20 days in Florida Itinerary

20 days in Florida Itinerary

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Route & dates

20 days in Florida Itinerary

Start: Milan
Fly + bus:  16​h 45​min
1
St. Augustine
— 1 night
Drive:  5​h 30​min
2
Panama City Beach
— 1 night
Fly:  5​h 45​min
3
Sanibel Island
— 1 night
Drive:  1​h 30​min
4
Marco Island
— 2 nights
ferry:  2​h 30​min
5
Key West
— 4 nights
bus:  1​h 15​min
6
Marathon
— 2 nights
Drive:  45​min
7
Islamorada
— 2 nights
Drive:  45​min
8
Key Largo
— 2 nights
shuttle + Fly:  16​h 30​min
End: Milan

1
night
St. Augustine

St. Augustine ©
SAINT AUGUSTINE | PONTE VEDRA on Florida's Historic Coast The Nation's oldest city (est. Kick off your visit on the 27th (Sat): look for all kinds of wild species at St. Augustine Alligator Farm Zoological Park, enjoy the sand and surf at St. Augustine Beach, and then explore and take pictures at Flagler College. On the 28th (Sun), you'll have a packed day of sightseeing: look for gifts at Market to Market, examine the collection at St. Augustine Pirate & Treasure Museum, then stroll through Frank Butler County Park West, and finally kick back and relax at Crescent Beach Public Beach.

To see reviews, maps, other places to visit, and tourist information, read St. Augustine road trip planning site .

Milan, Italy to St. Augustine is an approximately 17-hour combination of flight and bus. You can also do a combination of train, flight, and bus. The time zone difference when traveling from Milan to St. Augustine is minus 6 hours. Traveling from Milan in July, plan for somewhat warmer nights in St. Augustine, with lows around 28°C. Finish your sightseeing early on the 28th (Sun) so you can drive to Panama City Beach.

Things to do in St. Augustine

Parks Beaches Outdoors

Side Trip

Crescent Beach Public Beach
Highlights from your plan
St. Augustine Beach ©
St. Augustine Beach
St. Augustine Pirate & Treasure Museum ©

1
night
Panama City Beach

Panama City Beach ©
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 29th (Mon): do a tasting at Panama City Beach Winery, admire the majestic nature at St. Andrews State Park, and then get close to the beloved marine mammals with a swim-with-the-dolphins experience. Get ready for a full day of sightseeing on the next day: kick back and relax at Santa Rosa Beach, take in the exciting artwork at The Blue Giraffe, and then look for all kinds of wild species at Wildlife Areas.

To see where to stay, reviews, more things to do, and tourist information, use the Panama City Beach travel route planner.

Drive from St. Augustine to Panama City Beach in 5.5 hours. Alternatively, you can do a combination of bus and flight; or do a combination of bus, flight, and taxi. In July, daily temperatures in Panama City Beach can reach 38°C, while at night they dip to 27°C. Wrap up your sightseeing on the 30th (Tue) to allow time to travel to Sanibel Island.

Things to do in Panama City Beach

Outdoors Tours Wildlife

Side Trip

Santa Rosa Beach
Highlights from your plan
Panama City Beach Winery ©
Panama City Beach Winery
St. Andrews State Park ©
St. Andrews State Park
Swim with Dolphins

1
night
Sanibel Island

Sanibel Island ©
Take a trip to Sanibel Island if you like pretty sunsets and luxurious resorts.
Kick off your visit on the 31st (Wed): see the interesting displays at The Bailey-Matthews National Shell Museum, kick back and relax at Blind Pass Beach Park, and then kick back and relax at Captiva Beach. Here are some ideas for day two: look for gifts at Bailey's General Store, then stroll through Bowman's Beach, and then cast your line with a fishing tour.

To see photos, more things to do, other places to visit, and more tourist information, read our Sanibel Island driving holiday tool .

Getting from Panama City Beach to Sanibel Island by flight takes about 6 hours. Other options: drive. In July, plan for daily highs up to 38°C, and evening lows to 28°C. Cap off your sightseeing on the 1st (Thu) early enough to go by car to Marco Island.

Things to do in Sanibel Island

Outdoors Beaches Parks

Side Trip

Captiva Island
Highlights from your plan
Blind Pass Beach Park ©
Blind Pass Beach Park
Captiva Beach ©
Captiva Beach
Fishing Charters & Tours

2
nights
Marco Island

Marco Island is a city in Collier County, Florida, United States, located on an island by the same name in the Gulf of Mexico off the coast of Southwest Florida. Start off your visit on the 2nd (Fri): race across the water with a speed boat tour, get up close to creatures of the deep with a dolphin and whale watching tour, and then take a leisurely stroll along Goodland Boating Park - Collier County. Keep things going the next day: take in the exciting artwork at Malenda Trick Art Gallery, then see what you can catch with a fishing tour, and then get interesting insight from Tours.

For other places to visit, where to stay, and more tourist information, refer to the Marco Island trip itinerary planner.

You can drive from Sanibel Island to Marco Island in 1.5 hours. In August, daytime highs in Marco Island are 39°C, while nighttime lows are 28°C. Finish your sightseeing early on the 3rd (Sat) to allow enough time to ride a ferry to Key West.

Things to do in Marco Island

Tours Outdoors Wildlife

Side Trip

Speed Boats Tours
Highlights from your plan
Fishing Charters & Tours
Dolphin & Whale Watching
Waterskiing & Jetskiing

4
nights
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.
Discover out-of-the-way places like Stand-Up Paddleboarding and U.S. Coast Guard Cutter Ingham Maritime Museum. Get in touch with nature at Kayaking & Canoeing and Scuba & Snorkeling. Spend the 4th (Sun) exploring nature at Dry Tortugas National Park. There's still lots to do: examine the collection at The Ernest Hemingway Home and Museum, see majestic marine mammals with a dolphin and whale watching tour, get some thrills out on the water with a waterskiing or jet-skiing adventure, and view the masterpieces at 7 Artists & Friends.

For where to stay, ratings, and tourist information, go to the Key West trip itinerary builder app .

You can ride a ferry from Marco Island to Key West in 2.5 hours. Alternatively, you can drive. In August, plan for daily highs up to 38°C, and evening lows to 32°C. Finish your sightseeing early on the 7th (Wed) to allow enough time to take a bus to Marathon.

Things to do in Key West

Tours Outdoors Adventure
Highlights from your plan
Stand-Up Paddleboarding
Kayaking & Canoeing
The Ernest Hemingway Home and Museum ©

2
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.
On the 8th (Thu), see what you can catch with a fishing tour, tour the pleasant surroundings at Sombrero Beach, and then identify plant and animal life at The Turtle Hospital. Keep things going the next day: identify plant and animal life at Dolphin Research Center, then snap pictures at Seven Mile Bridge, and then immerse yourself in nature at Bahia Honda State Park.

To find photos and tourist information, refer to the Marathon trip itinerary planner .

Getting from Key West to Marathon by bus takes about 1.5 hours. Other options: drive. In August, daily temperatures in Marathon can reach 39°C, while at night they dip to 31°C. Wrap up your sightseeing on the 9th (Fri) to allow time to drive to Islamorada.

Things to do in Marathon

Parks Outdoors Wildlife

Side Trip

Bahia Honda State Park
Highlights from your plan
Dolphin Research Center ©
Dolphin Research Center
Bahia Honda State Park ©
Bahia Honda State Park
The Turtle Hospital ©
The Turtle Hospital

2
nights
Islamorada

Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
Kick off your visit on the 10th (Sat): see some colorful creatures with a scuba or snorkeling tour and then cast your line with a fishing tour. Get ready for a full day of sightseeing on the next day: take in the exciting artwork at Lobster Trap Art Gallery, get interesting insight from Tours, then explore the gorgeous colors at Alligator Reef Light House, and finally fly like a bird with a parasailing or paragliding tour.

To see more things to do, where to stay, traveler tips, and more tourist information, read our Islamorada online journey builder .

You can drive from Marathon to Islamorada in an hour. Another option is to take a bus. August in Islamorada sees daily highs of 39°C and lows of 31°C at night. Cap off your sightseeing on the 11th (Sun) early enough to go by car to Key Largo.

Things to do in Islamorada

Tours Outdoors Wildlife
Highlights from your plan
Scuba & Snorkeling
Waterskiing & Jetskiing
Parasailing & Paragliding

2
nights
Key Largo

Key Largo ©
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.
Kick off your visit on the 12th (Mon): identify plant and animal life at Florida Keys Wild Bird Rehabilitation Center, identify plant and animal life at Molasses Reef, and then explore the gorgeous colors at Spiegel Grove. Get ready for a full day of sightseeing on the 13th (Tue): look for all kinds of wild species at Grecian Rocks, look for gifts at Shell World Florida Keys, and then glide through the air with a parasailing or paragliding tour.

To see ratings, photos, other places to visit, and other tourist information, you can read our Key Largo route site .

Traveling by car from Islamorada to Key Largo takes an hour. Alternatively, you can do a combination of bus and taxi. August in Key Largo sees daily highs of 38°C and lows of 29°C at night. Wrap up your sightseeing on the 13th (Tue) early enough to travel back home.

Things to do in Key Largo

Wildlife Parks Tours
Highlights from your plan
Spiegel Grove ©
Spiegel Grove
Molasses Reef ©
Molasses Reef

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