Nantucket creeps into your soul and finds a home. Many aspects of the island are bound to capture your imagination and your heart. Let us help you find those points of connection — your brand of Nantucket lifestyle.
To help you on your way, we’re sharing some of our own favorite restaurants and lesser-known Nantucket Underground hints. But your vacation is your special time away. Let us know what inspires and interests you, what you've never seen before, or what you'd like to try again. We know this island inside and out and can help you craft a getaway to remember.
We also invite you to visit Nantucket magazine’s website, published by the hotel’s owner.
For exclusive travel to the island, check out Linear Air or Cape Air for unique air shuttle options.
Insider Activities Restaurants
The 76 Main insider scoop on lesser known Nantucket activities and attractions (those marked with an asterisk are best enjoyed from spring through early fall):
1. Sip the Sparkly*. Settle in at Topper’s Deck on a crystal clear late morning and work your way through the Bubble Brunch Menu. Enjoy stunning views of Nantucket Bay as you discover so many delightful ways to sip sparkling wine. Our favorite? It’s a tie between the Venice Spritz and the Mon Cherie. Trust us—cab it back to Main Street.
2. Walk the Wild Isle. Step deeply into Nantucket’s wilderness and tune into the island’s wiles of wanderlust with both feet. Delight in the primal necessity of being outdoors with these four “back woods” walks around “the rock.” Ask your concierge for directions and make sure you take along your camera:
- Squam Farm: 1.5 mile loop with option to extend
- Sanford Farm Pasture: 1.5-6 mile walk
- Sconset Bluff: 5 mile loop
3. Journey to the Edge. Rent a jeep and drive to Great Point. Of course, the rental car company will tell you not to… but since when do you listen to authority!? The sunrise is especially glorious.
4. Grab a Paddle*. Join the Nantucket Community Sailing’s outrigger club for an evening trip around the harbor. Test your endurance and rhythm with this experienced group of paddlers. Read more about the club and these timeless watercrafts.
5. Visit a Beloved Institution*. While the Whaling Museum certainly deserves its due, nothing is more emotionally rousing (and oh so very Nantucket) than the Shipwreck Museum. Exhibits chronicle the heroism of stalwart islanders who routinely braved all odds to rescue shipwrecked sailors. Memorable and moving.
6. Start Your Day Stretching*. Rise and shine for Yoga on the Beach, held every day but Sunday at 7 a.m. on Children’s Beach in season. The island is also home to several great yoga studios if you prefer to find your namaste indoors.
7. Rock at The Box. Get your groove on at The Chicken Box, hands down the best venue for live music on the island. Act like a real insider and only refer to it as “The Box” and don’t bother going before 10:00 pm. That’s when the real fun starts.
8. Explore Madaket*. Board the bus to Madaket for the afternoon. Browse the ‘giveaways’ at the little house at the Madaket Dump (or the Madaket Mall, as locals call it) for some of the finest castoffs in the world, and grab an ice cream cone at Millie's. See the real neighborhood of Mr. Rodgers at his summer cottage “The Crooked House.” End the evening watching the sunset. Madaket offers the only “all over the ocean” sunset this side of Santa Monica.
9. Picnic at the Point. Snag a bag of mussels to go (steamers or little necks from Sayle’s Seafood) and mosey over to the beach beside Brant Point Lighthouse. Nosh as you watch the ferries glide into the harbor.
10. Find Your Sun*. Whether you are searching for a pick-up volleyball game or a quiet place to loll in the rays, Nantucket offers a beach for every mood and inclination. Click here for a great Nantucket beach summary.
11. Take a 2-wheel Tour. Rent a bike from Nantucket Bike Shop and point your pedals in the direction of Cisco Brewery and Bartlett's Farm for beautiful views and tasty brews.
12. Watersports Adventure*. Learn how to fly with a kiteboarding lesson, take your first ever ride on a wakeboard, or watch your kids grin ear-to-ear as they go tubing behind a boat. Experience the remote corners of Nantucket few get to see while you get in your morning workout and learn how to paddle board. Check out Next Level Watersports for more info on all these outdoor water pursuits and more.