21 days in Hartford, New Haven & Bridgeport Itinerary

21 days in Hartford, New Haven & Bridgeport Itinerary

Created using Inspirock Connecticut route planner

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Make it your trip
Fly
1
Hartford
— 6 nights
Drive
2
New Haven
— 7 nights
Drive
3
Bridgeport
— 7 nights
Drive to La Guardia Airport, Fly to Orlando International Airport

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Hartford

— 6 nights
Hartford is the capital of the U.S. state of Connecticut. Family-friendly places like The Mark Twain House & Museum and Forest Park will thrill your kids. You'll find plenty of places to visit near Hartford: Springfield Museums (in Springfield), East Haddam (Ray of Light Farm & Gillette Castle State Park) and Hubbard Park (in Meriden). Next up on the itinerary: explore the world behind art at Wadsworth Atheneum Museum of Art, explore the engaging exhibits at Kidcity Children's Museum, gain insight at Old Sturbridge Village, and find something for the whole family at Six Flags New England.

To see traveler tips, maps, reviews, and more tourist information, go to the Hartford trip planner.

Orlando to Hartford is an approximately 6-hour flight. You can also drive; or take a bus. Expect cooler temperatures when traveling from Orlando in December; daily highs in Hartford reach 42°F and lows reach 28°F. Wrap up your sightseeing on the 7th (Mon) to allow time to drive to New Haven.

Things to do in Hartford

Museums · Parks · Historic Sites · Childrens Museums

Side Trips

New Haven

— 7 nights
New Haven, in the U.S. state of Connecticut, is the principal municipality in Greater New Haven, which had a total population of 862,477 in 2010. Kids will appreciate attractions like Yale University Art Gallery and Yale University. Explore New Haven's surroundings by going to Ocean Beach Park (in New London), Waterford (Pleasure Beach, Harkness Memorial State Park, &more) and Madison (The Shoreline Greenway Trail, RJ Julia Booksellers, &more). There's much more to do: take an in-depth tour of Blessed Michael McGivney Pilgrimage Center, stroll around East Rock Park, explore the world behind art at Yale Center for British Art, and tour the pleasant surroundings at Hammonasset Beach State Park.

To see traveler tips, reviews, where to stay, and more tourist information, go to the New Haven trip itinerary builder app.

You can drive from Hartford to New Haven in an hour. Alternatively, you can drive; or take a train; or take a bus. In December, plan for daily highs up to 44°F, and evening lows to 31°F. Cap off your sightseeing on the 14th (Mon) early enough to go by car to Bridgeport.

Things to do in New Haven

Museums · Parks · Outdoors · Historic Sites

Side Trips

Bridgeport

— 7 nights
Bridgeport is a seaport city in the U.S. state of Connecticut. Kids will appreciate attractions like Housatonic Museum of Art and Discovery Museum. Venture out of the city with trips to Mount Sinai (Cedar Beach & Ralph's Fishing Station), Port Jefferson (Maritime Explorium & Mather House Museum) and East Setauket Pond Park (in East Setauket). And it doesn't end there: admire nature's wide array of creatures at Beardsley Zoo, examine the collection at Bridgeport Public Library, visit a coastal fixture at Fayerweather Island Light, and kick back and relax at Compo Beach.

To see traveler tips, where to stay, photos, and tourist information, go to the Bridgeport holiday maker website.

Bridgeport is just a stone's throw from New Haven. In December, daytime highs in Bridgeport are 45°F, while nighttime lows are 32°F. You'll have a few hours on the 21st (Mon) to wrap things up before traveling home.

Things to do in Bridgeport

Parks · Museums · Outdoors · Beaches

Side Trips