First named “Cape Cod” by a British explorer in the early 1600s, the extreme tip of the Massachusetts peninsula has been a successful fishing community since the days of the Pilgrims. Provincetown has welcomed artists since the late 1800s and has a thriving theater scene. In recent decades, P’town has become a popular destination for the LGBT community. Its remoteness and natural beauty beckon to all visitors. Most cruises here are on smaller boats originating in Boston.
What We Love
Whale Watching: Many companies offer boat trips from the main pier that go deep into Cape Cod Bay, a breeding area for North Atlantic right whales. Humpbacks and fin whales can also be spotted April through October.
Whydah Pirate Museum: This outpost houses a bounty of booty from one of the world’s only authenticated pirate wrecks captained by Black Sam Bellamy.
Best Known For
Commercial Street: The benches in front of Town Hall are the best perches for viewing the veritable carnival of singers, actors, and drag queens strolling down the main street.
Province Lands: These beaches have towering dunes, bike trails, hiking paths, and some of the best sunset viewing on the planet. Dune buggy tours give you a guided look at the preserve.
Shop for Cruises
Who It's Best For
Nightlife Fanatics: What sets P’town’s robust arts scene apart are the epic drag shows and cabarets that have been entertaining locals and visitors alike for generations.
Book Worms: This small town has the highest concentration of bookstores on Cape Cod. The oldest is Provincetown Bookshop, which dates to 1932.
Don't Say We Didn't Warn You
P’town Pride: Salty fishermen and flamboyant artists get along swimmingly here. What they have in common — in addition to loving their idyllic enclave — is an often palpable disdain for outsiders. Don’t walk in the middle of Commercial Street, keep dillydallying to a minimum (and politeness to a maximum), and you’ll get along just fine.
Jenna Mahoney is a Brooklyn-based contributor to ShermansCruise who has also written for Allure.