The 76 Main insider scoop on lesser known Nantucket activities and attractions:

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:

  • Coskata Pond. Coskata-Coatue Wildlife Refuge. Moderate to Strenuous. 3.2 miles
  • Head of the Plains. Madaket. Moderate. 2.3 miles
  • Squam Swamp. Squam. Easy 1 mile.
  • Serengeti. West of ‘Sconset village. Moderate. 2 miles

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 view of the island from this angle is 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. 

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. 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 “to go” mussels, 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. Sip a Martini. Of course, you can do this anywhere, but why not with a winter wheat vodka that was “Born in Nantucket and raised in the Rocky Mountains?” Dune restaurant delivers decadent cocktails made with Lucky Dog Vodka, the brainchild of Nantucket local Greg Nichols. The incredibly smooth, crisp spirit is distilled with Rocky Mountain meltwater from the Snake River aquifer in Idaho. Plus, it won the Gold Medal at the 2011 New York Wine & Spirits Competition. Not too shabby! Read more about Lucky Dog Vodka and its maker, local, Greg Nichols.

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