A quintessential New England summer getaway, Nantucket is one of our members’ favorite destinations in the portfolio. And the most centrally located home to the harbor, beaches, and more of Nantucket’s best offerings is Whitesail.

Inspirato member Jenni S. and her family spent an August week there —read on for stellar Nantucket restaurant recommendations and some of the family’s favorite parts of their trip.


“We just spent a week on Nantucket at the Whitesail property. It is Inspirato’s closest single family home to downtown Nantucket (a four-minute walk to Main Street). Having teenage kids, this was amazing—they could easily be independent.

“We rented bikes for the week. We had some trouble with getting them delivered, getting helmets and receiving locks that didn’t work, but the concierge helped us navigate that. We rode our bikes to Cisco Brewers, Cisco Beach, Jetties Beach, and Sconset. One night we bought a picnic dinner from Born & Bread and took the Wave Shuttle ($3/person) to Madaket to watch the sunset.


(Photo courtesy of Jenni S.)

Albacore Charters Nantucket took all the boys fishing one morning and they had the best time. We used a different company in the past and Albacore was by far the better option. The boys caught tons of fish which the captain skinned and de-boned so we could make it for dinner that night.

“Another highlight of the trip was going to Sconset for lunch at The Summer House Inn. We enjoyed the beach and the pool after lobster rolls. Wandering around Sconset to see the darling historic cottages and having ice cream at Sconset Market’s Ice Cream Bar was the perfect end to the day.


(Photo courtesy of Jenni S.)

“Dining highlights included or, The Whale and The Pearl (for an adults-only night because it is pre fixe). Ice cream at the Juice Bar is a must-do. Go after lunch rather than after dinner to avoid the hourlong line. The Handlebar makes amazing coffee drinks and has tasty pastries just steps from the house. We ate at Sea Grille our last night and while it was a healthy walk away from town, it was well worth it—excellent food and even better service.

“We can’t wait to come back to Nantucket!”


Bookings for Whitesail and other Nantucket homes—like our new compound, Harborview—are already pouring in for next summer. If you’re interested in a trip to New England next summer, contact your Care team to begin planning today.

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