Nantucket, Massachusetts, seems like something out of a novel. There’s so much to explore and delve into—cobblestone streets, beautiful beaches, and an enchanting atmosphere—making it an incredible place for a day trip from Boston or a weekend-long stay with your significant other. Plan a trip with your loved one this summer—no matter how long you choose to stay, you’re sure to fall deeper in love with one another. We’ve listed out some of the most romantic locations in Nantucket—you’re sure to love them!
Storybook Settings in Nantucket
Where to Eat:
The food in Nantucket is insanely delicious. Almost everything is prepared fresh—especially the seafood. From casual spots to fine dining, the opportunities for scrumptious cuisine are endless. You’ll have many different restaurants to choose from, but we’ve laid out some of our favorite spots that are perfect for a date between sweethearts.
80 Center Street
Walk through the vine-covered trellis and into the warm and elegant interior of American Seasons. Known for serving Nantucket residents and visitors by candlelight, this fine dining spot oozes romance. Chef and owner Neil Ferguson brings culinary experience from Paris, New York City, and London, so you know that whatever you order is going to be excellent. All the food is local, seasonal, and thoughtfully prepared. Begin with roasted sea scallops to share, then dig into their braised lamb neck or line-caught halibut.
20 Broad Street
Serving upscale food in an elegant environment, Dune embodies Nantucket’s timelessness. It consistently wins awards, and for good reason. The seafood offerings range from global dishes to a simple lobster roll, and the menu is ever-changing. The wine list here is quite extensive, and they also have a sommelier on hand—wine pairing has never been so easy. Order a bottle and enjoy your meal together in this charming restaurant.
1 Straight Wharf
Nantucket’s premier oyster bar, CRU is the perfect spot for seafood lovers. The menu changes daily to fit the offerings of the sea, meaning every dish is ultra-fresh. CRU is casual and elegant, and it’s everything you could want for a romantic lunch date. Grab a glass of rosé, dig into your favorite dishes, and snap a picture together with the breathtaking view in the background—both the meal and the location will be something you’ll remember forever.
120 Wauwinet Road
Regarded as the best restaurant on Nantucket, Topper’s is a foodie destination located on the waters of Nantucket Bay. You and your partner are sure to find yourselves in the midst of a dazzling evening. Located at the beautiful Wauwinet Inn, Topper’s gives diners an authentic meal with fresh, local food. Their Retsyo oysters are cultivated just 300 yards away, so you know you’re getting them fresh!
Where to Drink:
Drinking in Nantucket is a varied affair, with dives and classy joints, beachfront spots and homes-turned-bars. Needless to say, you have a lot of places to choose from, so to help you and your loved one figure out the best spot for some late-night drinking or a refreshing cocktail, we’ve listed some of our favorites. Check them out!
54 Jefferson Avenue
Beachfront dining has never been more beautiful than at Galley Beach. After a walk along the beach, stop here for a refreshing glass of wine with an enthralling view of the ocean. If wine isn’t your thing, their cocktail list is terrific; each beverage pairs wonderfully with the sunset.
326 Madaket Road
You’ll find the best views of the sunset at Millie’s. It’s perfect for a casual date night where you can dig into a delicious Baja California menu and some unique and delicious cocktails. This spot offers plenty of barstools if you just want a quick drink, and their bartenders are just as friendly as the atmosphere. Not to mention, the drinks are social media-worthy, served in a mason jar and uber-colorful.
The Chicken Box
16 Daves Street
We had to include the dive bar that locals love most on this list. Simply known as The Box to islanders, it’s a place beloved by locals and tourists alike. They have the best live music on the island, bartenders who are genuinely excited to get to know you, and a lively scene that gets started after 10 p.m. Perfect for partners who love to party, this is definitely a place to go at the tail end of a big night out.
5 Bartlett Farm Road
No matter what kind of drink you’re feeling, Cisco Brewers has what you need to ignite your taste buds. They are Nantucket’s premier winery, brewery, and distillery. If you don’t mind the crowd, grab a drink from the brewery, where outdoor seating and good vibes abound. For more of an intimate feel, head to the winery, where you can enjoy tastings and private conversation.
What to Do:
To help you narrow down the romantic activities you and your loved one can do on Nantucket, we’ve compiled a few of our favorites. From sightseeing to sailing, we hope you and your partner will enjoy these activities.
Rent a Bike
A wonderful way to take in the gorgeous views of Nantucket is to hop on a bike and ride around the island. The island has several bike rental companies, and the bikes are all adorable. One of our favorite scenic loops is from downtown Nantucket to Siasconset (known to locals as ’Sconset). The 40-minute ride is perfect when you throw some snacks into the bike basket and pedal at a leisurely pace.
See the Lighthouses
Nantucket features three beautiful lighthouses, and we highly recommend going to see them on your trip. There’s Brant Point Light Station (the second-oldest lighthouse in the U.S.); Great Point Lighthouse (you’ll need to rent a Jeep with an over-sand permit); and Sankaty Head Lighthouse (in easternmost Nantucket). Pack a picnic, a blanket, and a bottle of wine, and you’ll be good to go!
Go on a Sailing Excursion
If you have the time, you and your partner should definitely think about going sailing during your trip to Nantucket. Head out on a sailing excursion around the island—it’s a wonderful way to see all the natural beauty Nantucket has to offer. The breathtaking island has some of the most jaw-dropping sunsets in the world, and sailing is the perfect way to see them.
Take a Cooking Class
Since the cuisine is one of the main things Nantucket is known for, you and your partner should try out a cooking class. Learn from the masters by taking a class at the Nantucket Culinary Center. Once you finish preparing your meal, you’ll head to the third floor of the building to enjoy a candlelit dinner overlooking downtown Nantucket. It’s simply the best.