From magnificent sunset boat cruises on the bay to wine-tasting at a local vineyard, guided tours of the pristine Cape Cod National Seashore dunes, plus date-night dinners, art-browsing, and live entertainment downtown, our Provincetown, MA bed and breakfast is perfect for planning your couples’ retreat. Get ready for the perfect getaway – full of romance, relaxation, and summer’s exceptional beauty on outer Cape Cod.

Experience Sunset on the Water in Provincetown

There’s nothing quite as romantic as watching the sunset with the one you love while sailing around the tip of the Cape peninsula, with majestic views of the iconic lighthouses on Cape Cod as you cruise from the Provincetown harbor into the open waters of the Atlantic. Although a few companies offer sunset boat excursions, the tour with Captain Bob Burns and his crew at Sail Cape Cod is truly unique. You’ll sail for 2 hours on their classic 73-foot schooner, Bay Lady II, with the sound of wind blowing against the massive sails as your soundtrack. The cruise takes place from 6:30-8:30 pm and culminates with a sunset worthy of endless photos. Captain Burns, a longtime native of Provincetown and sailor for over 50 years, will show you the beauty of Cape Cod from the deck of his cherished schooner.

As if the sunset cruise wasn’t already thrilling enough, you might spot some marine life while sailing. Dolphins, seals, and even whales commonly appear during the spring and summer, adding an exciting element to your boat tour. The crew encourages guests to bring drinks and snacks, so stop at the gourmet grocery store and Provincetown staple, Angel Foods, beforehand. Owned by Liz of Liz’s Cafe, one of our favorite Provincetown restaurants, this is the perfect place to pick up some gourmet cheeses, olives, bread, and a bottle of prosecco to enjoy on the boat during your sunset excursion.

If you’re traveling to Provincetown from Boston aboard the ferry (with the perk of skipping the summertime car traffic along Route 6 between Boston and Provincetown, MA), take advantage of the Boston Harbor Cruises Provincetown “fast ferry” schedule to time your trips around the sunset. The last crossing from Boston to Provincetown leaves at 7 p.m., while the last one from Provincetown to Boston departs at 5:30 p.m. – excellent timing to catch a sunset while on your 90-minute scenic trip across the bay.

Young couple hugging at sunset on boat with a sunset cruise

Date Night at a Vineyard and Sunset Dune Tours

Indulge your senses during your couples’ retreat to the outer Cape and take a scenic 15-minute drive south to the gorgeous 5-acre estate at Truro Vineyards. Do a guided tasting of their exquisite estate-grown wines, including a dry Maritime red, Cabernet Franc, and oaky, citrusy chardonnay (ideal for a warm summer day). Every Wednesday from July 3rd through August 28th, 2024, make your vineyard outing even more special by attending their Wine & Dine events, which combine a 5-course menu of locally sourced food, award-winning wine, and work from a different featured local artist each week and live music from 6:30-8:30 pm. As you sit under shaded outdoor tables next to the picturesque rows of grapes while eating delicious food, sipping your favorite wine and live music filling the air, it’s a lovely scene pulled right from a rom-com movie.

For a sunset experience equally as adventurous as a boat tour, head out on a sunset cruise on the dunes with Art’s Dune Tours. In business since 1946, Art’s is a family-run operation, and its tour guides are full of insight and knowledge about Provincetown’s stunning natural landscapes. The 2.5-hour sunset tour explores the miles of dunes within the Cape Cod National Seashore (75% of the outer Cape is protected land, preserving its wild habitat). You’ll spend the first hour crossing the dunes on their all-terrain vehicles, seeing unique sights like the historic Cape Cod dune shacks. Then, they’ll provide chairs for your group to relax on the shore of Herring Cove for the ultimate Cape Cod sunset view. If you want to make the dunes tour extra intimate, rent all six seats in the vehicle, and you’ll have a private tour with just you and your special someone.

Dinner and Art on the East End, Plus Music and Comedy Around the Block

The Provincetown restaurant scene is diverse and delicious, with several spots ideal for planning a romantic dinner for two. Stroll down Commercial St on the East End, where you’ll find two of the best eateries in town, both with breathtaking harbor views. At Fanizzi’s, they live up to their motto of being a “restaurant by the sea,” with their dining rooms perched directly over the water’s edge. Share appetizers like stuffed artichokes and crab cakes with chipotle sauce, followed by entrees like chicken parmigiana and lobster ravioli. Pair your meal with their fantastic selection of wines and cocktails, with an extra dessert treat of decadent tiramisu or warm peach crisp. At the Mews, just a few blocks from Fanizzi’s, you’ll find a similarly elegant ambiance, with top-notch delicacies like Wellfleet oysters, baked miso cod, and grilled lamb chop to match their spectacular bayside dining room vistas.

A couples’ retreat wouldn’t be complete without enjoying some of Provincetown’s legendary culture and nightlife, which come alive during summer. Browse the world-class art exhibits at the Provincetown Art Association and Museum, where entry is free every Friday evening (convenient for combining with dinner at nearby Fanizzi’s or the Mews, which are neighbors of PAAM on the East End), and browse the rows of renowned art galleries in Provincetown along Commercial St as you make your way back towards the marina.

Laugh together at live comedy events at the Provincetown Town Hall, right across the street from us – Jinkx Monsoon, Cheyenne Jackson, Audra McDonald, and other talents will perform on various weekends in July and August of 2024 – check the summer events calendar for dates and show info. Finish your evening next door with live tunes in a romantic setting, toasting your cocktails to the live lounge/jazz music at Tin Pan Alley, capping off an entertaining and memorable escape to Provincetown.

Stay with us and get away for a romantic couples’ summertime retreat to Provincetown, MA!