20 days in Florida Itinerary

20 days in Florida Itinerary

Created using Inspirock Florida journey planner

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Route & dates

20 days in Florida Itinerary

Start: Istanbul
Fly + shuttle:  16​h 45​min
1
Islamorada
— 3 nights
Drive:  45​min
2
Marathon
— 3 nights
bus:  1​h 15​min
3
Key West
— 6 nights
Fly + taxi:  2​h 45​min
4
Sanibel Island
— 2 nights
Drive:  1​h 15​min
5
Naples
— 3 nights
Drive:  2​h 15​min
6
Miami Beach
— 1 night
Fly:  15​h 30​min
End: Istanbul

3
nights
Islamorada

Islamorada ©
Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
You'll explore the less-touristy side of things at Florida Keys Wild Bird Rehabilitation Center and Windley Key Fossil Reef Geological State Park. Take a break from the city and head to A Lil' Tail Charters and Robbie's of Islamorada. Next up on the itinerary: take an in-depth tour of History of Diving Museum, get a taste of the local shopping with Old Road Gallery, look for gifts at Ocean Gardens, and sample the tasty concoctions at Islamorada Beer Company Brewery and Tasting Room.

To find maps, more things to do, other places to visit, and more tourist information, you can read our Islamorada travel route planner.

Istanbul, Turkey to Islamorada is an approximately 17-hour flight. You'll gain 7 hours traveling from Istanbul to Islamorada due to the time zone difference. Traveling from Istanbul in December, things will get much hotter in Islamorada: highs are around 29°C and lows about 22°C. Finish up your sightseeing early on the 23rd (Sat) so you can go by car to Marathon.

Things to do in Islamorada

Wildlife Outdoors Museums

Side Trip

Florida Keys Wild Bird Rehabilitation Center
Highlights from your plan
History of Diving Museum ©
History of Diving Museum

3
nights
Marathon

Marathon ©
A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
Your itinerary includes some good beach time at Bahia Honda State Park and Sombrero Beach. Discover out-of-the-way places like Dolphin Research Center and Scuba & Snorkeling. It doesn't end there: look for all kinds of wild species at Crane Point Museum & Nature Center and cast your line with a fishing tour.

Inspirock's itinerary builder makes planning a Marathon trip simple and quick.

Drive from Islamorada to Marathon in an hour. Alternatively, you can take a shuttle; or take a bus. Expect a daytime high around 31°C in December, and nighttime lows around 24°C. Wrap up your sightseeing on the 26th (Tue) to allow time to drive to Key West.

Things to do in Marathon

Wildlife Outdoors Parks

Side Trip

Bahia Honda State Park
Highlights from your plan
Dolphin Research Center ©
Dolphin Research Center
Crane Point Museum & Nature Center ©
Crane Point Museum & Nature Center
Bahia Honda State Park ©
Bahia Honda State Park

6
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.
Step off the beaten path and head to Stand-Up Paddleboarding and Waterskiing & Jetskiing. Step out of the city life by going to Dolphin & Whale Watching and Dry Tortugas National Park. There's still lots to do: take an in-depth tour of Key West Lighthouse and Keeper's Quarters Museum, see the interesting displays at Mel Fisher Maritime Museum, brush up on your military savvy at U.S. Coast Guard Cutter Ingham Maritime Museum, and stroll the grounds of Key West Cemetery.

To find more things to do, where to stay, ratings, and more tourist information, you can read our Key West attractions site .

Traveling by car from Marathon to Key West takes 1.5 hours. Alternatively, you can take a bus. Expect a daytime high around 30°C in December, and nighttime lows around 25°C. Finish your sightseeing early on the 1st (Mon) to allow enough time to travel to Sanibel Island.

Things to do in Key West

Tours Outdoors Museums
Highlights from your plan
The Ernest Hemingway Home and Museum ©
Dolphin & Whale Watching
Saint Mary Star of the Sea ©
Saint Mary Star of the Sea

2
nights
Sanibel Island

Sanibel Island ©
Take a trip to Sanibel Island if you like pretty sunsets and luxurious resorts.
Relax by the water at Captiva Beach and Fort Myers Beach. Explore hidden gems such as Lovers Key State Park and Sanibel Island Lighthouse.

For photos, where to stay, and more tourist information, read our Sanibel Island trip maker website .

You can do a combination of flight and taxi from Key West to Sanibel Island in 3 hours. Alternatively, you can do a combination of ferry and taxi; or drive. Plan for little chillier nights when traveling from Key West in January since evenings lows in Sanibel Island dip to 15°C. Finish your sightseeing early on the 3rd (Wed) to allow enough time to drive to Naples.

Things to do in Sanibel Island

Parks Beaches Outdoors

Side Trips

Fort Myers Beach, Captiva Beach
Highlights from your plan
Captiva Beach ©
Captiva Beach
Bowman's Beach ©
Bowman's Beach
Lovers Key State Park ©
Lovers Key State Park

3
nights
Naples

Naples ©
Naples is a city in Collier County, Florida, United States. Start off your visit on the 4th (Thu): look for gifts at Toucan's World, then identify plant and animal life at Barefoot Beach Preserve, and then get interesting insight from Tours. On the 5th (Fri), you'll have a packed day of sightseeing: don't miss a visit to Fifth Avenue South, then enjoy the sand and surf at Lowdermilk Beach, and then explore the world behind art at Artis—Naples.

To see where to stay, ratings, more things to do, and other tourist information, you can read our Naples holiday app .

You can drive from Sanibel Island to Naples in 1.5 hours. In January, plan for daily highs up to 28°C, and evening lows to 16°C. Finish your sightseeing early on the 6th (Sat) so you can drive to Miami Beach.

Things to do in Naples

Outdoors Beaches Parks

Side Trips

Waterskiing & Jetskiing, Barefoot Beach Preserve
Highlights from your plan
Barefoot Beach Preserve ©
Barefoot Beach Preserve
Lowdermilk Beach ©
Lowdermilk Beach
Artis-Naples ©
Artis-Naples

1
night
Miami Beach

Miami Beach ©
Separated by water from the neighboring city of Miami, Miami Beach sits on a barrier island between Biscayne Bay and the Atlantic Ocean.
Kick off your visit on the 6th (Sat): see the interesting displays at Vizcaya Museum & Gardens, then browse the different shops at Lincoln Road, and then wander the streets of Espanola Way. On the next day, wander the streets of Ocean Drive, then wander the streets of Art Deco Historic District, then kick back and relax at South Beach, and finally take a stroll through Collins Avenue.

To see maps, other places to visit, ratings, and tourist information, read our Miami Beach itinerary builder website .

Drive from Naples to Miami Beach in 2.5 hours. Alternatively, you can do a combination of flight, tram, and bus; or take a bus. In January in Miami Beach, expect temperatures between 29°C during the day and 19°C at night. Wrap up your sightseeing on the 7th (Sun) early enough to travel back home.

Things to do in Miami Beach

Neighborhoods Shopping Parks

Side Trip

Vizcaya Museum and Gardens
Highlights from your plan
South Beach ©
South Beach
Lincoln Road ©
Lincoln Road
Art Deco Historic District ©
Art Deco Historic District

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