Best Date Night Spots on the Cape and Islands
Planning the perfect date night on the Cape and Islands? We’ve got you covered — from ocean-view dinners to cozy local favorites. This guide highlights the best spots to make your evening truly unforgettable.
- 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!
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!
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.
Photo by @oceanedgeresort
- Cape Cod Central Railroad (Hyannis) - Cape Cod Central Railroad invites you to experience Romance on the Rails with two unforgettable dining adventures. On Saturday, February 14th, enjoy a relaxing evening ride featuring a special four-course gourmet dinner served on white table linens in traditional rail style. New this year, the celebration continues with a Valentine’s Weekend Sunday Brunch Train on February 15th, offering a three-course gourmet meal perfect for couples, friends, or families! *Update: these events are currently sold out for 2026*
Photo by @capecodcentralrailroad
- 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!
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! Enjoy an elegant assortment of breakfast options such as pastries, omelettes, pancakes, waffles, and more. A must-try is their Peach Melba French Toast, topped with compressed peaches, whipped cream, and raspberry crumble!
Photo by @chathambarsinn
- 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 @bleu_capecod
- 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, Montano's Restaurant has been serving fresh homemade pasta made daily, fresh local seafood, and Angus beef for over 35 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
- Siena Italian Bar & Grill (Mashpee) - With a true Italian spirit, Siena in Mashpee Commons offers the best Italian dining on the Cape! From the hills of Tuscany to the dunes of Mashpee, their kitchen brings the flavors of Italy to your table. They invite you to Live Well, Eat Well, and Be Social!
Photo by @phantomgourmet
- Sea Crest Beach Resort (North Falmouth) - celebrate Valentine's Day at The Lantern Room! Join them February 13th & 14th from 3-8 pm for specially curated Valentine's Day dishes, available alongside their brand-new full winter menu. On February 14th, make the special day even sweeter with live piano and jazz music from 4–8 PM, setting the perfect tone for a cozy, memorable night by the water.
Photo by @lanternroomcapecod
- The West End (Hyannis) - owned and operated by a husband and wife team and created out of a shared passion for excellent service and unique culinary experiences. The West End has been dedicated to creating something special for Cape Cod locals and visitors alike. Open year-round and now open for lunch as of February 12th, 2026!
Photo by @westendhyannis
- Cape Cod Winery (Falmouth) - their most-loved Valentine’s tradition is back and sweeter than ever! Join CCW Saturday, February 14th, for a fun and unforgettable Wine & Chocolate Pairing Experience, featuring their delicious partnership with local favorite Ghelfis Candies! Five incredible wines, five decadent handcrafted chocolates, and the perfect cozy vibe, whether you’re planning the ultimate date day or a festive Galentine’s outing. Spots are limited, grab your tickets on their website!
Photo by @capecodwinery
- Five Bays Bistro (Osterville) - Five Bays Bistro is located in the heart of one of the most picturesque villages on Cape Cod! They offer a sophisticated and mouth-watering award-winning contemporary New American cuisine in an inviting atmosphere worthy of a major city. Pictured below is a Five Bays staple, their delicious Lobster Mac & Cheese!
Photo by @fivebaysbistro
- 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.
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!
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 Valentine, your best friend, or join them solo at their Valentine's Day Tasting! Stop by Saturday, February 14th, from 11 AM–5 PM, where three Truro Vineyard's wines (plus a bonus pour of their Coco dessert wine) meet three Chill’s Cheesecakes for the ultimate sweet pairing.
Photo by @trurovineyardsofcapecod