26 days in New England Itinerary

26 days in New England Itinerary

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Route & dates

26 days in New England Itinerary

Prague
Fly:  14​h 15​min
Oak Bluffs, Martha's Vineyard
— 4 nights
ferry:  1​h 30​min
Nantucket
— 4 nights
ferry + taxi:  2​h 15​min
Provincetown
— 2 nights
Drive:  3​h 30​min
Bristol
— 2 nights
Drive:  1​h 15​min
Portland
— 3 nights
Drive:  3​h 45​min
Acadia National Park, Mount Desert Island
— 4 nights
taxi + Fly + bus:  3​h 15​min
Boston
— 2 nights
Drive:  30​min
Salem
— 3 nights
Fly:  13​h 15​min
Prague

4
days
Oak Bluffs, Martha's Vineyard

Oak Bluffs is a town located on the island of Martha's Vineyard in Dukes County, Massachusetts, United States. Relax by the water at Lighthouse Beach and Joseph Sylvia State Beach. Eschew the tourist crowds and head to Edgartown Lighthouse and Aquinnah Lighthouse. When in Oak Bluffs, make a side trip to see Gay Head Lighthouse in Aquinnah, approximately 44 minutes away. There's lots more to do: enjoy the sand and surf at Bend in the Road Beach, look for all kinds of wild species at Felix Neck Wildlife Sanctuary, don't miss a visit to Flying Horses Carousel, and tour the pleasant surroundings at Inkwell Beach.

For traveler tips, more things to do, reviews, and other tourist information, you can read our Oak Bluffs trip builder.

Prague, Czech Republic to Oak Bluffs is an approximately 14.5-hour flight. The time zone difference when traveling from Prague to Oak Bluffs is minus 6 hours. Traveling from Prague in September, expect nights in Oak Bluffs to be about the same, around 13°C, while days are somewhat warmer, around 26°C. Finish your sightseeing early on the 19th (Wed) so you can ride a ferry to Nantucket.

Things to do in Oak Bluffs

Outdoors Parks Beaches

Side Trips

Edgartown, Aquinnah
Highlights from your plan
Lighthouse Beach
Edgartown Lighthouse
Gay Head Lighthouse

3
days
Nantucket

Nantucket is an island 30mi south of Cape Cod, in the American state of Massachusetts. Museum-lovers will get to explore Whaling Museum and Nantucket Lightship Basket Museum. You'll get in some beach time at Madaket Beach and Jetties Beach. The adventure continues: enjoy the sea views from Sankaty Head Lighthouse, admire the natural beauty at Oldest House (Jethro Coffin House), see the interesting displays at Nantucket Shipwreck & Lifesaving Museum, and contemplate the long history of Greater Light.

To find ratings, photos, more things to do, and tourist information, use the Nantucket trip planner.

Traveling by ferry from Oak Bluffs to Nantucket takes 1.5 hours. In September, daytime highs in Nantucket are 24°C, while nighttime lows are 16°C. Finish your sightseeing early on the 23rd (Sun) to allow enough time to travel to Provincetown.

Things to do in Nantucket

Parks Historic Sites Beaches
Highlights from your plan
Whaling Museum
Sankaty Head Lighthouse

2
days
Provincetown

A small resort town with a year-round population of just 3,000, Provincetown draws nearly 60,000 annual visitors with its scenic beaches, art colonies, galleries, theaters, and shops.
Start off your visit on the 23rd (Sun): kick back and relax at Long Point, enjoy the sea views from Highland Light, and then stroll through Race Point Beach. Keep things going the next day: visit a coastal fixture at Nauset Lighthouse, take an in-depth tour of Salt Pond Visitor Center, and then stroll through Cape Cod Provincelands Trail.

To see more things to do, ratings, and tourist information, use the Provincetown travel itinerary creator.

Do a combination of ferry and taxi from Nantucket to Provincetown in 2.5 hours. Alternatively, you can do a combination of ferry and bus. In September, daily temperatures in Provincetown can reach 25°C, while at night they dip to 15°C. Wrap up your sightseeing on the 25th (Tue) early enough to travel to Bristol.

Things to do in Provincetown

Outdoors Parks Beaches

Side Trips

Eastham, Highland Light
Highlights from your plan
Race Point Beach
Long Point
Nauset Lighthouse

2
days
Bristol

Bristol is a town in Lincoln County, Maine, United States. Start off your visit on the 25th (Tue): do a tasting at Cellardoor Winery, then enjoy the sea views from Maine Lighthouse Museum, and then steep yourself in history at Colonial Pemaquid State Historic Site. On the 26th (Wed), you'll have a packed day of sightseeing: look for all kinds of wild species at Boothbay Region Land Trust, examine the collection at Boothbay Railway Village, and then don't miss a visit to Historic New England Castle Tucker.

For ratings, reviews, where to stay, and other tourist information, read Bristol itinerary planner.

You can drive from Provincetown to Bristol in 5.5 hours. Traveling from Provincetown in September, you can expect nighttime temperatures to be slightly colder in Bristol, with lows of 11°C. On the 27th (Thu), you'll travel to Portland.

Things to do in Bristol

Historic Sites Parks Museums

Side Trips

Colonial Pemaquid State Historic Site, Maine Lighthouse Museum, Cellardoor Winery, Historic New England Castle Tucker, Boothbay Railway Village
Highlights from your plan
Maine Lighthouse Museum
Cellardoor Winery

3
days
Portland

Maine's biggest and perhaps most vibrant city, Portland was established as a fishing village in 1633 and grew to become New England's largest port.
Escape the urban bustle at Ogunquit Beach and Casco Bay. We've included these beaches for you: Footbridge Beach and Kennebunk Beach. Get out of town with these interesting Portland side-trips: Marginal Way Walkway (in Ogunquit) and Goose Rocks Beach (in Cape Porpoise). The adventure continues: see the interesting displays at Portland Head Light.

To see ratings, other places to visit, traveler tips, and tourist information, read Portland online itinerary creator.

You can drive from Bristol to Portland in 1.5 hours. In September in Portland, expect temperatures between 25°C during the day and 13°C at night. Wrap up your sightseeing by early afternoon on the 30th (Sun) to allow time for the car ride to Acadia National Park.

Things to do in Portland

Beaches Outdoors Parks

Side Trips

Ogunquit, Kennebunk Beach, Goose Rocks Beach, Portland Head Light
Highlights from your plan
Ogunquit Beach
Portland Head Light
Marginal Way Walkway

4
days
Acadia National Park, Mount Desert Island

The first national park east of the Mississippi River, Acadia National Park draws visitors with its rugged landscape of ocean shoreline, low-slung granite mountains, dense woodlands, and pristine lakes.
Ship Harbor Nature Trail and St Saviour's Episcopal Church will appeal to history buffs. Step out of the city life by going to Gorham Mountain Trail and Precipice Trail. Next up on the itinerary: see the interesting displays at The Seal Cove Auto Museum, tour the pleasant surroundings at Heart of Acadia Loop, explore the striking landscape at Otter Cliff, and hike along Great Head Trail.

To find reviews, photos, and other tourist information, read our Acadia National Park sightseeing planner.

You can drive from Portland to Acadia National Park in 4 hours. Other options are to do a combination of bus, flight, and taxi; or do a combination of bus and taxi. In September, plan for daily highs up to 24°C, and evening lows to 12°C. Wrap up your sightseeing on the 4th (Thu) early enough to travel to Boston.

Things to do in Acadia National Park

Parks Outdoors Trails

Side Trips

Bar Harbor, The Seal Cove Auto Museum, Ship Harbor Nature Trail, Flying Mountain Hiking Trail
Highlights from your plan
Otter Cliff
The Seal Cove Auto Museum
Bar Island Trails

2
days
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.
Freedom Trail has been added to your itinerary. Start off your visit on the 5th (Fri): contemplate the long history of Adams National Historical Park, then tour the pleasant surroundings at Isabella Stewart Gardner Museum, and then wander the streets of Beacon Hill. Keep things going the next day: explore the different monuments and memorials at Granary Burying Ground, take a stroll through Waterfront, and then get to know the fascinating history of Freedom Trail.

To see traveler tips, reviews, maps, and more tourist information, you can read our Boston tour planner.

Traveling by combination of taxi, flight, and bus from Acadia National Park to Boston takes 3.5 hours. Alternatively, you can drive; or do a combination of taxi and bus. Expect somewhat warmer evenings in Boston when traveling from Acadia National Park in October, with lows around 11°C. Wrap up your sightseeing on the 6th (Sat) to allow time to drive to Salem.

Things to do in Boston

Historic Sites Neighborhoods Parks

Side Trip

Adams National Historical Park
Highlights from your plan
Freedom Trail
Isabella Stewart Gardner Museum
Adams National Historical Park

2
days
Salem

Best known for its 1692 witch trials, Salem has a number of significant historical sites, a bustling downtown, and many witch-themed attractions.
On the 7th (Sun), you'll have a packed day of sightseeing: see the interesting displays at Peabody Essex Museum, then get engrossed in the history at Salem Witch Museum, then steep yourself in history at The House of the Seven Gables, and finally stop by Omen: Psychic Parlor and Witchcraft Emporium.

To find where to stay, traveler tips, maps, and other tourist information, use the Salem travel itinerary planner.

Salem is just a short distance from Boston. October in Salem sees daily highs of 19°C and lows of 8°C at night. You'll have a few hours on the 9th (Tue) to wrap things up before traveling home.

Things to do in Salem

Museums Beaches Outdoors

Side Trips

Hampton Beach, Historic New England Beauport Sleeper--McCann House
Highlights from your plan
The House of the Seven Gables
Peabody Essex Museum
Hampton Beach

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