Nantucket is to New England what the Hamptons are to New York; an elite, elegant and chic escape from the city. But with nary a traffic light in sight, Nantucket entrances visitors with its old whaling town charm, and surprisingly low-key glamour.

  • Perfect for
    Families | Foodies | Romantics | Style Mavens
  • When to go
    June-August | September-November
  • Ideal length of stay
    3-5 Nights

Designing Your Journey

Work with Indagare to design the perfect itinerary for an immersive journey. Our travel experts know the destination inside and out, and they can make recommendations based on your travel needs and preferences.

  • 3 Days: Essential Nantucket-LP

    3 Days: Essential Nantucket

    Indagare can craft a customized itinerary on Nantucket with private boat charters, clambake beach dinners, surfing lessons, fishing excursions and guided touring of the island’s historic sites.

    • Day 1: Time in Town

      Spend the day leisurely at your hotel or ambling around the quaint town and harbor. Don’t miss the Whaling Museum for insight into the island’s rich history. Come sunset, head to the wharf for oysters and cocktails and after dinner, stop by the island’s favorite ice cream shop, known for its fragrant homemade waffle cones, before strolling back to your hotel.

    • Day 2: Boutiques and Beach Time

      Wake up early to put your name on the list at a classic establishment that serves the island’s best breakfast. Later, shop around town at longtime favorite boutiques as well as chic newcomers. In the afternoon, bring picnic supplies to one of the island’s many beautiful beaches and afterwards stop off at a popular brewery for drinks, oysters and live music.

    • Day 3: Siasconset

      After breakfast at your hotel, bike to Brant Point for beautiful views of the harbor. For a longer ride, head toward the quaint village of Siasconset. Here, enjoy lunch before exploring the town and its charming rose-covered cottages. Later, head out to Jetties Beach for a cocktail or dinner at the beach as the sun sets.

Where To Stay

We only feature hotels that we can vouch for first-hand. At many of them, Indagare members receive special amenities, including upgrades, early check-in, breakfast, spa credits and more. Look for the Indagare Plus logo in the reviews.

Ready to go and in need of expert trip planning? Contact us today.
Indagare Insider Jill Kargman
“The Whaling Museum on Nantucket is incredible; the architecture and collection are world-class. You can’t believe this treasure is on a tiny island!” Read the postcard.

What To Read

Everything we recommend is sourced first-hand by our well-traveled team and incredible network of insiders and resources around the world. Here are some the latest articles, interviews, and book and film recommendations not to be missed.

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