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Cruise Itinerary

Embark on an extraordinary sailing adventure aboard the renowned schooner Rebecca as you participate in the exhilarating Pat West Yacht Regatta, hosted by the esteemed Gannon and Benjamin Marine Railway in Vineyard Haven, Martha's Vineyard. This regatta merges the natural beauty of the island with the passion for sailing, creating a captivating experience. Vineyard Haven, a charming coastal town, holds a captivating history and offers a plethora of activities for visitors to enjoy.

Immerse yourself in the rich history of Vineyard Haven, which served as a prominent seaport during the 19th century. Explore the town's picturesque streets lined with beautiful Victorian homes and quaint shops. Visit the Martha's Vineyard Museum to delve deeper into the island's fascinating maritime heritage and local culture. Stroll along the idyllic shores, soak up the sun on the pristine beaches, or indulge in fresh seafood at waterfront restaurants.

The Pat West Yacht Regatta, hosted by the esteemed Gannon and Benjamin Marine Railway, showcases the craftsmanship and expertise of this renowned boatbuilding business. Gannon and Benjamin have a rich history of constructing and restoring classic wooden boats, including the iconic Rebecca. Engage with fellow sailors, revel in the camaraderie, and witness the artistry of traditional boatbuilding in action.

During your time in Martha's Vineyard, seize the opportunity to explore the island's captivating attractions. Discover the charming towns of Edgartown and Oak Bluffs, each offering unique experiences and architectural beauty. Take a bike ride through the picturesque landscapes, visit the iconic Martha's Vineyard lighthouses, or enjoy a leisurely hike along scenic trails. Indulge in the island's culinary delights, from fresh seafood to locally produced wines.

After an exhilarating day of sailing in the Pat West Yacht Regatta, join the lively prize giving and party at the Gannon and Benjamin Railroad Beach Shop in Vineyard Haven, Martha's Vineyard. This iconic establishment, renowned for its boatbuilding heritage, sets the stage for a memorable post-regatta celebration. Immerse yourself in the rustic charm of the beach shop as musicians fill the air with lively tunes, voices join in spirited sing-alongs, and sailors share stories of the day's races. Indulge in delectable food, refreshing drinks, and the company of like-minded individuals who appreciate the beauty of classic boats. Dance under the starry sky, revel in the maritime culture of Martha's Vineyard, and create lasting memories of camaraderie and joy in the sailing community.

Participating in the Pat West Yacht Regatta aboard Rebecca is not only a thrilling sailing experience but also an opportunity to immerse yourself in the rich history and enchanting allure of Vineyard Haven and Martha's Vineyard. Celebrate the legacy of Gannon and Benjamin Marine Railway, revel in the competitive spirit of the regatta, and embrace the idyllic charm of this beloved island destination.

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Package Calendar

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

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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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