15 days in New England Itinerary

With coastline on the west, south, and east, Newport is a maritime city with a rich history.

Kick off your visit on the 2nd (Mon): see the interesting displays at Newport Car Museum, then take a tour by water with Boat Tours & Water Sports, and then appreciate the extensive heritage of Cliff Walk. On your second day here, examine the collection at The Breakers, take a memorable drive along Ocean Drive Historic District, and then steep yourself in history at Lizzie Borden House.

For more things to do, other places to visit, photos, and more tourist information, refer to the Newport road trip planning site.

Indianapolis to Newport is an approximately 4-hour flight. You can also drive; or take a bus. Traveling from Indianapolis in September, you will find days in Newport are a bit cooler (74°F), and nights are about the same (58°F). Wrap up your sightseeing on the 3rd (Tue) to allow time to fly to Bar Harbor.

Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Start off your visit on the 4th (Wed): examine the collection at The Seal Cove Auto Museum, then trek along Precipice Trail, and then identify plant and animal life at Shore Path. Here are some ideas for day two: take your sightseeing to a higher altitude at Cadillac Mountain, hit the best photo ops around with an inspiring photography tour, and then get outside with Outdoor Activities.

For reviews, maps, more things to do, and tourist information, you can read our Bar Harbor road trip site.

Fly from Newport to Bar Harbor in 3 hours. Alternatively, you can drive; or take a bus. Traveling from Newport in September, plan for little chillier nights in Bar Harbor, with lows around 52°F. Finish your sightseeing early on the 5th (Thu) to allow enough time to drive to 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.

Start off your visit on the 6th (Fri): get outside with Fisherman's Walk, then explore the striking landscape at Perkins Cove, then appreciate the extensive heritage of Marginal Way Walkway, and finally kick back and relax at Ogunquit Beach.

To see where to stay, traveler tips, other places to visit, and other tourist information, read Ogunquit road trip planning app.

You can drive from Bar Harbor to Ogunquit in 4 hours. Other options are to do a combination of flight, train, and bus; or take a bus. In September, daytime highs in Ogunquit are 74°F, while nighttime lows are 48°F. Finish your sightseeing early on the 6th (Fri) so you can drive to Boston.

Rich in museums, restaurants, shops, and historical sites, Boston attracts over 16 million visitors each year.

Visit Freedom Trail and Granary Burying Ground for their historical value. Do some cultural sightseeing at Museum of Fine Arts and John F. Kennedy Presidential Museum & Library. Get out of town with these interesting Boston side-trips: Dolphin & Whale Watching (in Gloucester) and Louisa May Alcott's Orchard House (in Concord). The adventure continues: walk around Boston Public Garden, pause for some photo ops at New England Holocaust Memorial, admire the masterpieces at Otis House, and explore the different monuments and memorials at Mount Auburn Cemetery.

For where to stay, reviews, ratings, and more tourist information, you can read our Boston online attractions planner.

Getting from Ogunquit to Boston by car takes about 1.5 hours. Other options: take a bus; or do a combination of bus and train. Traveling from Ogunquit in September, plan for a bit warmer nights in Boston, with lows around 59°F. Wrap up your sightseeing on the 10th (Tue) to allow time to drive to Hyannis.

"The Capital of the Cape," Hyannis serves as Cape Cod's main transportation and commercial hub.

We've included these beaches for you: Nauset Beach and West Dennis Beach. Visit Atwood Museum and Edward Gorey House for their historical value. Venture out of the city with trips to Shining Sea Bikeway (in Falmouth) and Chatham Lighthouse Beach (in Chatham). There's lots more to do: get up close to creatures of the deep with Hyannis Whale Watcher Cruises, examine the collection at Heritage Museums & Gardens, engage your brain at Sandwich Glass Museum, and steep yourself in history at Captain Bangs Hallet House Museum.

To see reviews, ratings, maps, and more tourist information, refer to the Hyannis online travel planner.

Traveling by car from Boston to Hyannis takes 1.5 hours. Alternatively, you can take a bus; or fly. September in Hyannis sees daily highs of 73°F and lows of 57°F at night. Wrap up your sightseeing on the 13th (Fri) early enough to drive to 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.

You'll enjoy a bit of beach vacationing at Cape Cod National Seashore and Coast Guard Beach. Get outdoors at Nauset Light Beach and Marconi Beach. Next up on the itinerary: enjoy the sand and surf at Corn Hill Beach, look for all kinds of wild species at Art's Dune Tours, and stroll through Race Point Beach.

For where to stay, other places to visit, traveler tips, and more tourist information, you can read our Provincetown visit planner.

Getting from Hyannis to Provincetown by car takes about 1.5 hours. Other options: take a bus. September in Provincetown sees daily highs of 71°F and lows of 57°F at night. Finish up your sightseeing early on the 16th (Mon) so you can catch the flight back home.