14 days in New England Itinerary

14 days in New England Itinerary

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Route & dates

14 days in New England Itinerary

Start: Boston
ferry:  1​h 30​min
1
Provincetown
— 2 nights
Fly:  3​h 45​min
2
Rockland
— 2 nights
Drive:  2​h 15​min
3
Bar Harbor, Mount Desert Island
— 3 nights
Drive:  4​h 30​min
4
North Conway
— 1 night
Drive:  1​h 15​min
5
Franconia
— 2 nights
Drive:  4​h
6
Newport
— 2 nights
Drive:  3​h 45​min
End: New York City

2
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.
On the 21st (Tue), appreciate the extensive heritage of Wellfleet Bay Wildlife Sanctuary, get engrossed in the history at Salt Pond Visitor Center, then enjoy the sea views from Nauset Lighthouse, and finally enjoy the sea views from Highland Light. Get ready for a full day of sightseeing on the 22nd (Wed): get a sense of history and politics at Provincetown Town Hall and then tour the pleasant surroundings at Cape Cod Rail Trail.

For traveler tips, more things to do, ratings, and more tourist information, read our Provincetown visit planner.

Boston to Provincetown is an approximately 1.5-hour ferry ride. You can also fly; or drive. In May, plan for daily highs up to 63°F, and evening lows to 48°F. Cap off your sightseeing on the 23rd (Thu) early enough to travel to Rockland.

Things to do in Provincetown

Parks Outdoors Trails

Side Trips

Eastham, Highland Light, Cape Cod Rail Trail, Wellfleet Bay Wildlife Sanctuary
Highlights from your plan
Nauset Lighthouse ©
Nauset Lighthouse
Highland Light ©
Highland Light
Salt Pond Visitor Center ©
Salt Pond Visitor Center

2
nights
Rockland

Rockland ©
Rockland is a city in Knox County, Maine, in the United States. Kick off your visit on the 23rd (Thu): explore the galleries of Maine Lighthouse Museum, then do a tasting at Breakwater Vineyards, then examine the collection at Marshall Point Lighthouse Museum, and finally do a tasting at Cellardoor Winery. Here are some ideas for day two: tee off at Samoset Resort Golf Course, don't miss a visit to Curtis Island Light, and then take your sightseeing to a higher altitude at Mount Battie.

To see traveler tips, ratings, more things to do, and tourist information, read our Rockland route planning site .

Traveling by flight from Provincetown to Rockland takes 4 hours. Alternatively, you can do a combination of ferry and flight; or drive. Traveling from Provincetown in May, expect slightly colder with lows of 43°F in Rockland. Wrap up your sightseeing on the 25th (Sat) early enough to drive to Bar Harbor.

Things to do in Rockland

Outdoors Golf Wineries

Side Trips

Camden, Cellardoor Winery, Breakwater Vineyards, Marshall Point Lighthouse Museum, Samoset Resort Golf Course
Highlights from your plan
Maine Lighthouse Museum ©
Maine Lighthouse Museum
Marshall Point Lighthouse Museum ©
Marshall Point Lighthouse Museum
Cellardoor Winery ©
Cellardoor Winery

3
nights
Bar Harbor, Mount Desert Island

Bar Harbor ©
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Visiting Great Head Trail and Flying Mountain Hiking Trail will get you outdoors. Discover out-of-the-way places like Ship Harbor Nature Trail and Nature & Wildlife Tours. Step out of Bar Harbor with an excursion to Wonderland Trail in Southwest Harbor--about 32 minutes away. There's still lots to do: explore the activities along Eagle Lake Acadia National Park, take in the spiritual surroundings of St. Saviour's Church :, see the interesting displays at The Seal Cove Auto Museum, and take in the exciting artwork at Little Village Gifts.

To find ratings, traveler tips, reviews, and tourist information, read our Bar Harbor day trip planning website .

Getting from Rockland to Bar Harbor by car takes about 2.5 hours. Other options: take a bus. In May, daily temperatures in Bar Harbor can reach 60°F, while at night they dip to 43°F. Finish your sightseeing early on the 28th (Tue) to allow enough time to drive to North Conway.

Things to do in Bar Harbor

Outdoors Parks Trails

Side Trips

Acadia National Park, Southwest Harbor, The Seal Cove Auto Museum, Ship Harbor Nature Trail
Highlights from your plan
Eagle Lake Acadia National Park ©
Eagle Lake Acadia National Park
Great Head Trail ©
Great Head Trail
The Seal Cove Auto Museum ©
The Seal Cove Auto Museum

1
night
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.
Start off your visit on the 28th (Tue): glide through natural beauty at Great Glen Trails Outdoor Center, look and learn at Mount Washington Observatory Weather Discovery Center, then take in the dramatic scenery at Echo Lake State Park, and finally pause for some serene contemplation at The Little White Church.

To see other places to visit, maps, reviews, and more tourist information, read our North Conway trip planner .

You can drive from Bar Harbor to North Conway in 4.5 hours. Other options are to do a combination of flight and bus; or do a combination of bus and car. In May, daily temperatures in North Conway can reach 59°F, while at night they dip to 43°F. Finish up your sightseeing early on the 29th (Wed) so you can go by car to Franconia.

Things to do in North Conway

Parks Winter Sports Outdoors

Side Trips

Great Glen Trails Outdoor Center, The Little White Church, Echo Lake State Park
Highlights from your plan
Great Glen Trails Outdoor Center ©
Great Glen Trails Outdoor Center
Echo Lake State Park ©
Echo Lake State Park
The Little White Church ©
The Little White Church

2
nights
Franconia

Franconia is a town in Grafton County, New Hampshire, United States. On the 29th (Wed), admire the sheer force of Crawford Notch State Park, examine the collection at New England Ski Museum, then take in the dramatic scenery at Flume Gorge, and finally trek along Artist Bluff Trail. On the next day, explore and take pictures at The Frost Place, then whizz through the canopy at some of the top local zipline courses and adventure parks, and then cruise along Franconia Notch.

To see maps, ratings, more things to do, and tourist information, you can read our Franconia online holiday planner .

Traveling by car from North Conway to Franconia takes 1.5 hours. Alternatively, you can take a bus. While traveling from North Conway, expect a bit warmer days and about the same nights in Franconia, ranging from highs of 68°F to lows of 41°F. Finish your sightseeing early on the 31st (Fri) to allow enough time to drive to Newport.

Things to do in Franconia

Outdoors Parks Nature

Side Trips

Zipline, Crawford Notch State Park
Highlights from your plan
Zipline
Crawford Notch State Park ©
Crawford Notch State Park
Artist Bluff Trail ©
Artist Bluff Trail

2
nights
Newport

Newport ©
With coastline on the west, south, and east, Newport is a maritime city with a rich history.
On the 31st (Fri), appreciate the extensive heritage of Cliff Walk, then steep yourself in history at Chateau-sur-Mer, then pause for some serene contemplation at St. Mary's Catholic Church, and finally admire the majestic nature at Beavertail Lighthouse and Park. On your second day here, enjoy the sea views from Montauk Point Lighthouse and then cast your line with a fishing tour.

To see ratings, more things to do, reviews, and other tourist information, read our Newport travel route planner.

Getting from Franconia to Newport by car takes about 4 hours. Other options: take a bus; or take a bus. Expect a bit warmer evenings in Newport when traveling from Franconia in May, with lows around 49°F. Wrap up your sightseeing by early afternoon on the 2nd (Sun) to allow enough time to drive back home.

Things to do in Newport

Historic Sites Outdoors Parks

Side Trips

Montauk, Beavertail Lighthouse and Park, Cornelia Carey Sanctuary (The Knob)
Highlights from your plan
Chateau-sur-Mer ©
Chateau-sur-Mer
Beavertail Lighthouse and Park ©
Beavertail Lighthouse and Park
Fishing Charters & Tours

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