18 days in New York City & Massachusetts Itinerary

18 days in New York City & Massachusetts Itinerary

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Route & dates

18 days in New York City & Massachusetts Itinerary

Start: London
Fly:  10​h 45​min
1
New York City
— 4 nights
Fly:  3​h 45​min
2
Nantucket
— 4 nights
ferry:  1​h 30​min
3
Oak Bluffs, Martha's Vineyard
— 2 nights
ferry + taxi:  2​h
4
Chatham
— 5 nights
Drive:  2​h
5
Boston
— 1 night
bus + Fly:  9​h 45​min
End: London


4
nights
New York City

New York City ©
Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
Popular historic sites such as 9/11 Memorial and Ellis Island are in your itinerary. The Metropolitan Museum of Art and American Museum of Natural History are good opportunities to explore the local culture. Go for a jaunt from New York City to Central Valley to see Woodbury Common Premium Outlets about 1h 10 min away. The adventure continues: take a stroll through Fifth Avenue, browse the eclectic array of goods at Chelsea Market, don't miss a visit to Central Park, and examine the collection at New York Public Library.

To find reviews, maps, and other tourist information, go to the New York City online itinerary planner

London, UK to New York City is an approximately 11-hour combination of flight and bus. You can also do a combination of flight and train. Traveling from London to New York City, you'll gain 5 hours due to the time zone difference. Prepare for somewhat warmer weather when traveling from London in August: high temperatures in New York City hover around 34°C and lows are around 26°C. Wrap up your sightseeing by early afternoon on the 19th (Sun) to allow enough time to travel to Nantucket.

Things to do in New York City

Museums Parks Shopping

Side Trip

Woodbury Common Premium Outlets
Highlights from your plan
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art
9/11 Memorial ©
9/11 Memorial
American Museum of Natural History ©
American Museum of Natural History

4
nights
Nantucket

Nantucket ©
Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Satisfy your inner culture vulture at Whaling Museum and Egan Maritime's Nantucket Shipwreck & Lifesaving Museum. You'll explore the less-touristy side of things at Cisco Beach and Great Point Light. There's lots more to do: enjoy the sea views from Sankaty Head Lighthouse, examine the collection at Nantucket Lightship Basket Museum, don't miss a visit to Brant Point Lighthouse, and enjoy the sand and surf at Surfside Beach.

To see where to stay, traveler tips, ratings, and more tourist information, read Nantucket trip builder

You can fly from New York City to Nantucket in 4 hours. Other options are to do a combination of car and ferry; or ride a ferry. Plan for a bit cooler temperatures traveling from New York City in August, with highs in Nantucket at 28°C and lows at 20°C. Finish your sightseeing early on the 23rd (Thu) so you can ride a ferry to Oak Bluffs.

Things to do in Nantucket

Parks Outdoors Beaches
Highlights from your plan
Whaling Museum ©
Whaling Museum
Sankaty Head Lighthouse ©
Sankaty Head Lighthouse

2
nights
Oak Bluffs, Martha's Vineyard

Oak Bluffs ©
Oak Bluffs is a town located on the island of Martha's Vineyard in Dukes County, Massachusetts, United States. Visiting Menemsha Hills and Menemsha Public Beach will get you outdoors. Shop till you drop at Chilmark Chocolates and Alley's General Store. When in Oak Bluffs, make a side trip to see Gay Head Lighthouse in Aquinnah, approximately 44 minutes away. Next up on the itinerary: kick back and relax at Lighthouse Beach, look for gifts at Ben and Bill's Chocolate Emporium, and stroll through Lambert's Cove Beach.

To see maps, traveler tips, more things to do, and tourist information, refer to the Oak Bluffs travel route planner

You can ride a ferry from Nantucket to Oak Bluffs in 1.5 hours. Another option is to do a combination of ferry and taxi. In August, plan for daily highs up to 30°C, and evening lows to 19°C. Cap off your sightseeing on the 25th (Sat) early enough to travel to Chatham.

Things to do in Oak Bluffs

Parks Outdoors Beaches

Side Trips

Chilmark, West Tisbury, Black Dog Bakery, Menemsha Public Beach, Gay Head Lighthouse
Highlights from your plan
Chilmark Chocolates ©
Chilmark Chocolates
Menemsha Hills ©
Menemsha Hills
Gay Head Lighthouse ©
Gay Head Lighthouse

5
nights
Chatham

Chatham ©
Chatham is a town in Barnstable County, Massachusetts, United States, Barnstable County being coextensive with Cape Cod. You'll get in some beach time at Corn Hill Beach and Head of the Meadow Beach. Your cultural itinerary includes sights like Maps of Antiquity and Church of the Transfiguration. You'll find plenty of places to visit near Chatham: Provincetown (Race Point Beach & Dolphin & Whale Watching) and Duck Harbor Beach (in Wellfleet). And it doesn't end there: shop like a local with Chatham Pier and Fish Market, view the masterpieces at Addison Art Gallery, and stop by Chatham Candy Manor.

To find traveler tips, reviews, ratings, and more tourist information, you can read our Chatham trip planner

Traveling by combination of ferry and taxi from Oak Bluffs to Chatham takes 2 hours. Alternatively, you can do a combination of ferry and bus. In August in Chatham, expect temperatures between 30°C during the day and 20°C at night. Cap off your sightseeing on the 30th (Thu) early enough to go by car to Boston.

Things to do in Chatham

Outdoors Parks Beaches

Side Trips

Orleans, Provincetown, Truro, Duck Harbor Beach
Highlights from your plan
Maps of Antiquity ©
Maps of Antiquity
Race Point Beach ©
Race Point Beach
Dolphin & Whale Watching

1
night
Boston

Boston ©
Rich in museums, restaurants, shops, and historical sites, Boston attracts over 16 million visitors each year. New England's largest and most influential city, Boston ranks among the world's major centers of education and culture.
On the 30th (Thu), admire the masterpieces at Museum of Fine Arts, then look for gifts at Brookline Booksmith, and then admire the natural beauty at Boston Public Garden. Get ready for a full day of sightseeing on the next day: take in the pleasant sights at Quincy Market, shop like a local with Faneuil Hall Marketplace, then get engrossed in the history at Boston Tea Party Ships & Museum, and finally take a stroll through North End.

To find photos, reviews, maps, and more tourist information, refer to the Boston tour itinerary builder

Getting from Chatham to Boston by car takes about 2 hours. Other options: take a bus; or do a combination of bus and train. In August, plan for daily highs up to 32°C, and evening lows to 22°C. Wrap up your sightseeing on the 31st (Fri) early enough to travel back home.

Things to do in Boston

Museums Shopping Parks

Side Trip

Brookline Booksmith
Highlights from your plan
Museum of Fine Arts ©
Museum of Fine Arts
Boston Tea Party Ships & Museum ©
Boston Tea Party Ships & Museum
North End ©
North End

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