15 days in New England Itinerary

15 days in New England Itinerary

Created using Inspirock New England route maker

This plan was created by another user.  Make it your plan

Route & dates

15 days in New England Itinerary

Start: Winnipeg
Fly:  9​h 15​min
1
Boston
— 2 nights
ferry:  1​h 30​min
2
Provincetown
— 3 nights
Drive:  1​h 45​min
3
Falmouth
— 2 nights
Drive:  1​h 30​min
4
Newport
— 2 nights
Drive:  3​h
5
Ogunquit
— 1 night
Drive:  4​h
6
Bar Harbor, Mount Desert Island
— 3 nights
+2
shuttle + bus + Fly:  10​h 45​min
End: Winnipeg

2
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.
Deepen your sense of the past at sights like Freedom Trail and Orchard House. Museum-lovers will appreciate Museum of Fine Arts and The Paul Revere House. Get out of town with these interesting Boston side-trips: Walden Pond State Reservation (in Concord) and Dolphin & Whale Watching (in Gloucester). And it doesn't end there: admire all the interesting features of Fenway Park, explore the different monuments and memorials at Mount Auburn Cemetery, and take in nature's colorful creations at Boston Public Garden.

To find maps, traveler tips, and tourist information, read our Boston holiday maker site .

Winnipeg, Canada to Boston is an approximately 9.5-hour flight. You can also drive. You'll lose 1 hour traveling from Winnipeg to Boston due to the time zone difference. Expect a daytime high around 22°C in May, and nighttime lows around 11°C. Wrap up your sightseeing on the 28th (Tue) to allow time to ride a ferry to Provincetown.

Things to do in Boston

Historic Sites Museums Wildlife

Side Trips

Concord, Mount Auburn Cemetery, Dolphin & Whale Watching
Highlights from your plan
Museum of Fine Arts ©
Museum of Fine Arts
Freedom Trail ©
Freedom Trail
Orchard House ©
Orchard House

3
nights
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.
Museum-lovers will appreciate Pilgrim Monument & Provincetown Museum and Provincetown Art Association and Museum. Take a break from the city and head to Cape Cod National Seashore and Race Point Beach. Go for a jaunt from Provincetown to Eastham to see Captain Penniman House about 44 minutes away. Next up on the itinerary: stroll through Cape Cod Rail Trail, get a sense of history and politics at Provincetown Town Hall, and kick back and relax at Herring Cove Beach.

To find photos, traveler tips, other places to visit, and tourist information, refer to the Provincetown trip maker .

Traveling by ferry from Boston to Provincetown takes 1.5 hours. Alternatively, you can fly; or drive. In May, plan for daily highs up to 20°C, and evening lows to 10°C. Wrap up your sightseeing on the 31st (Fri) early enough to drive to Falmouth.

Things to do in Provincetown

Parks Outdoors Beaches

Side Trips

Cape Cod, Captain Penniman House
Highlights from your plan
Cape Cod National Seashore ©
Cape Cod National Seashore
Race Point Beach ©
Race Point Beach
Herring Cove Beach ©
Herring Cove Beach

2
nights
Falmouth

Falmouth ©
Falmouth is a town in Barnstable County, Massachusetts, United States; Barnstable County is coextensive with Cape Cod. Start off your visit on the 1st (Sat): steep yourself in history at Captain Bangs Hallet House Museum, then steep yourself in history at Edward Gorey House, then examine the collection at Heritage Museums & Gardens, and finally grab your bike and head to Shining Sea Bikeway. Get ready for a full day of sightseeing on the 2nd (Sun): get curious at Sandwich Glass Museum, then admire the masterpieces at Highfield Hall & Gardens, then admire all the interesting features of Cornelia Carey Sanctuary (The Knob), and finally enjoy the sand and surf at Old Silver Beach.

To find traveler tips, reviews, ratings, and tourist information, use the Falmouth trip itinerary planner.

Traveling by car from Provincetown to Falmouth takes 2 hours. Alternatively, you can take a bus. In May, plan for daily highs up to 21°C, and evening lows to 9°C. Wrap up your sightseeing on the 2nd (Sun) early enough to drive to Newport.

Things to do in Falmouth

Parks Museums Outdoors

Side Trips

Sandwich, Yarmouth Port
Highlights from your plan
Shining Sea Bikeway ©
Shining Sea Bikeway
Heritage Museums & Gardens ©
Heritage Museums & Gardens
Edward Gorey House ©
Edward Gorey House

2
nights
Newport

Newport ©
With coastline on the west, south, and east, Newport is a maritime city with a rich history.
Start off your visit on the 3rd (Mon): view the masterpieces at Thames Glass, then appreciate the extensive heritage of Ocean Drive Historic District, then see the interesting displays at The Breakers, and finally trek along Cliff Walk. Keep things going the next day: take in nature's colorful creations at Blithewold Mansion, Gardens & Arboretum, then admire the majestic nature at Colt State Park, and then admire the majestic nature at Beavertail Lighthouse and Park.

To see ratings, traveler tips, where to stay, and other tourist information, you can read our Newport day trip planning website .

You can drive from Falmouth to Newport in 1.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. Expect a daytime high around 26°C in June, and nighttime lows around 17°C. Cap off your sightseeing on the 4th (Tue) early enough to go by car to Ogunquit.

Things to do in Newport

Parks Historic Sites Nature

Side Trips

Bristol, Beavertail Lighthouse and Park
Highlights from your plan
Cliff Walk ©
Cliff Walk
The Breakers ©
The Breakers
Ocean Drive Historic District ©
Ocean Drive Historic District

1
night
Ogunquit

Ogunquit ©
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.
Kick off your visit on the 5th (Wed): take in the dramatic natural features at Perkins Cove, then appreciate the extensive heritage of Marginal Way Walkway, and then enjoy the sand and surf at Ogunquit Beach.

To see other places to visit, where to stay, ratings, and more tourist information, use the Ogunquit trip itinerary planner.

Traveling by car from Newport to Ogunquit takes 3 hours. Alternatively, you can take a bus; or do a combination of bus and train. Traveling from Newport in June, Ogunquit is a bit cooler at night with lows of 13°C. Finish your sightseeing early on the 5th (Wed) so you can drive to Bar Harbor.

Things to do in Ogunquit

Parks Beaches Outdoors
Highlights from your plan
Marginal Way Walkway ©
Marginal Way Walkway
Ogunquit Beach ©
Ogunquit Beach

3
nights
Bar Harbor, Mount Desert Island

Bar Harbor ©
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. On the 6th (Thu), explore the wealth of natural beauty at Acadia National Park. Get ready for a full day of sightseeing on the 7th (Fri): examine the collection at The Seal Cove Auto Museum, then step off the mainland to explore Mount Desert Island, and then trek along Champlain Mountain & Beehive Loop Trail.

To find traveler tips, more things to do, photos, and more tourist information, use the Bar Harbor trip itinerary planner .

Traveling by car from Ogunquit to Bar Harbor takes 4 hours. Alternatively, you can do a combination of bus and flight; or do a combination of bus, flight, and car. While traveling from Ogunquit, expect a bit cooler days and about the same nights in Bar Harbor, ranging from highs of 23°C to lows of 13°C. On the 8th (Sat), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Bar Harbor

Parks Nature Outdoors

Side Trips

Acadia National Park, The Seal Cove Auto Museum
Highlights from your plan
Acadia National Park ©
Acadia National Park
The Seal Cove Auto Museum ©
The Seal Cove Auto Museum
Cadillac Mountain ©
Cadillac Mountain

Similar Plans

17 days in New England BY A USER FROM UNITED KINGDOM October, culture, outdoors, romantic, beaches, historic sites, museums, wildlife, popular & hidden gems PREFERENCES: October, culture, outdoors, romantic, beaches, historic sites, museums, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 17 days in New England BY A USER FROM UNITED STATES September, culture, outdoors, relaxing, beaches, historic sites, wildlife, popular sights PREFERENCES: September, culture, outdoors, relaxing, beaches, historic sites, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 16 days in New England BY A USER FROM UNITED KINGDOM June, culture, outdoors, relaxing, beaches, historic sites, wildlife, popular sights PREFERENCES: June, culture, outdoors, relaxing, beaches, historic sites, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 16 days in New England BY A USER FROM UNITED STATES July, culture, outdoors, romantic, historic sites, wildlife, popular sights PREFERENCES: July, culture, outdoors, romantic, historic sites, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 16 days in New England BY A USER FROM UNITED STATES July, culture, outdoors, wildlife, popular sights PREFERENCES: July, culture, outdoors, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 17 days in New England BY A USER FROM AUSTRALIA September, teens, popular sights PREFERENCES: September, teens ATTRACTION STYLE: Popular sights PACE: Medium 21 days in New York City & New England BY A USER FROM UNITED STATES September, culture, outdoors, historic sites, museums, shopping, wildlife, slow & easy, popular & hidden gems PREFERENCES: September, culture, outdoors, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Slow & easy 11 days in New England BY A USER FROM UNITED STATES September, culture, relaxing, romantic, shopping, wildlife, slow & easy, hidden gems PREFERENCES: September, culture, relaxing, romantic, shopping, wildlife ATTRACTION STYLE: Hidden gems PACE: Slow & easy 19 days in New England BY A USER FROM UNITED STATES September, popular sights PREFERENCES: September ATTRACTION STYLE: Popular sights PACE: Medium 22 days in New England BY A USER FROM UNITED KINGDOM August, kids, outdoors, relaxing, beaches, wildlife, popular sights PREFERENCES: August, kids, outdoors, relaxing, beaches, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 31 days in New England BY A USER FROM ISRAEL September, culture, outdoors, romantic, beaches, historic sites, museums, popular sights PREFERENCES: September, culture, outdoors, romantic, beaches, historic sites, museums ATTRACTION STYLE: Popular sights PACE: Medium 6 days in New England BY A USER FROM UNITED STATES May, relaxing, romantic, beaches, wildlife, slow & easy, popular sights PREFERENCES: May, relaxing, romantic, beaches, wildlife ATTRACTION STYLE: Popular sights PACE: Slow & easy
View more plans