This leisurely journey takes you through some of the east coast of the USA’s most charming towns and villages. Enjoy a leisurely cruise in Hyannis, discover the lively artist colony of Provincetown, visit the six independent towns that make up Martha’s Vineyard and stroll around the charming villages in The Hamptons.

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Why We Love It

Visit the white sand beaches and picturesque seaside towns and villages that dot Maine's southern coast.

Enjoy an excursion to Martha's Vineyard to see a variety of landscapes and the historic independent towns.

Explore Cape Cod and its beaches, shopping, golf courses, hiking and biking trails, lighthouses and fine dining.

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Day by day Itinerary

New England Seaside Escape

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Day 1


Arrive in Boston, collect your rental car and make your way to your hotel.

Day 2

Boston - Hyannis - Yarmouth

This morning, depart for Cape Cod. In Hyannis, enjoy a leisurely one hour cruise on Lewis Bay and Hyannis Harbour. Sail past vistas of historical interest, scenic islands and beaches. Travel to the neighbouring village of Yarmouth. Centrally located on Cape Cod, it’s a short drive to all that Cape Cod has to offer.

Day 3

Yarmouth - Provincetown - Yarmouth

Today, visit the Cape Cod National Seashore to explore lighthouses, quaint coastal communities, and natural scenic beauty. Stroll through the charming village of Chatham before visiting the lively artist colony of Provincetown. Here you may wish to enjoy a whale watch, shop in the towns many eclectic art galleries and shops or spend the day relaxing at your hotel’s beach.

Day 4

Yarmouth - Martha’s Vineyard

Board the ferry with your vehicle in Woods Hole for the short ride to Martha’s Vineyard.

Day 5

Martha’s Vineyard

Enjoy an excursion of the Vineyard to see a variety of landscapes in the six independent towns whose separate histories form a composite tale of the island’s past. Visit “downisland”, the busy, fashionable eastern half of the Vineyard where Oak Bluffs, Edgartown, and Vineyard Haven lure the rich and famous and “upisland”, the sparsely populated and sleepy towns to the west.

Day 6

Martha’s Vineyard - Mystic - Old Saybrook

Depart the Vineyard for Connecticut. This afternoon, visit Mystic Seaport and the museum of America and the Sea.

Day 7

Old Saybrook - Riverhead

It’s a short ride to the Orient Point Ferry where you and your vehicle board for the 40 minute trip to the tip of Long Island. Upon arrival head into North Fork to visit wineries and explore the region. Then, travel to Riverhead and check-in to your hotel at the west end of the Hampton’s South Fork.

Day 8

The Hamptons

Today you can stroll around the charming villages filled with boutique shops and art galleries, have a picnic at an outdoor concert, visit the historic mansions, or just relax on the beach.

Day 9

Riverhead - New York

This morning, travel west towards New York where you’ll drop off the car at the end of your journey.

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