15 days in Southwest Florida Itinerary

15 days in Southwest Florida Itinerary

Created using Inspirock Southwest Florida trip planner
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Make it your trip
Fly to Southwest Florida International Airport, Drive to Fort Myers Beach
1
Fort Myers Beach
— 3 nights
Drive
2
Sanibel Island
— 2 nights
Drive
3
Siesta Key
— 3 nights
Drive
4
Anna Maria, Anna Maria Island
— 1 night
Drive
5
Marco Island
— 3 nights
Drive
6
Everglades City
— 2 nights
Drive to Miami International Airport, Fly to Kalamazoo

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Fort Myers Beach — 3 nights

Fort Myers Beach is a town located on Estero Island in Lee County, Florida, United States. Explore Fort Myers Beach's surroundings by going to Edison and Ford Winter Estates (in Fort Myers) and Naples (Lowdermilk Beach, Naples Pier, &more). The adventure continues: glide through the air with a parasailing or paragliding tour, get a taste of the local shopping with Harbour View Gallery, enjoy the sand and surf at Fort Myers Beach, and stroll through Lovers Key State Park.

To find more things to do, other places to visit, reviews, and tourist information, read our Fort Myers Beach online itinerary planner.

Kalamazoo to Fort Myers Beach is an approximately 7.5-hour combination of flight and car. You can also drive. Plan for a bit warmer temperatures traveling from Kalamazoo in May, with highs in Fort Myers Beach at 90°F and lows at 69°F. Finish your sightseeing early on the 11th (Wed) to allow enough time to drive to Sanibel Island.
Parks · Outdoors · Museums · Beaches
Side Trips

Sanibel Island — 2 nights

Take a trip to Sanibel Island if you like pretty sunsets and luxurious resorts.
Start off your visit on the 12th (Thu): cast your line with Whitney's Bait and Tackle, visit a coastal fixture at Sanibel Island Lighthouse, and then stop by Three Crafty Ladies. Here are some ideas for day two: stroll through J.N. "Ding" Darling National Wildlife Refuge, soothe aching muscles at some of the top local wellness centers, and then enjoy the sand and surf at Bowman's Beach.

For other places to visit, photos, more things to do, and tourist information, refer to the Sanibel Island trip website.

Sanibel Island is just a short distance from Fort Myers Beach. Expect a daytime high around 90°F in May, and nighttime lows around 69°F. Finish your sightseeing early on the 13th (Fri) so you can drive to Siesta Key.
Parks · Wildlife · Outdoors · Spas

Siesta Key — 3 nights

Siesta Key draws most of its visitors with soft, white-quartz sand beaches and translucent ocean water.
Venture out of the city with trips to Venice Fishing Pier (in Venice) and Horseback Riding Tours (in Bradenton). The adventure continues: tour the pleasant surroundings at Siesta Beach, don't miss a visit to Siesta Key Village, buy something for everyone on your list at St. Armands Circle, and glide peacefully along the water with some of the best stand-up paddleboarding in the area.

To find traveler tips, maps, ratings, and more tourist information, you can read our Siesta Key trip itinerary builder site.

You can drive from Sanibel Island to Siesta Key in 2 hours. Alternatively, you can do a combination of taxi and bus. Expect a daytime high around 87°F in May, and nighttime lows around 68°F. Finish your sightseeing early on the 16th (Mon) so you can drive to Anna Maria.
Outdoors · Parks · Tours · Adventure
Side Trips

Anna Maria, Anna Maria Island — 1 night

Anna Maria, is a city in Manatee County, Florida, United States. On the 17th (Tue), enjoy the sand and surf at Bean Point and then see majestic marine mammals with Anna Maria Island Dolphin Tours.

To see photos, where to stay, ratings, and more tourist information, you can read our Anna Maria trip app.

You can drive from Siesta Key to Anna Maria in an hour. Another option is to take a bus. In May in Anna Maria, expect temperatures between 87°F during the day and 68°F at night. Finish your sightseeing early on the 17th (Tue) so you can drive to Marco Island.
Outdoors · Parks · Tours · Wildlife

Marco Island — 3 nights

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. Marco Island is known for wildlife, adventure, and beaches. Your trip includes some of its best attractions: see majestic marine mammals with a dolphin and whale watching tour, contemplate the waterfront views at Capri Paddlecraft Park, enjoy the sand and surf at Tigertail Beach, and look for gifts at Keep In Touch.

Quickly create a custom-made itinerary for Marco Island using our trip planner.

Getting from Anna Maria to Marco Island by car takes about 3 hours. Other options: do a combination of taxi and bus; or do a combination of bus and taxi. Expect a daytime high around 88°F in May, and nighttime lows around 69°F. Finish up your sightseeing early on the 20th (Fri) so you can go by car to Everglades City.
Parks · Outdoors · Wildlife · Beaches

Everglades City — 2 nights

Everglades City is a city in Collier County, Florida, United States, of which it is the former county seat. Start off your visit on the 21st (Sat): trek along Loop Road and then shop like a local with Clyde Butcher's Big Cypress Gallery. On your second day here, race across the water with a speed boat tour.

To see reviews, ratings, where to stay, and tourist information, read our Everglades City trip builder app.

You can drive from Marco Island to Everglades City in an hour. In May in Everglades City, expect temperatures between 88°F during the day and 69°F at night. On the 22nd (Sun), wrap the sightseeing up by early afternoon so you can travel back home.
Outdoors · Trails · Shopping · Parks
Side Trip