Few destinations in the U.S. can compete when it comes to the storied history of Cape Cod, the hook-shaped peninsula that juts off the coast of Massachusetts into the Atlantic Ocean. Home to rich maritime history, awe-inspiring natural scenery, and countless lobster shacks, it’s no wonder the Cape has long been a favorite summer destination.
Longtime Cape visitors often have a favorite place to stay on the island, which is usually thought of as divided into three sections: Upper Cape, Mid Cape, and Lower and Outer Cape. Upper Cape and Mid Cape are closer to Boston than other towns and staying in Mid Cape provides an easy jumping off point for day trips to Martha’s Vineyard and Nantucket. Lower and Outer Capes are home to Chatham, Wellfleet, and other popular small towns.
Located on a private beach, the Chatham Bars Inn is a popular location for those wanting to indulge in Cape Cod luxury. As a Tradewind partner, Chatham Bars Inn guests who charter with Tradewind to Chatham also can receive an exclusive offer for their stay.
No matter where you stay, flying offers a clear advantage over traffic-filled driving, providing valuable time-savings and allowing more time to be spent on the Cape. Tradewind Aviation offers a seamless journey from many East Coast cities with its private charters to Barnstable Municipal Airport (HYA/KHYA), Chatham Municipal Airport (CQX/KCQX), and Provincetown Municipal Airport (PVC/KPVC).
Once your accommodations are decided, it’s time for the fun part—planning your Cape Cod itinerary. Here are 10 must-experience activities that should be on your list.
Go Whale Watching
From April through October, migratory humpback, finback, and minke whales can be found in the waters between Cape Cod and Cape Ann. The Stellwagen Bank National Marine Sanctuary is one of the best places in the world for whale watching, and numerous outfitters operate out of Cape Cod ports. The sanctuary advises choosing a tour company that’s recognized by Whale SENSE, a nonprofit organization that determines if an operator is using safe whale watching practices.
Tour a Lighthouse
An important symbol of Cape Cod’s maritime history, the 18 lighthouses that dot its coasts represent more than just a beautiful photo backdrop. Race Point Lighthouse, which is located in the outermost town on the Cape, Provincetown, is on the National Register of Historic Places, and its Keeper’s House and Whistle House are now available to rent as accommodations. In Eastham, tours of Nauset Lighthouse are available on Wednesdays and Sundays.
Bike Along Cape Cod Rail Trail
This 25-mile-long paved pathway runs from South Dennis in Mid Cape all the way to Wellfleet in Outer Cape. Rent bikes and enter the trail at one of its trailheads or numerous other entry points along the way (which often have free parking nearby). The trail winds past scenic ponds, public beaches, and seafood shacks, so you can easily make a full day out of exploring it.
Even those who don’t stay in Provincetown (known as P-Town to those in the know) will want to make a day trip to the Cape’s outermost hamlet. This historic haven was a stopping point for Pilgrim colonists more than 400 years ago, and today it’s known for its artsy culture and as a thriving LGBTQ+ tourism destination. Visitors can easily spend a day exploring the bustling town, which is home to coffee shops, boutiques, and some of the Cape’s best restaurants.
Climb Pilgrim Monument
While in P-Town, make a point to stop at this 252-foot tall monument, which was built to commemorate the Mayflower Pilgrims’ landing in Provincetown in 1620. It takes about 10 minutes to climb to the top of the monument, where you’ll be treated to 360-degree views of Provincetown, Cape Cod Bay, the Atlantic Ocean, and the rest of Cape Cod stretching to the south.
Watch a Movie Under the Stars
Since 1957 Wellfleet Cinemas has operated one of the Cape’s best family destinations. A drive-in movie theatre, indoor cinema, flea market, mini golf course, and ice cream stand make this retro spot a can’t-miss attraction. Watch a double feature under the stars at one of just 300 drive-in theatres left in the U.S.
Visit the Kennedy Museum
President John F. Kennedy famously spent his summers on Cape Cod, and the town of Hyannis is synonymous with the Kennedy name. Today it’s home to the John F. Kennedy Hyannis Museum, which shares the story of the 35th president’s connection to the Cape, as well as his family’s long history there.
Spot an Apex Predator in its Natural Habitat
Much has been made of the fact that great white sharks have returned to the waters surrounding Cape Cod. The Atlantic White Shark Conservancy (AWSC) exists to quell fears and educate tourists about the apex predators, which are one of the most misunderstood animals in the world (thanks, Jaws). The AWSC offers several opportunities to potentially see white sharks in the wild, including a receiver tour to track sharks’ movement, private white shark charters, and three summer expeditions hosted in partnership with the Whale and Dolphin Conservation. The summer expeditions are currently sold out, but spots on the waitlist are available.
Find the Best Clam Chowder
You can’t go wrong with any of the fresh seafood available on the Cape, but clam chowder is ubiquitous and delicious. Try a mug of prize-winning chowder at The Lobster Pot in P-Town, or grab a bowl at Mac’s Seafood, a local chain with locations all over the Cape. Most roadside lobster shacks will have chowder as well, so make it your mission to try as many versions as possible.
Catch a Performance at Cape Playhouse
Operating since 1927 and once host to Humphrey Bogart, the Cape Playhouse is the longest-running professional summer theatre in the country, and it’s considered one of the best small-stage theatres in America. Each summer brings a new lineup of musicals and plays to this Cape Cod fixture. This season’s standout shows include An American in Paris, Murder on the Orient Express, and The Fantasticks.
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