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Cruise Itinerary

Join the exhilarating Opera House Cup regatta aboard the magnificent schooner Rebecca. Experience the thrill of competing alongside passionate sailors from far and wide in one of the most prestigious races on the East Coast. Immerse yourself in the vibrant atmosphere of Nantucket as classic yachts gather to showcase their sailing prowess in this captivating event. Explore the island's timeless charm, indulge in its renowned dining scene, and discover its cultural treasures. Participate in the regatta, forge lasting connections, and create unforgettable memories in the heart of Nantucket's maritime legacy.

Embark on an extraordinary adventure aboard the magnificent schooner Rebecca as you set course for Nantucket, a captivating destination renowned for its annual Opera House Cup regatta. Sail across the sparkling waters and immerse yourself in the timeless charm of this island paradise. Nantucket's attractions await your discovery, from the iconic Brant Point Lighthouse to the cobblestone streets of the historic downtown. Explore the Nantucket Whaling Museum and delve into the island's captivating history, once a bustling hub of the whaling industry. Experience the enchantment of Nantucket's sandy beaches, picturesque landscapes, and idyllic coastal scenery that will leave you in awe.

As you approach Nantucket for the Opera House Cup regatta, be prepared for a thrilling spectacle. Classic yachts from far and wide gather to compete in this prestigious event, creating a vibrant display of sailing prowess against the backdrop of Nantucket Sound. Feel the adrenaline as you join the ranks of passionate sailors and showcase your skills in this highly anticipated race. Engage in friendly competition and forge lasting connections with fellow enthusiasts, all while experiencing the exhilaration of sailing in one of the most esteemed regattas on the East Coast.


After the races, the charm of Nantucket continues to captivate. Indulge in the island's renowned dining scene, where world-class restaurants offer culinary delights using fresh local ingredients. Explore the quaint streets lined with boutique shops, art galleries, and cultural treasures. Take in the island's natural beauty as you stroll along the sandy shores and witness breathtaking sunsets over the Atlantic Ocean. This extraordinary sailing experience aboard Rebecca will create memories to cherish, as you immerse yourself in the maritime legacy of Nantucket and revel in the enchantment of this timeless destination.

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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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