Gail’s Tours, Nantucket Island
The Sankaty Head coastline from the air — the red-banded lighthouse above the bluff, the moors and the Atlantic.

Nantucket, Massachusetts

YourguidetotherealNantucket.

A 1¾-hour narrated drive around the island with a sixth-generation islander.

Departures

10:00Morning
1:00Midday
3:00Afternoon
Daily, year round About 1¾ hours Pick-up at 25 Federal Street Up to fourteen guests

The Tour

One narrated loop of the island.

About 1¾ hours from pick-up to drop-off — town, moors, coast and back again — in a new Mercedes Sprinter van, narrated the whole way by Gail, a sixth-generation islander.

A sixth-generation narrator

Gail was born and raised on the island, and her family goes back six generations here. The stories are hers.

A new Mercedes Sprinter

Fourteen seats, tall windows and a quiet ride — small enough for questions and conversation. Pick-up at 25 Federal Street, so no need for a car.

Stops for photographs

The van pulls over at the best views, so you leave with photographs.

The Oldest House, a weathered shingled saltbox on a lawn under a blue sky.
The Oldest House, Sunset Hill.

Along the way

Six of the highlights.

  1. IThe Oldest HouseThe Jethro Coffin House on Sunset Hill, built in 1686 — the oldest house on the island still standing where it was raised.
  2. IIBrant Point LightThe little lighthouse at the mouth of the harbour, on a station first lit in 1746 — the second-oldest in the country.
  3. IIIThe Old MillBuilt in 1746 and still grinding corn on a windy day — the oldest working windmill in America.
  4. IVUpper Main StreetThe whaling captains’ mansions and the Three Bricks, from the years when Nantucket lit the world.
  5. V’SconsetThe historic fishing village at the east end — seventeenth-century fishermen’s shacks grown into rose-covered cottages.
  6. VISankaty Head LighthouseThe red-banded tower of 1850 above the bluffs, moved back from the eroding edge in 2007.

With the moors and the cranberry bogs on the road between. Weather, season and the day’s traffic permitting.

What guests say

★★★★★

“Gail gave us a phenomenal insider’s tour of Nantucket. As a multigenerational Nantucketer she was extremely knowledgeable of its history and resources.”

John Selby · Google, April 2023

★★★★★

“Gail is a wealth of knowledge about Nantucket as she was born and raised there. We saw so many historical sites and interesting tidbits.”

Irene McGinnis · Google, June 2024

★★★★★

“Very knowledgeable, a Nantucket native, witty and funny. She picked us up at our hotel and the tour was very fun.”

Kathy Webb · Google, May 2025

The island

Fourteen seats, three departures

See the island withsomeone who grew up on it.

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