10 days in New England Itinerary

Kick off your visit on the 19th (Wed): see where the action happens at Fenway Park, step aboard Boston Tea Party Ships & Museum, then get engrossed in the history at USS Constitution Museum, then wander the streets of North End, and finally get to know the fascinating history of Freedom Trail. On the 20th (Thu), you'll have a packed day of sightseeing: buy something for everyone on your list at Faneuil Hall Marketplace, get advice or help at John F. Kennedy Presidential Museum & Library, then admire the natural beauty at Boston Public Garden, and finally stroll around Boston Common.

For maps, where to stay, reviews, and tourist information, you can read our Boston trip maker site.

Des Moines to Boston is an approximately 6.5-hour flight. You can also drive; or do a combination of bus and train. Traveling from Des Moines to Boston, you'll lose 1 hour due to the time zone difference. In October, daytime highs in Boston are 64°F, while nighttime lows are 50°F. Wrap up your sightseeing on the 20th (Thu) to allow time to drive to Salem.

Kick off your visit on the 21st (Fri): stop by Hex: Old World Witchery, stop by Pentagram, stop by Omen: Psychic Parlor and Witchcraft Emporium, get a new perspective on things with Schooner FAME of Salem, then steep yourself in history at The House of the Seven Gables, and finally stroll around Salem Witch Trials Memorial. On the 22nd (Sat), you'll have a packed day of sightseeing: take in the waterfront activity at Pickering Wharf, then explore the different monuments and memorials at Old Burying Point Cemetery, then see the interesting displays at Salem Witch Museum, and finally look for gifts at Crow Haven Corner.

To find more things to do, traveler tips, maps, and other tourist information, read Salem trip app.

Getting from Boston to Salem by car takes about an hour. Other options: take a train; or take a bus. Plan for little chillier nights when traveling from Boston in October since evenings lows in Salem dip to 45°F. You will leave for Newport on the 23rd (Sun).

Start off your visit on the 23rd (Sun): examine the collection at The Breakers, then hike along Cliff Walk, and then look for gifts at Newport Scrimshanders. Keep things going the next day: take a tour by water with Fish'n Tales Adventures, then get to know the fascinating history of Ocean Drive Historic District, then tour the old-fashioned way with a train tour, and finally take a tour by water with Boat Tours & Water Sports.

For other places to visit, maps, and tourist information, read our Newport trip builder website.

You can drive from Salem to Newport in 2 hours. Alternatively, you can take a bus; or do a combination of train and bus. In October, daytime highs in Newport are 64°F, while nighttime lows are 50°F. Wrap up your sightseeing on the 24th (Mon) early enough to drive to Plymouth.

On the 25th (Tue), explore the striking landscape of Cape Cod National Seashore.

To find ratings, photos, traveler tips, and more tourist information, you can read our Plymouth trip planner.

Drive from Newport to Plymouth in 1.5 hours. Alternatively, you can drive; or take a bus; or do a combination of bus and train. Expect a daytime high around 65°F in October, and nighttime lows around 46°F. Finish your sightseeing early on the 25th (Tue) so you can drive to Provincetown.

On the 26th (Wed), take in the waterfront at MacMillan Wharf, then pause for some photo ops at Pilgrim Monument & Provincetown Museum, and then kick back and relax at Race Point Beach.

To see maps, traveler tips, reviews, and other tourist information, read Provincetown online attractions planner.

You can drive from Plymouth to Provincetown in 1.5 hours. Another option is to take a bus. Expect a daytime high around 63°F in October, and nighttime lows around 49°F. Wrap up your sightseeing on the 26th (Wed) to allow time to travel to Oak Bluffs.

On the 27th (Thu), gain insight with Greetings from Martha's Vineyard Tours.

To find more things to do, reviews, maps, and more tourist information, read Oak Bluffs road trip planner.

You can do a combination of taxi and ferry from Provincetown to Oak Bluffs in 3 hours. Other options are to do a combination of car and ferry; or do a combination of bus and ferry. October in Oak Bluffs sees daily highs of 65°F and lows of 46°F at night. Wrap up your sightseeing by early afternoon on the 27th (Thu) to allow time for the flight back home.