Boston’s sailing scene centers on two standout harbor tours. The Adirondack schooners (III and IV) run excellent 1.5-2 hour trips – we love their traditional sailing experience and route past city landmarks like the New England Aquarium and historic Castle Island.
Our favorite upscale option is the Trilogy, a 103-foot luxury yacht perfect for small groups up to 12 people, complete with jacuzzi and spa amenities.
Both operators offer hassle-free 24-hour cancellation policies.
Let’s explore these recommended Boston sailing tours in detail.
Key Points
- Boston Sailing Tours offers two main options: Adirondack schooners and Trilogy yacht, catering to different experiences and group sizes.
- Adirondack schooner tours provide a classic sailing experience around the Downtown Harbor, showcasing iconic landmarks and scenic views.
- Trilogy yacht offers a luxury private sailing adventure with amenities such as a jacuzzi, spa pool, and fully-equipped kitchen.
- Both sailing options receive positive reviews for their knowledgeable crew, personalized experiences, and flexible cancellation policies.
- Customers can easily book online and enjoy a range of payment options, ensuring a hassle-free sailing experience in Boston.
Boston: Downtown Harbor Sailing Cruise
Frequently, visitors to Boston can embark on a classic sailing schooner, either Adirondack III or IV, for a 1.5 to 2-hour cruise around the city’s Downtown Harbor.
These excursions provide an opportunity to experience the iconic Boston Harbor, passing by the Inner Harbor Islands and notable landmarks like the New England Aquarium, Moakley Federal Courthouse, Boston Fish Pier, and Castle Island.
During the cruise, guests can enjoy a round-trip sailing adventure while the knowledgeable captain and crew provide information about the sights and history.
Complimentary soda and water are provided, and adult beverages are available for purchase. Passengers are welcome to bring their own picnic onboard, and the small group size ensures a personalized sailing experience.
Prices start at $61.05 per person, with free cancellation up to 24 hours in advance and a reserve now, pay later option.
Reviews praise the knowledgeable crew and relaxing atmosphere, making this a highly-rated way to explore Boston’s harbor.
Read our full review: Boston: Downtown Harbor Sailing Cruise Review
Book now: Check availability
Luxurious Private Yacht Trilogy
For those seeking a truly luxurious and private sailing experience in Boston, the Trilogy yacht offers an unparalleled opportunity. Priced at $2,000 for groups of up to 12, this 103-foot Broward yacht provides an exceptional two-hour tour of the Boston Harbor and surrounding areas.
With a dedicated captain and crew, guests can enjoy an array of onboard amenities, including a jacuzzi hot tub, large foredeck spa pool, sunbed, and a fully-equipped kitchen and dining area. Passengers are welcome to bring their own food and beverages, or can contact recommended local caterers.
The Trilogy’s panoramic views from the plush interiors or sun-kissed deck offer a combination of adventure, relaxation, and luxury. Conveniently located at Dock R behind Victory Point Restaurant, the Trilogy isn’t suitable for babies under one year and comes with a few restrictions, such as no smoking or littering.
With free cancellation up to 24 hours in advance, this private yacht experience is a must-try for those seeking an unforgettable sailing adventure in Boston.
Read our full review: Luxurious Private Yacht Trilogy Review
Book now: Check availability
The Sum Up
Boston offers a variety of sailing experiences perfect for both novice and experienced sailors. From the Downtown Harbor Sailing Cruise‘s scenic city views to the luxurious Private Yacht Trilogy, there’s an option to suit every preference. Whether you’re looking for a relaxing afternoon or an exhilarating adventure, Boston’s sailing opportunities provide an unforgettable way to enjoy the city’s waterfront.