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Cruise Itinerary

Embark on a thrilling Regatta Cruise in Martha's Vineyard, where you'll join competitive races, hone your sailing skills, and celebrate with fellow sailors. Settle aboard Schooner Rebecca for a practice sail, followed by exhilarating regatta races and a festive Race Party. Conclude the cruise with a Pursuit Race and an awards ceremony. Get ready for an unforgettable sailing adventure filled with camaraderie

Day 1:Arrival and Practice Sail 9:00 am: Guests arrive and settle down aboard Schooner Rebecca. Enjoy a warm welcome and get acquainted with the crew and fellow sailors.

11:00 am: Set sail for a practice session, preparing for the upcoming regatta. Lunch will be served on board while enjoying the sailing experience. Afternoon: Take the opportunity to fine-tune sailing skills and maneuvers under the guidance of the captain. Once everyone is comfortable and the captain is satisfied with the boat's performance, head towards Vineyard Haven and anchor up.

Evening: Attend the competitors' meeting at 6:00 pm at Sail MV, gathering valuable information and instructions for the regatta. Enjoy a relaxing evening on board, savoring the tranquil atmosphere.

Day 2: Regatta Race Day and Celebration Morning: Rise early to prepare for the regatta. Leave the anchorage well before the regatta warning signal at 10:00 am. The focus will be on racing, giving your best performance, and aiming for a coveted trophy. Throughout the Day: Engage in thrilling races, putting your skills to the test amidst the stunning surroundings of Martha's Vineyard. Enjoy the excitement and competitive spirit of the regatta.

Evening: After an exhilarating day on the water, it's time to celebrate! Attend the Race Party at the Sail MV Boathouse, where delicious food and refreshing drinks will be served. A suggested donation of $20 per person can be paid at the event. Socialize, share stories, and revel in the accomplishments of the day.


Day 3: Pursuit Race and Awards Ceremony Morning: Prepare for the Pursuit Race, with the first boat warning signal at 10:30 am. Experience the thrill of chasing and being chased by fellow racers, showcasing your sailing prowess. Afternoon: Enjoy the final race of the cruise, giving it your all until the finish line. Once the racing concludes, relax on board and reflect on the unforgettable experiences of the past days.

Evening: Join the Awards Ceremony at Martha's Vineyard Shipyard. Celebrate the achievements of the participants, share in the camaraderie, and raise a toast to a successful regatta. Refreshments can be enjoyed at your own discretion.


Note: The itinerary is subject to weather conditions and may be adjusted by the captain for safety and optimal enjoyment of all participants.

Boothbay Classic Regatta 2022 by Patrick Sikes-17.jpg

Package Calendar

Find the Package and Date that works for you. Click it. Book it. It's that simple.

Boothbay Classic Regatta 2022 by Patrick Sikes-18.jpg

Package info

The charterer and client are responsible for providing the following:

  • Crew Gratuity: The charter package does not include crew gratuity. It is recommended to provide $100 to $150 per day per crew member, or a group gratuity of $200 to $300 per day. Cash in an envelope at the end of the charter is preferred, but Venmo is also accepted.

  • Alcoholic Beverages: The charterer (client) is responsible for supplying alcoholic beverages. Beverages other than water and a small soda selection are not included in the charter package. Bringing your own beverages (BYOB) is allowed and encouraged.

  • Dietary Restrictions and Allergies: The charterer and guests must inform the Owner and/or the Captain about any dietary restrictions or allergies at least 3 days prior to the charter.

  • Additional Expenses: The charterer is responsible for paying for any expenses not included in the package, such as restaurants, transportation to and from the boat, tours, excursions, and other costs that may arise during the charter.

  • Crew Meals: If the charterer takes the crew out to dinner, it is the charterer's responsibility to pay for the crew meals within reason.



Things to bring:


  • Sufficient clothing without excess, as storage is limited on a yacht. Include options for wet and cooler weather.

  • A bathing suit, a hat, sunglasses, and sun cream.

  • While a variety of snacks are provided on board, you are welcome to bring your favorite snacks if you have specific preferences.


What the Owner and charter package provide:


  • Fresh linens and towels.

  • Two crew members: a Captain and a Mate who share cooking and cleaning responsibilities.

  • Plates, cutlery, cookware, coolers, ice, glasses, and cups for the charter.

  • Provisions for three meals a day, including a light breakfast, sandwiches during racing and sailing, and dinner.

  • Water and Sodas.

  • Dockage and/or mooring fees included in the charter package.

  • Charter Registration and entry.

  • Insurance.


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