60 days in Naples, Key West & Fort Myers Itinerary

60 days in Naples, Key West & Fort Myers Itinerary

Created using Inspirock Florida tour itinerary planner
Make it your trip
Drive
1
Naples
— 2 nights
Taxi to Marco Island, FL, Ferry to Key West
2
Key West
— 3 nights
Ferry to Fort Myers Beach, FL, Taxi to Fort Myers
3
Fort Myers
— 54 nights
Drive

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Naples — 2 nights

Plan my day in Naples using traveler tips and tourist information provided by Inspirock.

Ocala to Naples is an approximately 4.5-hour car ride. You can also do a combination of shuttle and flight; or take a bus. Plan for a bit warmer nights when traveling from Ocala in May since evenings lows in Naples dip to 70°F. Wrap up your sightseeing on the 3rd (Wed) early enough to travel to Key West.
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Outdoors · Parks · Neighborhoods · Beaches
Find places to stay May 1 — 3:

Key West — 3 nights

Conch Republic

Located just 140 km (90 mi) from Cuba, Key West is an island only about 6.4 km (4 mi) long and 1.6 km (1 mi) wide.
Your day by day itinerary now includes Mallory Square. Family-friendly places like Fort Zachary Taylor and Bahia Honda State Park will thrill your kids. We've also included these beaches for you: Sombrero Beach and Calusa Beach. There's more to do: don't miss a visit to Duval Street.

To find more things to do, maps, photos, and tourist information, go to the Key West tour itinerary builder site.

You can do a combination of taxi and ferry from Naples to Key West in 4 hours. Alternatively, you can drive; or take a bus. Expect a bit warmer evenings in Key West when traveling from Naples in May, with lows around 77°F. On the 6th (Sat), you'll travel to Fort Myers.
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Parks · Outdoors · Beaches · Historic Sites
Side Trips
Find places to stay May 3 — 6:

Fort Myers — 54 nights

Your itinerary includes some good beach time at Siesta Beach and Fort Myers Beach. Kids will enjoy St. Pete Beach and Fishing Charters & Tours. Explore the numerous day-trip ideas around Fort Myers: Fort Myers Beach (Matanzas Pass Preserve, Mound House, &more), Sanibel Island (Hirdie Girdie Gallery, Sanibel Historical Museum and Village, &more) and Sarasota (St. Thomas More Catholic Church, Siesta Key Village, &more). Spend the 27th (Sat) spotting exotic species with Everglades Day Safari.

To see other places to visit, where to stay, maps, and more tourist information, go to the Fort Myers trip planner.

Do a combination of ferry and taxi from Key West to Fort Myers in 4.5 hours. Alternatively, you can drive; or take a bus. Traveling from Key West in May, expect slightly colder with lows of 69°F in Fort Myers. Wrap up your sightseeing on the 29th (Thu) early enough to drive back home.
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Parks · Outdoors · Wildlife · Museums
Side Trips
Find places to stay May 6 — Jun 29: