60 days in Southwest Florida Itinerary

60 days in Southwest Florida Itinerary

Created using Inspirock Southwest Florida trip planner
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Make it your trip
Fly
1
Everglades City
— 6 nights
Drive
2
Marco Island
— 11 nights
Drive
3
Fort Myers Beach
— 8 nights
Drive
4
Captiva Island
— 6 nights
Drive
5
Sanibel Island
— 13 nights
Drive
6
Bradenton
— 8 nights
Drive
7
Bradenton Beach, Anna Maria Island
— 7 nights
Fly

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Everglades City — 6 nights

Everglades City is a city in Collier County, Florida, United States, of which it is the former county seat. Get in touch with nature at Big Cypress National Preserve and Fakahatchee Strand Preserve State Park. Discover out-of-the-way places like Fishing Charters & Tours and Nature & Wildlife Tours. You'll find plenty of places to visit near Everglades City: Immokalee (Seminole Casino Hotel & Florida Panther National Wildlife Refuge) and Ochopee (Loop Road & Turner River Road). There's still lots to do: examine the collection at Museum of the Everglades, explore the galleries of Skunk Ape Research Center, contemplate the long history of Smallwood Store, and hike along Kirby Storter Roadside Park.

To see other places to visit, more things to do, photos, and other tourist information, you can read our Everglades City tour itinerary planner.

Portland to Everglades City is an approximately 6-hour flight. You can also drive; or do a combination of bus, train, and car. Traveling from Portland in November, expect Everglades City to be much hotter, temps between 81°F and 64°F. Wrap up your sightseeing on the 7th (Sun) early enough to drive to Marco Island.
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Wildlife · Parks · Outdoors · Museums
Side Trips

Marco Island — 11 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. You'll explore the less-touristy side of things at Native Guided Fishing Charters and South Marco Beach. Get a sense of the local culture at Marco Island Historical Museum and San Marco Catholic Church. There's still lots to do: enjoy the sand and surf at Keewaydin Island, stroll around Frank E. Mackle Park, indulge in some personalized pampering at some of the best spas, and explore the landscape on two wheels at Island Bike Shop & Bicycle Rentals.

To see other places to visit, reviews, maps, and more tourist information, go to the Marco Island route planner.

Traveling by car from Everglades City to Marco Island takes an hour. In November, daily temperatures in Marco Island can reach 81°F, while at night they dip to 64°F. Wrap up your sightseeing on the 18th (Thu) to allow time to drive to Fort Myers Beach.
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Parks · Outdoors · Wildlife · Beaches

Fort Myers Beach — 8 nights

Fort Myers Beach is a town located on Estero Island in Lee County, Florida, United States. Explore hidden gems such as Everglades Day Safari and Revs Institute. Get in touch with nature at Four Mile Cove Ecological Preserve and Cape Coral. You'll find plenty of places to visit near Fort Myers Beach: Fort Myers River District (in Fort Myers) and Naples (Clam Pass Park, Third Street South, &more). There's still lots to do: see some colorful creatures with Island Time Dolphin & Shelling Cruises, stroll around Lakes Regional Park, play a few rounds at Castle Golf, and enjoy the sand and surf at Bonita Springs Public Beach.

To find traveler tips, reviews, other places to visit, and more tourist information, refer to the Fort Myers Beach trip planner.

Drive from Marco Island to Fort Myers Beach in 1.5 hours. Alternatively, you can do a combination of taxi and bus; or do a combination of bus and taxi. In November, daily temperatures in Fort Myers Beach can reach 82°F, while at night they dip to 63°F. Wrap up your sightseeing on the 26th (Fri) early enough to drive to Captiva Island.
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Outdoors · Parks · Wildlife · Beaches
Side Trips

Captiva Island — 6 nights

Get some cultural insight at Captiva Chapel By-The-Sea and Jungle Drums Gallery on Captiva Island, FL. Escape the urban bustle at Captiva Beach and Captiva Pass.

To see photos, traveler tips, reviews, and more tourist information, you can read our Captiva Island day trip app.

Getting from Fort Myers Beach to Captiva Island by car takes about an hour. In November, plan for daily highs up to 82°F, and evening lows to 63°F. Wrap up your sightseeing by early afternoon on the 2nd (Thu) to allow time for the car ride to Sanibel Island.
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Parks · Shopping · Nature · Museums

Sanibel Island — 13 nights

Take a trip to Sanibel Island if you like pretty sunsets and luxurious resorts.
Explore hidden gems such as Sanibel Causeway and Tarpon Bay Beach. Sanibel Historical Museum and Village and Sanibel Island Lighthouse will appeal to history buffs. There's lots more to do: enjoy the sand and surf at Blind Pass Beach Park, tee off at The Dunes Golf & Tennis Club, relax and rejuvenate at some of the best spas, and see what you can catch with Whitney's Bait and Tackle.

For ratings, traveler tips, where to stay, and tourist information, read our Sanibel Island travel itinerary planner.

Sanibel Island is just a stone's throw from Captiva Island. December in Sanibel Island sees daily highs of 80°F and lows of 62°F at night. Finish your sightseeing early on the 15th (Wed) to allow enough time to drive to Bradenton.
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Parks · Outdoors · Wildlife · Shopping

Bradenton — 8 nights

Friendly City

Bradenton boasts a handful of historical buildings, but its real claim to fame is as the home of Tropicana Products and its quirky culture.
You'll discover tucked-away gems like Robinson Nature Preserve and Englewood Beach. Get some cultural insight at De Soto National Memorial and Sarasota National Cemetery. Explore the numerous day-trip ideas around Bradenton: Sarasota (Kayaking & Canoeing & Legacy Trail), Englewood (Stump Pass Beach State Park, Manasota Key Beach, &more) and Siesta Key (Spas, Crescent Beach, &more). And it doesn't end there: take a pleasant ride with a tour on horseback, kick back and relax at Nokomis Beach, and tour the pleasant surroundings at North Jetty Beach.

To find reviews, other places to visit, photos, and tourist information, you can read our Bradenton attractions planner.

Drive from Sanibel Island to Bradenton in 2.5 hours. Alternatively, you can do a combination of taxi and bus. In December in Bradenton, expect temperatures between 78°F during the day and 59°F at night. Cap off your sightseeing on the 23rd (Thu) early enough to go by car to Bradenton Beach.
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Outdoors · Parks · Beaches · Nature
Side Trips

Bradenton Beach, Anna Maria Island — 7 nights

Bradenton Beach is a city on Anna Maria Island in Manatee County, Florida, United States. Coquina Baywalk and Anna Maria Island Historical Museum are good opportunities to explore the local culture. You'll explore the less-touristy side of things at Bradenton Beach and Spas. There's lots more to do: see majestic marine mammals with Anna Maria Island Dolphin Tours, stroll around Joan M. Durante Community Park, enjoy the sand and surf at Holmes Beach, and tee off at Harbourside Golf Course.

For photos, ratings, and other tourist information, you can read our Bradenton Beach vacation planner.

Bradenton Beach is just a stone's throw from Bradenton. In December, daily temperatures in Bradenton Beach can reach 78°F, while at night they dip to 59°F. Finish your sightseeing early on the 30th (Thu) so you can fly back home.
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Parks · Outdoors · Beaches · Wildlife
Side Trips