36 days in New England Itinerary

36 days in New England Itinerary

Created using Inspirock New England tour planner

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Route & dates

36 days in New England Itinerary

Start: Sydney
Fly:  25​h
1
Boston
— 6 nights
Fly:  4​h 15​min
2
Acadia National Park, Mount Desert Island
— 5 nights
Drive:  4​h 45​min
3
North Conway
— 5 nights
Drive:  2​h
4
Ogunquit
— 5 nights
Drive:  3​h
5
Newport
— 4 nights
Drive:  1​h 15​min
6
Sandwich
— 4 nights
Drive:  1​h 15​min
7
Provincetown
— 4 nights
Fly:  27​h
End: Sydney

6
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.
Explore the numerous day-trip ideas around Boston: Salem (Peabody Essex Museum & The House of the Seven Gables) and Dolphin & Whale Watching (in Gloucester). The adventure continues: admire the masterpieces at Museum of Fine Arts, take a stroll through North End, traverse land and water with a duck tour, and appreciate the extensive heritage of Freedom Trail.

For maps, ratings, photos, and other tourist information, refer to the Boston trip planner.

Sydney, Australia to Boston is an approximately 25-hour flight. You can also do a combination of flight and bus; or do a combination of flight and ferry. You'll gain 15 hours traveling from Sydney to Boston due to the time zone difference. In May, daytime highs in Boston are 22°C, while nighttime lows are 11°C. Finish your sightseeing early on the 9th (Sat) so you can travel to Acadia National Park.

Things to do in Boston

Museums Parks Tours

Side Trips

Salem, Dolphin & Whale Watching, Mount Auburn Cemetery
Highlights from your plan
Museum of Fine Arts ©
Museum of Fine Arts
Boston Public Garden ©
Boston Public Garden
Boston Common ©
Boston Common

5
nights
Acadia National Park, Mount Desert Island

Acadia National Park ©
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.
Acadia National Park is known for nature, trails, scenic drive, beaches, and parks. Your plan includes some of its best attractions: take your sightseeing to a higher altitude at Cadillac Mountain, contemplate the waterfront views at Jordan Pond Path Trailhead, hike along Penobscot Mountain Trail, and identify plant and animal life at Jordan Cliffs Trail.

For maps, reviews, more things to do, and tourist information, use the Acadia National Park road trip planning site .

You can fly from Boston to Acadia National Park in 4.5 hours. Alternatively, you can do a combination of flight and car; or drive. Prepare for slightly colder weather when traveling from Boston in May: high temperatures in Acadia National Park hover around 18°C and lows are around 7°C. Finish your sightseeing early on the 14th (Thu) so you can drive to North Conway.

Things to do in Acadia National Park

Parks Outdoors Trails

Side Trip

Somesville Historical Museum and Gardens
Highlights from your plan
Cadillac Mountain ©
Cadillac Mountain
Champlain Mountain & Beehive Loop Trail ©
Carriage Roads ©
Carriage Roads

5
nights
North Conway

North Conway ©
North Conway combines colonial New England architecture with outlet shops selling goods from some of the world's most recognizable brands, all set amid the scenery of the White Mountains.
Get out of town with these interesting North Conway side-trips: West Rattlesnake Mountain (in Holderness), Santa's Village (in Jefferson) and Dog Mountain Home of Stephen Huneck Gallery (in Saint Johnsbury). There's lots more to do: take a memorable drive along Kancamagus Highway, look and learn at Mount Washington Observatory Weather Discovery Center, explore and take pictures at Mount Washington Auto Road, and immerse yourself in nature at Franconia Notch State Park.

Planning North Conway trip won't be overwheling when you use's Insprock itinerary maker.

You can drive from Acadia National Park to North Conway in 5 hours. Alternatively, you can do a combination of taxi, bus, and car; or do a combination of flight and bus. Expect a daytime high around 17°C in May, and nighttime lows around 7°C. Finish your sightseeing early on the 19th (Tue) to allow enough time to drive to Ogunquit.

Things to do in North Conway

Parks Nature Outdoors

Side Trips

Franconia, Lincoln, The Little White Church, White Mountain National Forest, Beyond Obsession
Highlights from your plan
West Rattlesnake Mountain ©
West Rattlesnake Mountain
Kancamagus Highway ©
Kancamagus Highway

5
nights
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.
Explore Ogunquit's surroundings by going to Portland (Allagash Brewing Company & Portland Museum of Art), The Wilson Memorial Chapel (in East Boothbay) and Old Orchard Beach (in Old Orchard Beach). And it doesn't end there: get to know the fascinating history of Marginal Way Walkway, look for gifts at The Salt Cellar, take in the dramatic natural features at Perkins Cove, and enjoy the sea views from Pemaquid Point Lighthouse.

For reviews, ratings, and tourist information, read Ogunquit tour builder .

You can drive from North Conway to Ogunquit in 2 hours. Alternatively, you can take a bus. When traveling from North Conway in May, plan for somewhat warmer days and about the same nights in Ogunquit: temperatures range from 22°C by day to 7°C at night. Finish your sightseeing early on the 24th (Sun) to allow enough time to drive to Newport.

Things to do in Ogunquit

Parks Historic Sites Outdoors

Side Trips

Boothbay, Portland, Pemaquid Point Lighthouse, Nubble Lighthouse, Old Orchard Beach
Highlights from your plan
Marginal Way Walkway ©
Marginal Way Walkway
Coastal Maine Botanical Gardens ©
Coastal Maine Botanical Gardens
Portland Head Light ©
Portland Head Light

4
nights
Newport

Newport ©
With coastline on the west, south, and east, Newport is a maritime city with a rich history.
Explore the numerous day-trip ideas around Newport: Mystic (Mystic Aquarium & Mystic Seaport Museum), Main Street Park, Essex Village (in Essex) and Lizzie Borden House (in Fall River). There's still lots to do: examine the collection at The Breakers, relax in the rural setting at Wright's Dairy Farm and Bakery, contemplate the long history of The Elms, and get lost in a book at Seekonk Public Library.

Ask Inspirock to suggest an itinerary and make planning a trip to Newport fast, fun, and easy.

Traveling by car from Ogunquit to Newport takes 3 hours. Alternatively, you can take a bus; or do a combination of bus and train. Traveling from Ogunquit in May, Newport is a bit warmer at night with lows of 11°C. Wrap up your sightseeing on the 28th (Thu) early enough to drive to Sandwich.

Things to do in Newport

Historic Sites Museums Parks

Side Trips

Mystic, Lizzie Borden House, Main Street Park, Essex Village, Wright's Dairy Farm and Bakery, Colt State Park
Highlights from your plan
The Breakers ©
The Breakers
Mystic Seaport Museum ©
Mystic Seaport Museum
Ocean Drive Historic District ©
Ocean Drive Historic District

4
nights
Sandwich

Sandwich ©
Sandwich is a town in Barnstable County, Massachusetts, United States. Explore the numerous day-trip ideas around Sandwich: Falmouth (Highfield Hall & Gardens & Cornelia Carey Sanctuary (The Knob)), Nickerson State Park (in Brewster) and Captain Bangs Hallet House Museum (in Yarmouth Port). There's lots more to do: see the interesting displays at Heritage Museums & Gardens, grab your bike and head to Shining Sea Bikeway, tour the pleasant surroundings at Cape Cod Rail Trail, and get engrossed in the history at Plimoth Plantation.

For maps, traveler tips, ratings, and more tourist information, read Sandwich tour itinerary website .

You can drive from Newport to Sandwich in 1.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. Expect a daytime high around 21°C in May, and nighttime lows around 9°C. Finish your sightseeing early on the 1st (Mon) to allow enough time to drive to Provincetown.

Things to do in Sandwich

Parks Museums Trails

Side Trips

Plymouth, Falmouth, Cape Cod Canal, Monomoy National Wildlife Refuge, John F Kennedy Hyannis Museum
Highlights from your plan
Cape Cod Rail Trail ©
Cape Cod Rail Trail
Heritage Museums & Gardens ©
Heritage Museums & Gardens
Sandwich Glass Museum ©
Sandwich Glass Museum

4
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.
Get out of town with these interesting Provincetown side-trips: Eastham (Coast Guard Beach & Salt Pond Visitor Center) and Nauset Beach (in Orleans). There's much more to do: see the interesting displays at Pilgrim Monument & Provincetown Museum, enjoy the sand and surf at Herring Cove Beach, get lost in a book at Provincetown Library, and see majestic marine mammals with a dolphin and whale watching tour.

For ratings, where to stay, reviews, and tourist information, you can read our Provincetown trip website .

Traveling by car from Sandwich to Provincetown takes 1.5 hours. Alternatively, you can take a bus. In June in Provincetown, expect temperatures between 26°C during the day and 15°C at night. Finish your sightseeing early on the 5th (Fri) so you can travel back home.

Things to do in Provincetown

Outdoors Parks Beaches

Side Trips

Eastham, Marconi Beach, Cape Cod National Seashore, Nauset Beach
Highlights from your plan
Cape Cod National Seashore ©
Cape Cod National Seashore
Race Point Beach ©
Race Point Beach

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