19 days in East Coast of USA Itinerary

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

Kick off your visit on the 18th (Wed): get a taste of local nightlife at Cocktails & Cannoli, get engrossed in the history at New England Holocaust Memorial, appreciate the history behind Bunker Hill Monument, then gain insight with Salem Walking Tours, then take a stroll through North End, and finally contemplate the long history of Longfellow House Washington's Headquarters National Historic Site. Keep things going the next day: ponder the world of politics at Old State House, then stop by Back Bay, then take in the spiritual surroundings of Trinity Church, and finally tour the pleasant surroundings at Castle Island.

Quickly create a custom-made itinerary for Boston using our trip planner.

Bel Air to Boston is an approximately 6-hour car ride. You can also drive. Expect little chillier temperatures when traveling from Bel Air in May; daily highs in Boston reach 67°F and lows reach 50°F. Finish your sightseeing early on the 19th (Thu) so you can drive to Salem.

Best known for its 1692 witch trials, Salem has a number of significant historical sites, a bustling downtown, and many witch-themed attractions.

Kick off your visit on the 20th (Fri): gain interesting insight with Hocus Pocus Tours, catch a live performance at Haunted Dinner Theater, browse for treasures at Fivehands Curiosity Shoppe, stroll the grounds of Old Burying Point Cemetery, then contemplate the long history of The Jeremiah Lee Mansion, and finally learn insider's secrets on Salem Food Tours. Here are some ideas for day two: contemplate the long history of Saugus Iron Works, then steep yourself in history at The Custom House, and then go for a stroll along the water at Pickering Wharf.

To see maps, traveler tips, where to stay, and more tourist information, go to the Salem travel route tool.

You can drive from Boston to Salem in an hour. Alternatively, you can take a train; or take a bus. In May, daily temperatures in Salem can reach 67°F, while at night they dip to 48°F. Finish your sightseeing early on the 21st (Sat) to allow enough time to drive to Gloucester.

The still waters off the Gloucester shore are immortalized in paintings and prints produced by the hundreds of artists who visit this town.

You'll discover tucked-away gems like Hammond Castle Museum and Long Point. You'll visit kid-friendly attractions like Eastern Point Lighthouse and Fishermen's Memorial Monument. Explore Gloucester's surroundings by going to Salem (Salem Maritime National Historic Site & The House of the Seven Gables), Newburyport (Plum Island Lighthouse & Taste Newburyport Food Tour) and Provincetown (Pilgrim Monument & Provincetown Museum, Dolphin & Whale Watching, &more). There's much more to do: see the interesting displays at Beauport, the Sleeper-McCann House, stroll around Stage Fort Park and Beach, look for all kinds of wild species at Crane Wildlife Refuge on the Crane Estate, and make a trip to Gloucester Fishermen's Wives Memorial.

To find ratings, reviews, traveler tips, and other tourist information, you can read our Gloucester trip planner.

Gloucester is very close to Salem. May in Gloucester sees daily highs of 67°F and lows of 48°F at night. Wrap up your sightseeing on the 26th (Thu) to allow time to drive to Kennebunkport.

Kennebunkport is a town in York County, Maine, United States. Kick off your visit on the 26th (Thu): take a tour by water with Boat Tours & Water Sports and then appreciate the extensive heritage of Parson's Way.

For where to stay, maps, ratings, and tourist information, use the Kennebunkport tour itinerary planner.

You can drive from Gloucester to Kennebunkport in 2 hours. Other options are to do a combination of train and bus; or do a combination of train and bus. Traveling from Gloucester in May, expect a bit cooler with lows of 43°F in Kennebunkport. Finish your sightseeing early on the 26th (Thu) so you can drive to Portland.

Maine's biggest and perhaps most vibrant city, Portland was established as a fishing village in 1633 and grew to become New England's largest port.

Kick off your visit on the 27th (Fri): look for gifts at Lisa-Marie's Made in Maine, then stroll the grounds of Eastern Cemetery, and then sample the tasty concoctions at Rising Tide Brewing Company.

To see more things to do, maps, other places to visit, and other tourist information, go to the Portland trip planner.

Getting from Kennebunkport to Portland by car takes about an hour. Other options: do a combination of taxi and train; or do a combination of taxi and bus. In May, daytime highs in Portland are 64°F, while nighttime lows are 45°F. On the 28th (Sat), you're off to Freeport.

Freeport is a town in Cumberland County, Maine, United States. Popular historic sites such as Skolfield-Whittier House and Seguin Island and Lighthouse are in your itinerary. Kids will appreciate attractions like Wolfe's Neck Woods State Park and Winslow Memorial Park Camping and Public Beach. There's still lots to do: contemplate in the serene atmosphere at First Parish Church, revel in the low prices at Freeport Shopping Outlets, and relax in the rural setting at Wolfe's Neck Farm.

For reviews, ratings, where to stay, and tourist information, go to the Freeport trip maker.

Freeport is just a stone's throw from Portland. In May, daily temperatures in Freeport can reach 64°F, while at night they dip to 43°F. On the 31st (Tue), you'll travel to Rockland.

Rockland is a city in Knox County, Maine, in the United States. You'll visit kid-friendly attractions like Rockland Breakwater Light and High Street Historic District. Discover out-of-the-way places like Maine Lighthouse Museum and Cellardoor Winery. There's still lots to do: examine the collection at Sail Power and Steam Museum, walk around Buoy Park, and get a new perspective on things with A Morning In Maine.

To see more things to do, reviews, other places to visit, and other tourist information, refer to the Rockland travel route website.

Traveling by car from Freeport to Rockland takes 1.5 hours. Alternatively, you can do a combination of train and bus. When traveling from Freeport in May, plan for little chillier days in Rockland, with highs around 59°F, while nights are about the same with lows around 43°F. You will leave for Bar Harbor on the 3rd (Fri).

Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Kick off your visit on the 3rd (Fri): visit a coastal fixture at Egg Rock Light.

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

Getting from Rockland to Bar Harbor by car takes about 2.5 hours. Other options: drive; or take a bus. In June in Bar Harbor, expect temperatures between 68°F during the day and 52°F at night. You'll have a few hours on the 4th (Sat) to wrap things up before traveling home.