Provincetown’s small footprint, surrounded by Cape Cod Bay and the Atlantic Ocean on either side, makes it easily walkable and perfect to explore on foot. From the always-active marina and towering Pilgrim Monument in the center of town, centuries-old houses alongside seaside lanes on the west end, and art of every style on the east end, you’ll experience several chapters of Provincetown’s fascinating history during your memorable stroll. 

Our Provincetown bed and breakfast is ideally located for walking in any direction, blocks away from the water, and the perfect home base for your tour of Provincetown.

MacMillan Pier, Portuguese Heritage, and a Fishing Culture That Runs Deep

Custard cups or pasteis de nata are a very traditional portuguese pastrie, won't miss it during your visit to out B&B.

Begin your day with a casual jaunt down to the MacMillan Pier and Marina – just a couple blocks away from our Provincetown hotel – Provincetown’s cultural hub and center of action for hundreds of years, with ships always coming and going. During the early 1800s, Provincetown was one of the busiest ports in the world for whaling, as massive “whalers” set out from the harbor and fished the bounty of whales off the coast of Cape Cod. These whaling ships brought back expert ocean-faring men and their families from the Azores and mainland Portugal, imbuing Provincetown with their Portuguese food, music, and culture. 

Walk out on the marina, listening to the sounds of sea birds and crews readying their boats, to the “They Also Faced the Sea” art memorial at the end of the pier. You’ll see beautiful black-and-white photos of the female matriarchs of these Portuguese fishing families, paying homage to how they held the community together while their husbands were at sea for long periods. 

After enjoying the sea breeze and watching the fishing boats bring in their daily catch (which you can then enjoy fresh for dinner at Mac’s Fish House, one of our favorite restaurants), stop by the Provincetown Portuguese Bakery near the marina. You can get a culinary taste of our Portuguese heritage with their malasadas (Portuguese fried dough, a close cousin to the French beignet), sweet rolls, or almond croissants, all made with the same original recipes since they opened over 100 years ago.

Centuries-Old Cape Cod Houses, Where the Pilgrims Came Ashore, and a Towering Monument to Our History

Next, walk down Commercial St. along the bay, heading towards the end of the Cape Cod peninsula. This thoroughfare is one of the most charming stretches of Provincetown, with seaside cottages dating back to yesteryear and our town’s beloved “dog beach” (see our recent blog for everything you need to know about pet-friendly Provincetown.). History is on full display in the houses you’ll pass by, like the one at 72 Commercial St, which dates back to the mid-1700s – legend has it that the original builders made the house using the wood of shipwrecked sea vessels, an authentic living piece of P-Town folklore.

At the end of Commercial St., you’ll get to Pilgrims’ First Landing Park, where a plaque marks the very spot where the Mayflower Pilgrims landed ashore in 1620 after over two months of voyaging from England. It’s a visceral feeling to look out over the calm waters of Cape Cod Bay, imagining the Pilgrims landing four centuries ago and exhilarated to find the “New World,” communing with the Native American Wampanoag tribe and celebrating the first Thanksgiving shortly after that.

As you stroll back to central P-Town, stop at the Joon Bar for appetizers (try the fried Spanish olives and crispy artichoke hearts) and delicious cocktails. Finish the day by heading to the top of the 252-foot-high Pilgrim Monument, a landmark to Provincetown’s important role in our nation’s history. In addition to the spectacular views from the top viewing deck (the last trip allowed up every day is at 4 p.m., so plan to get to the tower base by then), browse the museum collections below the tower, which explore the complicated intersection of Pilgrim and Native American cultures, Provincetown’s evolution as a whaling port, and our city’s vibrant LGBTQ+ history.

Cape Cod Lighthouse view, with a very well preserved old New England house.

Exploring the East Side, Discovering P-Town Art, and Lights in the Winter

For the next chapter of your tour of Provincetown, head the opposite way toward the “east side” of town, where you’ll find much more to explore. Get some caffeine and a tasty snack at Wired Puppy – their menu has unique drinks like a salted caramel latte, iced lavender chai tea, homemade cookies, muffins, and pastries. Continue down Commercial St. to the Provincetown Art Association and Museum, the home base for all things art. Their always-growing collection includes paintings and sculptures from hundreds of artists inspired by Cape Cod’s beautiful landscapes while spending time in and near Provincetown. They are closed on Tuesdays, but if you happen to be taking your walk on a Friday, visit after 6 p.m., when admission is free.

Return by foot to the town center, enjoying the salty air blowing off Cape Cod Bay, and stop in for a meal and drinks at Provincetown Brewing Company. Split some lemongrass chicken wings and nachos, or try one of their delicious burgers alongside a frosty pint from their extensive beer menu, which ranges from double IPAs and sours to lagers and stouts. Their outdoor patio is shaded on warmer days and heated in the winter, so post up there and wind down after your pleasant afternoon out and about. They also donate 15% of every pint sold to progressive and LGBTQ+ causes, reflecting Provincetown’s tight-knit community spirit.

Finish off the day by walking back down to the marina for the sunset, framing the harbor with the glow of late afternoon light. During the winter months, check out the quirky and iconic Lobster Pot Christmas Tree in nearby Lopes Square, made from actual l

Lobster traps and celebrating the hardworking lobstermen and lobsterwomen who have been pillars of P-Town’s culture for generations. Starting in mid-November, the Provincetown Monument shines brightly, with its lights extending up the tower throughout the winter – a lovely sight when ending your leisurely and memorable tour of Provincetown.

Stay with us and explore Provincetown on foot, with unique history and culture along every block!