The 5 Day Trips from Boston That Earn the Road Time

1.Boston to Martha’s Vineyard Day Trip with Optional Island Tour

★★★★★★★★★★4.5 · 3,162 reviews · 12 hours (approx.) · from $129Our pick

Ride from Boston to Falmouth in a 24-passenger minibus, cross Vineyard Sound by ferry, then explore Martha’s Vineyard for 5.5 to 6 hours. Choose free time or add a narrated island tour to see Edgartown, Aquinnah, Gay Head Light, and all six island towns.

“Not much to see on Martha's Vineyard. Best part of the tour was the shuttle driver to and from the ferry. It's a 2 hour drive from Boston to Woods Hole and our guide, Johnny Boston was both entertaining and informative. He helped the time pass quickly. Unfortunately once we got off the ferry the island itself was a big letdown. There is one scenic view, the Aquinnah Cliffs and lighthouse. Other than that it mostly looking at tree lined gravel drive ways that lead to unseen mansions of famous rich people and expensive boutiques in unremarkable small towns. There is a long rather boring beach where Jaws was filmed.”

Check availability →Read our full review

2.Boston: Martha’s Vineyard Day Trip with Optional Island Tour

★★★★★★★★★★4.6 · 573 reviews · 13 hours · from $129

Ride from downtown Boston to Falmouth, cross by ferry, then explore Martha’s Vineyard for about six hours. Choose free time or a three-hour island tour led by local guides such as Tom or Anthony, with stops in Oak Bluffs, Edgartown, and Aquinnah.

“Jay our driver was fabulous, few stories on the way made it a fun trip ,”

Check availability →Read our full review

3.Martha’s Vineyard Day Trip with Optional Island Tour from Boston

★★★★★★★★★★4.5 · 407 reviews · 13 hours (approx.) · from $130

You’ll leave Boston early with guides such as Keith, Rory, Matt, or Paul, travel through Cape Cod, visit Nobska Lighthouse, and take the ferry to Oak Bluffs. Choose six hours on your own or add a three-hour island tour, then return to Boston the same evening.

“much confusion on pick up driver was 20 minutes down road, boss finally called him made him turn bavk to hotel for gursts that "may" be there. They were not. Barely made it to ferry. Return trip hit major congestion in Biston. Driver did not attempt alternate route or seek guidance just plowed into traffic and crawled thru Boston. we arrived at hotel 1 1/2 hours late. Spent 3 hours total on return trip. Company too automated and not organized”

Check availability →Read our full review

4.Boston to Plymouth Day-Trip including Quincy, Plimoth Patuxet and Mayflower II

★★★★★★★★★★5.0 · 407 reviews · 11 hours (approx.) · from $165Top rated

Spend about 11 hours exploring Plymouth and Boston’s South Shore by small coach. You’ll visit Plimoth Patuxet, Plymouth Rock, the Forefathers Monument, Quincy, Scituate Lighthouse, and Mayflower II, with guides such as Chris Fisher bringing the route to life.

“I wanted to see the Pilgrim Museum in town. Did not realize "museum" referred to the Indian village. This is mis-leading, If the guide had told me I could have made other arrangements. I suggest that you make the visit to the Museum and the trip to the village an option. I could have seen it on my lunch 2 1/2 break. The guide was very good, though he could have pointed out the chance to visit the museum.”

Check availability →Read our full review

5.Boston to Newport Small-Group Day Trip with Breakers & Marble House Admission

★★★★★★★★★★4.5 · 266 reviews · 11 hours (approx.) · from $155

Travel from downtown Boston to Newport in a small group of up to 24 people. Guide Tim, Chris, or Lucia may lead the day, with mansion audio tours, narrated sightseeing, Cliff Walk views, Ocean Drive, and free time in town.

“The tour director was exceptional. Touring the different mansions were enjoyable but had to download the app on phone to get audio description of each room. That was a little cumbersome. The three hour stroll in Newport shopping area was too long.”

Check availability →Read our full review