5 days in Connecticut Itinerary

5 days in Connecticut Itinerary

Created using Inspirock Connecticut trip itinerary planner
Make it your trip
Drive
1
Kent
— 1 day
Drive
2
Chester
— 1 night
Drive
3
New London
— 1 night
Drive
4
Mystic
— 1 night
Drive
5
Old Saybrook
Drive
6
Madison
— 1 night
Drive

S M T W T F S
10
11
12
13
14
15
16
17
18
19
20
21
22
23

Kent — 1 day

Kent is a town in Litchfield County, Connecticut, alongside the border with New York. For ratings, more things to do, maps, and more tourist information, go to the Kent tour planning website.

Albany to Kent is an approximately 2-hour car ride. Expect a daytime high around 85°F in July, and nighttime lows around 64°F. On the 14th (Thu), you're off to Chester.
more
Parks · Outdoors · Museums · Nature

Chester — 1 night

Chester is a town in Middlesex County, Connecticut, United States. To find more things to do, where to stay, and tourist information, read our Chester online itinerary planner.

Traveling by car from Kent to Chester takes 2 hours. Alternatively, you can drive. In July in Chester, expect temperatures between 81°F during the day and 66°F at night. On the 15th (Fri), you'll travel to New London.
more
Shopping · Parks · Nightlife · Nature

New London — 1 night

New London is a seaport city and a port of entry on the northeast coast of the United States. To find traveler tips, maps, other places to visit, and tourist information, refer to the New London online attractions planner.

New London is just a stone's throw from Chester. July in New London sees daily highs of 80°F and lows of 66°F at night. You'll set off for Mystic on the 16th (Sat).
more
Parks · Outdoors · Historic Sites · Nature

Mystic — 1 night

A historical leading seaport, Mystic has maintained a strong respect for the past.
On the 16th (Sat), have some family-friendly fun at Watch Hill Merry-Go-Round and then get outside with Outdoor Activities.

For other places to visit, where to stay, traveler tips, and more tourist information, you can read our Mystic road trip tool.

Mystic is just a short distance from New London. In July, daytime highs in Mystic are 80°F, while nighttime lows are 66°F. Finish your sightseeing early on the 17th (Sun) so you can drive to Old Saybrook.
more
Fun & Games · Outdoors · Tours
Side Trip

Old Saybrook

Old Saybrook is a town in Middlesex County, Connecticut, United States. To find reviews, ratings, where to stay, and other tourist information, refer to the Old Saybrook trip planner.

Old Saybrook is just a short distance from Mystic. July in Old Saybrook sees daily highs of 81°F and lows of 66°F at night. You'll set off for Madison on the 17th (Sun).
more
Parks · Outdoors · Historic Sites · Shopping

Madison — 1 night

Madison is a town in the southeastern corner of New Haven County, Connecticut, United States, occupying a central location on Connecticut's Long Island Sound shoreline. Kick off your visit on the 17th (Sun): don't miss a visit to Guilford Art Center and then steep yourself in history at Hyland House Museum. On your second day here, relax in the rural setting at Field House Farm.

To find reviews, ratings, more things to do, and other tourist information, read Madison trip planner.

Madison is just a short distance from Old Saybrook. In July, daytime highs in Madison are 81°F, while nighttime lows are 66°F. On the 18th (Mon), wrap the sightseeing up by early afternoon so you can drive back home.
more
Historic Sites
Side Trip

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.
more