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Best Date Night Spots on the Cape and Islands

  • Pelham House Resort (Dennis Port) - if you're looking for the perfect spot with stunning views and delicious food, look no further! The Rooftop at Pelham is your go-to oceanfront dining experience on Cape Cod. Fully heated and open year-round, it's the perfect spot to enjoy the perks of summer weather or take in the peacefulness of the off-season. We recommend visiting multiple times throughout the year, as the menu crafted by their talented culinary team has new additions every season!

Pelham House Resort

Photo by @travelingfooders

  • La Bella Vita (Orleans) - nestled in the heart of Orleans, La Bella Vita Kitchen & Bar offers a unique fusion of Italian-inspired cuisine. The menu is carefully crafted, made with the freshest ingredients, and catered to all tastes, ensuring there is something for everyone. They pride themselves on a warm and inviting atmosphere that is perfect for a romantic date night or a fun night out with friends and family. Enjoy your evening on their outdoor patio, and sip on a smooth espresso martini by the fire pits!

La Bella Vita

Photo by @labellavitavcapecod

  • Ocean Edge Resort (Brewster) - dine at Ocean Edge Resort for an upscale and intimate evening. The Roscommon Room at Ocean Edge allows you to relax and recharge. It is a gleaming wooden room with views of the ocean. Sip, take a bite, and enjoy quality time with your loved ones while marveling at the views of Cape Cod Bay. Reservations are required.

Ocean Edge

Photo by @oceanedgeresort

  • Osteria La Civetta (Falmouth) - a celebration of Italian food, wine, and hospitality, all combined with fresh and local ingredients. Every dish prepared is rooted in or inspired by their mothers and grandmothers, as well as, by the fishermen and farmers of Italy. Come into La Civetta for an intimate, relaxing, and delicious dining experience!

Osteria La Civetta

Photo by @osterialacivetta

  • Chatham Bars Inn (Chatham) - Stars Restaurant at Chatham Bars Inn is inspired by stunning views of the Atlantic Ocean and is an experience that will excite all of the senses. We highly recommend visiting here for brunch year-round. Our personal favorite item on the brunch menu is their Brioche French Toast - frangipane, poached pears, candied almonds, and whipped cream!

Chatham Bars Inn

Photo by @capeology

  • Bleu (Mashpee) - experience a little bit of France on Cape Cod while dining at Bleu. Executive Chef/Owner Frederic Feufeu, a native of the Lorie Valley, is known for his authentic French bistro fare and contemporary cuisine. Stop in to experience a lovely atmosphere and enjoy dinner paired with an award-winning selection of wine. 


Photo by @blue_restaurant

  • Bucatino’s (Falmouth) - it takes more than great cooking to make a great meal, and Bucatino's has got that covered! They offer an Italian ambiance and all meals are prepared with fresh local ingredients. Join Bucatino's on Valentine's Day for a specially curated menu, including a selection of appetizers, entrees, and desserts. Reservations are recommended. 


Photo by @bucatinofalmouth

  • Montano's Restaurant (Truro) - established in 1988 by Chef and Owner Bob Montano, Montano's Restaurant has been serving fresh homemade pasta made daily, fresh local seafood, and Angus beef for over 25 years. Join them for your next date night and enjoy delectable Italian fare. We highly recommend their Calamari Fritti and Pepper and their Rigatoni Vodka!


Photo by @montanosma

  • The Chatham Cut (Chatham) - culinary excellence meets impeccable service. Discover a haven of flavors where each dish tells a story and every moment is a celebration to savor. Indulge in an exquisite dining experience that goes beyond the ordinary. Pick from their carefully curated wine list with regions from all around the world and enjoy a delicious meal prepared by their team of passionate chefs during your next date night!

Chatham Cut

Photo by @thechathamcut

  • Fin (Dennis) - located in Dennis Village, Fin serves contemporary seafood, refreshing drinks, and much more in their two-story antique home. All food is prepared with local ingredients from fish to farm. Fin has a quaint, romantic ambiance that will quickly become a go-to date night spot. Reopening for the season in the Spring!

Fin Cape Cod

Photo by @fincapecod

  • The Glass Onion (Falmouth) - one of Falmouth's hidden gems. They offer a delicious, upscale menu in a charming yet elegant setting. Not only is it a perfect setting for a special occasion or romantic date night, but they serve nothing but the best fare. Reservations are recommended throughout the year. 

Glass Onion

Photo by @planet.payton

  • Trevi Cafe & Wine Bar (Mashpee) - embodies a contemporary ambiance with an authentic dash of European romance. Their Mediterranean-style cuisine is composed of the season's freshest ingredients, while the wines from their diverse, unique collection pair seamlessly with each meal. Come spend your Valentine's Day with your special someone at Trevi and enjoy their February 14th special menu!

    Trevi Cafe & Wine Bar

    Photo by @trevi_cafe_winebar

    • Truro Vineyards of Cape Cod - their vineyard is situated next to 44,600 acres of National Seashore. Make a reservation for wine and spirits tastings, or stop by for the weekly wine flight. Bring your Honey and visit Truro Vineyards on Valentine's Day for a special Paint & Sip. Led by the talented Colin McGuire, paint your own masterpiece while sipping on wine and snacks. Open year-round, but make sure to check their hours of operation in the off-season!

    Truro Vineyards

    Photo by @trurovineyardsofcapecod

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