35 days in Fort Myers, Key West & St. Augustine Itinerary

35 days in Fort Myers, Key West & St. Augustine Itinerary

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35 days in Fort Myers, Key West & St. Augustine Itinerary

Start: Fort Myers
1
Fort Myers
— 28 nights
ferry:  4​h
2
Key West
— 3 nights
Fly + Drive:  5​h 45​min
3
St. Augustine
— 3 nights
Drive:  5​h
End: Fort Myers

28
nights
Fort Myers

Fort Myers ©
Fort Myers is the county seat and commercial center of Lee County, Florida, United States. Naples Historical Society and Smallwood Store will appeal to history buffs. Step off the beaten path and head to Stand-Up Paddleboarding and Nokomis Beach. Change things up with these side-trips from Fort Myers: Estero (Coconut Point Mall & Happehatchee Center), Siesta Key (Turtle Beach, Crescent Beach, & more) and Englewood (Manasota Key Beach, Englewood Beach, & more). There's still lots to do: tour the pleasant surroundings at Captiva Beach, shop like a local with Third Street South, cast your line with a fishing tour, and kick back and relax at Bonita Springs Public Beach.

To find reviews, maps, photos, and other tourist information, use the Fort Myers travel route tool .

The Route module shows you travel options from your home to Fort Myers. In October, daily temperatures in Fort Myers can reach 86°F, while at night they dip to 70°F. Wrap up your sightseeing on the 11th (Mon) to allow time to travel to Key West.

Things to do in Fort Myers

Parks Outdoors Beaches

Side Trips

Naples, Sarasota, Cape Coral, Punta Gorda, Siesta Key
Highlights from your plan
Englewood Beach ©
Englewood Beach
Crescent Beach ©
Crescent Beach
Stump Pass Beach State Park ©
Stump Pass Beach State Park

3
nights
Key West

Key West ©
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.
On the 12th (Tue), find your balance on the water with some of the best stand-up paddleboarding in the area, then examine the collection at The Ernest Hemingway Home and Museum, and then pause for some serene contemplation at Saint Mary Star of the Sea. On the 13th (Wed), you'll have a packed day of sightseeing: enjoy the sand and surf at Fort Zachary Taylor, then take an in-depth tour of Key West Firehouse Museum, and then tour the pleasant surroundings at Smathers Beach.

To find more things to do, where to stay, maps, and tourist information, read our Key West trip itinerary planner.

Traveling by ferry from Fort Myers to Key West takes 4 hours. Alternatively, you can do a combination of bus and flight; or drive. Expect a bit warmer evenings in Key West when traveling from Fort Myers in November, with lows around 73°F. On the 14th (Thu), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Key West

Outdoors Parks Beaches
Highlights from your plan
The Ernest Hemingway Home and Museum ©
Vandenberg Wreck ©
Vandenberg Wreck
Key West Firehouse Museum ©
Key West Firehouse Museum

3
nights
St. Augustine

St. Augustine ©
SAINT AUGUSTINE | PONTE VEDRA on Florida's Historic Coast The Nation's oldest city (est. Start off your visit on the 15th (Fri): kick back and relax at Jacksonville Beach, then take in the spiritual surroundings of Mission of Nombre de Dios, then view the masterpieces at High Tide Gallery Art & Gifts, and finally take in the architecture and atmosphere at Memorial Presbyterian Church. Keep things going the next day: get engrossed in the history at Medieval Torture Collection, then see the interesting displays at The Ximenez-Fatio House, then enjoy the sand and surf at Vilano Beach, and finally see the interesting displays at World Golf Hall of Fame.

For more things to do, where to stay, photos, and more tourist information, read St. Augustine online travel planner .

Getting from Key West to St. Augustine by combination of flight and car takes about 6 hours. Other options: do a combination of flight and bus; or drive. Traveling from Key West in November, expect St. Augustine to be little chillier, temps between 73°F and 59°F. Wrap up your sightseeing by early afternoon on the 17th (Sun) to allow time for the car ride back home.

Things to do in St. Augustine

Outdoors Beaches Parks

Side Trips

Crescent Beach Public Beach, Jacksonville Beach
Highlights from your plan
Jacksonville Beach ©
Jacksonville Beach
Vilano Beach ©
Vilano Beach
Memorial Presbyterian Church ©
Memorial Presbyterian Church

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