5 days in Massachusetts Itinerary

5 days in Massachusetts Itinerary

Created using Inspirock Massachusetts tour planner

Make it your trip
— 1 night
New Bedford
Yarmouth Port
— 2 nights
— 1 night



— 1 night


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.
Your day by day itinerary now includes Little Brewster Island and Lighthouse, Boston Public Garden and Sleepy Hollow Cemetery. Start off your visit on the 21st (Wed): get engrossed in the history at USS Constitution Museum, take in nature's colorful creations at Boston Public Garden, and then explore the different monuments and memorials at Sleepy Hollow Cemetery.

To see reviews, maps, and tourist information, go to the Boston trip planner.

The Route module shows you travel options from your home to Boston. In October, daily temperatures in Boston can reach 64°F, while at night they dip to 50°F. Wrap up your sightseeing by early afternoon on the 22nd (Thu) to allow time for the car ride to New Bedford.

Things to do in Boston

Historic Sites · Parks · Nature · Museums

Side Trip

New Bedford

New Bedford is a city in Bristol County, Massachusetts, United States. You've now added New Bedford Whaling Museum to your itinerary. Kick off your visit on the 22nd (Thu): examine the collection at New Bedford Whaling Museum.

To find ratings and tourist information, go to the New Bedford trip planner.

Drive from Boston to New Bedford in 1.5 hours. Alternatively, you can drive. Traveling from Boston in October, you can expect nighttime temperatures to be little chillier in New Bedford, with lows of 45°F. Finish up your sightseeing early on the 22nd (Thu) so you can travel to Yarmouth Port.

Things to do in New Bedford

Highlights from your trip

Yarmouth Port

— 2 nights
Yarmouth Port is a census-designated place (CDP) in the town of Yarmouth in Barnstable County, Massachusetts, United States. Your day by day itinerary now includes Bass Hole Boardwalk, Edward Gorey House and Devil's Purse Brewing Company. Start off your visit on the 23rd (Fri): contemplate the long history of Edward Gorey House, appreciate the extensive heritage of Bass Hole Boardwalk, and then indulge your thirst for a good beer at Devil's Purse Brewing Company.

For ratings, traveler tips, photos, and other tourist information, read our Yarmouth Port trip planning website.

Traveling by car from New Bedford to Yarmouth Port takes an hour. Expect a daytime high around 64°F in October, and nighttime lows around 48°F. Wrap up your sightseeing on the 24th (Sat) to allow time to drive to Salem.

Things to do in Yarmouth Port

Historic Sites · Museums · Breweries & Distilleries

Side Trip


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.
Your day by day itinerary now includes The House of the Seven Gables as well as Old Burying Point Cemetery. Start off your visit on the 24th (Sat): stroll the grounds of Old Burying Point Cemetery and then contemplate the long history of The House of the Seven Gables.

To plan Salem vacation without wasting time, ask Inspirock to design an itinerary.

Traveling by car from Yarmouth Port to Salem takes 2 hours. October in Salem sees daily highs of 64°F and lows of 45°F at night. Wrap up your sightseeing by early afternoon on the 24th (Sat) to allow enough time to drive to Newburyport.

Things to do in Salem

Historic Sites · Museums


— 1 night
Newburyport is a small coastal city in Essex County, Massachusetts, United States, northeast of Boston. Your day by day itinerary now includes The Pink House as well as Plum Island. On the 24th (Sat), step off the mainland to explore Plum Island.

For photos, reviews, other places to visit, and other tourist information, use the Newburyport attractions planner.

Drive from Salem to Newburyport in an hour. Alternatively, you can drive. In October, plan for daily highs up to 64°F, and evening lows to 46°F. You'll have a few hours on the 25th (Sun) to wrap things up before traveling home.

Things to do in Newburyport

Nature · Parks · Historic Sites

Massachusetts travel guide

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

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.