When you only have a weekend in Provincetown–the colorful town on the sandy fist of Cape Cod– try to arrive well before the weekend rush hour traffic onto the Cape, especially during high season. I like to turn up in Provincetown before lunch in order to get convenient wharf parking and ease into this fabulous town chock full of history, art, architecture, and beaches. Provincetown’s welcoming vibe and openness to all lifestyles makes it one of the most gay-friendly cities in the country.

Friday: First things first. Get a lay of the land. Check in to your hotel and spend some time wandering P’town’s colorful streets. Pick up a copy of the Historic Provincetown Walking Tour map from the Tourism Office located at 330 Commercial Street or from the Historical Association at Town Hall. The fold-open map features fifty buildings that tell the story of Provincetown’s evolution through its architectural history. For a deeper look into the town’s social and architectural development, get a copy of the book, Building Provincetown: A Cultural History Block-by-Block, by David W. Dunlap.  
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When it’s time for lunch, there is no shortage of places to eat, but during peak season you may want to do a little restaurant research and make reservations if possible. We recommend lunch or appetizers at the iconic Lobster Pot. Can’t miss the neon glowing sign at its narrow entrance opening to a two story restaurant and bar overlooking the bay. The Lobster Pot also has a limited carry out menu offering the standards: lobster rolls, clam chowder and Portuguese kale soup.

Work off lunch, by climbing through history to the top of the 252-foot Pilgrim Monument (c.1910), the country’s tallest granite structure. The Italian-inspired tower commemorates the pilgrims’ first landing in Provincetown before sailing on to Plymouth. The view is worth the effort! We chanted “derrière extraordinaire” as we spiraled up the 116 steps and 60 ramps (probably 500 steps total) to magnificent vistas over the town and bay. The Chamber of Commerce weather allowed us to see out over the Province Land Dunes with view of the lakes and glimpses of the ocean. It was hard to tear ourselves away from the bird’s eye view, but going down the steps was much easier!

In keeping with the classic and historical theme of the day, enjoy a dinner of modern and traditional Italian at the intimate Front Street restaurant, one of P’town’s oldest and most endeared eateries.

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Start the day with Portuguese pastries, such as a fried malasada, or breakfast sandwiches and coffee from the iconic Portuguese Bakery. So much of the local cuisine, especially the liguiça and kale soup, is a reminder of the strong connections with the Portuguese fisherman who settled in Provincetown more than a century ago. Grab some carry out from any number of restaurants or pack a picnic and escape the hustle and bustle of Commercial Street by hitting the beaches.

Rent a bike from Arnold’s rather than traveling by car to explore miles of shoreline protected by the Cape Cod National Seashore in the Provincetown area. You’ll see more this way and not have to wrangle for limited and sometimes expensive parking. Avid cyclists can take to the dunes through the beautiful Province Lands Dunes, which speaking from experience, are hilly and require effort. Those of us who prefer a leisurely peddle will not have any problem biking to a scenic sandy spot.

Beaches of choice? The sweeping stretch of Herring Cove Beach or the dune lined Race Point Beach with its Old Harbor Life Saving Station Museum. The interesting building was relocated from Chatham to the hillside above Race Point Beach and contains a tour guide and interpretive exhibits related to ocean rescue. From here, make your way down the sandy hillside to a great stretch of Atlantic-facing beach.

For a memorable dinner, slurp local Wellfleet oysters at the Red Inn.

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Take the morning to shop the many art and craft galleries in Provincetown. What I appreciate most about retail here (and throughout Cape Cod) is the clear support of independently-owned stores, restaurants, and shops. Very few chains are found, even in the year-round towns. Photography, ceramics, painting, hand-crafted food, and textiles are among the sundries to be had. Pick up an autographed copy of my history-meets-travel book, Discover Cape Cod at the Provincetown Bookshop. Check out Bill Evaul Studios and Gallery at 347 Commercial Street for his unique Provincetown twist on white-line woodblock printmaking.

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Hop aboard a Dolphin Fleet whale watching trip to round out all of the different activities Provincetown has to offer. Read about our experience seeing almost 50 humpback whales on one phenomenal tour from Provincetown into the Stellwagon Marine Sanctuary.

Time to get your weekend Wanderlust on in Provincetown!