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Whether you would like to book this exact holiday or to tailor-make it to better suit you, please contact one of our knowledgeable experts on:
Boston to New York by the Beaches
Two great cities interspersed with seaside resorts and luxury retreats.
This Boston to New York by the beaches fly-drive holiday does just what it says on the tin. You will be able to compare and contrast Boston and New York but also have time to explore the delights of Cape Cod, Martha’s Vineyard and the Hamptons. Accommodation can be in intimate b&bs or one of the very luxurious resorts that abound in this area. Wherever you stay, the ocean will not be far away; indeed your holiday includes several ferries.
This itinerary is flexible and can be tailor-made to suit you; if you want to add extra days in one area, extend the holiday or maybe change the direction of travel. Talk to one of our experts about how to make this holiday the perfect one for you.
Mr Burns - Travelled to New England"The itinerary too was good"
Please accept my thanks for organising our trip to New England etc. All arrangements worked exactly as arranged and we were particularly pleased with the standard of hotels used.
The itinerary too was good and we loved Kennebunkport, Stowe and Jackson. We were well looked after in all locations, although slightly less so at Von Trapp hotel that was less personal because of their size, but the experience itself was welcome.
Itinerary (9 Nights)
Here’s a day-by-day guide to your itinerary. Feel free to ask us to add other days or ideas and excursions by contacting us directly, so we can give you the best price.
Days 1-2
Arrive in Boston and transfer to your hotel for a 2 night stay. Take a...
Days 1-2
Boston
Arrive in Boston and transfer to your hotel for a 2 night stay. Take a stroll through Boston’s lively neighbourhoods and discover some of the city’s great restaurants.
2 nights in Boston
Day 3
Boston to Hyannis
This morning, depart for Cape Cod, stopping on the way in Plymouth to see where...
Day 3
Boston
to Hyannis
This morning, depart for Cape Cod, stopping on the way in Plymouth to see where the Pilgrims landed and visit the Plimoth Patuxet Plantation living history museum. In Hyannis, take a leisurely one hour cruise on Lewis Bay and Hyannis Harbour (included in the price of your holiday). The accompanying commentary points out the highlights and interesting anecdotes as you sail past vistas of historical interest, scenic islands, beaches and even two presidential summer homes. Spend two nights in or near Hyannis. Centrally located on Cape Cod, it’s a short drive to all that Cape Cod has to offer; beaches, biking/hiking trails, golf, shopping and fine dining.
2 nights in Hyannis
Day 4
Hyannis
Today, visit the Cape Cod National Seashore to explore lighthouses, quaint coastal communities and natural...
Day 4
Hyannis
Today, visit the Cape Cod National Seashore to explore lighthouses, quaint coastal communities and natural scenic beauty. Stroll the charming and upscale village of Chatham before visiting the lively artist colony of Provincetown. Here you can go whale watching, shop the many eclectic art galleries and shops or spend the day on one of the long sandy beaches. Don’t leave New England without feasting on Lobster, steamers, corn-on-the- cob and all the trimmings!
Day 5
Hyannis to Marthas Vineyard
Take the ferry from Woods Hole for the 45-minute ride across to Martha’s Vineyard. Take...
Day 5
Hyannis
to
Marthas Vineyard
Take the ferry from Woods Hole for the 45-minute ride across to Martha’s Vineyard. Take the remainder of the afternoon to relax and familiarize yourself with the area, before checking in to your island hotel.
2 nights Marthas Vineyard
Day 6
Today, drive around the Vineyard to see a variety of landscapes in the six independent...
Day 6
Marthas Vineyard
Today, drive around 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. Tour “downisland”, the busy and fashionable eastern half of the Vineyard where Oak Bluffs, Edgartown, and Vineyard Haven lure the rich and famous; and up-island, the sparsely populated and sleepy towns to the west. Aquinnah is known for its beautiful clay cliffs and quiet natural serenity and the beach is one of the few nude beaches left in the U.S.
Day 7
Day 7
Marthas Vineyard to Mystic
Take the ferry back to the mainland for a three hour drive via Providence to...
Day 7
Day 7
Marthas Vineyard
to Mystic
Take the ferry back to the mainland for a three hour drive via Providence to Mystic, although you might prefer to take the longer (and rather prettier) route through Rhode Island where you could spend a couple of nights if you wish. Do visit Mystic Seaport, depicting 17th century seafaring history with some fascinating ships to explore.
1 night in Mystic
Days 8-9
Days 8-9
Mystic to Southampton
Another ferry today! The Orient Point Ferry takes just 40 minutes from New London to...
Days 8-9
Days 8-9
Mystic
to Southampton
Another ferry today! The Orient Point Ferry takes just 40 minutes from New London to Orient Point at the tip of Long Island. Take your time exploring the North Fork, visiting some of many wineries, and explore the region on your way to Southampton on the South Fork of Long Island.
You will have a full day to visit the charming villages filled with boutique shops and art galleries, have a picnic at an outdoor concert, tour the historic mansions, or just relax on the beach.
2 nights in Southampton
Day 10
This morning, travel west toward New York City, stopping on the way to explore Long...
Day 10
New York City
This morning, travel west toward New York City, stopping on the way to explore Long Beach – full of famous homes, film sites, Gatsby’s Gold Coast Mansions and lighthouses.
If you want to fly home today, JFK Airport is on your way to New York or you can extend your holiday in New York.
J Smith - Travelled New York to TorontoI have just returned from a tailor made holiday made possible by Jeannette Dembrey. This was the first time I had ever organised such a major holiday and as it was a gift for my children after my retirement it was really important to get things right. I went to quite a few agencies but Jeannette was way better than any of the people who I spoke to. She was so professional and wanted me to get the best from the money I could afford. The holiday was absolutely amazing and everything went like clockwork. Jeannette had thought of everything even the connections between places and the things we would do in each town. We stayed in 6 hotels altogether starting in New York and ending in Toronto. I am amazed at how smoothly it went. Even my son who has travelled all over the world was impressed with the way things had been organised. I cannot praise Jeannette enough for her professionalism. Thank you Jeannette. I would recommend you to anyone with the satisfaction of knowing that you did an amazing job. Thank you.
