4 days in Connecticut, Rhode Island & Massachusetts Itinerary

4 days in Connecticut, Rhode Island & Massachusetts Itinerary

Created using Inspirock United States sightseeing planner

This plan was created by another user.  Make it your plan

Route & dates

4 days in Connecticut, Rhode Island & Massachusetts Itinerary

Start: New York City
Drive:  1​h 45​min
1
New Haven
— 1 day
Drive:  2​h 15​min
2
Newport
— 1 night
Drive:  1​h 30​min
3
Boston
— 2 nights
Fly + bus:  3​h
End: New York City

1
day
New Haven

New Haven ©
New Haven, in the U.S. Kick off your visit on the 24th (Fri): learn more about the world around you at Yale Peabody Museum of Natural History, browse the collection at Beinecke Rare Book & Manuscript Library, and then explore the world behind art at Yale University Art Gallery.

To see other places to visit, more things to do, reviews, and tourist information, read our New Haven trip maker app .

New York City to New Haven is an approximately 2-hour car ride. You can also take a train; or take a bus. Plan for little chillier nights when traveling from New York City in May since evenings lows in New Haven dip to 50°F. Finish up your sightseeing early on the 24th (Fri) so you can go by car to Newport.

Things to do in New Haven

Museums
Highlights from your plan
Yale University Art Gallery ©
Yale University Art Gallery
Yale Peabody Museum of Natural History ©

1
night
Newport

Newport ©
With coastline on the west, south, and east, Newport is a maritime city with a rich history.
Kick off your visit on the 25th (Sat): get to know the fascinating history of Cliff Walk, then examine the collection at The Breakers, then cruise along Ocean Drive Historic District, and finally take in the exciting artwork at Thames Glass.

To see where to stay, traveler tips, photos, and other tourist information, read our Newport itinerary planner.

Drive from New Haven to Newport in 2.5 hours. Alternatively, you can take a train; or take a bus. In May, daytime highs in Newport are 65°F, while nighttime lows are 49°F. Cap off your sightseeing on the 25th (Sat) early enough to go by car to Boston.

Things to do in Newport

Historic Sites Outdoors Museums
Highlights from your plan
Ocean Drive Historic District ©
Ocean Drive Historic District
The Breakers ©
The Breakers

2
nights
Boston

Boston ©
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.
Start off your visit on the 26th (Sun): appreciate the history behind New England Holocaust Memorial, explore the world behind art at Museum of Fine Arts, and then explore and take pictures at Fenway Park. Get ready for a full day of sightseeing on the 27th (Mon): walk around Boston Common, then take in nature's colorful creations at Boston Public Garden, then buy something for everyone on your list at Faneuil Hall Marketplace, and finally get to know the fascinating history of Freedom Trail.

To see other places to visit, traveler tips, ratings, and other tourist information, read Boston trip itinerary planner .

Traveling by car from Newport to Boston takes 1.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. In May, daily temperatures in Boston can reach 67°F, while at night they dip to 50°F. Finish your sightseeing early on the 27th (Mon) so you can travel back home.

Things to do in Boston

Museums Parks Historic Sites
Highlights from your plan
Freedom Trail ©
Freedom Trail
Fenway Park ©
Fenway Park
Museum of Fine Arts ©
Museum of Fine Arts

Similar Plans

8 days in Rhode Island BY A USER FROM UNITED STATES June, teens, kids, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems PREFERENCES: June, teens, kids, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 8 days in Boston, Philadelphia & Lancaster BY A USER FROM UNITED STATES June, teens, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems PREFERENCES: June, teens, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 7 days in Rhode Island, Boston & Essex BY A USER FROM UNITED STATES May, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems PREFERENCES: May, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 8 days in Boston BY A USER FROM UNITED STATES June, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular sights PREFERENCES: June, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 7 days in Boston BY A USER FROM UNITED STATES May, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems PREFERENCES: May, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 5 days in Connecticut BY A USER FROM UNITED STATES June, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems PREFERENCES: June, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 5 days in Boston BY A USER FROM CANADA August, teens, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, popular sights PREFERENCES: August, teens, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 9 days in Seattle & Boston BY A USER FROM UNITED STATES June, teens, kids, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, slow & easy, popular & hidden gems PREFERENCES: June, teens, kids, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Slow & easy 8 days in New England & Albany BY A USER FROM UNITED KINGDOM October, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, wildlife, popular & hidden gems PREFERENCES: October, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 6 days in United States BY A USER FROM POLAND October, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular sights PREFERENCES: October, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 8 days in Boston BY A USER FROM UNITED STATES July, culture, outdoors, relaxing, historic sites, museums, shopping, wildlife, popular & hidden gems PREFERENCES: July, culture, outdoors, relaxing, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 5 days in Boston BY A USER FROM UNITED STATES June, culture, outdoors, relaxing, romantic, historic sites, museums, shopping, wildlife, popular sights PREFERENCES: June, culture, outdoors, relaxing, romantic, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium
View more plans