16 days in United States Itinerary

16 days in United States Itinerary

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Route & dates

16 days in United States Itinerary

Start: Chicago
Fly:  5​h 45​min
1
Tampa
— 2 nights
bus:  30​min
2
St. Petersburg
— 4 nights
Drive:  1​h 15​min
3
Siesta Key
— 3 nights
Drive:  2​h 30​min
4
Marco Island
— 5 nights
bus + Fly:  7​h 30​min
End: Chicago

2
nights
Tampa

Tampa ©
Tampa ranks among the country's most livable cities, attracting newcomers with its growing economy and status as a major port on the Gulf of Mexico.
Start off your visit on the 7th (Thu): contemplate in the serene atmosphere at Wat Mongkolrata Temple. Keep things going the next day: get up close and personal with brilliant marine life at The Florida Aquarium, wander the streets of Ybor City, and then test your team's savvy at popular escape rooms.

To find out how to plan a trip to Tampa, use our trip itinerary maker.

Chicago to Tampa is an approximately 6-hour flight. You can also do a combination of flight and bus; or drive. The time zone changes from Central Standard Time (CST) to Eastern Standard Time (EST), which is usually a 1 hour difference. Prepare for somewhat warmer weather when traveling from Chicago in May: high temperatures in Tampa hover around 89°F and lows are around 71°F. Wrap up your sightseeing on the 9th (Sat) to allow time to drive to St. Petersburg.

Things to do in Tampa

Parks Beaches Historic Sites

Side Trip

Sunset Beach
Highlights from your plan
The Florida Aquarium ©
The Florida Aquarium
Ybor City ©
Ybor City
Wat Mongkolrata Temple ©
Wat Mongkolrata Temple

4
nights
St. Petersburg

St. Petersburg ©
Located on a peninsula between Tampa Bay and the Gulf of Mexico, St.
Get some cultural insight at Duncan McClellan Gallery and Murielle Winery. Your itinerary includes some good beach time at Clearwater Beach and Saint Pete Beach. And it doesn't end there: see the interesting displays at The Dali Museum, glide through the air with a parasailing or paragliding tour, learn about winemaking at Florida Orange Groves and Winery, and explore the world behind art at Chihuly Collection.

To find reviews, other places to visit, more things to do, and other tourist information, go to the St. Petersburg trip itinerary builder .

St. Petersburg is just a short distance from Tampa. In May, daytime highs in St. Petersburg are 86°F, while nighttime lows are 73°F. Finish your sightseeing early on the 13th (Wed) to allow enough time to drive to Siesta Key.

Things to do in St. Petersburg

Outdoors Museums Parks

Side Trips

Clearwater, St. Pete Beach, Parasailing & Paragliding, Treasure Island Beach
Highlights from your plan
Duncan McClellan Gallery ©
Duncan McClellan Gallery
Clearwater Beach ©
Clearwater Beach
Saint Pete Beach ©
Saint Pete Beach

3
nights
Siesta Key

Siesta Key ©
Siesta Key draws most of its visitors with soft, white-quartz sand beaches and translucent ocean water.
You'll enjoy a bit of beach vacationing at Siesta Beach and Crescent Beach. Get some cultural insight at Sarasota National Cemetery and AlexArt International Art Gallery. There's much more to do: explore the world behind art at The Ringling, look for gifts at Silver City Sarasota, enjoy the sand and surf at Siesta Key Beach, and get to know the fascinating history of Marie Selby Botanical Gardens.

To find photos, more things to do, and other tourist information, refer to the Siesta Key visit planner.

You can drive from St. Petersburg to Siesta Key in 1.5 hours. Alternatively, you can take a bus. Traveling from St. Petersburg in May, expect little chillier with lows of 68°F in Siesta Key. Wrap up your sightseeing on the 16th (Sat) early enough to drive to Marco Island.

Things to do in Siesta Key

Parks Beaches Outdoors

Side Trip

Sarasota
Highlights from your plan
Sarasota National Cemetery ©
Sarasota National Cemetery
Siesta Beach ©
Siesta Beach
Crescent Beach ©
Crescent Beach

5
nights
Marco Island

Marco Island is a city in Collier County, Florida, United States, located on an island by the same name in the Gulf of Mexico off the coast of Southwest Florida. We've included these beaches for you: South Marco Beach and Tigertail Beach. Your cultural itinerary includes sights like Marco Island Historical Museum and San Marco Catholic Church. Explore the numerous day-trip ideas around Marco Island: Speed Boats Tours (in Everglades City) and Smallwood Store (in Chokoloskee). There's lots more to do: get up close to creatures of the deep with a dolphin and whale watching tour, find your balance on the water with some of the best stand-up paddleboarding in the area, fly like a bird with a parasailing or paragliding tour, and look for gifts at Keep In Touch.

To find maps, ratings, where to stay, and other tourist information, refer to the Marco Island journey website .

Traveling by car from Siesta Key to Marco Island takes 2.5 hours. Alternatively, you can take a bus. In May in Marco Island, expect temperatures between 88°F during the day and 69°F at night. Wrap up your sightseeing on the 21st (Thu) early enough to travel back home.

Things to do in Marco Island

Outdoors Tours Wildlife

Side Trips

Speed Boats Tours, Smallwood Store
Highlights from your plan
Dolphin & Whale Watching
South Marco Beach ©
South Marco Beach
Tigertail Beach ©
Tigertail Beach

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