top of page

Cruise Itinerary

Boothbay, located on the picturesque coast of Maine, is a charming destination that offers a unique experience for sailors and cruising enthusiasts. Known for its natural beauty, quaint coastal villages, and vibrant maritime heritage, Boothbay is a perfect setting for the Boothbay Classic Yacht Regatta.

Cruising to Boothbay allows you to immerse yourself in the enchanting coastal scenery and enjoy the pleasures of sailing. As you navigate the pristine waters, you'll be greeted by stunning vistas of rugged coastlines, rocky islands, and serene harbors. The region's calm waters and favorable winds provide an ideal environment for a memorable sailing adventure.

Arriving in Boothbay, you'll be captivated by its authentic New England charm. The town is characterized by historic waterfront buildings, bustling harbors filled with sailboats, and an inviting atmosphere. Stroll along the picturesque streets, explore local boutiques and art galleries, and indulge in fresh seafood at waterfront restaurants.

Boothbay is also known for its maritime attractions, including the renowned Maine Maritime Museum. Discover the rich seafaring history of the area, explore exhibits on boatbuilding, and learn about the region's lobstering traditions.

During the Boothbay Classic Yacht Regatta, the town comes alive with the spirit of sailing. Join fellow sailors and racing enthusiasts as you compete in thrilling regatta races, showcasing your skills and passion for sailing. The event brings together a vibrant community of sailors, offering an opportunity to connect, share experiences, and celebrate the joy of sailing.

Beyond the regatta, Boothbay offers a host of activities for visitors. Take a scenic cruise to explore the nearby islands, such as Burnt Island or Monhegan Island, and enjoy their natural beauty and wildlife. Embark on a lobster boat tour to gain insight into the local lobster industry and even try your hand at hauling traps.

Whether you're participating in the Boothbay Classic Yacht Regatta or cruising to Boothbay for leisure, this charming coastal destination promises an unforgettable sailing experience. From the thrill of the races to the tranquility of the coastal scenery, Boothbay captures the essence of maritime adventure on the stunning Maine coast.

Below is the general a plan for Boothbay Classics:


Day 1: Arrival and Practice Sail

  • Guests arrive in the morning and settle down aboard Schooner Rebecca.

  • Set sail for a practice session, fine-tuning sailing maneuvers and skills.

  • Enjoy a delicious lunch while out sailing.

  • Head back to the dock and secure the schooner for the evening.


  • Attend the registration and socialize with fellow participants.

  • Join the owners and skippers for cocktails and dinner, building camaraderie.

Day 2: Regatta Race Day and Post-Race Reception

  • Check-in and fuel up with breakfast snacks.

  • Gather for the skippers' meeting to receive race instructions.

  • Embark on an exhilarating day of racing, showcasing your sailing skills.

  • Compete for a chance to win coveted trophies.


  • Celebrate the day's accomplishments at the post-race reception.

  • Enjoy refreshments, share stories, and connect with other sailors.

Day 3: Boat Parade, Racing, and Awards Ceremony Morning:

  • Participate in the boat parade, adding to the vibrant display.

  • Prepare for an exciting day of racing, giving your best on the water.


  • Engage in the final races, showcasing your sailing prowess.

  • Reflect on the unforgettable experiences of the past days.


  • Join the highly anticipated awards ceremony and party.

  • Celebrate the achievements of the participants and enjoy the festive atmosphere.

  • Guest will need to depart that evening or very early in the morning the next day as Rebecca will be leaving at first light for Newport RI.

Note: The itinerary is subject to weather conditions and may be adjusted 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.


bottom of page