The Perfect Summer Weekend Getaway in Nantucket

Depending on where you’re traveling from, you can fly directly to Nantucket from New York or Boston or take the ferry. Pro tip: If your hotel doesn’t provide transportation, hop on the free Wave Shuttle from the airport to town. Ubers, taxis, and rental cars are also available.

Once you arrive, head to your hotel and settle in. From there, you can head to town to grab a light and fresh lunch at Lemon Press (dine-in or grab-and-go). I recommend the matcha and chicken salad—it is the perfect easy lunch after traveling all morning. After lunch, you can either relax at your hotel or wander through town to explore the shops and cobblestone streets.

After a little bit of exploring, head back to your hotel to freshen up for the evening. I recommend heading to The Gazebo for a Mudslide (a Nantucket classic!).

After a drink or two, head over to dinner. On my first night, we went to Or, The Whale. We loved it! I recommend the street corn, lamb wontons, and duck carnitas—perfect for sharing with a small group. Other recommended dinner options: Nautilus, Galley Beach, or Millie’s.

After dinner, you can keep it low-key or head to grab a drink at The Club Car, The Gaslight, or Brotherhood of Thieves for drinks and live music.

It is your first full day in Nantucket! You must start your day with a coffee and pastry at Handlebar Café. If you want a full sit-down breakfast, get on the waitlist at Black Eyed Susan’s.

After breakfast, walk down Main Street, enter some more shops, admire historic homes, and, if you are up for it, visit the Nantucket Whaling Museum.

Alternative option: If you want to be more active, venture out to Sconset for the Bluff Walk and lighthouse views.

Later in the afternoon, spend a few hours at Cisco Brewers—it is a must-do! Drink some local beers (or cocktails), enjoy live music, and try the food trucks. The lobster and scallop rolls from Lobster Trap were 10/10!

This evening, head over to Sister Ship for dinner. It is gorgeous, with great outdoor seating, and is the perfect spot for small or large parties (if you are with a large group, they offer two prix fixe menus). My favorite bites from the prix fixe my group did were the pil-pil shrimp, patatas bravas, Nantucket lettuce, spicy pork ragu, and the chocolate budino. It was amazing and super filling!

After dinner, it is time to head to the best bar on the island, The Chicken Box. I recommend getting there early to avoid the line. Play some pool, but stay for the live band around 11 pm. Shoutout to The Beat Drops—they were amazing! Spend the rest of the night there dancing and singing along.

After a late night out, you need a good breakfast. My favorite place we had breakfast on my trip was Born & Bread: Mercantile and Bakery. The coffee was strong, the cinnamon roll was out of this world, and my friend and I couldn't decide which sandwich to get since they all sounded amazing (seriously, you can't go wrong), so we split the Bianco and the cold tuna. The fresh sourdough bread they use is out of this world!

This afternoon, we planned to spend the day at the beach. We picked up pre-ordered sandwiches from Something Natural and headed to Jetties Beach. This beach was great with a large group since you could also go over to The Sandbar right on the beach to grab more food, snacks, or drinks.

After a nice afternoon at the beach, head back to town and stop at Jack & Charlie’s for some amazing post-beach ice cream.

For your final night, go to Cru for dinner. The atmosphere is lively and upscale. My favorite dishes were the scallops and the lobster roll, and you must get the famous CRUcumber-tini (strong and delicious!). You can spend the rest of the night here at the back bar or head out to another bar.

On your last morning, grab coffee and a sandwich from Fresh Nantucket (the Island Mambo was amazing). If your ferry or flight is later in the day, make the most of it and make one last stop at the beach. You can head back to Jetties, or try a different beach—Madaket, Cisco, or Ladies Beach are all great choices.

When it’s time to leave, take the free Wave Shuttle or an Uber to the airport or ferry terminal.