9 days in New England Itinerary

9 days in New England Itinerary

Created using Inspirock New England trip itinerary planner

Make it your trip
Fly
1
Boston
— 2 nights
Drive
2
Ogunquit
— 1 night
Drive
3
Newport
— 2 nights
Drive
4
Sandwich
— 2 nights
Drive
5
Provincetown
— 1 night
Ferry to World Trade Center Pier, Boston, MA, Fly to Milwaukee

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Boston

— 2 nights

Beantown

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.
Boston is known for historic sites, museums, and parks. Your plan includes some of its best attractions: explore the world behind art at Museum of Fine Arts, take a stroll through North End, stroll around Boston Common, and get engrossed in the history at Boston Tea Party Ships & Museum.

To see other places to visit, traveler tips, more things to do, and more tourist information, use the Boston route app.

Milwaukee to Boston is an approximately 5-hour flight. You can also drive; or take a train. Traveling from Milwaukee to Boston, you'll lose 1 hour due to the time zone difference. In June, daytime highs in Boston are 76°F, while nighttime lows are 60°F. Cap off your sightseeing on the 7th (Mon) early enough to go by car to Ogunquit.

Things to do in Boston

Museums · Parks · Historic Sites · Zoos & Aquariums

Ogunquit

— 1 night
Ogunquit means "beautiful place by the sea" in the language of the Native Americans who inhabited the region long ago, and this remains an accurate description of this holiday destination today.
Start off your visit on the 8th (Tue): visit a coastal fixture at Nubble Lighthouse, take in the dramatic natural features at Perkins Cove, and then appreciate the extensive heritage of Marginal Way Walkway.

To see maps, photos, where to stay, and other tourist information, go to the Ogunquit day trip planning app.

Traveling by car from Boston to Ogunquit takes 1.5 hours. Alternatively, you can do a combination of train and taxi; or take a bus. Expect little chillier evenings in Ogunquit when traveling from Boston in June, with lows around 52°F. Wrap up your sightseeing on the 8th (Tue) to allow time to drive to Newport.

Things to do in Ogunquit

Historic Sites · Parks · Nature

Side Trip

Newport

— 2 nights

City by the Sea

With coastline on the west, south, and east, Newport is a maritime city with a rich history.
On the 9th (Wed), take a memorable drive along Ocean Drive Historic District, then see the interesting displays at The Breakers, and then get to know the fascinating history of Cliff Walk. On the 10th (Thu), you'll have a packed day of sightseeing: tour in style with a train tour, then indulge your taste buds at Rhode Island Red Food Tours, and then take a tour by water with Boat Tours & Water Sports.

For where to stay, traveler tips, other places to visit, and more tourist information, refer to the Newport trip planner.

You can drive from Ogunquit to Newport in 3 hours. Other options are to take a bus; or do a combination of bus and train. Traveling from Ogunquit in June, expect somewhat warmer with lows of 58°F in Newport. Finish your sightseeing early on the 10th (Thu) to allow enough time to drive to Sandwich.

Things to do in Newport

Tours · Outdoors · Historic Sites · Breweries & Distilleries

Sandwich

— 2 nights
Sandwich is a town in Barnstable County, Massachusetts, United States. Kick off your visit on the 11th (Fri): get up close to creatures of the deep with Hyannis Whale Watcher Cruises, see the interesting displays at John F Kennedy Hyannis Museum, and then engage your brain at Sandwich Glass Museum. On the 12th (Sat), you'll have a packed day of sightseeing: examine the collection at Heritage Museums & Gardens, explore the world behind art at Highfield Hall & Gardens, then tour the pleasant surroundings at Shining Sea Bikeway, and finally appreciate the history behind Plymouth Rock.

For reviews, traveler tips, where to stay, and tourist information, use the Sandwich trip itinerary builder site.

Drive from Newport to Sandwich in 1.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. June in Sandwich sees daily highs of 73°F and lows of 55°F at night. Finish your sightseeing early on the 12th (Sat) to allow enough time to drive to Provincetown.

Things to do in Sandwich

Outdoors · Museums · Tours · Wildlife

Side Trips

Provincetown

— 1 night

Birthplace of American Liberty

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.
Kick off your visit on the 13th (Sun): examine the collection at Pilgrim Monument & Provincetown Museum, then take a leisurely stroll along MacMillan Wharf, then see majestic marine mammals with a dolphin and whale watching tour, and finally kick back and relax at Race Point Beach.

For ratings, more things to do, maps, and more tourist information, read our Provincetown itinerary planner.

You can drive from Sandwich to Provincetown in 1.5 hours. Alternatively, you can take a bus. In June, plan for daily highs up to 72°F, and evening lows to 56°F. Wrap up your sightseeing on the 13th (Sun) to allow time to travel back home.

Things to do in Provincetown

Outdoors · Parks · Beaches · Tours