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Cruise Itinerary

Cruising into Marblehead on sailboat Rebecca provides a delightful opportunity to explore a charming coastal town. Experience the historic beauty of Old Town, soak in the picturesque views of Marblehead Harbor, and enjoy the welcoming ambiance of the Corinthian Yacht Club. Discover Marblehead's sailing heritage, relax on its beaches, and savor the local cuisine and boutique shops. Don't miss the chance to immerse yourself in the vibrant community events and regattas that showcase the town's maritime spirit.

Day 1: Arrival, Practice Sail, and Yacht Club Experience 9:00 am: Guests arrive and settle down aboard Schooner Rebecca, eagerly anticipating the sailing adventure ahead. Feel the excitement build as you step on board and get acquainted with the crew and fellow sailors. 11:00 am: Set sail for a practice session, honing your skills and familiarizing yourself with the boat. While sailing, enjoy a delicious lunch with freshly made sandwiches, savoring the flavors amidst the stunning coastal scenery. Afternoon: As the day progresses, everyone onboard Rebecca becomes more comfortable with their roles and the boat's maneuvers. With the captain's approval, head towards Marblehead and secure a mooring. Grab the yacht club launch for the the Corinthian Yacht Club, a renowned institution in Marblehead, and unwind with a refreshing drink, taking in the vibrant atmosphere and mingling with fellow sailors. Evening:  Celebrate the beginning of an exciting weekend of racing and revel in the welcoming ambiance of the Corinthian Yacht Club.

Day 2: Full Day of Racing and Evening Celebration Morning: Wake up to the anticipation of a day filled with exhilarating races. Prepare yourselves and your boat for a thrilling day on the water, aiming to showcase your skills and compete for a coveted trophy. Throughout the Day: Engage in intense and competitive racing, navigating the challenging course with determination and finesse. Feel the rush of adrenaline as you maneuver through the waves, harnessing the power of the wind to propel you towards victory. Evening: As the sun sets on a day of thrilling races, it's time to unwind and celebrate. Join the dinner and party at the Corinthian Yacht Club, surrounded by fellow sailors and regatta participants. Share stories, laughter, and the joy of a day well spent on the water. The Corinthian Yacht Club provides the perfect backdrop for a memorable evening of camaraderie and celebration.

Day 3: Final Race and Awards Ceremony Morning: Sunday marks the last day of racing, bringing a mix of excitement and bittersweet anticipation. Prepare yourselves for the final challenge, showcasing your skills and determination in the pursuit of victory. Evening: The regatta culminates with an awards ceremony and party, where participants gather to celebrate their achievements. Join in the festivities and cheer for fellow sailors as trophies and recognition are bestowed. Embrace the sense of accomplishment and the bonds forged during this unforgettable sailing adventure.

 Marblehead's rich maritime heritage and the Corinthian Yacht Club's welcoming atmosphere provide the perfect backdrop for an incredible sailing experience.

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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