30 days in New England Itinerary

30 days in New England Itinerary

Created using Inspirock New England planner

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Make it your trip
Fly
1
Nantucket
— 4 nights
Ferry to Ocean Street Terminal, Hyannis, MA, Taxi to Eastham
2
Eastham
— 4 nights
Drive
3
Newport
— 6 nights
Fly
4
Bar Harbor, Mount Desert Island
— 7 nights
Drive
5
Rockland
— 4 nights
Drive
6
Kennebunkport
— 4 nights
Fly

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Nantucket

— 4 nights
Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Your cultural itinerary includes sights like Cisco Brewers and Sankaty Head Lighthouse. Your inner history buff will appreciate Brant Point Lighthouse and Great Point Light. There's still lots to do: kick back and relax at Madaket Beach, stroll through Surfside Beach, and see the interesting displays at Nantucket Shipwreck & Lifesaving Museum.

To see reviews, where to stay, traveler tips, and tourist information, refer to the Nantucket trip app.

Birmingham to Nantucket is an approximately 7-hour flight. You can also fly; or do a combination of car and ferry; or do a combination of train, bus, and ferry. The time zone difference when traveling from Birmingham to Nantucket is 1 hour. Expect little chillier temperatures when traveling from Birmingham in September; daily highs in Nantucket reach 71°F and lows reach 59°F. Finish your sightseeing early on the 5th (Sun) so you can travel to Eastham.

Things to do in Nantucket

Beaches · Parks · Outdoors · Historic Sites

Eastham

— 4 nights
Eastham is a town in Barnstable County, Massachusetts, United States, Barnstable County being coextensive with Cape Cod. Get in touch with nature at Nauset Beach and Chatham Lighthouse Beach. Do some cultural sightseeing at Nauset Lighthouse and Captain Penniman House. There's lots more to do: get engrossed in the history at Salt Pond Visitor Center, tour the pleasant surroundings at Nauset Light Beach, enjoy the sand and surf at Marconi Beach, and get to know the fascinating history of Wellfleet Bay Wildlife Sanctuary.

To find other places to visit, photos, reviews, and more tourist information, read Eastham travel planner.

You can do a combination of ferry and taxi from Nantucket to Eastham in 2.5 hours. Another option is to do a combination of ferry and bus. In September, daily temperatures in Eastham can reach 72°F, while at night they dip to 59°F. Cap off your sightseeing on the 9th (Thu) early enough to go by car to Newport.

Things to do in Eastham

Parks · Beaches · Outdoors · Historic Sites

Side Trips

Newport

— 6 nights

City by the Sea

With coastline on the west, south, and east, Newport is a maritime city with a rich history.
Lizzie Borden House and Heritage Museums & Gardens are good opportunities to explore the local culture. Get in touch with nature at Shining Sea Bikeway and National Monument to the Forefathers. Explore Newport's surroundings by going to Nobska Point Lighthouse (in Woods Hole), Sandwich Glass Museum (in Sandwich) and Falmouth (Spohr Gardens & Highfield Hall & Gardens). The adventure continues: get a new perspective on things with Fish'n Tales Adventures, explore the activities along Cape Cod Canal, take a stroll through Thames Street, and examine the collection at Rosecliff.

To find maps, traveler tips, and tourist information, use the Newport trip itinerary planning website.

Getting from Eastham to Newport by car takes about 2.5 hours. Other options: take a bus. Expect a daytime high around 74°F in September, and nighttime lows around 58°F. Finish up your sightseeing early on the 15th (Wed) so you can catch the flight to Bar Harbor.

Things to do in Newport

Historic Sites · Museums · Parks · Outdoors

Side Trips

Bar Harbor, Mount Desert Island

— 7 nights
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. The Natural History Center has been added to your itinerary. You'll discover tucked-away gems like Thunder Hole and Kayaking & Canoeing. Escape the urban bustle at Sand Beach and Champlain Mountain & Beehive Loop Trail. The adventure continues: trek along Ocean Path, stroll through Carriage Roads, pause for some serene contemplation at St. Saviour's Church :, and capture your vacation like a pro with an inspiring photography tour.

To see maps, reviews, where to stay, and more tourist information, go to the Bar Harbor tour builder site.

You can fly from Newport to Bar Harbor in 3 hours. Other options are to drive; or take a bus. Traveling from Newport in September, expect little chillier with lows of 52°F in Bar Harbor. Wrap up your sightseeing on the 22nd (Wed) to allow time to drive to Rockland.

Things to do in Bar Harbor

Outdoors · Parks · Trails · Tours

Side Trip

Rockland

— 4 nights
Rockland is a city in Knox County, Maine, in the United States. Visiting Camden Hills State Park and Boat Tours & Water Sports will get you outdoors. Popular historic sites such as Farnsworth Art Museum and Owls Head Lighthouse are in your itinerary. Step out of Rockland with an excursion to Marshall Point Lighthouse Museum in Port Clyde--about 34 minutes away. There's still lots to do: enjoy the sea views from Maine Lighthouse Museum, do a tasting at Cellardoor Winery, and examine the collection at Owls Head Transportation Museum.

To see ratings, photos, reviews, and more tourist information, read our Rockland trip builder app.

Traveling by car from Bar Harbor to Rockland takes 2.5 hours. Alternatively, you can take a bus. In September, daily temperatures in Rockland can reach 69°F, while at night they dip to 51°F. Finish your sightseeing early on the 26th (Sun) so you can drive to Kennebunkport.

Things to do in Rockland

Museums · Historic Sites · Parks · Shopping

Side Trips

Kennebunkport

— 4 nights
Kennebunkport is a town in York County, Maine, United States. Take a break from the city and head to Wells Beach and Ocean Ave. Popular historic sites such as Strawbery Banke Museum and St. Ann's Episcopal Church are in your itinerary. When in Kennebunkport, make a side trip to see Long Sands Beach in York Beach, approximately York Beach away. There's lots more to do: take a memorable drive along Walker's Point, stroll through Rachel Carson National Wildlife Refuge, and get a new perspective on things with Boat Tours & Water Sports.

To find photos, where to stay, reviews, and tourist information, read our Kennebunkport online visit planner.

You can drive from Rockland to Kennebunkport in 2.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. September in Kennebunkport sees daily highs of 74°F and lows of 48°F at night. Cap off your sightseeing on the 30th (Thu) early enough to catch the flight back home.

Things to do in Kennebunkport

Outdoors · Parks · Historic Sites · Beaches

Side Trips

Cape Cod travel guide

4.4
Beaches · Dolphin & Whale Watching · Specialty Museums
Located on the southern shore of Massachusetts, Cape Cod contains some 15 towns and two islands. The arm-shaped peninsula is a popular holiday destination throughout the year because of its historical attractions, art galleries, award-winning restaurants, and a scenic coastline dotted by sandy beaches. Start your sightseeing in Provincetown, located at the very tip of the cape and famous for being the site of the first Pilgrims' landing in 1620. From there you can hit up all of the Cape's other small towns, renowned for their comfortable bed and breakfasts and distinctive cuisine of fresh fish and oyster dishes. This maritime community features more than a dozen lighthouses. Part of experiencing the Cape means a trip to its two islands--which showcase several lighthouses and numerous restaurants.