Experience the Charm of Boston’s Waters with the T/T Trilogy – 24’ Family Sportsman
Imagine cruising along the Boston waterfront on a comfortable, well-equipped boat, with your family or friends. For just $700, up to six people can enjoy a 2-hour private trip aboard the T/T Trilogy, a 24-foot Family Sportsman boat designed for fun, relaxation, and adventure. Whether you’re into watersports, fishing, or simply soaking up the views, this experience offers something for all.
What we especially appreciate about this tour is how it combines versatility and comfort. The boat has a bathroom onboard—yes, real privacy and convenience—and a cooler for your drinks and snacks. Plus, the tow hitch and tube make it easy to add some adrenaline with waterskiing or tubing. On the flip side, a potential consideration might be that the duration is only two hours, which may feel brief if you’re eager for a full day on the water. However, this short window makes it easy to fit into a busy schedule and still enjoy a memorable trip.
This adventure suits families, small groups, or anyone looking for a relaxed yet engaging outing in Boston’s scenic coastal waters. If you love stunning skyline views, beautiful coastlines, and the chance to enjoy watersports or fishing with a crew that’s friendly and professional, you’ll find plenty to love here.
Key Points
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- Private and Flexible: Book a private 2-hour outing for up to 6 people, with morning, afternoon, or evening options.
- Well-Equipped Boat: Features include a bathroom, cooler, tow hitch, and room for watersports gear.
- Activities for All: From cruising and sightseeing to waterskiing, tubing, or fishing—the boat adapts to your interests.
- Comfort and Convenience: Ample seating, a bow lounge, and onboard amenities make for a relaxed experience.
- Expert Crew: The captain and crew guide your trip, ensuring safety and a personalized experience.
- Beautiful Views: Expect stunning skyline vistas, secluded coves, and the chance to spot Boston’s iconic waterfront landmarks.
A Practical Look at the T/T Trilogy Experience
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Planning more time in Boston? We've covered other experiences worth considering.
Starting Your Boston Waterfront Adventure
Your journey begins at Dock R, behind Victory Point Restaurant, a convenient spot right along the Boston waterfront. The process is straightforward—just show up with your group, and you’ll be greeted by the captain who’s eager to make your trip memorable. The reservation is flexible; you can book now and pay later, which is perfect if your plans are still taking shape.
Once onboard, the captain will give a quick safety briefing and show you how everything works. The boat’s layout is designed for comfort, with seats for up to six passengers and a bow lounge that’s perfect for relaxing and taking in the scenery.
The Cruise Along Boston’s Iconic Coastline
As the boat gently pulls away from the dock, you’ll notice how quickly the city’s skyline begins to shrink in the distance. The views of Boston’s downtown, the historic harbor, and the surrounding waterfront neighborhoods are impressive. Expect to see some of the city’s most recognizable sights—harbor islands, the USS Constitution, perhaps even the Boston Tea Party ships if they’re nearby.
The sea breeze and the rhythmic rocking of the boat create a calming effect, perfect for unwinding. If you chose to include watersports, the tow hitch and tube are ready for action. Many reviewers mention how fun it is to speed across the water on a tube, with one saying, “The kids loved bouncing around and giggling as we skied and tubed.”
Activities and Amenities
The boat’s onboard amenities align well with a laid-back day or an active one. With the bathroom onboard, you can comfortably spend the full two hours without running ashore. The cooler allows you to keep drinks and snacks handy, adding to the relaxed vibe.
If fishing appeals to you, the boat is equipped with 4 SS trolling rod holders and large storage to keep your catch. The fiberglass swim platform and ladder are perfect for a quick dip, which many guests find refreshing after some watersports or simply lounging in the sun.
More Great Tours NearbyUnwinding and Reflection
As your time winds down, the setting sun over Boston’s skyline adds a magical touch. Many reviews highlight how peaceful and picturesque the experience is, especially during the evening cruise. Watching the city light up from the water creates a memorable end to your trip.
Returning and Disembarking
When it’s time to head back, the captain navigates the boat smoothly to the dock, leaving you with plenty of photos and stories to share. The entire experience provides a balanced mix of adventure and relaxation—ideal for those who want a taste of Boston’s waters without committing to a full-day charter.
What Sets the T/T Trilogy Apart
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While many boat rentals in Boston offer just the boat, the T/T Trilogy stands out because it’s a full experience. The included amenities make it family-friendly and practical, while the option for watersports adds an element of thrill. The private group format ensures your outing is tailored to your pace and interests, and having a professional captain means safety and local knowledge are assured.
The stunning views are frequently praised by travelers. One reviewer shares, “The scenery was breathtaking, and we loved watching the city fade into the distance as the sun set.” It’s this combination of spectacular scenery, comfort, and versatility that makes this tour a worthwhile choice for many visitors.
Who Should Consider This Experience?

This tour is perfect for families with children, small groups of friends, or couples wanting a relaxing yet engaging outing. If you enjoy photographing skyline vistas, trying watersports, or simply cruising in comfort, the T/T Trilogy checks all the boxes. It’s also a good choice if you’re looking for a flexible, private experience that won’t break the bank at $700 for six people—offering a great value given the amenities and personalized service.
The Sum Up
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The T/T Trilogy offers a compact yet comprehensive way to enjoy Boston’s scenic coast and waterfront. Its amenities, versatility, and stunning views make it a favorite for those wanting a memorable day on the water. It’s especially suited for families or small groups seeking a comfortable and active outing, with plenty of opportunities for fun, relaxation, and impressive photo ops.
While the duration is only two hours, the experience remains rich and varied—whether you’re tubing, fishing, or simply soaking up the views. The friendly crew and well-equipped boat make everything smooth and enjoyable. If you’re after a manageable, private adventure that balances thrill and tranquility, this is a solid pick.
FAQ
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How long is the trip?
The tour lasts 2 hours, providing a perfect window for sightseeing, watersports, or relaxing with family.
Where do I meet the boat?
Your departure point is Dock R behind Victory Point Restaurant, a convenient location in Boston’s waterfront area.
Is the trip suitable for kids?
Yes, this private trip is family-friendly. The boat features amenities like a bathroom and seating for six, making it suitable for children.
Can I include watersports?
Absolutely. The boat has a tow hitch with a tube available, making it easy to add waterskiing or tubing to your day.
What’s included in the price?
Your fee covers the boat, captain and crew, amenities like the cooler and bathroom, and equipment for fishing and watersports.
Are drinks and food provided?
No, but you can bring your own food and beverages onboard, as there’s a cooler provided. Alcohol is not included but allowed to bring along.
Is it a group experience or can I book solo?
It’s a private group experience for up to six people, so it’s ideal for friends or family wanting exclusivity.
Can I cancel if my plans change?
Yes, you can cancel up to 24 hours in advance for a full refund, providing flexibility if your plans shift.
The T/T Trilogy offers an authentic slice of Boston waterside life, blending scenic beauty with the chance for fun and activity. Whether you’re after a relaxed day with family or a quick dose of adventure, this trip delivers on all fronts.
You can check availability for your dates here:More Tour Reviews in Boston
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- Boston Harbor Fall Foliage Brunch Cruise
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