5 days in Southwest Florida Itinerary

5 days in Southwest Florida Itinerary

Created using Inspirock Southwest Florida journey planner

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Make it your trip
Drive
1
Englewood
— 1 day
Drive
2
Fort Myers Beach
— 1 night
Drive
3
Captiva Island
— 1 night
Drive
4
Bradenton Beach, Anna Maria Island
— 2 nights
Drive

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Englewood

— 1 day
Englewood is a census-designated place (CDP) in Charlotte and Sarasota counties in the U.S. state of Florida. Start off your visit on the 24th (Wed): get a dose of the wild on a nature and wildlife tour, then kick back and relax at Stump Pass Beach State Park, and then kick back and relax at Englewood Beach.

For more things to do, photos, traveler tips, and tourist information, refer to the Englewood journey planner.

Orlando to Englewood is an approximately 2.5-hour car ride. You can also do a combination of bus and taxi; or do a combination of train, bus, and taxi. Expect a daytime high around 79°F in November, and nighttime lows around 62°F. Wrap up your sightseeing on the 24th (Wed) early enough to drive to Fort Myers Beach.

Things to do in Englewood

Outdoors · Parks · Beaches · Nature

Fort Myers Beach

— 1 night
Fort Myers Beach is a town located on Estero Island in Lee County, Florida, United States. Kick off your visit on the 25th (Thu): cruise along Sanibel Causeway and then discover the deep blue sea with Island Time Dolphin & Shelling Cruises.

To see maps, where to stay, ratings, and tourist information, read Fort Myers Beach trip planner.

Drive from Englewood to Fort Myers Beach in 2 hours. Alternatively, you can take a bus. November in Fort Myers Beach sees daily highs of 82°F and lows of 63°F at night. Cap off your sightseeing on the 25th (Thu) early enough to go by car to Captiva Island.

Things to do in Fort Myers Beach

Outdoors · Wildlife · Tours · Scenic Drive

Side Trip

Captiva Island

— 1 night
On the 26th (Fri), kick back and relax at Captiva Beach, head outdoors with Outdoor Activities, and then contemplate in the serene atmosphere at Captiva Chapel By-The-Sea.

To find reviews, photos, other places to visit, and tourist information, go to the Captiva Island vacation planning app.

Drive from Fort Myers Beach to Captiva Island in an hour. In November, daily temperatures in Captiva Island can reach 82°F, while at night they dip to 63°F. Finish your sightseeing early on the 26th (Fri) to allow enough time to drive to Bradenton Beach.

Things to do in Captiva Island

Outdoors · Historic Sites · Parks · Wildlife

Bradenton Beach, Anna Maria Island

— 2 nights
Bradenton Beach is a city on Anna Maria Island in Manatee County, Florida, United States. On the 27th (Sat), tour the pleasant surroundings at Bean Point and then see majestic marine mammals with Anna Maria Island Dolphin Tours. Get ready for a full day of sightseeing on the next day: enjoy the sand and surf at Coquina Beach, browse the eclectic array of goods at Beach Market at Coquina Beach, and then kick back and relax at Bradenton Beach.

For ratings, reviews, and tourist information, you can read our Bradenton Beach trip planner.

Drive from Captiva Island to Bradenton Beach in 3 hours. Alternatively, you can do a combination of taxi and bus. In November, daily temperatures in Bradenton Beach can reach 80°F, while at night they dip to 62°F. Finish up your sightseeing early on the 28th (Sun) so you can go by car back home.

Things to do in Bradenton Beach

Outdoors · Parks · Beaches · Wildlife

Side Trip