third event of the national regatta series is the first major event of the Chesapeake Bay spring sailing season, so there will certainly be heightened anticipation as 160 teams get set for three days of racing across 13 individual classes.

Two classes new to the regatta, which has been held in Annapolis for 33 years, are the Melges 15 and Wayfarer classes, doublehanded dinghies that originated more than 50 years apart. The Melges 15 , considered to be the fastest growing dinghy class in the US, has attracted family, coed, and youth teams to its winter regatta series in Florida, and some of these sailors will be taking to the Chesapeake for the first time alongside a few new owners. The Wayfarer , originally designed in 1957, has stood the test of time and is enjoying a resurgence with concentration of owners in the Southeast and Michigan, and the Annapolis regatta will serve as an opportunity for these traveling teams to meet one another on the big stage.

While many competitors will be traveling in from afar, Annapolis is home to robust one-design fleets that produce a unique concentration of class champions alongside some of the sport’s top professional sailors. The largest turnouts for this year’s regatta are in the J/70, J/80 and J/105 classes, which is to be expected in this sailing-obsessed city. The J/105 contingent, with 22 entries to date, will have all eyes on Cedric Lewis and Fredrik Salvesen’s Mirage , overall winners of the 2022 regatta, especially Ray Wulf’s Patriot , which was runner-up to Mirage in last year’s two-race series, truncated on account of the absence of wind over the three days.

The J/80 fleet only managed a pair of races in 2022 as well, with Will and Marie Crump and Thomas Klok’s R80 beating Thomas and Jennifer Kopp’s Kopp-Out, from Grosse Pointe Farms, by a mere 2 points. While the Crumps will not be in attendance to defend, several past winners, notably Conor Hayes’s More Gostoso , from Meredith, New Hampshire, will take up the challenge alongside 21 other teams, including five teams that have entered as part of the concurrent NorthU Regatta Experience. This immersive race-training program run by the American Sailing Association features two days of clinics and coaching for participants before the regatta and onboard coaching during the races themselves.

Over the weekend, two legacy classes will contest their annual championships: The East Championship for the J/30s and the Maple Leaf Championship for the classic Alberg 30 s, both of which have been a regular presence at the regatta for many years. For the Alberg 30s especially, this is the major kick off for their Chesapeake season with teams traveling in from throughout the region.

While the Etchells fleet is small in size following its World Championship in Miami last month, the Viper 640 s, having contested their Worlds in New Orleans in March, are back to near strength with 17 entries, including the 2022 regatta winner Evil Hiss , helmed by local favorite Mary Ewenson. The 1-boat J/22 fleet is packed with top local teams, including multiple-time defending champion Jeffrey Todd, as well as four experienced all-junior teams supported and kitted out by event organizers and Helly Hansen as part of the regatta series’ effort to bolster youth participation at all locations.

The J/70s will also have plenty of young sailors spread amongst the teams, many of which are using the regatta as training opportunity for the high-stakes J/70 World Championship in Florida in November. The leading contender, Brian Keane’s Savasana, which has won all the major winter events to date, will be in attendance, focusing on refining its program and keeping its momentum on the long road to the Worlds.

One new addition to the regatta is two days of distance racing for local PHRF and ORC sailors. These 11 teams will sail Saturday and Sunday only, completing one long race per day over courses that span the Chesapeake Bay for as many 12 miles, or as many hours as needed to get them a quality race and back in time for the nightly parties hosted at the Annapolis YC. With so many classes and racecourses to manage, the club works in partnership with Eastport YC and the Severn Sailing Association for on-water and race committee support.

In addition to planned social activities for the sailors, friends and locals, the Regatta Series and Sailing World will host its third Speaker Series event with American Magic, the New York challenge for the 37 th America’s Cup in Barcelona in 2024. Terry Hutchinson, American Magic’s skipper and president of sailing operations, will be on stage Thursday evening to share the team’s progress and provide exclusive insight into their formidable Cup challenge. Quantum Sails, the official sailmaker of the series has a full complement of support planned for competitors, from daily weather briefings, on-the-water coaching and debriefs and sail-repair services and title sponsor Helly Hansen will have an on-site store open daily to fit competitors and club members for the season with the latest sailing gear and accessories.

• More: Helly Hansen Sailing World Regatta Series , Helly Hansen Sailing World Regatta Series Annapolis
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2024 Sailing Season is coming! See you April 13, 2024!

Welcome Aboard!

Join us on our two beautiful, wooden, 74-foot schooners, Woodwind and Woodwind II , for a true sailing experience in Annapolis, Maryland.

Located in the heart of the Chesapeake Bay, Annapolis is “America’s Sailing Capital.” Help raise the sails, steer the boat, or simply sit back and relax as Woodwind sails from the historic Annapolis waterfront, past the Naval Academy and cruises into the Chesapeake Bay. As a family business, we take great pride in making your sailing experience a memorable one. Our captains and crew are engaging and enthusiastic. Sail away with us!

Make your sailing experience a memorable one! Sail away with us!