Exploring Boston by Water: A Review of the T/T Trilogy – 24 Family Sportsman
If you’re thinking about spending some quality time on Boston’s waters, the T/T Trilogy – 24 Family Sportsman offers a pretty flexible way to do it. Whether you’re into watersports, fishing, or just looking for a relaxed cruise with family or friends, this boat adventure has some notable perks worth considering. We’ve looked into what makes this experience tick, and it’s clear that it’s designed to deliver a fun, customizable outing quite close to the city.
What really caught our eye are the amenities onboard—a bathroom, coolers, and plenty of seating—making it a practical choice for spending a good chunk of the day on the water. Plus, the boat is equipped for watersports, with a tow hitch and tube available, so thrill-seekers can get their adrenaline fix. On the flip side, it’s only a 2-hour trip, which might feel a bit short if you’re craving a full day of adventure, but it’s perfect for a quick escape. This tour works well for small groups or families who want a tailored, intimate experience without the hassle of planning a big trip.
If your idea of a good day involves scenic views, some fun in the water, and a relaxed atmosphere, this could be a great fit. It’s especially suited to those who value comfort and convenience, as everything is included in the price—except alcohol and food, which you can bring along. Just keep in mind, since it’s a private group experience, there’s room for some customization, making it a flexible option for different interests.
Key Points

- Perfect for families and small groups seeking a flexible, waterside adventure
- Includes amenities like a bathroom, cooler, and comfortable seating
- Equipped for watersports with a tow hitch and tube, ideal for thrill-seekers
- Scenic views of Boston’s skyline and coastlines make for memorable moments
- Duration of 2 hours suits short, active visits—less ideal for full-day plans
- Includes captain and crew, so you don’t need to stress about navigation or safety
A Closer Look at the Boston Boat Experience

When we imagine exploring Boston’s scenic coastlines, it’s tempting to picture long, leisurely days filled with sightseeing and activities. The truth is, a 2-hour boat trip like this doesn’t offer a comprehensive tour of Boston’s waters but instead delivers a focused, enjoyable experience that’s easy to fit into a busy schedule. Think of it as a taste of the water—enough time to relax, have fun, and enjoy some stellar views without feeling overwhelmed.
The boat itself, the 23’9” Family Sportsman, is built for comfort and practicality. With seats for up to 6 people, it’s a cozy environment that fosters bonding, whether you’re sharing a laugh during watersports or quietly marveling at the Boston skyline. The onboard amenities are straightforward but thoughtful: a bathroom, a large cooler for drinks and snacks, and storage for gear. For families, or groups that like to keep things simple and stress-free, this setup really hits the mark.
The crew and captain are included, which means you don’t have to worry about navigation or safety—just focus on the fun. The captain is described as experienced and passionate about making your experience memorable, which is reassuring when you’re out on unfamiliar waters. You can expect a friendly welcome and smooth sailing, whether you’re speeding across the waves for some tubing or drifting quietly off the coast.
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What to Expect During Your Trip
The adventure begins at Dock R, behind Victory Point Restaurant, where you’ll meet your crew and get ready for your outing. As the boat pulls away from the dock, you’ll instantly appreciate the stunning views of Boston’s skyline shrinking in the background. This is the perfect setting for photos—both of the city and of your group having a good time on the water.
The boat is equipped for watersports, with a tow hitch and available tube, making it a hit for thrill-seekers or families with kids eager to try tubing. If fishing is more your vibe, the boat’s four trolling rod holders and large live well suggest that casual fishing could be part of your day, although specifics about fishing gear rentals aren’t detailed.
For those wanting a more relaxed experience, the bow lounge and aft bench seats are comfortable spots to soak in the scenery or enjoy snacks from the cooler. Since there’s a bathroom onboard, you won’t need to cut your trip short for bathroom breaks, which is a definite plus for comfort, especially if you’re out for more than an hour or two.
As the trip winds down, you’ll head back towards dock R. The sunset views over the Boston skyline are often mentioned as a highlight, adding that extra magic to your experience.
What’s Included and What’s Not

Everything you need for a smooth trip is included: the boat, a captain and crew, water sports gear, a cooler, and seating. This level of all-inclusiveness helps you budget better, with no surprises. The boat is also equipped with storage boxes, rod holders, and a swim platform, making it well-suited for different activities.
However, keep in mind that alcohol and food aren’t included, though you’re encouraged to bring your own. Tipping the crew is also not included in the price, so factor that into your budget if you’re pleased with their service.
Is This Experience Worth the Price?

At $700 for up to six people, this experience breaks down to about $117 per person—which, considering you’re getting a private boat, a crew, and amenities, is pretty reasonable. If you’re seeking a quick, fun escape with ease and comfort, this can be a good value. Plus, the ability to customize your day—whether you want to focus on watersports, fishing, or simple cruising—adds to its appeal.
It’s particularly suitable for small groups or families who want a hassle-free outing without the need to rent or bring along their own gear. The included amenities and crew support also mean you’re freed from the challenges of navigating unfamiliar waters, making it accessible even for less experienced boaters.
More Great Tours NearbyWho Would Love This Trip?
This tour is best suited for those who want a short, flexible, and enjoyable day on Boston’s waters. Families with kids who are comfortable on boats should find it a manageable, fun outing—especially with the onboard bathroom and amenities. Groups of friends or couples who want a private adventure with some watersports thrown in will also appreciate the tailored nature of the trip.
If you’re after a scenic cruise with the option of water-based activities, but not a full-day commitment, this offers a good balance. However, if you’re looking for a longer, more in-depth tour, or a comprehensive city sightseeing experience, you might want to look elsewhere.
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The Sum Up
All in all, the T/T Trilogy – 24 Family Sportsman stands out as a practical, well-equipped way to enjoy Boston’s waters without the fuss. It offers a cozy, private setting with amenities that make the experience comfortable and enjoyable—whether you’re tubing with kids or fishing with friends. The inclusion of a captain and crew means you can relax and just focus on having fun, and the scenic views of Boston’s skyline provide a perfect backdrop to your day.
While it’s only a 2-hour trip, that’s enough time to get a taste of the water, feel the breeze, and make some memories. It’s especially great if you’re traveling with a small group that appreciates flexibility and comfort. But for those seeking a longer, more comprehensive tour, you might find this just a little short.
If you’re after a manageable, family-friendly, and scenic outing that balances adventure and relaxation, this trip on the Family Sportsman boat could be just what you need for a memorable day in Boston.
T/T Trilogy – 24 Family Sportsman
FAQ

Is this tour suitable for families with children?
Yes, it’s a good option for families, especially those comfortable on boats. The boat has amenities like a bathroom and seating designed for comfort, making it suitable for kids.
Can I include watersports in my trip?
Absolutely. The boat has a tow hitch and tube available, so you can enjoy tubing and watersports if you’re looking for some excitement.
What is the duration of the trip?
The trip lasts about 2 hours, which is perfect for a quick, engaging outing without being too long for kids or tight schedules.
Where do I meet the boat?
You’ll find the boat at Dock R, behind Victory Point Restaurant.
What’s included in the price?
The trip includes the boat, captain, crew, water sports gear, cooler, seating, and amenities like a bathroom and storage.
Are food and drinks included?
No, but you’re welcome to bring your own food and beverages, including alcohol. Note that gratuity for the crew is not included.
Is this a private group experience?
Yes, it’s a private rental for your group, offering a tailored experience without other strangers onboard.
What should I bring?
Bring your own food, beverages, towels, and any personal gear you want for watersports or relaxing.
Is tipping necessary?
Tipping is customary but not included in the price. If you’re happy with the service, a tip is appreciated.
Can I cancel my booking?
Yes, cancellations are free if made at least 24 hours in advance, allowing you flexibility if plans change.
If you’re after a straightforward, enjoyable way to explore Boston’s waters with a bit of adventure and comfort, the T/T Trilogy offers a solid choice. Whether it’s a family outing or a small group’s day of fun, this boat experience is worth considering for a memorable day on the water.
You can check availability for your dates here:More Tour Reviews in Boston
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