25 days in New England Itinerary

25 days in New England Itinerary

Created using Inspirock New England trip planner

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Make it your trip
Fly
1
North Conway
— 3 nights
Drive
2
Ogunquit
— 2 nights
Drive
3
Boothbay Harbor
— 5 nights
Drive
4
Bar Harbor, Mount Desert Island
— 4 nights
Fly
5
Sandwich
— 3 nights
Drive
6
Provincetown
— 4 nights
Fly
7
Newport
— 3 nights
Fly

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North Conway

— 3 nights
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.
Bring the kids along to Kancamagus Highway and Franconia Notch State Park. Get out of town with these interesting North Conway side-trips: Mt. Washington Auto Road (in Gorham), The Basin at Franconia Notch State Park (in Franconia) and Flume Gorge (in Lincoln). The adventure continues: tour the pleasant surroundings at White Mountain National Forest, get great views at Cathedral Ledge, find something for the whole family at Story Land, and take in the dramatic scenery at Diana's Baths.

To see photos, where to stay, more things to do, and tourist information, read our North Conway itinerary planner.

Jacksonville to North Conway is an approximately 6-hour flight. You can also drive; or do a combination of train and bus. Plan for slightly colder temperatures traveling from Jacksonville in September, with highs in North Conway at 70°F and lows at 54°F. Wrap up your sightseeing on the 4th (Sat) to allow time to drive to Ogunquit.

Things to do in North Conway

Nature · Parks · Scenic Drive · Outdoors

Side Trips

Ogunquit

— 2 nights
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.
On the 5th (Sun), take in the dramatic natural features at Perkins Cove, get to know the fascinating history of Marginal Way Walkway, and then kick back and relax at Ogunquit Beach. Get ready for a full day of sightseeing on the next day: enjoy the sea views from Nubble Lighthouse, kick back and relax at Wells Beach, then get outside with Outdoor Activities, and finally take in the architecture and atmosphere at St. Ann's Episcopal Church.

To find more things to do, traveler tips, and more tourist information, you can read our Ogunquit driving holiday planner.

Drive from North Conway to Ogunquit in 2 hours. Alternatively, you can take a bus. Traveling from North Conway in September, you can expect nighttime temperatures to be slightly colder in Ogunquit, with lows of 48°F. Finish your sightseeing early on the 6th (Mon) so you can drive to Boothbay Harbor.

Things to do in Ogunquit

Historic Sites · Parks · Outdoors · Beaches

Side Trips

Boothbay Harbor

— 5 nights
Boothbay Harbor is a town in Lincoln County, Maine, United States. You'll visit kid-friendly attractions like Cap'n Fish's Cruises and Pemaquid Point Lighthouse. You'll find plenty of places to visit near Boothbay Harbor: Sheepscot Links (in Whitefield), Colby College Museum of Art (in Waterville) and Swan Island Wildlife Management Area (in Richmond). And it doesn't end there: go for a walk through Coastal Maine Botanical Gardens, take in the awesome beauty at Mount Battie, look for gifts at FIORE Artisan Olive Oils and Vinegars, and enjoy the sand and surf at Popham Beach State Park.

For reviews, other places to visit, maps, and tourist information, read our Boothbay Harbor online trip itinerary builder.

Traveling by car from Ogunquit to Boothbay Harbor takes 2 hours. Alternatively, you can do a combination of taxi and train; or do a combination of bus and taxi. In September, daytime highs in Boothbay Harbor are 73°F, while nighttime lows are 51°F. Finish your sightseeing early on the 11th (Sat) to allow enough time to drive to Bar Harbor.

Things to do in Boothbay Harbor

Parks · Nature · Outdoors · Wildlife

Side Trips

Bar Harbor, Mount Desert Island

— 4 nights
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Kids will enjoy Boat Tours & Water Sports and Shore Path. When in Bar Harbor, make a side trip to see Schoodic Point in Winter Harbor, approximately Winter Harbor away. There's much more to do: take in the awesome beauty at Cadillac Mountain, see the interesting displays at The Seal Cove Auto Museum, trek along Precipice Trail, and take in the dramatic natural features at Schoodic Peninsula.

To find where to stay, traveler tips, more things to do, and tourist information, use the Bar Harbor day trip website.

Drive from Boothbay Harbor to Bar Harbor in 3 hours. Alternatively, you can do a combination of taxi and bus. September in Bar Harbor sees daily highs of 70°F and lows of 52°F at night. Finish up your sightseeing early on the 15th (Wed) so you can catch the flight to Sandwich.

Things to do in Bar Harbor

Parks · Outdoors · Nature · Trails

Side Trips

Sandwich

— 3 nights
Sandwich is a town in Barnstable County, Massachusetts, United States. You'll visit kid-friendly attractions like Heritage Museums & Gardens and Plymouth Rock. Next up on the itinerary: get outside with Hyannis Whale Watcher Cruises, examine the collection at John F Kennedy Hyannis Museum, steep yourself in history at Hoxie House, and get engrossed in the history at Mayflower II.

To find ratings, maps, and more tourist information, read Sandwich trip planner.

Traveling by flight from Bar Harbor to Sandwich takes 3 hours. Alternatively, you can drive; or take a bus. September in Sandwich sees daily highs of 73°F and lows of 55°F at night. Wrap up your sightseeing on the 18th (Sat) early enough to drive to Provincetown.

Things to do in Sandwich

Museums · Outdoors · Parks · Wildlife

Side Trips

Provincetown

— 4 nights

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.
Kids will appreciate attractions like Pilgrim Monument & Provincetown Museum and Cape Cod National Seashore. Explore Provincetown's surroundings by going to Nauset Beach (in Orleans) and Eastham (Nauset Light Beach, Coast Guard Beach, &more). There's still lots to do: tour the pleasant surroundings at Race Point Beach, see majestic marine mammals with a dolphin and whale watching tour, admire the masterpieces at Provincetown Art Association and Museum, and kick back and relax at Marconi Beach.

To see ratings, photos, where to stay, and tourist information, read Provincetown holiday builder site.

Traveling by car from Sandwich to Provincetown takes 1.5 hours. Alternatively, you can take a bus. In September in Provincetown, expect temperatures between 71°F during the day and 57°F at night. Finish your sightseeing early on the 22nd (Wed) so you can fly to Newport.

Things to do in Provincetown

Outdoors · Beaches · Parks · Museums

Side Trips

Newport

— 3 nights

City by the Sea

With coastline on the west, south, and east, Newport is a maritime city with a rich history.
Attractions like The Breakers and Ocean Drive Historic District make great kid-friendly stops. You'll find plenty of places to visit near Newport: Bristol (Herreshoff Marine Museum & Colt State Park). There's much more to do: hike along Cliff Walk, examine the collection at Newport Car Museum, contemplate the long history of The Elms, and take a tour by water with Boat Tours & Water Sports.

To find where to stay, maps, ratings, and other tourist information, read Newport trip itinerary planning tool.

Traveling by flight from Provincetown to Newport takes 2 hours. Alternatively, you can drive; or do a combination of ferry and bus. September in Newport sees daily highs of 74°F and lows of 58°F at night. Cap off your sightseeing on the 25th (Sat) early enough to catch the flight back home.

Things to do in Newport

Historic Sites · Museums · Outdoors · Parks

Side Trips