Provincetown takes on a tranquil and relaxed feeling in the wintertime, with a quieter and less hectic atmosphere, perfect for getting away for a few days with your special someone. Free from the summertime crowds, you’ll find intimate solitude at beautiful beaches and on nearby trails, while indulgences like couples’ massages are just blocks away, and plenty of options await for date-night dining and live music. With our lower Provincetown bed and breakfast wintertime rates, there’s never been a better time to plan your Provincetown romantic getaway and delightful escape to the Cape together.


Two bikes parked in front of our Provincetown lodging

Brunch Bites, Strolling Near the Marina, and Unwinding With a Couples Massage

After a restful night (all of our Gabriel’s rooms have plush Tempur-Pedic mattresses) and a laidback start to the morning, stroll a couple of blocks over to a variety of charming local restaurants for a delicious brunch. Along Commercial Street, where Provincetown’s culinary heritage thrives, numerous food establishments await, inviting you to sample the rich tradition of omelets, french toast, and different types of Eggs Benedict (choose the salmon or lobster for a taste of the Cape’s famous seafood). Order two signature bloody marys, made with just the right kick and spice, and raise a toast to your Provincetown romantic getaway.

After your meal, head out for a walk together near the marina, one of the most picturesque places on Cape Cod. In Lopes Square, a gathering place during every season, you’ll find the one-of-a-kind Lobster Pot Tree if you visit over the holidays. Made from buoys and lobster traps, it pays homage to the generations of lobster-fishing families in town, a charming touch and a quirky part of Provincetown culture. Stroll along Commercial St, stop into renowned art galleries, enjoy the quiet winter ambiance, and finish the day with a visit to the Blu Day Spa. Have their expert team of massage therapists, all with over 20 years of experience, give you a couples massage – sink into soothing tranquility together while you both get a 30, 60, or 90-minute massage. Swedish massage is classic but opt for their couples’ deep tissue massage if you want an extra therapeutic session. Blissed out after your dual massage, just walk a couple blocks back to your room, where you can continue your romantic relaxation near the fireplace (most of our rooms have in-room fireplaces).

Wine-tasting, a Picnic on the Dunes, and a Sunset To Remember

Start the next day with our continental breakfast (served on Sat and Sun during the winter) before taking a scenic drive together to Truro Vineyards for a wine tasting. As you go from P-Town to Truro, the next town over and just 8 miles away, enjoy the views of the pristine bay water on one side and the preserved beauty of the Cape Cod National Seashore out the other window. Try their flight of five wines to taste all their unique varietals, including reds aged 1-2 years in oak barrels and whites like chardonnay and sauvignon blanc that pair perfectly with seafood.

Buy a bottle or two of your favorite wine from their impressive selection and return to P-Town to finish the day at Race Point Beach, one of New England’s most striking stretches of coastline. Pick up some picnic bites like housemade hummus and Caprese salad at Far Land Provisions on the way to Race Point, normally jam-packed in the summer months but serene and quiet during the wintertime. Walk hand-in-hand down the dunes and set up on the sand with your picnic food and wine, with breathtaking views of the iconic Race Point Light as the sun begins to set, a postcard-perfect romantic scene.

aerial view of Provincetown covered in snow

An Afternoon on the Trails Followed by a Date Night Downtown

After spending the day exploring the nearby hiking trails and taking in the natural beauty surrounding P-Town, enjoy an evening on the town with dinner and live entertainment. At the Mews, which will celebrate 60 years in business in 2024, the quality of service is as impeccable as the food, which ranges from decadent dishes like roasted cornish hen and duck leg confit served with sweet potato gnocchi to Vietnamese-inspired shaking beef with onions and scallions. Share a plate of raw oysters, equally delicious when served traditionally or with their sweet and spicy tomato sauce. Whether you sit in their first or second-floor dining room, you’ll have views directly out over the glimmering bay water, making your date night extra special.

After dinner, stroll back a half-mile on Commercial St towards the marina area, where you can catch live music at Tin Pan Alley. With everything from soulful lounge singers to jazz and Sunday night traditional swing tunes, musicians bring top-notch playing to their elegant and classy space, which stays open until 12:30 am every night, even throughout the winter months. Order a bottle from their extensive wine list and savor the romantic setting as sweet tunes fill the bar. You’ll be just a block away from your room, where you can wind down and relax, bookending a memorable and affectionate few days together on the outer Cape.

Stay with us and surprise your love with a Provincetown romantic getaway!