The island
Town is 2.5 miles. Surfside and Nobadeer are five minutes. The bike path starts at the end of the street.
Day 1
Arrive on the afternoon ferry from Hyannis and settle into the house after the 4 PM arrival. On your way from the ferry, stop at Bartlett's Farm to pick up groceries and island provisions for the week.
After settling in, head into Town for dinner at Cru overlooking the harbor. Finish the evening with a walk through the cobblestone streets before returning home to relax and ease into island time.
Day 2
Start the morning with coffee from Handlebar Café or breakfast at home before hopping on the nearby bike path for a ride toward Surfside Beach.
Pack sandwiches from Provisions or Something Natural and enjoy a relaxed beach afternoon.
Dinner tonight is at American Seasons, one of Nantucket's most beloved restaurants.
Day 3
Begin the day with a bike or drive out to Siasconset to explore the famous Bluff Walk, one of the most scenic walks on the island. Afterwards, stop at Claudette's in the center of 'Sconset for breakfast sandwiches.
Spend time exploring the charming village of Siasconset, browsing shops and rose covered cottages while enjoying the quieter side of the island.
Return to Town in the evening for dinner at The Proprietors Bar & Table, known for its creative seasonal menu.
Day 4
Spend the morning exploring downtown Nantucket, including a visit to the Whaling Museum. If whales are not your thing, there are several hidden gem spots that many visitors to the island often miss.
In the afternoon, head out to Cisco Brewers for live music, local beer, and a fun island atmosphere that's welcoming for families and groups alike.
Dinner tonight is casual and lively at Brotherhood of Thieves, a longtime Nantucket favorite.
Day 5
Rent a Jeep and drive across the sand out to Great Point Lighthouse, one of the most memorable adventures on Nantucket.
Spend the afternoon at beaches like Nobadeer or Forty-First Pole, both accessible by Jeep with a beach driving permit.
Back at the house, fire up the grill for a relaxed cookout using steaks or seafood from Nantucket Meat & Fish Market.
Day 6
Start the morning with breakfast at Island Kitchen, Lemon Press, or Born & Bread. All are delicious.
Spend the afternoon at Jetties Beach, perfect for families and lunch at the Sandbar, or head to Cisco Beach for a more classic Nantucket surf experience.
Dinner tonight is at Ventuno, a longtime Nantucket favorite for Italian cuisine.
If you're up for nightlife later, stop by The Chicken Box or The Gaslight for live music.
Day 7
Spend your final morning exploring some of Nantucket's natural beauty with a walk at Sanford Farm & Ram Pasture, Tupancy Links, or Squam Swamp.
Later in the day, take a harbor sailing tour with Captain Jim aboard the Endeavor.
After dinner, grab ice cream at the Juice Bar or Island Kitchen, then head to Madaket Beach for one of the island's unforgettable sunsets.
If the skies are clear, finish the night stargazing at the Maria Mitchell Observatory.
For the quieter corners, read the Hidden Nantucket guide.
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