13 days in Massachusetts Itinerary

13 days in Massachusetts Itinerary

Created using Inspirock Massachusetts trip planner

Make it your trip
Train to New York JFK, Fly to Martha's Vineyard
1
Edgartown
— 1 day
Bus to Oak Bluffs, Martha's Vineyard, MA, Ferry to Nantucket
2
Nantucket
— 1 night
Ferry to Hyannis, MA, Taxi to Provincetown
3
Provincetown
— 3 nights
Drive
4
Plymouth
— 2 nights
Drive
5
Gloucester
— 1 night
Drive
6
Salem
— 1 night
Drive
7
Boston
— 3 nights
Drive
8
Springfield
— 1 night
Drive

S M T W T F S
13
14
15
16
17
18
19
20
21
22
23
24
25
26

Edgartown

— 1 day
Edgartown is a town located on Martha's Vineyard in Dukes County, Massachusetts, United States. Start off your visit on the 13th (Sun): visit a coastal fixture at Edgartown Lighthouse, then steep yourself in history at Trinity Park Tabernacle, then make a trip to Flying Horses Carousel, and finally tee off at Farm Neck Golf Club.

For other places to visit, more things to do, traveler tips, and tourist information, read Edgartown journey planning app.

Philadelphia to Edgartown is an approximately 5-hour combination of train and flight. You can also fly; or do a combination of car and ferry. In June, Edgartown is slightly colder than Philadelphia - with highs of 73°F and lows of 54°F. Finish your sightseeing early on the 13th (Sun) to allow enough time to travel to Nantucket.

Things to do in Edgartown

Historic Sites · Outdoors · Golf

Side Trip

Nantucket

— 1 night
Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Kick off your visit on the 14th (Mon): don't miss a visit to St Paul's Episcopal Church, then see the interesting displays at Whaling Museum, then enjoy the sand and surf at Jetties Beach, and finally make a trip to Nantucket Founders Burial Ground.

To find traveler tips, other places to visit, more things to do, and more tourist information, read our Nantucket trip itinerary app.

You can do a combination of bus and ferry from Edgartown to Nantucket in 2.5 hours. Expect a daytime high around 69°F in June, and nighttime lows around 57°F. Cap off your sightseeing on the 14th (Mon) early enough to travel to Provincetown.

Things to do in Nantucket

Outdoors · Beaches · Parks · Museums

Provincetown

— 3 nights

Birthplace of American Liberty

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 find plenty of places to visit near Provincetown: Eastham (Nauset Light Beach, Salt Pond Visitor Center, &more). The adventure continues: appreciate the history behind Pilgrim Monument & Provincetown Museum, get a sense of history and politics at Provincetown Town Hall, kick back and relax at Race Point Beach, and explore the world behind art at Provincetown Art Association and Museum.

To find ratings, traveler tips, photos, and more tourist information, go to the Provincetown online trip itinerary planner.

You can do a combination of ferry and taxi from Nantucket to Provincetown in 3 hours. Another option is to do a combination of ferry and bus. In June in Provincetown, expect temperatures between 72°F during the day and 56°F at night. Wrap up your sightseeing on the 17th (Thu) to allow time to drive to Plymouth.

Things to do in Provincetown

Outdoors · Beaches · Parks · Museums

Side Trips

Plymouth

— 2 nights

America's Hometown

Rightly calling itself "America's Hometown," Plymouth holds a prominent place in the nation's history and culture as the site of the first Puritan colony.
Start off your visit on the 18th (Fri): get up close to creatures of the deep with Hyannis Whale Watcher Cruises, then examine the collection at Heritage Museums & Gardens, and then pause for some photo ops at Plymouth Rock. Here are some ideas for day two: take an in-depth tour of Plimoth Patuxet, get curious at Sandwich Glass Museum, and then grab your bike and head to Shining Sea Bikeway.

For where to stay, maps, and more tourist information, read our Plymouth trip maker app.

You can drive from Provincetown to Plymouth in 1.5 hours. Another option is to take a bus. In June, plan for daily highs up to 76°F, and evening lows to 56°F. Finish your sightseeing early on the 19th (Sat) so you can drive to Gloucester.

Things to do in Plymouth

Museums · Outdoors · Tours · Wildlife

Side Trips

Gloucester

— 1 night

Sandy Bay

The still waters off the Gloucester shore are immortalized in paintings and prints produced by the hundreds of artists who visit this town.
Start off your visit on the 20th (Sun): identify plant and animal life at Halibut Point State Park, then explore the different monuments and memorials at Old First Parish Burying Ground, and then see majestic marine mammals with a dolphin and whale watching tour.

To see traveler tips, photos, maps, and tourist information, read Gloucester road trip planning app.

Traveling by car from Plymouth to Gloucester takes 1.5 hours. Alternatively, you can take a train. Expect a daytime high around 76°F in June, and nighttime lows around 56°F. Finish up your sightseeing early on the 20th (Sun) so you can go by car to Salem.

Things to do in Gloucester

Wildlife · Outdoors · Tours · Nature

Side Trip

Salem

— 1 night

Witch City

Best known for its 1692 witch trials, Salem has a number of significant historical sites, a bustling downtown, and many witch-themed attractions.
On the 21st (Mon), steep yourself in history at The House of the Seven Gables, gain some tasty knowledge on Salem Food Tours, then get engrossed in the history at Salem Witch Museum, and finally stop by Crow Haven Corner.

To see reviews, more things to do, photos, and other tourist information, you can read our Salem trip planner.

Salem is very close to Gloucester. June in Salem sees daily highs of 76°F and lows of 56°F at night. Cap off your sightseeing on the 21st (Mon) early enough to go by car to Boston.

Things to do in Salem

Museums · Breweries & Distilleries · Wineries · Shopping

Boston

— 3 nights

Beantown

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.
Take a break from Boston with a short trip to Marginal Way Walkway in Ogunquit, about 1h 25 min away. Next up on the itinerary: admire the masterpieces at Museum of Fine Arts, walk around Boston Common, explore the galleries of Boston Tea Party Ships & Museum, and buy something for everyone on your list at Faneuil Hall Marketplace.

For reviews, traveler tips, photos, and more tourist information, you can read our Boston road trip planner.

You can drive from Salem to Boston in an hour. Alternatively, you can take a train; or take a bus. In June, daily temperatures in Boston can reach 76°F, while at night they dip to 60°F. Finish your sightseeing early on the 24th (Thu) so you can drive to Springfield.

Things to do in Boston

Parks · Museums · Historic Sites · Zoos & Aquariums

Side Trip

Springfield

— 1 night
Springfield is a city in western New England, and the seat of Hampden County, Massachusetts, United States. Kick off your visit on the 25th (Fri): pause for some photo ops at Dr. Seuss National Memorial Sculpture Garden, walk around Stanley park, then take in nature's colorful creations at Grandmother's Garden, and finally get in on the family fun at Six Flags New England.

Discover how to plan a Springfield trip in just a few steps with Inspirock's itinerary builder.

Traveling by car from Boston to Springfield takes 2 hours. Alternatively, you can take a bus; or take a train. Expect a bit cooler evenings in Springfield when traveling from Boston in June, with lows around 54°F. Finish up your sightseeing early on the 25th (Fri) so you can go by car back home.

Things to do in Springfield

Parks · Theme Parks

Side Trips

Massachusetts travel guide

4.3
History Museums · Art Museums · Historic Walking Areas
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.

Cape Cod travel guide

4.4
Beaches · Dolphin & Whale Watching · Specialty Museums
Located on the southern shore of Massachusetts, Cape Cod contains some 15 towns and two islands. The arm-shaped peninsula is a popular holiday destination throughout the year because of its historical attractions, art galleries, award-winning restaurants, and a scenic coastline dotted by sandy beaches. Start your sightseeing in Provincetown, located at the very tip of the cape and famous for being the site of the first Pilgrims' landing in 1620. From there you can hit up all of the Cape's other small towns, renowned for their comfortable bed and breakfasts and distinctive cuisine of fresh fish and oyster dishes. This maritime community features more than a dozen lighthouses. Part of experiencing the Cape means a trip to its two islands--which showcase several lighthouses and numerous restaurants.