Sag Harbor (Hamptons) to Nantucket


Sag Harbor in the Hamptons offers an easy departure on the ultimate summer getaway for city folks needing a sea air breather.  This suggested itinerary offers enchanted harbor-hopping along the New York, Connecticut, Rhode Island and Massachusetts coastline. Tailor it to suit your interests.

Suggested itinerary, from the Hamptons to Nantucket

Sag Harbor Hamptons to Nantucket luxury yacht charter map

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This one is based on 7nights/8days.  To get the most of your yacht vacation, we recommend 10-14 days, unless you plan to board your yacht in Newport.  This itinerary is a gem.

  1. Fishers Island historic beginnings were home to America’s wealthiest families (before we collected taxes).  It still has  private estates but the small village offers scenic routes for hiking, biking and exploring beaches.
  2. Mystic Seaport has claimed the largest Maritime Museum in the world.  You can walk through history of the greatest sailing ships, Captains, sea shanty music offered during the summer months.
  3. Stonington is home to a vital Historical Society, antique shopping at its finest, and a variety of restaurants.
  4. Block Island offers biking, birding and Captain Kidd buried treasures (according to Block Island history).  The best arrival dock is Great Salt Pond  to avoid the Ferry Dock chaos of day trippers.
  5. Nantucket is the St. Barth’s of New England where you can see and be seen.  The Nantucket Boat Basin requires reservations in advance, so be sure to let your Captain know ahead of time your itinerary plans.  If you choose to end your charter here, you can fly home from Nantucket Memorial Airport (ACK).
  6. Martha’s Vineyard encompasses sophisticated Edgartown (where Jaws was filmed), Chappy, Oak Bluffs with its charming Gingerbread houses, Vineyard Haven (a “dry” town) with great shops including The Simon Art Gallery where Peter Simons continues to teach photography, Menemsha fishing village, and Gay Head, home to the Wampanoag Indian tribe.  Have your Captain arrange a lobster bake on the island (we know where it can happen).  
  7. The Elizabeth Islands include day stops for swimming and walking.  The lazy days of summer here will propel your childhood memories.  Special stops we recommend include Tarpaulin Cove and Cuttyhunk.  The “Story of Cuttyhunk”, written by Louise Haskell, is mentioned in the Brief History of Naushon reviewed by Alice Forbes Howland.  The only way to get there is by boat!

As you might imagine, taking your time cruising this route offers benefits for every age.  You will step back into time while relaxing, reading, eating, drinking and experiencing the cruising lifestyle.

Cruising is better than a beach or a hotel, because you are moving effortlessly.

Book it!  Be sure to tell your ideas to our complimentary planning service today.

Newport Castle Hill