10 days in Chester, Key West & St. Augustine Itinerary

10 days in Chester, Key West & St. Augustine Itinerary

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Route & dates

10 days in Chester, Key West & St. Augustine Itinerary

Start: Richmond
Drive:  30​min
1
Chester
— 1 night
Fly:  6​h 45​min
2
Key West
— 3 nights
Fly + Drive:  5​h 45​min
3
St. Augustine
— 3 nights
bus + Fly:  8​h 30​min
End: Richmond

1
night
Chester

Chester ©
Chester is a census-designated place (CDP) in Chesterfield County, Virginia, United States. Kick off your visit on the 9th (Sat): see the interesting displays at Pocahontas Island Black History Museum, contemplate the long history of Farmers Bank, explore the different monuments and memorials at Blandford Church and Cemetery, then see the interesting displays at Keystone Tractor Works, and finally stroll through Roslyn Landing Park. Get ready for a full day of sightseeing on the 10th (Sun): contemplate the long history of Henricus Historical Park, explore the different monuments and memorials at Cold Harbor National Cemetery, and then have some family-friendly fun at Ironbridge Sports Park.

To find where to stay, ratings, reviews, and other tourist information, read our Chester journey planning tool .

Richmond to Chester is an approximately half hour car ride. In February, daily temperatures in Chester can reach 51°F, while at night they dip to 31°F. Finish your sightseeing early on the 10th (Sun) to allow enough time to travel to Key West.

Things to do in Chester

Historic Sites Museums Fun & Games

Side Trips

Petersburg, Colonial Heights, Cold Harbor National Cemetery
Highlights from your plan
Farmers Bank ©
Farmers Bank
Keystone Tractor Works ©
Keystone Tractor Works
Henricus Historical Park ©
Henricus Historical Park

3
nights
Key West

Key West ©
Located just 140 km (90 mi) from Cuba, Key West is an island only about 6.4 km (4 mi) long and 1.6 km (1 mi) wide.
Key West is known for adventure, museums, nightlife, wildlife, and nature. Your plan includes some of its best attractions: see the interesting displays at The Ernest Hemingway Home and Museum, identify plant and animal life at Key West Butterfly & Nature Conservatory, take a memorable drive along The Overseas Highway, and cast your line with a fishing tour.

To see maps, other places to visit, and tourist information, go to the Key West online vacation planner .

Explore your travel options from Chester to Key West with the Route module. Traveling from Chester in February, things will get much warmer in Key West: highs are around 78°F and lows about 68°F. Finish your sightseeing early on the 14th (Thu) to allow enough time to travel to St. Augustine.

Things to do in Key West

Outdoors Tours Museums
Highlights from your plan
The Ernest Hemingway Home and Museum ©
Mallory Square ©
Mallory Square

3
nights
St. Augustine

St. Augustine ©
SAINT AUGUSTINE | PONTE VEDRA on Florida's Historic Coast The Nation's oldest city (est. Step out of St. Augustine to go to DeLand and see Stetson Mansion, which is approximately 1h 35 min away. Next up on the itinerary: brush up on your knowledge of spirits at St. Augustine Distillery, tour the water at your own pace with Red Boat Water Tours, LLC, explore and take pictures at Flagler College, and look for all kinds of wild species at St. Augustine Alligator Farm Zoological Park.

To find maps, traveler tips, photos, and other tourist information, you can read our St. Augustine holiday website .

Traveling by combination of flight and car from Key West to St. Augustine takes 6 hours. Alternatively, you can do a combination of flight and bus; or drive. Expect a bit cooler temperatures when traveling from Key West in February; daily highs in St. Augustine reach 68°F and lows reach 51°F. Wrap up your sightseeing by early afternoon on the 18th (Mon) to allow time for travel back home.

Things to do in St. Augustine

Parks Historic Sites Wildlife

Side Trip

Stetson Mansion
Highlights from your plan
Stetson Mansion ©
Stetson Mansion
St. Augustine Distillery ©
St. Augustine Distillery

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