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🌿 RelaxedLong weekend · from Boston, MA

Nantucket: Cobblestones, Cisco Brewers & Moors

Nantucket, 30 miles offshore in the Atlantic, is the most complete surviving 19th-century whaling port in the world — 800 pre-Civil War buildings on a 14-by-3.5-mile island with no traffic lights and no chain stores. The grey-shingled character of the town and the moors in the island's interior have been maintained by the Nantucket Historic District Commission since 1955.

Day 1 — Nantucket, MADay 2 — Cisco Brewers & 'Sconset Village, MADay 3 — Nantucket — Departure Day & Hyannis
Day 1Nantucket, MA

Day 1Nantucket, MA

🚗 1 hr 30 min driving📍 6 stops
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Morning
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Drive
Boston, MAHyannis Ferry Terminal
1 hr 30 min8:00 AM9:30 AM
Nantucket Ferry — Steamship Authority
Nantucket Ferry — Steamship Authority
4.3
The Steamship Authority's high-speed ferry from Hyannis takes 1 hour to Nantucket; the traditional ferry takes 2 hours and 15 minutes. The high-speed ferry is the standard choice for day visitors; the slow ferry is preferred by those bringing bicycles. The approach to Nantucket through the harbor entrance, with the town's grey-shingled waterfront visible above the Great Point marshes, is one of the best maritime arrivals in the US.
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Lunch
Nantucket Historic District — Straight Wharf
Nantucket Historic District — Straight Wharf
The cobblestone waterfront district runs from Straight Wharf to Old South Wharf — a compact area of original 18th and 19th-century commercial buildings housing restaurants, galleries, and the Nantucket Whaling Museum. The museum occupies the 1847 candle factory, with a 46-foot sperm whale skeleton suspended from the roof and the actual tryworks that rendered whale oil in a 19th-century Pacific voyage.
The Proprietors Bar & Table
The Proprietors Bar & Table
4.4
A Nantucket restaurant on India Street, serving New American cuisine with serious wine and cocktail programs in a room that attracts the island's year-round residents as much as the summer visitors. The oyster selection rotates between Nantucket Harbor farms and the off-island suppliers; the charcuterie is made in-house.
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Afternoon
Nantucket Moors & Sanford Farm
Nantucket Moors & Sanford Farm
The 767-acre Sanford Farm conservation property preserves the open moorland that covers the island's interior — a landscape of heath, kettle ponds, and blueberry barrens that the Wampanoag named 'Nantucket' ('the faraway land') for its visual character. The 6-mile Sanford Farm trail system reaches Ram Pasture on the south shore; the ocean view from the Ram Pasture bluff faces the open Atlantic with no land between Nantucket and Spain.
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Evening
🍽️ Dinner5:00 PM
The Galley on Cliffside Beach
The Galley on Cliffside Beach
A seasonal restaurant on Cliffside Beach, operating from a converted fishing shack since 1956, with umbrella tables on the beach and a menu of lobster, raw bar, and grilled fish served within arm's reach of the surf. The lobster bisque and the grilled swordfish with tomato and basil are the summer anchors.
4.2Seafood restaurant📍 Maps →
4 options · tap to switch
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White Elephant or Vanessa Noel Hotel
The White Elephant on Easton Street is a classic Nantucket resort with harbor views and a full spa — the most established luxury option on the island. The Vanessa Noel Hotel on Federal Street is the smallest and most design-forward option, with 8 rooms and a fashion boutique at street level.
Day 2Cisco Brewers & 'Sconset Village, MA

Day 2Cisco Brewers & 'Sconset Village, MA

🚗 20 min driving📍 6 stops
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Morning
Cisco Brewers, Nantucket Vineyard & Triple Eight Distillery
Cisco Brewers, Nantucket Vineyard & Triple Eight Distillery
4.4
A campus of three craft producers in the Cisco area of Nantucket's agricultural interior: Cisco Brewers (producing ales and wheat beers since 1995), Nantucket Vineyard (estate wines from 12 acres of Marquette and Cayuga grapes), and Triple Eight Distillery (vodka, rum, and whiskey using Nantucket grain and water). The outdoor beer garden operates year-round; the combined campus is the most visited non-beach destination on the island.
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Lunch
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Drive
Cisco, Nantucket'Sconset Village
20 min9:00 AM9:20 AM
Siasconset Village
Siasconset Village
The eastern end of Nantucket — called 'Sconset by locals — is a colony of rose-covered fishing shacks that evolved into summer cottages in the 18th century and have been designated a historic district since 1972. The Sankaty Head Lighthouse (1849) at the bluff's edge is the most powerful light on the New England coast; the 'Sconset Bluff Walk follows the erosion edge above the Atlantic for half a mile.
Claudette's Sandwich Shop
Claudette's Sandwich Shop
4.5
A 'Sconset institution since 1974, operating from the original Siasconset Market building, with a menu of made-to-order sandwiches and house-made soups. The lobster salad sandwich — on house-baked bread, with Nantucket butter lettuce — is the island's best sandwich outside the Straight Wharf lobster roll.
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Afternoon
Great Point — Coskata-Coatue Wildlife Refuge
Great Point — Coskata-Coatue Wildlife Refuge
4.9
A 16-mile round-trip accessible only by four-wheel-drive or a 4-mile walk from Wauwinet — the barrier spit at Nantucket's northern tip, with the 1818 Great Point Lighthouse at the tip. The refuge encompasses one of the most significant seabird nesting areas in the Northeast; the rip at Great Point's tip is one of the most productive striped bass fishing spots on the East Coast. Access requires a 4WD vehicle with a beach driving permit (available from the Trustees of Reservations) or a guided tour — Great Point is not reachable on foot without an 8-mile round-trip beach walk.
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Evening
🍽️ Dinner5:00 PM
Topper's at The Wauwinet
Topper's at The Wauwinet
The Wauwinet inn's restaurant on the remote north shore of Nantucket — 9 miles from town by road — serving the island's most formal and most accomplished cuisine. The dining room faces Nantucket Harbor and the inner harbor estuary; the tasting menu draws from Nantucket waters and the island's small farm community.
4.3American restaurant📍 Maps →
4 options · tap to switch
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White Elephant or Vanessa Noel Hotel
Second night on Nantucket, allowing a slow morning at the Saturday farmers market before the return ferry to Hyannis.
Day 3Nantucket — Departure Day & Hyannis

Day 3Nantucket — Departure Day & Hyannis

🚗 3 hr driving📍 2 stops
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Morning
Nantucket Farmers & Artisans Market
Nantucket Farmers & Artisans Market
A Saturday and Sunday outdoor market on the Nantucket Wharf, running from mid-June through mid-October, with 50 vendors selling Nantucket-grown produce, handmade crafts, baked goods, and prepared foods. The Saturday market is the larger; the Sunday is quieter and more local in character.
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Lunch
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Drive
Nantucket, MAHyannis, MA
1 hr 30 min9:00 AM10:30 AM
Return ferry from Nantucket to Hyannis.
Embargo Bar & Grille — Hyannis
Embargo Bar & Grille — Hyannis
4.3
A waterfront restaurant on the Hyannis Inner Harbor, serving Cape Cod seafood in an open-air setting above the ferry dock. The chowder is made from the morning's catch; the lobster roll is the full-belly Cape Cod style — a split-top bun with warm butter-dressed claw and knuckle meat.
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Afternoon
🚗
Drive
Hyannis, MABoston, MA
1 hr 30 min12:00 PM1:30 PM
Return via US-6 west and I-93 north through Brockton and into Boston.
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