Perfect Long Weekend on Nantucket for Couples

Bike ride to ‘Sconset

Rent a bike from Nantucket Bike Shop on Broad Street in town (or borrow one from your hotel–many have them available for guests) and bike 45 minutes to the ‘Sconset area of Nantucket. You’ll enjoy picturesque scenery along the way! If you don't feel up for the ride back to town, catch the free bus that goes around the island (complete with bike racks).

‘Sconset Bluff Walk

The ‘Sconset Bluff Walk is an iconic Nantucket experience! In the village of Siasconset, there is a public walking path that winds along the backyards of impressive homes, and on the other side, you’ll see exquisite ocean views from the bluffs. To get started on the trail, turn right after 21 Front Street and make an immediate left.

Boat ride to lunch at Toppers

Make lunch special by adding a boat ride along the coast of Nantucket! Topper’s is a restaurant at the Wauwinet hotel (located about 20 minutes from town) that’s known for fine dining and cocktails on the lawn overlooking the water. Instead of driving there for lunch, you can book a complimentary 50-minute sail aboard the Wauwinet Lady, which departs from the resort’s sister property in town, the White Elephant, and transports diners directly to the restaurant.

Cisco Brewers

A brewery, distillery, and winery all in one! You can also find food trucks from many of the popular restaurants in town.

Beach day

Visit Ladies Beach, a gorgeous spot that will likely be less crowded than popular Surfside Beach. To make it a picnic, pick up provisions from Bartlett’s Farm on the way!

Drinks at Club Car

Fun, centrally located spot to grab a drink and/or small plates. Stay late for a lively evening and great people-watching.

Ice cream at the Juice Bar

Most popular ice cream spot on the island that locals swear by!

Shopping in town

Save time (and space in your suitcase) for shopping in town. They have everything from local boutiques and bookshops to designer stores.

• Lunch at Galley Beach: You’ll feel like you are at a European beach club when having lunch at Galley Beach. Reservations recommended.

• Ventuno: The best Italian restaurant on the island and located in a charming, historic building. Before or after dinner, sip on a cocktail at their outdoor patio or the wine bar upstairs.

• Lunch at The Chanticleer: Enjoy lunch in the delightful garden at the Chanticleer in the charming village of ‘Sconset. We did this after our bike ride from town! Be sure to reserve a table outside.

• Dinner at The Company of the Cauldron: If you are okay with a prefix menu, you’ll love the Company of the Cauldron for a romantic dinner! They gave us complimentary Champagne and a fantastic table when we told them it was our anniversary. The queen of beach reads herself, Elin Hilderbrand (IYKYK), dubbed this the most romantic restaurant on Nantucket and in my opinion, she’s not wrong!

• Dinner at CRU: A chic, trendy spot with waterfront views and amazing lobster rolls.

• Lemon Press: A casual but charming spot for breakfast or lunch serving breakfast sandwiches, smoothies, and the like. We had a short wait but we got in quickly.