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 much more to do: enjoy the sand and surf at Siasconset Beach, stroll through Surfside Beach, examine the collection at Nantucket Lightship Basket Museum, and take an in-depth tour of Nantucket Shipwreck & Lifesaving Museum.

To find maps, ratings, reviews, and tourist information, you can read our Nantucket vacation site.

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. Due to the time zone difference, you'll lose 1 hour traveling from Birmingham to Nantucket. Expect little chillier temperatures when traveling from Birmingham in September; daily highs in Nantucket reach 71°F and lows reach 59°F. Wrap up your sightseeing on the 5th (Sun) early enough to travel to Eastham.

Things to do in Nantucket

Outdoors · Parks · Beaches · 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 still lots to do: get to know the fascinating history of Wellfleet Bay Wildlife Sanctuary, get all the information you need at Salt Pond Visitor Center, enjoy the sand and surf at Marconi Beach, and tour the pleasant surroundings at Nauset Light Beach.

To find traveler tips, more things to do, ratings, and more tourist information, refer to the Eastham trip app.

Traveling by combination of ferry and taxi from Nantucket to Eastham takes 2.5 hours. Alternatively, you can do a combination of ferry and bus. In September, plan for daily highs up to 72°F, and evening lows to 59°F. Wrap up your sightseeing on the 9th (Thu) early enough to drive to Newport.

Things to do in Eastham

Parks · Outdoors · Beaches · 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 Cape Cod Canal. Explore Newport's surroundings by going to Sandwich Glass Museum (in Sandwich), Falmouth (Spohr Gardens & Highfield Hall & Gardens) and Nobska Point Lighthouse (in Woods Hole). There's lots more to do: don't miss a visit to International Tennis Hall of Fame, wander the streets of Thames Street, steep yourself in history at Rough Point Museum, and see what you can catch with Fish'n Tales Adventures.

For maps, photos, reviews, and more tourist information, go to the Newport sightseeing planning tool.

You can drive from Eastham to Newport in 2.5 hours. Another option is to take a bus. September in Newport sees daily highs of 74°F and lows of 58°F at night. Wrap up your sightseeing on the 15th (Wed) early enough to fly 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 Sand Beach. Escape the urban bustle at Ocean Path and Kayaking & Canoeing. And it doesn't end there: hike along Gorham Mountain Trail, identify plant and animal life at Wildlife Areas, tee off at Pirate's Cove Miniature Golf, and tour the pleasant surroundings at Bubble Rock.

Make your Bar Harbor itinerary with Inspirock to find out what to see and where to go.

Traveling by flight from Newport to Bar Harbor takes 3 hours. Alternatively, you can drive; or take a bus. Traveling from Newport in September, expect slightly colder with lows of 52°F in Bar Harbor. Cap off your sightseeing on the 22nd (Wed) early enough to go by car 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 Marshall Point Lighthouse Museum are in your itinerary. Next up on the itinerary: enjoy the sea views from Maine Lighthouse Museum, examine the collection at Owls Head Transportation Museum, look for gifts at Owls Head Lighthouse, and learn about winemaking at Cellardoor Winery.

To find maps, ratings, and more tourist information, use the Rockland driving holiday website.

You can drive from Bar Harbor to Rockland in 2.5 hours. Alternatively, you can take a bus. In September in Rockland, expect temperatures between 69°F during the day and 51°F at night. Wrap up your sightseeing on the 26th (Sun) early enough to drive to Kennebunkport.

Things to do in Rockland

Museums · Historic Sites · Shopping · Parks

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 Walker's Point. 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 tour by water with Boat Tours & Water Sports, stroll through Rachel Carson National Wildlife Refuge, and cruise along Ocean Ave.

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.