Ask any Cape Cod parent where their kids want to go by boat and you'll quickly notice a pattern.
It's usually not the fanciest marina. It's not the longest boat ride. And it's definitely not the destination with the best cocktails.
Kids remember the places where they jumped off a bridge, found a sand dollar, chased crabs, rode a carousel, or spent hours swimming until they were exhausted.
At Bosun's Marine in Mashpee, we spend all summer talking with local boaters about where they're heading next. Whether you own a boat, are considering your first boat, or have started thinking about upgrading to fit a growing family, these are some of the destinations Cape Cod families return to year after year.
Cape Cod Family Boating Guide
Destination | Best For | Why Kids Love It | Why Parents Love It |
Martha's Vineyard | Full-Day Adventure | Jaws Bridge, Flying Horses Carousel, beaches, ice cream, exploring Oak Bluffs | Feels like a vacation without booking one, restaurants, shopping, walkable towns |
Bassett's Island | Swimming & Beach Days | Shallow water, swimming, paddleboards, beach games | Easy anchorage, close to Mashpee, lunch at The Chart Room |
Washburn Island | Nature & Exploring | Shell collecting, trails, wildlife, beach adventures | Quiet, uncrowded, feels miles away from everyday life |
Jeremy Point | Sandbar Adventures | Tide pools, giant sandbars, exploring, running free | Stunning scenery, fewer crowds, unique Cape Cod experience |
Tarpaulin Cove | Swimming & Water Sports | Crystal-clear water, snorkeling, paddleboarding | Beautiful anchorage, peaceful atmosphere, great for a full-day trip |
Provincetown | Older Kids & Teens | Whale watches, street performers, ice cream, harbor activity | Restaurants, galleries, shopping, one of the most unique towns in New England |
Best Overall Family Adventure
Martha's Vineyard
If there were a "greatest hits" destination for Cape Cod families, Martha's Vineyard would probably win.
The biggest draw for kids is the famous Jaws Bridge in Edgartown, where generations of visitors have jumped into the water below. Oak Bluffs is home to the Flying Horses Carousel, the oldest operating carousel in America, along with ice cream shops, candy stores, and plenty of places to explore.
Parents love that one boat trip can keep the entire family entertained for an entire day. Between Edgartown, Oak Bluffs, and Vineyard Haven, there is always something to do, see, or eat. Many local boaters say a Vineyard trip is what finally convinced them that boat ownership was worth it.
Best For: Families with kids of all ages
Best Family Beach Day
Bassett's Island
Ask local boaters where they take the kids on a hot July afternoon and Bassett's Island is usually near the top of the list.
The calm water and sandy shoreline make it perfect for swimming, floating, paddleboarding, and simply spending the day outdoors. Local boaters have been anchoring here for generations for picnics, swimming, and relaxing on the beach.
When everyone gets hungry, many families make the short dinghy ride to the waterfront Chart Room, which has become a summer tradition for Cape Cod boaters.
Best For: Families with younger children
Best Hidden Nature Adventure
Washburn Island
Not every boating day needs restaurants and crowds.
Washburn Island feels like the Cape Cod many people remember from years ago. Kids can explore trails, look for wildlife, collect shells, and spend hours discovering things on their own.
Parents love the slower pace. It's one of the easiest places to disconnect from schedules, phones, and the everyday rush of summer.
Best For: Families who love nature
Best Sandbar Adventure
Jeremy Point
Jeremy Point is the place kids talk about all week after visiting.
At low tide, the area transforms into a massive network of sandbars and shallow water. Kids can run, explore, search for shells, and play beach games while feeling like they've discovered their own private island.
The catch? Timing matters. Local boaters know Jeremy Point is all about the tides.
Best For: Curious kids who love exploring
Best Swimming Destination
Tarpaulin Cove
Located on Naushon Island, Tarpaulin Cove feels completely different from most Cape Cod boating destinations.
The water is remarkably clear, making it a favorite for swimming, paddleboarding, floating, and snorkeling. Many local boaters describe it as one of the most beautiful anchorages in Southern New England.
For families with older kids, it's the kind of destination that turns into an all-day adventure.
Best For: Water-loving families
Best Destination for Teens
Provincetown
Teenagers can be tough to impress.
Provincetown helps.
Commercial Street is packed with shops, restaurants, ice cream stops, street performers, and constant activity. Add whale watches, harbor cruises, and one of the most vibrant waterfronts on Cape Cod, and it's easy to understand why older kids love spending the day here.
Parents appreciate that Provincetown offers something for everyone, making it one of the easiest family boating destinations on Cape Cod.
Best For: Families with teens
The Real Reason Families Get Into Boating
The best family boating destinations on Cape Cod all have one thing in common:
The memories start long before you arrive.
They're made during the boat ride, when kids are spotting seals, helping navigate, looking for sharks' teeth on the beach, or asking if they can jump in the water the second the anchor drops.
At Bosun's Marine, we see it every day. Families who start with short trips around Mashpee eventually find themselves spending weekends on Martha's Vineyard, exploring hidden beaches, and discovering places they never knew existed.
Whether you're looking for your first family boat, considering a larger model as your kids grow, or simply searching for new Cape Cod boating destinations, there's never been a better time to spend more days on the water.
Because years from now, your kids won't remember what boat you owned.
They'll remember where it took them.