It’s fun to imagine what the hardy band of Puritans who first visited the idyllic natural harbor of Provincetown back in 1620 would have thought of the place these days. What was once a desolate stretch of dunes, scrub oak, poison ivy and pitch pine surrounded by saltwater is now a bustling tourist destination and thriving artist community. Sure, the winter months can be quiet, but summer feels like a cacophonous, never-ending mardi gras, with drag queens patrolling Commercial Street amid noisy throngs of foreign tourists and family vacationers. Numerous restaurants, galleries and boutiques now line the streets, alleys and wharves that were once the sole domain of commercial fishermen and whalers.


It’s safe to say that mariners have appreciated P-town long before it became known for its thriving art scene, tourism industry and gay community. The deep natural harbor offers excellent protection from the wind and seas in virtually all directions.


The harbor approaches are deep and free of obstructions, and the inner harbor can easily accommodate large yachts and commercial vessels. Moorings and slips are available via the two marinas — Flyers and Provincetown Marina—along with launch service and dinghy docks. However, be sure to call ahead for reservations, especially during the summer and early fall. Ice, fuel, and repair services are available as well. Transient boaters can also anchor inside the protected arm of Long Point, where they’ll find good holding ground.


Day-trip boating options from P-town include runs to Stellwagen Bank, the southwest tip of which lies a scant three miles offshore. Here you can view humpback, minke and finback whales at close range (just be sure to stay 300 feet from the whales, as per federal law). Ocean sunfish, bluefin tuna and basking sharks also gather over the bank to feed during the summer, when the surrounding waters teem with plankton and baitfish. Boaters can also cruise along the Outer Cape beaches, as long as they remain mindful of the sandbars and surf, which can run heavy after a storm or during strong easterly winds. Trips nearby Wellfleet Harbor, to the south, are an option as well.

Of course, shoreside activities and events abound in P-town. You can climb to the top of the 252-foot-tall Pilgrim Monument (built in 1910), also home to the Provincetown Museum, for a spectacular view of the Cape and surrounding waters. If you like eclectic stores, be sure to stop in at Marine Specialties, a P-town institution selling everything from mooring balls to fishnet stockings and located in an old fishing-net shop in the heart of Commercial Street.


The athletically inclined can rent a bike and ride through the towering dunes and pitch pine forests just outside town, or visit one of the former lifesaving stations along the Outer Cape, such as the one at Race Point Light. If you like to walk, you can hike along the West End breakwater (actually a long stone dike), which was built in 1911 by the Army Corps of Engineers. Cruises of the harbor are available through several companies, but kids will love the pirate ship cruises aboard Pirate Adventures. Nightlife abounds in town, with numerous cabaret performances each night during the summer and fall.

Speaking of fall, September and early October may be the best time to travel by boat to P-town. The harbor is less crowded, and you’re more likely to find a mooring or slip on short notice. Also, the throngs of tourists will have ebbed, leaving you more room to explore the town. Lastly, early autumn weather can be fantastic in this part of New England.