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New England Coastal Road Trip

Boston, Cape Cod, Martha's Vineyard & Rhode Island, USA

Best time to travel
Jun - Oct
Ideal length
10 nights
Perfect for
From (incl flights)
€2,649 pp

At a glance

  • International return flights from Dublin to Boston.
  • 10 days' pre-arranged car rental in a Hyundai Elantra, or similar as well as all private vehicle transfers and shared ferry transfers.
  • 10 nights’ luxury accommodation in Boston, Cape Cod, Martha’s Vineyard and Newport, Rhode Island.
  • Private guided city tour of Boston and an adventurous sailing experience in Newport.
  • Explore Martha’s Vineyard with a private guided tour of the filming locations of Jaws and a private kayaking adventure.
Let's plan your trip!


Off the coast of New England, whales dominate the wild waters of the Atlantic and create a sensational setting for us to witness them in all their glory. Venturing along the coastline, the famous sandy shores of Cape Cod and Martha’s Vineyard are bathed in unique beauty. Quaint colonial towns and charming seaside villages are home to folks as friendly as they come. On this suggested itinerary, enjoy a road trip down this charming coastline and celebrate its many highlights. Begin in Massachusetts’ historic Boston, before making your way along the Cape to appreciate its marine wildlife. Ferry out to Martha’s Vineyard to step into the set of iconic Jaws before you end your adventure in Rhode Island, where another nautical adventure awaits.

View all of our luxury holidays to the USA.

Trip Overview

Depart from Dublin to Boston.

Upon arrival, privately transfer to your luxury hotel in the heart of the city. Spend two nights here, exploring historic landmarks and sampling the tantalising array of cuisine the city has to offer.

Discover the beloved and the overlooked of Boston.

On a privately guided tour of the city, stop by the iconic landmarks of the Freedom Trail and learn about their part in Boston’s history. Your expert private guide will also take you to some off the beaten path locations where you can appreciate the stunning architecture.

North End, Boston
Pick up your rental car and drive to the coastal town of Falmouth.

Spend three nights in this charming town along Cape Cod, one of the world’s best whale watching destinations. Spot these magnificent mammals for yourself as you set out on a privately guided whale watching tour. If you’re lucky, you may spot a breaching humpback whale.

humpback whale, cape cod
Ride the ferry to Martha’s Vineyard.

Spend three nights on this Cape Cod island, famously the setting of celebrated thriller film, Jaws. Privately tour the filming locations and beaches of the island. Revisit your favourite scenes from the movie and learn insider stories from its production.

Martha's Vineyard
Float atop blue waters under the setting sun.

On a privately guided kayaking adventure, explore the waters of Martha’s Vineyard. Admire the wildlife and beauty of the coastline as you glide along the water. Watch the dancing colours of the sunset as you land for a beach picnic.

Kayaking Martha's Vineyard
Head to Rhode Island.

Spend two nights in the city of Newport. Enjoy an unforgettable nautical adventure as you board an authentic America’s Cup yacht. Sail past Newport’s main attractions including the Pell Bridge, Rose Island Lighthouse and Fort Adams. Try your hand at sailing alongside the expert crew.

Newport, Rhode Island
Drive to the airport for your flight home.

Drop off your rental car and board your flight home. Arrive in Dublin.

Tailoring your holiday

OROKO Itineraries are created with you in mind and no two are the same. These can be used to help plan your trip - or we can design a completely different itinerary to suit you.

Let's plan your trip!

Where to rest your head

Looking for the best accommodation? We've got the contacts

Fairmont Copley Plaza

Fairmont Copley Plaza

Overlooking Copley Square, this refined historic hotel is ideally located near many historic landmarks such as the Boston Public Library and shopping spots such as Newbury Street.

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Inn on the Square

Inn on the Square

Tucked inside a picturesque colonial-style mansion and bursting with quintessential Cape Cod charm, Inn on the Square is a traditional hotel situated in the heart of Falmouth.

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kelley house

Kelley House

First opened in 1792, the Kelley House is one of the most iconic historic hotels of Martha’s Vineyard. The hotel offers traditional, homey rooms and suites spread across four federal-style buildings.

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Newport Beach Hotel & Suites

Newport Beach Hotel & Suites

Featuring stunning panoramic views overlooking the Atlantic, the Newport Beach Hotel & Suites is a luxurious oceanfront property that combines Newport’s historic charm with contemporary sophistication.

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What people are saying

Dara at OROKO booked the most fantastic trip for my daughter and I to Athens. It was our first time in Greece. Between Acropolis, museum, and gallery visits, to quiet times at a beachside boutique hotel, it was the most perfect Easter break for us both. Thanks OROKO.

Fiona & Ava – Athens, 2022


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