Nantucket is a perennial favorite among Indagare travelers, and it’s easy to see why. Off the southern coast of Cape Cod, this 14-mile-long island has preserved a sense of place that few American destinations can match—cobblestone streets are lined with gray-shingled houses, wild rose hedges spill over white picket fences and the harbor still looks much as it did in its whaling heyday. The appeal is equal parts nostalgia and polish: days unfold at the beach with a lobster roll in hand, strolling through historic hamlets or biking the flat, sun-drenched paths between town and the eastern bluffs.
What keeps travelers coming back is the island’s effortless mix of relaxation and sophistication. The dining scene ranges from unfussy sandwich shops and raw bars on the wharf to candlelit harborside restaurants with serious wine lists and seasonal New England menus. The shopping is compelling, too: independent boutiques and design-driven stores that reward an afternoon of browsing. And the hotels, from historic inns to waterfront properties, tend toward intimate and well-appointed rather than large-scale. It adds up to a destination with real character, and a quietly chic atmosphere that never tries too hard. Here is Indagare’s guide to the essentials.
Sleep
The classic White Elephant offers waterfront resort amenities paired with an in-town setting. The hotel is fresh off a recent renovation.
Experience
Don’t miss an easy, laid-back day at one of Nantucket’s best beaches. Unlike nearby Martha’s Vineyard, the most beautiful beaches here are public, not private.
Splurge
A Nantucket boat charter opens up the island’s full coastline—including beaches and sandbars only reachable by boat. Sunset from the water is sublime.
Eat
Nantucket’s top tables range from sandwiches and lobster rolls (Slip 14 is a favorite) to elegant New England cuisine at Cru.
Drink
Enjoy a sundowner with a view at The Wauwinet, either on the terrace at its restaurant Topper’s or out on its fabulous waterfront lawn.
Savor
See the island at a slower pace by exploring via bike. Many hotels offer complimentary bikes, and a number of independent shops offer affordable rentals by the hour, half- or full-day.
Visit
Nantucket Whaling Museum gives a deep dive on the island’s fascinating history and how the whaling industry made—and later destroyed—its economy.
See
Siasconset is a hamlet on the southeastern corner of Nantucket. It’s famed for its charming gray-shingled cottages, wandering rose-covered fences and red-and-white Sankaty Lighthouse.
Shop...
Coastal-chic fashion boutiques in Nantucket town include ASHA, Nantucket Looms and Salt.
Indagare’s Guide to Nantucket
Explore Indagare’s complete guide to Nantucket, including recommendations for where to stay and what to see and do.
Published onJuly 29, 2026
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We only feature hotels that we can vouch for first-hand. At many of them, Indagare members receive special amenities.
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