The Handlebar is one of our favorite coffee shops on the island. It's on a cozy little corner near the water, and the coffee is great.
If you are in the mood for some history, the Whaling Museum is a great spot to check out. It's right in town, too.
This is our favorite restaurant on island. Not only is the food extremely creative and delicious, but the space itself is within an old home right in town, so it's very cozy.
The Nautilus is one of our favorite restaurants on the island. The Asian-inspired menu is delicious, and the cocktails are just as good. Reservations open two weeks in advance and are sometimes difficult to secure. (Pro tip: Arrive early and get a spot at the bar when they open.)
Nantucket Conservations Foundation owns, protects, and maintains thousands of acres of land across Nantucket, all of which can be enjoyed by the public. They have various reservations and trails that are all lovely places to go for a walk, run, or bike ride. This website lists all of the places to explore. (Lily Pond Park is a highlight.)
Brotherhood has been around since 1972, and it's the perfect place to stop for a cup of chowder, a beer, or both in the fall. This is one of Daniel's favorite haunts; you'll know why the second you step inside.
Steps is a wonderful beach right near town. If the weather is decent, we highly recommend heading over here for a sunset or a cold plunge.
If you wish to play a round of golf while here for the weekend, we recommend playing at Miacomet Golf Club. This is a beautiful course that's pretty easy to get a tee time at.
This is one of the oldest golf courses in the country, and another good option if you wish to play nine holes while on island.