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The Sun, The Wind, The Islands: Sailing to Nantucket

(trip #21)

5 days in Nantucket, MA ($$$$) — A 5 day, 4 night sailing trip to Nantucket on board a chartered catamaran. Explore the island by land and sea. Discover quiet anchorages, historic spots, and gorgeous beaches. Learn the basics of sailing and enjoy island bounty at highly acclaimed restaurants. A half-day deep sea fishing adventure is included. An excellent opportunity to reconnect with a small group of friends. This trip is designed for a group of 6. Catamarans work best for couples, most have double beds. The sail boats listed as options below have mostly twins plus bunk beds so they might be better for buddies. Discuss food and drinks with the captain, a couple of days include Breakfast on board. Best time to visit is end of June-early July when water is warm enough to swim and the summer crowds are not yet in. Early September is also great.

How to use

Day 1

Day 1 9:00AM  Set Sail to Nantucket
at In the Wild

Set sail for a great cruise to Nantucket on your own charted Catamaran or Sail Boat. This trip is ideally suited for 6 people maximum.

Day 1 8:00PM  Dinner at the Ropewalk.
at The Ropewalk

Once the boat is docked, enjoy a great dinner at this popular boaters hang out. Opens April 18 for 2007 season. Located on the waterfront, serving pr... more »

Day 2

Day 2 8:00AM  Breakfast Starter on the Boat
at On Board

Start the day off with a little breakfast on your boat.

Day 2 10:00AM  Jeep Tour of Nantucket
at Arastours

Driving tour includes all well known stops on the island with plenty of time to explore. Bring your camera.

Day 2 1:00PM  Museum
at The Whaling Museum & Historic Sights

Museum has been recently redone and houses the skeleton of a male sperm whale.

Day 2 8:00PM  Dinner at Oran Mor
at Oran Mor

Chef owned and a favorite of the locals.. Dress is smart casual (please-no shorts).

Day 3

Day 3 6:00AM  Breakfast at the Even Keel Cafe
at Even Keel Cafe

A favorite spot for Breakfast which opens at 7am. Large terrace in the back. To go is also available so pack some goodies for lunch on the boat.

Day 3 10:00AM  Sailing Around Nantucket

Explore secluded coves. Anchor the boat and take a private group swim. Interested in taking the Helm? Your captain will explain the basics of saili...

Day 3 8:00PM  Dinner at the Sea Grille
at Sea Grille

Seafood restaurant with famous chowder. Dress is smart casual.

Day 4

Day 4 8:00AM  Breakfast on-board, Day 4
at On Board
Day 4 10:00AM  Biking
at Young's Bicycle Shop

Explore the island by bike. Head west on the Madaket path (green arrows), then follow Eel Point Rd to Dionis Beach and stop for a swim to cool off (ab... more »

Day 4 8:00PM  Dinner at Toppers
at Toppers at the Wauwinet Inn

Cruise on the open-top boat shuttle (Wauwinet Lady) to the Inn and back. Transportation is included with dinner reservations, but your group must re... more »

Day 5

Day 5 9:00AM  Set Sail for Home
at In the Wild

Sail home.

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