4 days in Southwest Florida Itinerary

4 days in Southwest Florida Itinerary

Created using Inspirock Southwest Florida vacation planner
Make it your trip
Fly
1
Siesta Key
— 1 night
Drive
2
Naples
— 1 night
Drive
3
Marco Island
— 1 night
Fly

S M T W T F S
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Siesta Key — 1 night

Siesta Key draws most of its visitors with soft, white-quartz sand beaches and translucent ocean water.
Kick off your visit on the 19th (Thu): explore the world behind art at The Ringling, then stroll through Save Our Seabirds, and then browse the different shops at St. Armands Circle. On the 20th (Fri), you'll have a packed day of sightseeing: don't miss a visit to Siesta Key Village, then enjoy the sand and surf at Siesta Beach, and then glide peacefully along the water with some of the best stand-up paddleboarding in the area.

For ratings, traveler tips, reviews, and more tourist information, refer to the Siesta Key online sightseeing planner.

Chicago to Siesta Key is an approximately 4.5-hour flight. You can also drive; or do a combination of bus, subway, and taxi. Due to the time zone difference, you'll lose 1 hour traveling from Chicago to Siesta Key. Traveling from Chicago in May, things will get a bit warmer in Siesta Key: highs are around 87°F and lows about 68°F. Finish your sightseeing early on the 20th (Fri) to allow enough time to drive to Naples.
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Outdoors · Parks · Beaches · Adventure
Side Trip

Naples — 1 night

Start off your visit on the 21st (Sat): admire the natural beauty at Naples Botanical Garden, glide peacefully along the water with some of the best stand-up paddleboarding in the area, and then take a leisurely stroll along Naples Pier.

For other places to visit, reviews, where to stay, and more tourist information, go to the Naples trip planner.

Traveling by car from Siesta Key to Naples takes 2 hours. Alternatively, you can do a combination of bus and taxi. In May, daytime highs in Naples are 88°F, while nighttime lows are 70°F. Finish up your sightseeing early on the 21st (Sat) so you can go by car to Marco Island.
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Parks · Adventure · Outdoors · Tours

Marco Island — 1 night

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. Start off your visit on the 22nd (Sun): head outdoors with Outdoor Activities and then kick back and relax at Keewaydin Island.

To see other places to visit, more things to do, reviews, and other tourist information, read our Marco Island trip planner.

Marco Island is just a stone's throw from Naples. In May, daytime highs in Marco Island are 88°F, while nighttime lows are 69°F. Wrap up your sightseeing on the 22nd (Sun) early enough to fly back home.
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Outdoors · Beaches · Wildlife · Tours