20 days in Florida Itinerary

20 days in Florida Itinerary

Created using Inspirock Florida trip planner

Make it your trip
Drive
1
Naples
— 2 nights
Drive
2
St. Augustine
— 5 nights
Drive
3
Panama City Beach
— 1 night
Drive
4
Fort Walton Beach
— 4 nights
Fly
5
Key West
— 3 nights
Drive
6
Marathon
— 2 nights
Drive
7
Key Largo
— 2 nights
Drive

S M T W T F S
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31

Naples

— 2 nights
Step out of the city life by going to Bowman's Beach and Lovers Key State Park. Museum-lovers will get to explore The Bailey-Matthews National Shell Museum and Edison and Ford Winter Estates.

To find ratings, where to stay, other places to visit, and tourist information, refer to the Naples driving holiday planner.

Fort Lauderdale to Naples is an approximately 2-hour car ride. You can also take a bus. October in Naples sees daily highs of 87°F and lows of 71°F at night. Wrap up your sightseeing on the 14th (Wed) to allow time to drive to St. Augustine.

Things to do in Naples

Parks · Outdoors · Wildlife · Museums

Side Trips

St. Augustine

— 5 nights
St. Get a sense of the local culture at The Oldest Store Museum and Old Jail. Eschew the tourist crowds and head to First Colony and Shrimping Museum. Explore St. Augustine's surroundings by going to Beach at Daytona Beach (in Daytona Beach), Fernandina Beach (Amelia Island Horseback Riding & Fort Clinch State Park) and Ponce de Leon Inlet Lighthouse & Museum (in Ponce Inlet). There's lots more to do: contemplate in the serene atmosphere at Cathedral Basilica of St. Augustine, gain insight at Flagler College, examine the collection at Lightner Museum, and don't miss a visit to St. George Street.

To find photos, reviews, where to stay, and other tourist information, use the St. Augustine trip planner.

Drive from Naples to St. Augustine in 6 hours. Alternatively, you can fly; or take a bus. Traveling from Naples in October, expect nights in St. Augustine to be about the same, around 67°F, while days are a bit cooler, around 80°F. Finish your sightseeing early on the 19th (Mon) so you can drive to Panama City Beach.

Things to do in St. Augustine

Parks · Historic Sites · Museums · Outdoors

Side Trips

Panama City Beach

— 1 night

World's Most Beautiful Beaches

Boasting 43 km (27 mi) of white sandy beaches and plenty of sunshine, Panama City Beach is an ideal choice for a relaxing holiday.
Kick off your visit on the 20th (Tue): do a tasting at Panama City Beach Winery, then discover the deep blue sea with a scuba or snorkeling tour, and then admire the majestic nature at St. Andrews State Park.

To find where to stay, ratings, more things to do, and more tourist information, refer to the Panama City Beach trip planner.

Getting from St. Augustine to Panama City Beach by car takes about 5.5 hours. Other options: fly. Expect slightly colder evenings in Panama City Beach when traveling from St. Augustine in October, with lows around 59°F. Cap off your sightseeing on the 20th (Tue) early enough to go by car to Fort Walton Beach.

Things to do in Panama City Beach

Outdoors · Tours · Wildlife · Parks

Fort Walton Beach

— 4 nights
Fort Walton Beach is a city in southern Okaloosa County, Florida, United States. Visiting Navarre Beach and Henderson Beach State Park will get you outdoors. Satisfy your inner culture vulture at Air Force Armament Museum and Fort Pickens Area. You'll find plenty of places to visit near Fort Walton Beach: The Graffiti Bridge (in Pensacola) and Pensacola Beach (in Pensacola Beach). The adventure continues: step off the mainland to explore Okaloosa Island, get close to the beloved marine mammals with AJ's Water Adventures, walk around Dog Park, and surround yourself with nature on Fudpucker's Gator Beach.

To see other places to visit, where to stay, photos, and tourist information, refer to the Fort Walton Beach day trip planning app.

Getting from Panama City Beach to Fort Walton Beach by car takes about 1.5 hours. You'll gain 1 hour traveling from Panama City Beach to Fort Walton Beach due to the time zone difference. October in Fort Walton Beach sees daily highs of 80°F and lows of 60°F at night. Wrap up your sightseeing on the 24th (Sat) to allow time to travel to Key West.

Things to do in Fort Walton Beach

Outdoors · Parks · Beaches · Nature

Side Trips

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.
Visiting Dry Tortugas National Park and Dolphin & Whale Watching will get you outdoors. Satisfy your inner culture vulture at U.S. Coast Guard Cutter Ingham Maritime Museum and Key West Lighthouse and Keeper's Quarters Museum. Next up on the itinerary: stroll through Audubon House & Tropical Gardens, explore the different monuments and memorials at Key West Cemetery, indulge in some personalized pampering at some of the best spas, and get up close and personal with brilliant marine life at Florida Keys Eco-Discovery Center.

To see traveler tips, maps, more things to do, and tourist information, refer to the Key West tour builder tool.

You can fly from Fort Walton Beach to Key West in 6.5 hours. Other options are to drive; or do a combination of bus and shuttle. The time zone difference moving from Central Standard Time to Eastern Standard Time is 1 hour. Prepare for a bit warmer weather when traveling from Fort Walton Beach in October: high temperatures in Key West hover around 86°F and lows are around 77°F. Finish your sightseeing early on the 27th (Tue) so you can drive to Marathon.

Things to do in Key West

Parks · Nature · Museums · Outdoors

Marathon

— 2 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.
On the 28th (Wed), discover the deep blue sea with a scuba or snorkeling tour, then look for all kinds of wild species at The Turtle Hospital, and then shop like a local with Shady Palm Art Gallery & Photography. On your second day here, look for all kinds of wild species at Dolphin Research Center and then see the interesting displays at Crane Point Museum & Nature Center.

To find maps and more tourist information, refer to the Marathon trip planning site.

You can drive from Key West to Marathon in 1.5 hours. Alternatively, you can take a bus. October in Marathon sees daily highs of 87°F and lows of 77°F at night. Wrap up your sightseeing on the 29th (Thu) to allow time to drive to Key Largo.

Things to do in Marathon

Wildlife · Parks · Outdoors · Tours

Key Largo

— 2 nights

Diving Capital of the World

The northernmost island of the Florida Keys, Key Largo provides stunning scenery, a number of watersports opportunities, and plenty of areas to relax on vacation.
On the 30th (Fri), stop by Robert Is Here, take an in-depth tour of History of Diving Museum, and then fulfill a lifelong dream with Theater of the Sea. Keep things going the next day: identify plant and animal life at Capt. Sterling's Everglades Eco-Tours, then look for all kinds of wild species at Molasses Reef, and then identify plant and animal life at Florida Keys Wild Bird Rehabilitation Center.

To find where to stay, reviews, photos, and other tourist information, read Key Largo itinerary planning website.

You can drive from Marathon to Key Largo in 1.5 hours. Alternatively, you can take a bus. In October in Key Largo, expect temperatures between 85°F during the day and 73°F at night. Wrap up your sightseeing on the 31st (Sat) to allow time to drive back home.

Things to do in Key Largo

Wildlife · Outdoors · Tours · Parks

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.