25 days in Florida Itinerary

25 days in Florida Itinerary

Created using Inspirock Florida travel route planner

Make it your trip
Drive
1
St. Augustine
— 5 nights
Drive
2
Fort Walton Beach
— 3 nights
Fly
3
Islamorada
— 2 nights
Drive
4
Marathon
— 3 nights
Drive
5
Key West
— 4 nights
Ferry to Marco Island, FL, Taxi to Naples
6
Naples
— 4 nights
Drive
7
Sarasota
— 3 nights
Drive

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St. Augustine

— 5 nights
St. Eschew the tourist crowds and head to Vilano Beach and Andy Romano Beachfront Park. Attractions like Crescent Beach Public Beach and World Golf Hall of Fame make great kid-friendly stops. Take a break from St. Augustine with a short trip to The Casements in Ormond Beach, about 58 minutes away. There's much more to do: see the interesting displays at St. Photios Greek Orthodox National Shrine, steep yourself in history at Old St. Augustine Village, get engrossed in the history at Spanish Military Hospital Museum, and browse the exhibits of The Oldest House Museum Complex.

To find photos, where to stay, ratings, and tourist information, go to the St. Augustine online holiday planner.

Orlando to St. Augustine is an approximately 2-hour car ride. You can also take a bus. When traveling from Orlando in November, plan for a bit cooler days and about the same nights in St. Augustine: temperatures range from 73°F by day to 59°F at night. Wrap up your sightseeing on the 6th (Fri) early enough to drive to Fort Walton Beach.

Things to do in St. Augustine

Museums · Historic Sites · Outdoors · Parks

Side Trips

Fort Walton Beach

— 3 nights
Fort Walton Beach is a city in southern Okaloosa County, Florida, United States. Explore hidden gems such as Indian Temple Mound and Museum and Blue Mountain Beach. Family-friendly places like Goofy Golf and Garnier Post Office will thrill your kids. Step out of Fort Walton Beach with an excursion to Waterfront Gifts and Art in Miramar Beach--about 30 minutes away. There's lots more to do: cast your line with O Sea D Fishing Charters, stroll around Destin Dog Park, and get in on the family fun at Wild Willy's Adventure Zone.

For ratings, reviews, more things to do, and other tourist information, read our Fort Walton Beach trip planner.

Traveling by car from St. Augustine to Fort Walton Beach takes 6.5 hours. Alternatively, you can fly; or take a bus. The time zone difference when traveling from St. Augustine to Fort Walton Beach is minus 1 hour. Expect a bit cooler evenings in Fort Walton Beach when traveling from St. Augustine in November, with lows around 49°F. Cap off your sightseeing on the 9th (Mon) early enough to travel to Islamorada.

Things to do in Fort Walton Beach

Outdoors · Parks · Beaches · Wildlife

Side Trips

Islamorada

— 2 nights

The Village of Islands

Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
Start off your visit on the 10th (Tue): take an in-depth tour of History of Diving Museum, view the masterpieces at Rain Barrel Village, then stop by Bella Sol Fragrance Bar and Gifts, and finally walk around Founders Park. On the 11th (Wed), you'll have a packed day of sightseeing: take in the exciting artwork at Lobster Trap Art Gift Shop and Gallery, relax and rejuvenate at Island Flow Yoga, then get some thrills out on the water with a waterskiing or jet-skiing adventure, and finally indulge your thirst for a good beer at Islamorada Brewery & Distillery.

For traveler tips, ratings, and tourist information, use the Islamorada road trip planner.

Traveling by flight from Fort Walton Beach to Islamorada takes 6 hours. Alternatively, you can drive; or do a combination of bus and shuttle. The time zone changes from Central Standard Time to Eastern Standard Time, which is usually a 1 hour difference. Traveling from Fort Walton Beach in November, expect nights in Islamorada to be warmer, around 72°F, while days are a bit warmer, around 82°F. Wrap up your sightseeing on the 11th (Wed) to allow time to drive to Marathon.

Things to do in Islamorada

Museums · Shopping · Parks · Adventure

Marathon

— 3 nights

Heart of the Florida Keys

A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
Kids will enjoy Sunset Park Beach and Curry Hammock State Park. Explore hidden gems such as Florida Keys Aquarium Encounters and Crane Point Museum & Nature Center. There's still lots to do: identify plant and animal life at Sombrero Reef, pause for some serene contemplation at San Pablo Catholic Church, take in the views from Old Seven Mile Bridge, and take a memorable tour with Dive Duck Key.

For photos, ratings, maps, and other tourist information, use the Marathon trip itinerary maker site.

You can drive from Islamorada to Marathon in an hour. Other options are to drive; or take a bus. In November in Marathon, expect temperatures between 82°F during the day and 72°F at night. Finish your sightseeing early on the 14th (Sat) so you can drive to Key West.

Things to do in Marathon

Parks · Wildlife · Outdoors · Zoos & Aquariums

Side Trips

Key West

— 4 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.
You'll explore the less-touristy side of things at Peppers of Key West and Florida Keys Eco-Discovery Center. Attractions like Key West Historic Seaport and Vandenberg Wreck make great kid-friendly stops. And it doesn't end there: brush up on your military savvy at U.S. Coast Guard Cutter Ingham Maritime Museum, go for a walk through West Martello Tower, admire the natural beauty at Key West Garden Club, and appreciate the history behind Key West AIDS Memorial.

For traveler tips, ratings, reviews, and tourist information, go to the Key West trip planner.

Traveling by car from Marathon to Key West takes 1.5 hours. Alternatively, you can drive; or take a bus. In November, plan for daily highs up to 81°F, and evening lows to 73°F. Wrap up your sightseeing on the 18th (Wed) early enough to travel to Naples.

Things to do in Key West

Wildlife · Parks · Museums · Historic Sites

Naples

— 4 nights
Bring the kids along to Native Guided Fishing Charters and LaPlaya Golf Course. Explore hidden gems such as Golisano Children's Museum of Naples and Naples Historical Society. Step out of Naples with an excursion to Winterberry Park in Marco Island--about 34 minutes away.

For photos, reviews, and tourist information, use the Naples online travel route planner.

You can do a combination of ferry and taxi from Key West to Naples in 4 hours. Other options are to drive; or take a bus. Plan for slightly colder nights when traveling from Key West in November since evenings lows in Naples dip to 65°F. Wrap up your sightseeing on the 22nd (Sun) early enough to drive to Sarasota.

Things to do in Naples

Museums · Outdoors · Parks · Wildlife

Side Trip

Sarasota

— 3 nights
Sarasota is a city in Sarasota County on the southwestern coast of the U.S. Step off the beaten path and head to Blind Pass Beach and Save Our Seabirds. Kids will appreciate attractions like North Jetty Beach and Food Tours. Explore Sarasota's surroundings by going to Venice (Ideal Classic Cars Museum & Showroom & Spas & Wellness). There's much more to do: admire nature's wide array of creatures at The Cat Depot, look for gifts at Just/Because, and do sightseeing your way with Sarasota Saltwater Adventures.

To find traveler tips, other places to visit, more things to do, and other tourist information, refer to the Sarasota day trip planner.

Traveling by car from Naples to Sarasota takes 2 hours. Alternatively, you can take a bus; or do a combination of bus and taxi. November in Sarasota sees daily highs of 80°F and lows of 62°F at night. Wrap up your sightseeing on the 25th (Wed) early enough to drive back home.

Things to do in Sarasota

Parks · Outdoors · Beaches · Tours

Side Trips

Florida travel guide

4.4
Disney Parks & Activities · Beaches · Theme Parks
The Sunshine State
The “Sunshine State,” Florida became a favorite winter destination for the affluent crowd over a century ago. Today, the state attracts visitors from around the world with its golden beaches and modern theme parks. You can spend your entire vacation enjoying the state's highly developed seaside areas, but remember that some of Florida's best-kept secrets are in secluded locations. Visit the big cities and their comfortable resorts offering top-notch dining and nightlife, but leave some time to see the peninsula's swampy landscape, filled with wild creatures and native plants. Farther away from the tourist-packed urban areas, the untamed wetlands of Florida offer a selection of things to do, such as kayaking, boat rides, and numerous other outdoor activities.