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304 North Cardinal St.
Dorchester Center, MA 02124

Experience Boston Harbor on a private yacht with options for sightseeing, fishing, lobstering, or cruising, led by Captain Riccardo aboard the Trinacria.

The Fishing or Cruising Boston Harbor on the private yacht Trinacria offers a personalized adventure with a focus on flexibility and privacy. Priced at $2,000 per group (up to 6 guests), this tour provides a 3 to 5-hour experience that can include sightseeing, fishing, lobstering, or simply cruising. The tour departs from Boston and is notable for its intimate setting, with most Boston tours being shared, making this option stand out.
One of the many strengths of this tour is the ability to bring your own food and beverages, allowing for a tailored experience. The flexible pickup options and capacity to accommodate special requests add to its appeal. With a highly praised guide and stunning views of historic Boston landmarks, this trip is ideal for those seeking an exclusive and customizable outing in Boston Harbor.
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The Trinacria is a private yacht owned and operated by Captain Riccardo, who leads the tours with a reputation for professionalism. This yacht offers an unshared experience, ensuring that each group enjoys the boat’s full privacy, unlike typical tours that host large crowds. Captain Riccardo is highly regarded for his knowledge of both Boston’s history and the best fishing spots, which boosts the tour’s appeal.
The yacht itself is equipped to provide a smooth and comfortable ride, with pickup offered from various locations and mobile tickets making the process straightforward. The tour’s flexibility extends to choosing specific activities or requesting special arrangements, including burial at sea ceremonies with all US Government notifications handled free of charge.

The itinerary offers an immersive view of Boston’s historic and cultural sites. The Boston skyline is the first sight most will enjoy, providing a striking backdrop for photos. The USS Constitution, the oldest active ship in the world, is a highlight, with the tour pausing nearby for memorable photos.
The Bunker Hill Monument is another significant site, symbolizing one of the first major battles of the American Revolutionary War. The Mystic River and Charles River are included in the cruise, giving an insight into Boston’s natural waterways and their importance, especially for rowing and academic institutions like Harvard and MIT.
Plus, the USS Cassin Young, a World War II destroyer now preserved as a memorial, is visible from the boat. The Zakim Bridge, a modern engineering feat, is also featured, while iconic sports venues like the TD Boston Garden and historic sites such as the Boston Navy Yard add further context to the city’s rich past.

The tour makes a point to showcase Castle Island, built in 1632, which historically served as a defensive site and a prison. Its shoreline is often visible from the boat, offering a glimpse into Boston’s early defenses and military history. The Deer Island facility, established in 1634 as a refuge and later a prison, is seen from afar. Today, Deer Island operates as one of the largest sewage treatment plants in the United States, generating its own electricity and using waste as fertilizer.
Although these sites are viewed from the boat rather than visited, they add significant historical and modern operational context to the cruise. The viewing distance is clear on a good weather day, making these landmarks an interesting part of the overall experience.

The highlight of the tour is the passage to Boston Light on Little Brewster Island. Established in 1716 and rebuilt in 1783, Boston Light is the oldest lighthouse in the United States still in operation. The lighthouse is manually staffed, with a Coast Guard keeper still present despite automation since 1998.
Cruising past Boston Light offers visitors an up-close view of this historic structure, which is designated as a National Historic Landmark. The lighthouse adds a charming maritime touch to the overall experience, connecting guests with Boston’s longstanding relationship with the sea.
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The USS Cassin Young, launched in 1943, is a memorial ship that served in World War II and the Korean War. The yacht’s slow cruise allows for photo opportunities while passing this historic vessel. Its presence emphasizes the harbor’s naval history.
The Zakim Bridge is another notable sight, known for its modern architectural design. The tour pauses to give a good perspective of this cable-stayed bridge, which symbolizes Boston’s bridge-building efforts and civil rights activism, named after Leonard P. Zakim.

The Mystic River, historically significant for Native American tribes and the Battle of Bunker Hill, is included in the cruise route. This tidal river’s name originates from the Native American term Missi-Tuk, meaning great tidal river. The boat travels through its waters, offering views of the Mystic River’s historical and cultural importance.
The Charles River marks the confluence with Boston Harbor. Known for the Head of the Charles Regatta, the largest long-distance rowing event in the world, the Charles River is home to Harvard, Brandeis, Boston University, and MIT. The boat’s route includes this scenic waterway, highlighting Boston’s academic and athletic traditions.

The TD Boston Garden and the Boston Navy Yard are viewed from the harbor, giving context to Boston’s sporting and naval heritage. The Boston Garden is home to iconic teams like the Boston Celtics and Boston Bruins. The Navy Yard, established in 1801, served as one of the oldest shipbuilding facilities in the US Navy, decommissioned in 1974.
These sites underscore Boston’s dual identity as a sports-loving city and a historic naval port, enriching the sightseeing experience with local pride and history.
The Castle Island, built in 1632, was a key defensive point during the War of 1812. Its shoreline, often visible from the boat, also bears the marks of previous military uses, including the rebuilding efforts led by Lieutenant Paul Revere. The island’s current name and structure, Fort Independence, reflect its longstanding military significance.
Deer Island, once a refuge for deer and then a prison, now functions as a major sewage treatment facility. The Pelletized waste generated there is used as fertilizer, and the plant supplies treatment for the entire Boston area. Although primarily viewed from a distance, Deer Island’s presence adds modern relevance to the harbor’s landscape.
The Nantucket Lightship, commissioned in 1936, is the last of its kind and currently undergoing renovation as a floating museum. The yacht passes closely by this vessel, offering a unique sightseeing opportunity. The cruise concludes with a return to the initial meeting point, having covered a broad spectrum of Boston’s maritime history, landmarks, and natural beauty.
The tour departs at 9:00 am, with the meeting point flexible based on preferences. The tour is most often booked 27 days in advance, indicating its popularity. The maximum group size is 6, suitable for those seeking an intimate experience.
Included in the fare are fishing rods, tackle, bait, drinks, and all necessary notifications for special ceremonies, such as ash scattering. The tour is non-refundable, but weather-related cancellations offer options for rescheduling or full refunds.
This exclusive private yacht experience is perfect for guests who value privacy, personalized service, and a combination of sightseeing and activity options. It suits those interested in Boston’s history, maritime heritage, or simply wanting a peaceful day on the water with tailored arrangements. The flexibility to bring your own food and the professional guidance from Captain Riccardo make this a memorable outing for small groups.
The Fishing or Cruising Boston Harbor on the Trinacria stands out as a highly customizable, private experience that combines marine sightseeing, historical landmarks, and recreational activities. Its intimate setting and flexible itinerary make it a strong choice for those seeking a personalized day on Boston’s waters.
While it advances a premium price point, the full privacy and exclusive access to landmarks like Boston Light and the USS Constitution justify the cost for many. The knowledgeable guide and beautiful views ensure a worthwhile adventure, especially for those interested in history, scenery, or fishing.
“Captain Riccardo is a true professional in every sense of the word. From the history of Boston to knowing right where the best spots were to fish. …”
How many people can fit on the yacht?
The tour accommodates up to 6 guests, providing an exclusive and private experience.
What activities can I choose during the tour?
Options include sightseeing, fishing, lobstering, or just cruising. Activities vary in duration and can be customized.
Can I bring my own food and drinks?
Yes, the tour allows bringing your own food and beverages onboard, making the trip highly personalized.
How long does the tour last?
The standard duration is 3 to 5 hours, depending on activities chosen. A minimum of 4 hours is recommended if fishing or lighthouse stops are included.
Are fishing rods and tackle provided?
Yes, the tour includes fishing rods, tackle, bait, and drinks with no extra charge.
Is the tour suitable for children or service animals?
Yes, service animals are allowed, and most travelers can participate, though specific physical requirements are not detailed.
What is the cancellation policy?
The tour is non-refundable, but if canceled due to poor weather, a full refund or rescheduling is offered.
Is there any historical significance to the stops?
Yes, stops include USS Constitution, Bunker Hill Monument, Castle Island, and more, all rich with Boston’s maritime and revolutionary history.
Do I need any special skills or experience?
No prior experience is necessary; the guides are knowledgeable, and all gear is provided for fishing.
How do I book this tour?
Booking can be done in advance, with most trips scheduled 27 days ahead, via the provided platform or contact details.