We highly recommend making dinner reservations 30 days in advance for the restaurants that accept them as it’s a very busy weekend on island.
Provisions ($)- Casual and quick sandwiches/salads in town
Cru ($$$)- Rated #1 Lobster Roll in Nantucket by Caroline and Mitchener with prime location overlooking the harbor
The Sandbar at Jetties ($$)- Casual beach bar with full raw bar, burgers and more. We love spending an afternoon on Jetties Beach and then posting up here for a late lunch.
Brant Point Grill ($$$)- Waterfront restaurant at the iconic White Elephant Hotel (walking distance from town)
The Tavern ($$) - Casual lunch/dinner spot in town. The Gazebo next door is our favorite drink spot.
Galley Beach ($$$$)- Our favorite restaurant with fine dining right on the beach. It is closed for private events on Friday and Saturday of our weekend, but highly recommend any one on the island longer to make a reservation.
Lola 41 ($$$)- Lively sushi and burger spot in town that takes only same day reservations. Call right at 4PM to try and book a table for that night or recommend visiting in-person to put your name on the list.
Cru ($$$)- See above. Reservations for our weekend will become available in August.
Brant Point Grill ($$$)- See above. Reservations for our weekend are available via Open Table currently.
Ventuno ($$$)- Best Italian food on the island. Reservations are available online one month in advance.
The Nautilus ($$)- Dinner-only spot in town that takes same-day reservations.
The Club Car ($$$)- Housed in a club car from the original Nantucket Railroad, Club Car is a fun spot in town for cocktails and delicious small plates. Bonus- It turns into a piano bar at night!
For more dining recommendations, we love this guide from Veranda Magazine that's updated for the 2021 season.
We HIGHLY recommend renting bikes or a Vespa and exploring the island one morning or afternoon. You can rent from Young’s, Cooks Cycles or Nantucket Bike Shop right in town, and they’ll share various path options. The island has incredible bike paths leading out of town to Surfside Beach and all the way to Sconset, but it’s also fun to rent a Vespa and cruise over the cobblestones more comfortably :)
Our favorite day activity is to head all the way out to the charming village of Sconset (10 mile, fairly easy bike ride). Once there, have lunch at Summer House and make sure to see the Sankaty Lighthouse. The Sconset Bluff Walk (also known as the Cliff Walk) is a breathtaking public walking path that’s an “only on Nantucket” experience.
If you’re looking for a shorter ride, you can head the other direction out of town towards Madaket and stop at Millie’s on the way for lunch.
Enjoy drinks and live music at Cisco Brewers. There is a free shuttle from town every 30 minutes at 23 Federal Street (Nantucket Visitor Center). We recommend going earlier in the day as there tends to be a long line to get into Cisco's in the afternoon, especially on Saturdays.
Steps Beach and Jetties Beach are the closest to town and favorites. Sandbar at Jetties Beach (see above under Lunch spots) is a favorite casual dining spot to grab lunch with your feet in the sand.
Seeing the island by boat is a treat! We recommend booking a sail boat ride on The Endeavor.
Courses open to the public include Miacomet Golf Course (18-hole) or Sconset “Skinner’s” Golf Course (9-hole)