16 days in New England Itinerary

Start off your visit on the 9th (Fri): visit a coastal fixture at Sankaty Head Lighthouse, get engrossed in the history at Nantucket Shipwreck & Lifesaving Museum, see the interesting displays at Nantucket Lightship Basket Museum, then enjoy the sand and surf at Madaket Beach, and finally don't miss a visit to Brant Point Lighthouse.

To see other places to visit, where to stay, reviews, and other tourist information, read Nantucket trip itinerary builder.

Philadelphia to Nantucket is an approximately 3-hour flight. You can also do a combination of train and flight; or do a combination of car and ferry. Expect little chillier temperatures when traveling from Philadelphia in June; daily highs in Nantucket reach 69°F and lows reach 57°F. Finish up your sightseeing early on the 9th (Fri) so you can travel to Eastham.

Start off your visit on the 10th (Sat): enjoy the sand and surf at Skaket Beach, tour the pleasant surroundings at Nauset Beach, engage your brain at Marconi-RCA Wireless Museum, then explore the world behind art at Atwood Museum, and finally enjoy the sand and surf at Marconi Beach. Here are some ideas for day two: take an in-depth tour of Salt Pond Visitor Center, tour the pleasant surroundings at Nauset Light Beach, enjoy the sea views from Nauset Lighthouse, then enjoy the sand and surf at Coast Guard Beach, and finally see what you can catch with a fishing tour.

To find more things to do, maps, ratings, and tourist information, read Eastham day trip planning website.

You can do a combination of ferry and taxi from Nantucket to Eastham in 2.5 hours. Alternatively, you can do a combination of ferry and bus. In June in Eastham, expect temperatures between 72°F during the day and 57°F at night. Finish your sightseeing early on the 11th (Sun) so you can drive to Newport.

Start off your visit on the 12th (Mon): stroll around Fort Adams State Park, see the interesting displays at Rosecliff, examine the collection at International Tennis Hall of Fame, then appreciate the extensive heritage of Cliff Walk, and finally visit a coastal fixture at Beavertail Lighthouse and Park. Get ready for a full day of sightseeing on the 13th (Tue): see the interesting displays at The Breakers, then examine the collection at New Bedford Whaling Museum, then contemplate the long history of Lizzie Borden House, and finally enjoy the sand and surf at Sachuest Beach (Second Beach).

For maps, ratings, more things to do, and more tourist information, go to the Newport trip planner.

You can drive from Eastham to Newport in 2 hours. Another option is to take a bus. In June, plan for daily highs up to 73°F, and evening lows to 58°F. Wrap up your sightseeing on the 13th (Tue) to allow time to drive to Pittsfield.

Kick off your visit on the 14th (Wed): kick your exploration up a notch at some of the top local zipline courses and adventure parks, admire the masterpieces at MASS MoCA, then explore the world behind art at The Clark Art Institute, and finally admire the masterpieces at Williams College Museum of Art. Get ready for a full day of sightseeing on the 15th (Thu): tour the pleasant surroundings at Herman Melville's Arrowhead, see the interesting displays at Berkshire Museum, contemplate the long history of The Mount, Edith Wharton's Home, then explore the world behind art at Norman Rockwell Museum, and finally admire the masterpieces at Chesterwood Museum.

To find photos, reviews, maps, and other tourist information, refer to the Pittsfield tour itinerary planner.

Getting from Newport to Pittsfield by car takes about 3 hours. Expect little chillier evenings in Pittsfield when traveling from Newport in June, with lows around 53°F. Wrap up your sightseeing on the 15th (Thu) to allow time to drive to Boston.

Kick off your visit on the 16th (Fri): contemplate the long history of Plymouth Rock, examine the collection at The Jenney, take in the architecture and atmosphere at King's Chapel, then explore the world behind art at Museum of Fine Arts, and finally get to know the fascinating history of Freedom Trail. Keep things going the next day: stop by Waterfront, steep yourself in history at The Old Manse, witness the site of a historic battle at Minute Man National Historical Park, then explore the galleries of Louisa May Alcott's Orchard House, and finally admire the natural beauty at Boston Public Garden.

For where to stay, photos, other places to visit, and tourist information, use the Boston itinerary builder.

Drive from Pittsfield to Boston in 2.5 hours. Expect somewhat warmer evenings in Boston when traveling from Pittsfield in June, with lows around 60°F. Wrap up your sightseeing on the 17th (Sat) to allow time to drive to Portland.

On the 18th (Sun), appreciate the extensive heritage of Marginal Way Walkway, take an in-depth tour of USS Albacore Museum, browse the exhibits of Strawbery Banke Museum, then tour the pleasant surroundings at Long Sands Beach, and finally enjoy breathtaking views from Portland Observatory. Keep things going the next day: pause for some serene contemplation at St. Ann's Episcopal Church, then take a tour by water with Boat Tours & Water Sports, then stroll through Wells Beach, and finally take a stroll through Old Port.

For ratings, where to stay, and more tourist information, use the Portland trip planner.

You can drive from Boston to Portland in 2 hours. Other options are to drive; or take a bus; or take a train. Expect a bit cooler evenings in Portland when traveling from Boston in June, with lows around 54°F. Wrap up your sightseeing on the 19th (Mon) to allow time to drive to Rockland.

Start off your visit on the 20th (Tue): visit a coastal fixture at Maine Lighthouse Museum, see the interesting displays at Owls Head Transportation Museum, then admire the majestic nature at Camden Hills State Park, and finally take an in-depth tour of Boothbay Railway Village. Get ready for a full day of sightseeing on the next day: explore the world behind art at Farnsworth Art Museum, enjoy the sea views from Owls Head Lighthouse, then visit a coastal fixture at Rockland Breakwater Light, and finally take a tour by water with Boat Tours & Water Sports.

To find ratings, more things to do, maps, and tourist information, refer to the Rockland travel itinerary planner.

Drive from Portland to Rockland in 2 hours. Alternatively, you can drive; or take a bus; or do a combination of train and bus. While traveling from Portland, expect slightly colder days and about the same nights in Rockland, ranging from highs of 68°F to lows of 51°F. Finish your sightseeing early on the 21st (Wed) so you can drive to Bar Harbor.

Step off the beaten path and head to Jordan Pond Path Trailhead and Sand Beach.

To find reviews, where to stay, other places to visit, and other tourist information, read our Bar Harbor day trip planning website.

Traveling by car from Rockland to Bar Harbor takes 2.5 hours. Alternatively, you can take a bus. Expect a daytime high around 68°F in June, and nighttime lows around 52°F. Wrap up your sightseeing on the 24th (Sat) to allow time to fly back home.