Kerry Hucul

Newport Yacht Charter Itinerary New England

Newport Yacht Charter Itinerary offers 400 years of history, hundreds of islands, miles of pristine beaches, and postcard-perfect harbors! A perfect place to “get-away” from it all in the summer.

Watch the trawlers go out to sea

In a 7-day yachting itinerary, you can only capture the spirit of New England; the saltiness of the ocean air, the seabirds at cocktail hour, the clambakes and fresh lobster, wailing gulls and whaling museums.

This Newport Yacht Charter Itinerary leaves from Newport, Rhode Island the bustling seaport town. Historical wonders and modern daily life are seen in the same breath. Yachting enthusiasts will revel in the beautiful sailing yachts that you can see here.

Enjoy watching yacht races, deserted beaches, trails for hiking and biking, with a charming downtown area to poke around in.

Some of the mansions you can visit include The BreakersThe ElmsMarble House and Rosecliff.

Plan a day or two before or after your yacht charter to enjoy Newport. You will not run out of things to do or see!

Mansions of Newport
Yacht Charter Itinerary

Day 1: Newport to Sag Harbor

Sag Harbor, New York, is a protected hamlet with a dramatic maritime history. This Long Island superyacht hide-away, positioned on the north coast, is unique.

Due to preservation efforts, centuries-old buildings showing you the lifestyle of early settlers, whaling captains, and wealthy industrialists remain charmingly intact.

Main Street is the quintessential New England Main Street, where period buildings house fine boutiques, galleries, and restaurants.

Dock at the Sag Harbor Yacht Club and you’re steps from Sag Harbor Village shopping, dining, and the Bay Street Theater. Pull in among head-turning superyachts and sailing yachts.

Sailing and History enthusiasts can visit the Whaling and Historical Museum.

Cuttyhunk Harbor Newport Yacht Charter Itinerary

Day 2: Sag Harbor to Block Island 

This windswept island is like no other destination on your Newport Yacht Charter Itinerary. Block Island is located south of Mainland Rhode Island.

Summertime ocean enthusiasts swarm Block Island in great numbers for the yacht races and fishing tournaments! But large areas of protected land are empty of crowds.

Crisscrossed by trails, the parks and preserves are excellent for hiking and bird spotting.

You can drop your anchor off remote beaches, picnic at lighthouse beaches, let kids wade in the gentle surf of protected beaches, or try your hand surfing.

The Great Salt Pond and Old Harbor, just a mile apart, have shops and galleries to explore, pubs to crawl, and restaurants to enjoy New England seafood.

The Island North Lighthouse was built in 1867 and well worth a wander around.

North Lighthouse Block Island
Newport Yacht Charter Itinerary, North Lighthouse on Block Island

Day 3: Block Island to Cuttyhunk MA 

Cuttyhunk is the perfect place to do a whole bunch of nothing at all. Just a mile and a half long and less than a mile wide. Enjoy the wildlife, including deer and rabbits. Explore by hiking or biking the trails and small, winding dirt roads.

The area is a sportfishing mecca, with plenty of striped basses to fish between May and October. Your yacht charter crew happily catch and serve fresh fish whenever possible.

Located between Buzzards Bay to the north and Vineyard Sound to the south, this area has been famous for fishing since the mid-1800s.

Visitors cannot bring cars onto the island, and only a few of the permanent residents drive. This makes the island particularly enjoyable to explore.

  1. Go ashore to relax, enjoy nature, and serenity. Maybe your crew can prepare a delicious beach barbecue in the evening.
  2. Climb up Lookout Hill at 154′ above sea level and have a picnic. The Coast Guard had placed six defensive bunkers in the second world war years there.
  3. Build a bonfire and dance around the flames.
  4. Have sunset cocktails in the sand.
  5. Watch a billion stars appear in the night sky.
  6. Enjoy a traditional Clam Bake
Traditional clam and lobster bake on the beach
Traditional clam and lobster bake on the beach

Day 4: Cuttyhunk to Nantucket

Nantucket is beloved by all! Despite its popularity, it offers privacy, anonymity, great boating and fishing, rolling dunes, and beautiful beaches.

The wharves and cobblestoned streets of the Town of Nantucket are lined with restaurants, high-end boutiques, and steepled churches. The town’s Whaling Museum recounts the island’s role as a 19th-century whaling hub.

Herman Melville wrote dramatic tales of Nantucket’s whaling heritage in “Moby Dick.” Don’t forget to visit the Whaling Museum on Broad Street.

Take a stroll through Nantucket’s Art Galleries located near the harbor. Collectors will find classic landscape and coastal subjects as well as contemporary works by local and regional artists.

Surfside is a favorite beach for swimming and surfing.

Head toward the Nantucket Wildlife Refuge, a narrow peninsula on the island’s northernmost tip. The Atlantic side has high surfing waves while the bayside is calm enough for waterskiing and shell collecting.

Visit Award-winning Topper’s Restaurant at the Wauwinet Hotel for an exceptional dining experience in a historical setting. Your yacht charter crew can tender you directly up to their private dock!

Check out Chef Kyle’s Recipe and wine blogs here.

Wauwinet Hotel on Block Island
Wauwinet Hotel on Block Island

DAY 5-6: Nantucket to Martha’s Vineyard

Marthas’ Vineyard is located just south of Cape Cod. It is only available by boat or air.

Martha’s Vineyard is a 96-square-mile island that is an exclusive summertime playground with amenities befitting the wealthy and ultra-rich.

For others, it is a low-key island of bicycles and beaches, hiking trails and rolling hills, fishing villages, and stonewall fenced farms.

Don’t forget to visit the historic towns on the Island’s east end, which include Vineyard Haven, Oak Bluffs, and Edgartown.

Vineyard Haven 

The island’s main port is on a picturesque harbor bedecked with tall ships and private yachts.

Stroll the length of Main Street for collectibles, dining, and historic sites.

New England Yacht Charters Lighthouse

Oak Bluffs 

Oak Bluffs is a typical boardwalk town. There are food and souvenir stores, and the town is well known for its quaint gingerbread cottages.

Look for a thriving artist colony at Oak Bluffs.

Edgartown 

The preferred locale for high-profile vacationers. The historic town is beautiful, peaceful, and luxurious.

Admire the Greek revival homes of ship captains. Visit museums. Dine and shop at upscale businesses housed in historic buildings.

Edgartown is known for its rich whaling tradition and Chappaquiddick Island is considered part of Edgartown.

Beach Dunes on Nantucket

Day 7: Martha’s Vineyard to Newport RI

Relax on deck, keeping your camera close at hand. The New England shore transitions from romantic landscapes to quaint fishing harbors and dramatic cliffs.

Anchor off the beach at Quicks Hole on Nashawena Island for a picnic lunch and a swim. Savor the beauty of Narragansett Bay one last time before arriving back in Newport.

From a casual sailing charter to a luxury yacht charter, New England this summer, the islands of Nantucket are waiting for you to explore.


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Book my Newport Yacht Charter Itinerary New England

Call Stephanie, your New England luxury charter yacht broker

+1 954 271 3005 (US)
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Check out some of our yachts that will be plying the waters of New England this summer, and let’s get out and enjoy the beauty that is close to home.


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