If I Had a Day in Provincetown: My Favorite Things to See, Eat and Do

flagImagine an idyllic New England village by the sea with beautiful homes and  quaint shops. There are sail boats float in the harbor. Lobster and New England clam chowder is readily available. Beaches and sand dunes are abundant. The town is alive with diversity, art, good food and playful celebration. Regardless of age, weight, race or orientation — all are welcome here. Sounds perfect, right? Well, that place is Provincetown, Massachusetts. It was the first place the pilgrims landed on the Mayflower in 1620, and it is the place of my annual New England pilgrimage.

Actually, Provincetown is a special place in my life at any time of the year. While thousands throng to this charming seaside town in the warmer summer months, I find that the off-season months and the winter season can be just as inviting and enjoyable for different reasons. Summer brings the possibility of beachside tanning, bicycle rides through the village, hikes along the dunes, whale watches and outdoor revelry. The crowds are away in the winter, and those who remain are passionate locals who love their town no matter the temperature. The colder months allow for more engagement with these locals, reading by the fireplace, and good food at one of the restaurants that remains open year around. For a wonderful introduction to Provincetown, read Michael Cunningham’s autobiographical At Land’s End.

I have been going to Provincetown for years, and I would like to share what I would eat and do if I had a day in this wonderful place.


Getting to Provincetown is not easy, and it takes some planning. Most visitors arrive one of two ways: First, you can drive. Provincetown is approximately 2 to 2 1/2 hours from downtown Boston or Providence due to the traffic and two-lane highways. Secondly, you can take the 90 minute ferry from Boston with multiple departures round-trip every day in the summer (Bay State Ferry is the preferred company with a “fast” ferry option).



Provincetown has some wonderful homes and duplexes to rent for a family or groups, but couples or singles likely will enjoy one of its many inns or bed and breakfasts. My favorite inns are The Brass Key Guest House, The Waterford Inn, and Land’s End Inn. The Gaslamp Inn has a wonderful breakfast, a large hot tub, and managed by an hospitable couple. Provincetown Inn is a more reasonable option near Pilgrim’s Point that also has a pool and an happening scene.



There is something to do for everyone in Provincetown, from visiting art galleries on the East End to whale watching on the North Atlantic. Here are a few of my favorites:

  • Bike ride in the village or among the dunes of the National Seashore (See Ptown Bikes for bike rentals)
  • Whale watch from Provincetown Harbor on the Dolphin Fleet
  • Enjoy afternoon “tea” (rum punch) at the daily Boat Slip Tea Dance from 5-7 pm
  • Hike across Pilgrim Point bay on a rock wall over a mile long
  • Visit the Cape Cod National Seashore and the Provincetown Lighthouse
  • Bask in the summer sun at the Provincetown Inn pool while enjoying the delicious food and libations at the bar
  • Sing show tunes by the piano nightly at the storied Crown and Anchor
  • Climb the Pilgrim Monument for a view over P-Town and the Seashore



Breakfast and Coffee: Relish, Provincetown Portuguese Bakery, Liz’s Cafe Anybody’s Bar, Kohi Coffee Company

Lunch: The Canteen (lobster roll is a must), Spiritus Pizza, Yolqueria, Relish, Front Street Cafe

Happy Hour: From oysters, to wine and cocktails, to a stunning view — there is no comparison to The Red Inn in the West End. If you can stand to miss Tea Dance.

Dinner: Mew’s, The Red Inn, Strangers and Saints, Jimmy’s Hideaway, Canteen, 9 Ryder Street (behind Lobster Pot). Note: Lobster Pot is touristy. There are much better options.



Wellfleet Bookstore and Restaurant

Chatham Lighthouse and the restaurant Chatham Squire

Nausset Beach near Orleans is a beautiful wide beach

Martha’s Vineyard, Hyannis and Nantucket



This blog entry is part of a larger series of travel articles on Toddbouldin.com called “If I Had a Day” covering New York City, New Orleans, Nashville and Los Angeles.

Todd is available for travel consultation and reservations to these cities and more for a negotiated rate per hour. Todd is a travel writer and Yelp Elite based on his restaurant and travel reviews. If you are interested, please contact Todd at Todd@toddbouldin.com.

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