11 days in United States Itinerary

11 days in United States Itinerary

Created using Inspirock United States tour itinerary builder

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Route & dates

11 days in United States Itinerary

Start: Jacksonville
+2
bus + Fly + bus:  6​h 45​min
1
Portland
— 1 night
Drive:  1​h
2
Portsmouth
— 1 night
Drive:  1​h
3
Boston
— 3 nights
ferry:  1​h 30​min
4
Provincetown
— 1 night
Drive:  1​h
5
Orleans
— 1 night
Drive:  30​min
6
Chatham
— 1 day
Drive:  45​min
7
Barnstable
— 1 night
Drive:  30​min
8
Sandwich
— 1 night
Drive:  1​h
9
Oak Bluffs
— 1 night
Fly + bus:  7​h
End: Jacksonville

1
night
Portland

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.
To find ratings, traveler tips, where to stay, and other tourist information, read Portland trip site .

Jacksonville to Portland is an approximately 7-hour combination of flight and bus. You can also fly; or drive. Traveling from Jacksonville in August, things will get little chillier in Portland: highs are around 79°F and lows about 59°F. Wrap up your sightseeing on the 3rd (Fri) early enough to drive to Portsmouth.

Things to do in Portland

Historic Sites

Side Trip

Portland Head Light
Highlights from your plan
Portland Head Light ©
Portland Head Light

1
night
Portsmouth

Portsmouth ©
Portsmouth is a city in Rockingham County, New Hampshire, in the United States. Start off your visit on the 3rd (Fri): stroll through Long Sands Beach and then kick back and relax at Wallis Sands State Beach.

To find more things to do, maps, and tourist information, read Portsmouth travel planner .

Traveling by car from Portland to Portsmouth takes an hour. Alternatively, you can take a bus. In August, plan for daily highs up to 80°F, and evening lows to 61°F. Finish your sightseeing early on the 4th (Sat) to allow enough time to take a bus to Boston.

Things to do in Portsmouth

Beaches Parks Outdoors

Side Trips

Wallis Sands State Beach, Long Sands Beach
Highlights from your plan
Wallis Sands State Beach ©
Wallis Sands State Beach
Long Sands Beach ©
Long Sands Beach

3
nights
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.
Head to Faneuil Hall Marketplace and Brookline Booksmithfor some retail therapy. Visit Freedom Trail and Orchard House for their historical value. The adventure continues: explore the world behind art at Museum of Fine Arts, take a stroll through Newbury Street, explore and take pictures at Fenway Park, and get engrossed in the history at John F. Kennedy Presidential Museum & Library.

To find out how to plan a trip to Boston, use our trip itinerary maker.

Getting from Portsmouth to Boston by bus takes about an hour. Other options: drive. In August in Boston, expect temperatures between 81°F during the day and 65°F at night. Finish up your sightseeing early on the 7th (Tue) so you can catch the ferry to Provincetown.

Things to do in Boston

Museums Shopping Historic Sites

Side Trips

Brookline Booksmith, Louisa May Alcott's Orchard House, Harvard Book Store
Highlights from your plan
Faneuil Hall Marketplace ©
Faneuil Hall Marketplace
Museum of Fine Arts ©
Museum of Fine Arts
Freedom Trail ©
Freedom Trail

1
night
Provincetown

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 7th (Tue): stroll through Race Point Beach and then kick back and relax at Corn Hill Beach.

To see more things to do, where to stay, photos, and more tourist information, read Provincetown trip maker tool .

You can ride a ferry from Boston to Provincetown in 1.5 hours. Other options are to do a combination of bus and flight; or drive. Expect a daytime high around 78°F in August, and nighttime lows around 63°F. Wrap up your sightseeing on the 8th (Wed) to allow time to travel to Orleans.

Things to do in Provincetown

Beaches Parks Outdoors

Side Trip

Corn Hill Beach
Highlights from your plan
Corn Hill Beach ©
Corn Hill Beach
Race Point Beach ©
Race Point Beach

1
night
Orleans

Orleans ©
Orleans is a town in Barnstable County, Massachusetts, which is co-extensive with Cape Cod. Kick off your visit on the 8th (Wed): enjoy the sand and surf at Coast Guard Beach, contemplate the long history of Captain Penniman House, and then kick back and relax at Nauset Beach.

To see more things to do, reviews, ratings, and other tourist information, read our Orleans trip website .

You can drive from Provincetown to Orleans in an hour. In August, daily temperatures in Orleans can reach 78°F, while at night they dip to 64°F. Finish your sightseeing early on the 9th (Thu) to allow enough time to travel to Chatham.

Things to do in Orleans

Beaches Parks Outdoors

Side Trip

Eastham
Highlights from your plan
Nauset Beach ©
Nauset Beach
Coast Guard Beach ©
Coast Guard Beach
Captain Penniman House ©
Captain Penniman House

1
day
Chatham

Chatham ©
Chatham is a town in Barnstable County, Massachusetts, United States, Barnstable County being coextensive with Cape Cod. Kick off your visit on the 9th (Thu): play a few rounds at Cranberry Valley Golf Course and then kick back and relax at Chatham Lighthouse Beach.

To find photos, where to stay, traveler tips, and more tourist information, use the Chatham route maker website .

Chatham is just a stone's throw from Orleans. In August, plan for daily highs up to 78°F, and evening lows to 64°F. Finish up your sightseeing early on the 9th (Thu) so you can travel to Barnstable.

Things to do in Chatham

Outdoors Golf Beaches

Side Trip

Cranberry Valley Golf Course
Highlights from your plan
Cranberry Valley Golf Course ©
Cranberry Valley Golf Course

1
night
Barnstable

Barnstable ©
Barnstable is a city, referred to as the Town of Barnstable, in the U.S. On the 10th (Fri), tour the pleasant surroundings at Gray's Beach, steep yourself in history at Edward Gorey House, then contemplate the long history of Captain Bangs Hallet House Museum, then see the interesting displays at John F Kennedy Hyannis Museum, and finally have fun at Wackenhammer's Clockwork Arcade.

To see traveler tips, more things to do, where to stay, and tourist information, read Barnstable itinerary builder website .

Getting from Chatham to Barnstable by car takes about an hour. In August in Barnstable, expect temperatures between 78°F during the day and 63°F at night. Cap off your sightseeing on the 10th (Fri) early enough to travel to Sandwich.

Things to do in Barnstable

Beaches Parks Outdoors

Side Trips

Yarmouth Port, Hyannis
Highlights from your plan
Edward Gorey House ©
Edward Gorey House
Captain Bangs Hallet House Museum ©
Captain Bangs Hallet House Museum
John F Kennedy Hyannis Museum ©
John F Kennedy Hyannis Museum

1
night
Sandwich

Sandwich ©
Sandwich is a town in Barnstable County, Massachusetts, United States. On the 11th (Sat), contemplate the long history of Mayflower II, take an in-depth tour of Plimoth Plantation, and then examine the collection at Heritage Museums & Gardens.

To see other places to visit, maps, and more tourist information, refer to the Sandwich road trip planning site .

Sandwich is just a short distance from Barnstable. In August, daytime highs in Sandwich are 78°F, while nighttime lows are 61°F. Finish your sightseeing early on the 11th (Sat) to allow enough time to travel to Oak Bluffs.

Things to do in Sandwich

Museums Historic Sites

Side Trip

Plymouth
Highlights from your plan
Heritage Museums & Gardens ©
Heritage Museums & Gardens
Plimoth Plantation ©
Plimoth Plantation
Mayflower II ©
Mayflower II

1
night
Oak Bluffs

Oak Bluffs ©
Oak Bluffs is a town located on the island of Martha's Vineyard in Dukes County, Massachusetts, United States. Start off your visit on the 12th (Sun): kick back and relax at Lambert's Cove Beach, enjoy the sea views from Edgartown Lighthouse, and then contemplate the long history of Trinity Park Tabernacle.

To see photos, maps, ratings, and other tourist information, go to the Oak Bluffs online tour itinerary builder .

Getting from Sandwich to Oak Bluffs by combination of taxi and ferry takes about an hour. Other options: do a combination of bus and ferry. In August in Oak Bluffs, expect temperatures between 79°F during the day and 61°F at night. Wrap up your sightseeing on the 12th (Sun) to allow time to travel back home.

Things to do in Oak Bluffs

Beaches Parks Outdoors

Side Trips

Lambert's Cove Beach, Edgartown Lighthouse
Highlights from your plan
Lambert's Cove Beach ©
Lambert's Cove Beach
Edgartown Lighthouse ©
Edgartown Lighthouse
Trinity Park Tabernacle ©
Trinity Park Tabernacle

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