8 days in Massachusetts Itinerary

8 days in Massachusetts Itinerary

Created using Inspirock Massachusetts planner
Make it your trip
— 2 nights
— 1 night
— 2 nights
Taxi to Harwich Port, Harwich, MA, Ferry to Nantucket
— 2 nights


Boston — 2 nights


Rich in museums, restaurants, shops, and historical sites, Boston attracts over 16 million visitors each year. New England's largest and most influential city, Boston ranks among the world's major centers of education and culture.
Explore hidden gems such as Lizzie Borden House and Old State House. Deepen your sense of the past at sights like Swan Point Cemetery and Trinity Church. Step out of Boston to go to Providence and see Boat Tours & Water Sports, which is approximately 1 hour away. There's still lots to do: get to know the fascinating history of Freedom Trail, steep yourself in history at Castle Island, contemplate in the serene atmosphere at Old South Church, and take a tour of Charlestown Navy Yard.

To find reviews, ratings, more things to do, and more tourist information, you can read our Boston online trip builder.

Philadelphia to Boston is an approximately 3.5-hour flight. You can also drive; or take a train. When traveling from Philadelphia in October, plan for slightly colder days in Boston, with highs around 64°F, while nights are about the same with lows around 50°F. Wrap up your sightseeing on the 24th (Mon) to allow time to drive to Falmouth.
Historic Sites · Parks · Outdoors · Museums
Side Trips

Falmouth — 1 night

Falmouth is a town in Barnstable County, Massachusetts, United States; Barnstable County is coextensive with Cape Cod. Start off your visit on the 25th (Tue): get engrossed in the history at Sandwich Glass Museum, take in nature's colorful creations at Highfield Hall & Gardens, then enjoy the sea views from Nobska Point Lighthouse, and finally grab your bike and head to Shining Sea Bikeway.

To find traveler tips, other places to visit, ratings, and tourist information, read Falmouth online visit planner.

Getting from Boston to Falmouth by car takes about 1.5 hours. Other options: take a bus. October in Falmouth sees daily highs of 64°F and lows of 46°F at night. Finish your sightseeing early on the 25th (Tue) to allow enough time to drive to Chatham.
Parks · Museums · Trails · Outdoors
Side Trip

Chatham — 2 nights

Chatham is a town in Barnstable County, Massachusetts, United States, Barnstable County being coextensive with Cape Cod. On the 26th (Wed), enjoy the sand and surf at Chatham Lighthouse Beach and then visit a coastal fixture at Chatham Lighthouse. Here are some ideas for day two: explore the world behind art at Atwood Museum, take in the waterfront at Chatham Pier and Fish Market, and then stroll through Nauset Beach.

To find reviews, other places to visit, traveler tips, and other tourist information, read our Chatham holiday planner.

Traveling by car from Falmouth to Chatham takes 1.5 hours. Alternatively, you can take a bus. In October in Chatham, expect temperatures between 63°F during the day and 50°F at night. Wrap up your sightseeing on the 27th (Thu) to allow time to travel to Nantucket.
Parks · Beaches · Outdoors · Historic Sites
Side Trip

Nantucket — 2 nights

Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Kick off your visit on the 28th (Fri): visit a coastal fixture at Brant Point Lighthouse and then enjoy the sand and surf at Madaket Beach. Here are some ideas for day two: see the interesting displays at Nantucket Lightship Basket Museum, then visit a coastal fixture at Sankaty Head Lighthouse, and then visit a coastal fixture at Great Point Light.

To find other places to visit, reviews, more things to do, and tourist information, use the Nantucket road trip site.

You can do a combination of taxi and ferry from Chatham to Nantucket in 2.5 hours. Another option is to do a combination of bus and ferry. October in Nantucket sees daily highs of 64°F and lows of 51°F at night. Cap off your sightseeing on the 29th (Sat) early enough to catch the flight back home.
Historic Sites · Parks · Beaches · Outdoors

Massachusetts travel guide

History Museums · Nightlife · Art Museums
The Bay State
Known as the "Bay State" because of the three bays dominating its coastline, Massachusetts has played a significant cultural and commercial role through most of the country's history. An increasingly popular vacation destination for foreign travelers, Massachusetts offers numerous places to visit, ranging from historical sites to modern urban centers famous for their culinary, art, and nightlife scenes. With the majority of its population living in and around the city of Boston, in the 20th century Massachusetts went from a state largely dependent on fishing and agriculture to the country's leader in higher education, healthcare, high technology, and financial services. Home to renowned universities and research centers, the state's cities attract a young crowd of students, scientists, artists, and business professionals.