5 days in Florida, Jekyll Island & Maryland Itinerary

5 days in Florida, Jekyll Island & Maryland Itinerary

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Route & dates

5 days in Florida, Jekyll Island & Maryland Itinerary

Start: Tampa
Drive:  1​h 30​min
1
Orlando
— 1 night
Drive:  3​h 45​min
2
Jekyll Island
— 1 night
bus + Fly:  7​h 45​min
3
Baltimore
— 1 day
+2
train + subway + Fly:  5​h 30​min
4
Key West
— 1 night
Fly:  4​h 15​min
End: Tampa


Learn more about your trip

1
night
Orlando

Orlando ©
For most people, any mention of Orlando immediately conjures up images of sprawling theme parks filled with characters plucked right out of popular animated movies.
Start off your visit on the 31st (Wed): get in on the family fun at Universal Orlando Resort. Here are some ideas for day two: get in on the family fun at Walt Disney World Resort, make an unforgettable trip to Happily Ever After Fireworks, and then test your problem-solving skills at The Escape Game Orlando.

To find other places to visit, where to stay, and tourist information, you can read our Orlando route planner.

Tampa to Orlando is an approximately 1.5-hour car ride. You can also take a bus; or take a train. In July in Orlando, expect temperatures between 91°F during the day and 75°F at night. Cap off your sightseeing on the 1st (Thu) early enough to go by car to Jekyll Island.

Things to do in Orlando

Theme Parks Fun & Games Nightlife
Highlights from your plan
Walt Disney World Resort ©
Walt Disney World Resort
Universal Orlando Resort ©
Universal Orlando Resort
Happily Ever After Fireworks ©
Happily Ever After Fireworks

1
night
Jekyll Island

A vacation on Jekyll Island allows visitors to discover the lifestyle of American aristocrats from the 19th century.
Kick off your visit on the 2nd (Fri): get up close to creatures of the deep with a dolphin and whale watching tour and then see what you can catch with a fishing tour.

To find other places to visit, more things to do, photos, and other tourist information, you can read our Jekyll Island online trip itinerary builder .

Getting from Orlando to Jekyll Island by car takes about 4 hours. Other options: do a combination of train and car; or fly. In August in Jekyll Island, expect temperatures between 89°F during the day and 76°F at night. Finish up your sightseeing early on the 2nd (Fri) so you can travel to Baltimore.

Things to do in Jekyll Island

Tours Wildlife Outdoors

Side Trip

Fishing Charters & Tours
Highlights from your plan
Dolphin & Whale Watching
Fishing Charters & Tours

1
day
Baltimore

Baltimore ©
A major center for tourism and travel, Baltimore is famous as the city where amateur poet Francis Scott Key wrote the lyrics for the United States' national anthem.
On the 3rd (Sat), try to win big at Horseshoe Casino and then brush up on your knowledge of spirits at Sagamore Spirit Distillery.

For ratings, photos, traveler tips, and tourist information, read Baltimore trip itinerary builder app .

Traveling by combination of bus and flight from Jekyll Island to Baltimore takes 8 hours. Alternatively, you can do a combination of bus, flight, and train; or drive. Expect a bit cooler evenings in Baltimore when traveling from Jekyll Island in August, with lows around 71°F. Finish up your sightseeing early on the 3rd (Sat) so you can travel to Key West.

Things to do in Baltimore

Fun & Games Casinos Breweries & Distilleries
Highlights from your plan
Sagamore Spirit Distillery ©
Sagamore Spirit Distillery
Horseshoe Casino ©
Horseshoe Casino

1
night
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.
Kick off your visit on the 4th (Sun): examine the collection at The Ernest Hemingway Home and Museum, look for all kinds of wild species at Key West Butterfly & Nature Conservatory, then shop like a local with 7 Artists & Friends, and finally fly like a bird with a parasailing or paragliding tour.

Ask Inspirock to suggest an itinerary and make planning a trip to Key West fast, fun, and easy.

You can do a combination of train and flight from Baltimore to Key West in 5.5 hours. Other options are to fly; or drive. Traveling from Baltimore in August, expect a bit warmer with lows of 81°F in Key West. Finish your sightseeing early on the 4th (Sun) to allow enough time to travel back home.

Things to do in Key West

Museums Tours Parks
Highlights from your plan
7 Artists & Friends ©
7 Artists & Friends
The Ernest Hemingway Home and Museum ©

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