At a glance
- Duration:
- 9 Days
- Start/End:
- Round Trip Boston
- From:
- $6,350
- Time of Year:
- April - September

Embark on an 9-day Cape Codder Cruise, sailing roundtrip from Boston, MA. This unforgettable journey takes you from Boston to Cape Cod, where charming gray-shingle cottages, serene beaches, and lively clam shacks set the stage for the perfect getaway.
Explore the artistic vibe of Provincetown, a vibrant seaport filled with quirky galleries and exciting whale-watching tours. Discover the charming villages and delightful gingerbread cottages of Martha’s Vineyard, with expert island guides showing you around. Walk the grand grounds of Newport’s lavish seaside mansions.
Set sail aboard our modern small ships to New Bedford, MA, known as “The Whaling City”, a bustling seaport with a lively fishing fleet and a peaceful waterfront scene. And don’t miss the highlight of the Cape Codder itinerary: a traditional lobster bake luncheon. Savor freshly caught lobster, steamed clams, and mouthwatering corn on the cob, all prepared over coals and kelp gathered that very morning.
Cape Codder Cruise Highlights
- Round-trip from Boston, MA: start and end in a historic, vibrant city.
- Day cruising: enjoy relaxing ship time as you transit along the New England coast.
- Provincetown, MA: artistic, eclectic town with galleries, street performances, and dune adventures.
- Plymouth, MA: see Plymouth Rock, walk historic trails, and explore the Mayflower II replica.
- Visit the Massachusetts Maritime Academy: tour the campus, simulators, labs, and enjoy scenic views of Cape Cod Canal.
- Newport, RI: explore sumptuous mansions (e.g., The Breakers), historic Fort Adams, and Newport’s yachting legacy.
- Martha’s Vineyard, MA: guided island exploration, Edgartown’s colonial architecture, rugged cliffs, and nature.
- New Bedford, MA: known as “The Whaling City” — walk the historic waterfront, visit whaling museums, and see maritime art.
- Lobsterbake Luncheon: traditional New England lobster bake with fresh lobster, steamed clams, and corn over coals.
- Onboard amenities: panoramic sun deck, walking track, sky lounge, and bow terrace for scenic views.
- Comfortable staterooms: balcony suites (Veranda, Vista, Premium) with modern amenities and floor-to-ceiling windows.
Cape Codder Cruise Details
Day-to-Day Itinerary
Day 1: Boston, MA
Arrive and enjoy your hotel accommodations. Later, explore this historic and culturally rich city known for its colonial landmarks, prestigious universities, and vibrant neighborhoods. Walk the Freedom Trail to explore sites from the American Revolution or enjoy the scenic views along the Charles River. Discover a blend of old and new, with cobblestone streets and modern innovation coexisting side by side. From world-class museums to fresh seafood at Quincy Market, Boston provides a memorable experience for every traveler.
An optional hotel upgrade is available at the Four Seasons Hotel Boston. Call your Cruise Specialist 1-888-815-5428 for pricing and availability.
Day 2: Day of Cruising
Board your modern vessel amongst the cobblestone streets and 18th-century architecture that makes this city the perfect place to push off for a New England adventure.
As we welcome you onboard for your voyage, we’ll share a toast to you, meet the crew, and get excited for the days to come.
Day 3: Provincetown, MA
Originally founded as a haven for creative minds, Provincetown has grown into a vibrant summer destination on Cape Cod. Known for its eclectic shops, brightly painted buildings, and serene beaches, Provincetown offers a chance to immerse yourself in the lively culture of historic Cape Cod. The town’s energetic street performances and thriving art galleries showcase its artistic heritage, providing a wealth of entertainment and cultural experiences.
Day 4: Plymouth, MA
Plymouth, a historic coastal town, is the site of the first Pilgrim settlement, founded in 1620. The iconic Plymouth Rock, located within Pilgrim Memorial State Park, marks the believed landing place of these early settlers. Nearby, the Mayflower II, a painstakingly crafted full-scale replica of the ship that carried the Pilgrims across the Atlantic, is often docked at the park, providing a tangible connection to this defining moment in history. The surrounding landscape boasts expansive Atlantic views and miles of shoreline, showcasing the natural beauty that greeted the Pilgrims. Lush green forests and scenic trails around the town offer ample opportunities for outdoor exploration and peaceful moments in nature.
Day 5: Mass Maritime Academy, MA
Founded in 1891 in Boston, MA, Massachusetts Maritime Academy (MMA) is the oldest and largest operational maritime academy in the United States. Explore this distinctive “special mission” campus, featuring advanced simulators and labs, while engaging with MMA cadets and staff. Experience cutting-edge technologies such as the 360-degree Full Bridge Simulator, the Emergency Operations Training Center, and the Marine Engineering Labs. Throughout the tour, learn about the Academy’s rich history and the surrounding area from expert insiders. Located on the picturesque shores of Cape Cod, the Academy offers breathtaking views of the Cape Cod Canal and Buzzards Bay.
Day 6: Newport, RI
Nestled in the heart of Narragansett Bay, Newport is celebrated as the world’s yachting capital. Stroll along its scenic coastlines, discovering its charming historic districts, lively docks, and stunning waterfront views. Newport offers a rich variety of experiences for every traveler. Immerse yourself in its maritime heritage at the Herreshoff Marine Museum and America’s Cup Hall of Fame. Explore Newport’s illustrious past as you admire the grand coastal estates along the famous “Avenue of the Mansions.” Walk marble staircases, explore elegant ballrooms, and step back in time to when these magnificent homes were the summer retreats of America’s wealthiest families.
Day 7: Martha's Vineyard, MA
Martha’s Vineyard, once a thriving hub for whaling and trade, welcomed ships carrying goods from around the world. Today, the island has become a cherished New England getaway, home to six distinctive towns, from the tranquil Chilmark to the lively Vineyard Haven. Edgartown, with its refined charm, stands as the island’s most elegant town, boasting well-preserved colonial architecture and meticulously landscaped gardens. Throughout the island, rolling hills and lush oak forests frame serene sandy beaches. If you’re fortunate, you may even spot ospreys soaring above as the waves crash along the shore.
Day 8: New Bedford, MA
In the mid-19th century, New Bedford was the undisputed center of the global whaling industry, captivating the imagination of Herman Melville and inspiring his iconic novel, Moby Dick, published in 1841.
Today, New Bedford continues to embrace its legacy as “The Whaling City,” with a picturesque waterfront bordered by historic cobblestone streets, alongside modern ships in its bustling harbor. Vibrant public art and colorful murals bring energy to this historic city, while green spaces offer tranquil havens within the urban landscape.
Day 9: Boston, MA
As we return to Boston, we bid farewell to this unforgettable Massachusetts journey. While your Cape Cod adventure may be coming to a close, the historic streets of Boston are still yours to explore. Our crew is happy to assist you with directions to local landmarks, attractions, or your travel accommodations.






