21 days in Florida Itinerary

21 days in Florida Itinerary

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Route & dates

21 days in Florida Itinerary

Start: Melbourne
Fly + shuttle:  27​h
1
Islamorada
— 2 nights
Drive:  45​min
2
Marathon
— 2 nights
bus:  1​h 15​min
3
Key West
— 3 nights
ferry:  2​h 30​min
4
Marco Island
— 3 nights
Drive:  1​h 45​min
5
Sanibel Island
— 1 night
Drive:  45​min
6
Fort Myers Beach
— 1 night
Drive:  5​h 30​min
7
St. Augustine
— 3 nights
Drive:  2​h
8
Orlando
— 3 nights
Fly:  26​h
End: Melbourne

2
nights
Islamorada

Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
On the 15th (Sun), view the masterpieces at Lobster Trap Art Gift Shop and Gallery, take a tour by water with Boat Tours & Water Sports, then identify plant and animal life at Florida Keys Wild Bird Rehabilitation Center, and finally sample the tasty concoctions at Islamorada Brewery & Distillery. On the 16th (Mon), you'll have a packed day of sightseeing: see some colorful creatures with a scuba or snorkeling tour, then get close to the beloved marine mammals with a swim-with-the-dolphins experience, and then stop by Petals With Pizzazz.

To find maps, more things to do, reviews, and other tourist information, read Islamorada day trip website .

Melbourne, Australia to Islamorada is an approximately 27-hour combination of flight and shuttle. You can also do a combination of train, flight, and shuttle. Traveling from Melbourne to Islamorada, you'll gain 15 hours due to the time zone difference. Traveling from Melbourne in December, expect somewhat warmer with lows of 25°C in Islamorada. Finish up your sightseeing early on the 16th (Mon) so you can go by car to Marathon.

Things to do in Islamorada

Wildlife Tours Outdoors

Side Trip

Key Largo
Highlights from your plan
Fishing Charters & Tours
Swim with Dolphins

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 17th (Tue), tour the pleasant surroundings at Sombrero Beach, identify plant and animal life at The Turtle Hospital, and then admire the majestic nature at Bahia Honda State Park. On the next day, cast your line with a fishing tour, then look for all kinds of wild species at Dolphin Research Center, and then take in the views from Seven Mile Bridge.

For ratings, other places to visit, more things to do, and tourist information, read Marathon trip maker site .

Traveling by car from Islamorada to Marathon takes an hour. Alternatively, you can take a bus. In December, plan for daily highs up to 31°C, and evening lows to 25°C. Finish your sightseeing early on the 18th (Wed) so you can take a bus to Key West.

Things to do in Marathon

Parks Outdoors Wildlife

Side Trip

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

3
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.
You'll discover tucked-away gems like Dry Tortugas National Park and Scuba & Snorkeling. Step out of the city life by going to Dolphin & Whale Watching and Stand-Up Paddleboarding. There's much more to do: look for all kinds of wild species at Key West Butterfly & Nature Conservatory, fly like a bird with a parasailing or paragliding tour, enjoy the sea views from Key West Lighthouse and Keeper's Quarters Museum, and take in the exciting artwork at 7 Artists & Friends.

To find other places to visit, reviews, photos, and more tourist information, you can read our Key West trip builder website .

You can take a bus from Marathon to Key West in 1.5 hours. Another option is to drive. December in Key West sees daily highs of 30°C and lows of 25°C at night. Finish your sightseeing early on the 21st (Sat) so you can ride a ferry to Marco Island.

Things to do in Key West

Tours Outdoors Wildlife
Highlights from your plan
Dry Tortugas National Park ©
Dry Tortugas National Park
Dolphin & Whale Watching
Stand-Up Paddleboarding

3
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. Discover out-of-the-way places like Speed Boats Tours and Waterskiing & Jetskiing. Shop till you drop at Marco Island Farmers Market-Wednesday- Mid November to Mid April and Clyde Butcher's Big Cypress Gallery. There's still lots to do: take a memorable tour with Tours, fly like a bird with a parasailing or paragliding tour, look for all kinds of wild species at Capri Paddlecraft Park, and glide peacefully along the water with some of the best stand-up paddleboarding in the area.

To find ratings, more things to do, photos, and more tourist information, read our Marco Island trip itinerary app .

You can ride a ferry from Key West to Marco Island in 2.5 hours. Alternatively, you can drive. Traveling from Key West in December, expect little chillier with lows of 19°C in Marco Island. Finish up your sightseeing early on the 24th (Tue) so you can go by car to Sanibel Island.

Things to do in Marco Island

Tours Outdoors Wildlife

Side Trips

Speed Boats Tours, Clyde Butcher's Big Cypress Gallery
Highlights from your plan
Waterskiing & Jetskiing
Dolphin & Whale Watching
Stand-Up Paddleboarding

1
night
Sanibel Island

Sanibel Island ©
Take a trip to Sanibel Island if you like pretty sunsets and luxurious resorts.
On the 25th (Wed), look for gifts at Gene's Bookstore, tour the pleasant surroundings at Bowman's Beach, and then tour the pleasant surroundings at Captiva Beach.

For maps, photos, reviews, and tourist information, you can read our Sanibel Island itinerary planning app .

Traveling by car from Marco Island to Sanibel Island takes 2 hours. Expect a daytime high around 31°C in December, and nighttime lows around 19°C. Finish your sightseeing early on the 25th (Wed) to allow enough time to drive to Fort Myers Beach.

Things to do in Sanibel Island

Beaches Parks Outdoors

Side Trip

Captiva Beach
Highlights from your plan
Bowman's Beach ©
Bowman's Beach
Captiva Beach ©
Captiva Beach

1
night
Fort Myers Beach

Fort Myers Beach ©
Fort Myers Beach is a town located on Estero Island in Lee County, Florida, United States. Start off your visit on the 26th (Thu): look for all kinds of wild species at Lovers Key State Park, see majestic marine mammals with a dolphin and whale watching tour, and then stop by Rick's Trading Post.

To see more things to do, ratings, other places to visit, and other tourist information, read our Fort Myers Beach trip itinerary maker website .

Traveling by car from Sanibel Island to Fort Myers Beach takes an hour. In December in Fort Myers Beach, expect temperatures between 31°C during the day and 19°C at night. Finish up your sightseeing early on the 26th (Thu) so you can go by car to St. Augustine.

Things to do in Fort Myers Beach

Wildlife Tours Parks

Side Trip

Rick's Trading Post
Highlights from your plan
Lovers Key State Park ©
Lovers Key State Park
Dolphin & Whale Watching
Rick's Trading Post ©
Rick's Trading Post

3
nights
St. Augustine

St. Augustine ©
SAINT AUGUSTINE | PONTE VEDRA on Florida's Historic Coast The Nation's oldest city (est. You'll discover tucked-away gems like St. Augustine Beach and Fort Clinch State Park. Get outdoors at Fort Matanzas National Monument and St. Augustine Alligator Farm Zoological Park. Take a break from St. Augustine with a short trip to Ormond Beach in Ormond Beach, about 56 minutes away. There's more to do: enjoy the sand and surf at Vilano Beach and view the masterpieces at High Tide Gallery Art & Gifts.

To see ratings, reviews, photos, and more tourist information, read our St. Augustine online trip maker .

Getting from Fort Myers Beach to St. Augustine by car takes about 5.5 hours. Other options: do a combination of bus, flight, and car; or do a combination of bus and flight. In December, St. Augustine is a bit cooler than Fort Myers Beach - with highs of 24°C and lows of 15°C. Cap off your sightseeing on the 29th (Sun) early enough to go by car to Orlando.

Things to do in St. Augustine

Parks Beaches Outdoors

Side Trips

Ormond Beach, Fort Clinch State Park
Highlights from your plan
Fort Clinch State Park ©
Fort Clinch State Park
St. Augustine Beach ©
St. Augustine Beach
Ormond Beach ©
Ormond Beach

3
nights
Orlando

Orlando ©
For most people, any mention of Orlando immediately conjures up images of sprawling theme parks filled with characters plucked right out of popular animated movies.
You'll discover tucked-away gems like The Escape Game Orlando and International Drive. Head to World of Disney and Orlando Vineland Premium Outletsfor some retail therapy. The adventure continues: find something for the whole family at Walt Disney World Resort, try out the rides at Discovery Cove, and make an unforgettable trip to Happily Ever After Fireworks.

To see where to stay, maps, more things to do, and more tourist information, read our Orlando trip planner .

Traveling by car from St. Augustine to Orlando takes 2 hours. Alternatively, you can take a bus. While traveling from St. Augustine, expect somewhat warmer days and about the same nights in Orlando, ranging from highs of 29°C to lows of 17°C. Cap off your sightseeing on the 1st (Wed) early enough to travel back home.

Things to do in Orlando

Theme Parks Shopping Beaches
Highlights from your plan
Walt Disney World Resort ©
Walt Disney World Resort
The Escape Game Orlando ©
The Escape Game Orlando
Discovery Cove ©
Discovery Cove

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