21 days in Connecticut Itinerary

21 days in Connecticut Itinerary

Created using Inspirock Connecticut trip itinerary planner
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Make it your trip
Fly to Logan International Airport, Drive to Mystic
1
Mystic
— 6 nights
Drive
2
Simsbury
— 6 nights
Drive
3
New Haven
— 7 nights
Train to South Station, Fly to Dubai

S M T W T F S
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Mystic — 6 nights

A historical leading seaport, Mystic has maintained a strong respect for the past.
You'll find plenty of places to visit near Mystic: Main Street Park, Essex Village (in Essex), East Haddam (Allegra Farm And The Horsedrawn Carriage And Sleigh Museum Of New England & Gillette Castle State Park) and Machimoodus State Park (in Moodus). There's lots more to do: look and learn at Mystic Seaport Museum, step aboard Charles W. Morgan, take in the views from Mystic River Bascule Bridge, and steep yourself in history at Olde Mistick Village.

Plan a Mystic trip in moments using our itinerary builder.

Dubai, United Arab Emirates to Mystic is an approximately 23.5-hour combination of flight and car. You can also do a combination of flight and train. Due to the time zone difference, you'll gain 9 hours traveling from Dubai to Mystic. In September, Mystic is much colder than Dubai - with highs of 28°C and lows of 17°C. Cap off your sightseeing on the 15th (Thu) early enough to go by car to Simsbury.
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Parks · Historic Sites · Nature · Museums
Side Trips

Simsbury — 6 nights

Simsbury is an affluent town in Hartford County, Connecticut, United States. Explore the numerous day-trip ideas around Simsbury: Vernon Rails-to-Trails (in Vernon), Lake Compounce (in Bristol) and The Lodge at Crandall Park (in Tolland). Next up on the itinerary: tour the pleasant surroundings at Talcott Mountain State Park, trek along West Hartford Reservoir, identify plant and animal life at White Memorial Conservation Center, and take in the dramatic scenery at Kent Falls State Park.

For photos, traveler tips, ratings, and more tourist information, refer to the Simsbury road trip website.

Getting from Mystic to Simsbury by car takes about 1.5 hours. In September, plan for daily highs up to 30°C, and evening lows to 14°C. Wrap up your sightseeing on the 21st (Wed) to allow time to drive to New Haven.
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Parks · Outdoors · Trails · Wildlife
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. You'll find plenty of places to visit near New Haven: Wickham Park (in Manchester), The Mark Twain House & Museum (in Hartford) and Gotta's Farm and Cider Mill (in Portland). The adventure continues: explore the world behind art at Yale University Art Gallery, enjoy the sand and surf at Hammonasset Beach State Park, admire the majestic nature at Silver Sands State Park, and get outside with Outdoor Activities.

For where to stay, reviews, traveler tips, and tourist information, you can read our New Haven journey planner.

Traveling by car from Simsbury to New Haven takes 1.5 hours. In September, daytime highs in New Haven are 29°C, while nighttime lows are 17°C. Finish your sightseeing early on the 28th (Wed) to allow enough time to travel back home.
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Parks · Outdoors · Nature · Trails
Side Trips

Connecticut travel guide

4.3
Historic Sites · Aquariums · Theaters
The Constitution State
Perhaps best known for its renowned private and public universities, Connecticut was once home to the country's first law school and still boasts one of the oldest secondary schools in America. More than just a small state packed with students, Connecticut offers visitors a chance to explore some of New England's finest tourist attractions while on vacation, including lighthouses, beaches, theaters, museums, galleries, and restaurants. Despite its small size, the state also boasts two large casino complexes, both located on Native American reservations. Rich in history and natural beauty, Connecticut draws newcomers from around the world, with large Polish, Chinese, and Hispanic communities.
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