25 days in Florida Itinerary

25 days in Florida Itinerary

Created using Inspirock Florida travel route planner

Plan created by another user. Make it yours
1
St. Augustine
— 5 nights
2
Fort Walton Beach
— 3 nights
3
Islamorada
— 2 nights
4
Marathon
— 3 nights
5
Key West
— 4 nights
6
Naples
— 4 nights
7
Sarasota
— 3 nights

S M T W T F S
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5
nights
St. Augustine

St. Augustine ©
St. Eschew the tourist crowds and head to Vilano Beach and Andy Romano Beachfront Park. Attractions like Crescent Beach Public Beach and St. Photios Greek Orthodox National Shrine 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 lots more to do: see the interesting displays at World Golf Hall of Fame, pause for some serene contemplation at Memorial Presbyterian Church, take a memorable tour with Tours, and get engrossed in the history at Spanish Military Hospital Museum.

To find more things to do, other places to visit, maps, and more tourist information, go to the St. Augustine route planner.

Orlando to St. Augustine is an approximately 2-hour car ride. You can also take a bus. While traveling from Orlando, expect slightly colder days and about the same nights in St. Augustine, ranging from highs of 73°F to lows of 59°F. Finish your sightseeing early on the 6th (Fri) to allow enough time to drive to Fort Walton Beach.

Things to do in St. Augustine

Museums · Historic Sites · Outdoors · Beaches

Side Trips

Highlights from your trip

3
nights
Fort Walton Beach

Fort Walton Beach ©
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

Highlights from your trip
©
Golf Course
Goofy Golf
4.5

2
nights
Islamorada

Islamorada ©

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 · Outdoors · Parks
Highlights from your trip
©
History Museum
History of Diving Museum
4.8
©
Waterskiing / Jetskiiing
Waterskiing & Jetskiing
4.7

3
nights
Marathon

Marathon ©

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 Florida Keys Aquarium Encounters. Explore hidden gems such as Sombrero Reef and Crane Point Museum & Nature Center. There's still lots to do: immerse yourself in nature at Curry Hammock State Park, view the masterpieces at Shady Palm Art Gallery & Photography, snap pictures at Old Seven Mile Bridge, and see some colorful creatures with Dive Duck Key.

To see ratings, where to stay, and tourist information, use the Marathon online journey maker.

Getting from Islamorada to Marathon by car takes about an hour. Other options: drive; or take a bus. In November, daytime highs in Marathon are 82°F, while nighttime lows are 72°F. 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

Highlights from your trip
©
Must see
Sunset Park Beach
4.6
©
Scuba / Snorkeling
Dive Duck Key
4.4

4
nights
Key West

Key West ©

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 Key West Historic Seaport. Attractions like U.S. Coast Guard Cutter Ingham Maritime Museum and Vandenberg Wreck make great kid-friendly stops. And it doesn't end there: observe the fascinating underwater world at Florida Keys Eco-Discovery Center, 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

Highlights from your trip

4
nights
Naples

Naples ©
Bring the kids along to Native Guided Fishing Charters and Cambier Park. Explore hidden gems such as Golisano Children's Museum of Naples and Collier Museum at Government Center. Step out of Naples with an excursion to Winterberry Park in Marco Island--about 34 minutes away.

To see other places to visit, where to stay, reviews, and other tourist information, go to the Naples trip itinerary planning tool.

Getting from Key West to Naples by combination of ferry and taxi takes about 4 hours. Other options: drive; or take a bus. Traveling from Key West in November, plan for a bit cooler nights in Naples, with lows around 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

Highlights from your trip

3
nights
Sarasota

Sarasota ©
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 North Jetty Beach. Kids will appreciate attractions like Food Tours and The Cat Depot. Explore Sarasota's surroundings by going to Venice (Ideal Classic Cars Museum & Showroom & Spas & Wellness). The adventure continues: look for all kinds of wild species at Save Our Seabirds, look for gifts at Just/Because, and discover the deep blue sea with Sarasota Saltwater Adventures.

To see photos, ratings, other places to visit, and more tourist information, read our Sarasota trip itinerary planner.

You can drive from Naples to Sarasota in 2 hours. Alternatively, you can take a bus; or do a combination of bus and taxi. Expect a daytime high around 80°F in November, and nighttime lows around 62°F. Wrap up your sightseeing on the 25th (Wed) to allow time to drive back home.

Things to do in Sarasota

Parks · Outdoors · Beaches · Tours

Side Trips

Highlights from your trip

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