38 days in Florida Itinerary
Created using Inspirock Florida itinerary planner
Start: Adelaide
Fly
1
Key Largo
— 4 nights
Drive
2
Islamorada
— 3 nights
Drive
3
Marathon
— 2 nights
Drive
4
Key West
— 5 nights
Fly
5
Sarasota
— 3 nights
Drive
6
Naples
— 4 nights
Drive
7
Marco Island
— 3 nights
Fly
8
Orlando
— 4 nights
Drive
9
Crystal River
— 2 nights
Drive
10
St. Augustine
— 5 nights
Fly
End: Adelaide
Wed, Dec 27 - Fri, Feb 2
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Key Largo — 4 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.You'll explore the less-touristy side of things at Anhinga Trail and Swim with Dolphins. Head to Robert Is Here and Sandal Factory Outletfor plenty of shopping. Step out of Key Largo with an excursion to Everglades Alligator Farm in Homestead--about 44 minutes away. There's lots more to do: get a dose of the wild on Capt. Sterling's Everglades Eco-Tours, learn about winemaking at Keys' Meads, pause for some serene contemplation at Saint Justin Martyr Catholic Church, and step aboard African Queen Canal Cruise.
To see maps, more things to do, reviews, and more tourist information, go to the Key Largo online route builder.
Adelaide, Australia to Key Largo is an approximately 26-hour flight. You'll gain 14.5 hours traveling from Adelaide to Key Largo due to the time zone difference. Traveling from Adelaide in December, Key Largo is somewhat warmer at night with lows of 22°C. Wrap up your sightseeing on the 31st (Sun) to allow time to drive to Islamorada.
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Islamorada — 3 nights
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.Museum-lovers will appreciate History of Diving Museum and Gallery Morada. Do your shopping at Pasta Pantaleo Signature Gallery and Zero Dress Code Boutique. Next up on the itinerary: cast your line with a fishing tour, take in the exciting artwork at Old Road Gallery, shop like a local with Rain Barrel Village, and admire the majestic nature at Lignumvitae Key Botanical State Park.
Plan my Islamorada trip by asking Inspirock to come up with tips and suggestions.
Islamorada is just a short distance from Key Largo. In December in Islamorada, expect temperatures between 31°C during the day and 25°C at night. Wrap up your sightseeing on the 3rd (Wed) to allow time to drive to Marathon.
Highlights from your trip
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 4th (Thu), pick up some local products at Paradise Produce, tour the pleasant surroundings at Sombrero Beach, then look for all kinds of wild species at The Turtle Hospital, and finally head outdoors with Outdoor Activities. On your second day here, look for all kinds of wild species at Dolphin Research Center and then kick back and relax at Bahia Honda State Park.
To see reviews, photos, more things to do, and other tourist information, you can read our Marathon trip planner.
Getting from Islamorada to Marathon by car takes about an hour. Other options: take a bus. Expect a daytime high around 29°C in January, and nighttime lows around 22°C. Cap off your sightseeing on the 5th (Fri) early enough to go by car to Key West.
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Key West — 5 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.Shop till you drop at We Cycle and 7 Artists & Friends Key West. Get some historical perspective at Saint Mary Star of the Sea and Key West Lighthouse and Keeper's Quarters Museum. Spend the 10th (Wed) exploring nature at Dry Tortugas National Park. There's still lots to do: get up close to creatures of the deep with a dolphin and whale watching tour, relax and rejuvenate at some of the best spas, explore the different monuments and memorials at Key West Cemetery, and brush up on your military savvy at U.S. Coast Guard Cutter Ingham Maritime Museum.
To see photos, other places to visit, maps, and other tourist information, go to the Key West trip itinerary builder website.
Traveling by car from Marathon to Key West takes 1.5 hours. Alternatively, you can take a bus. In January, daily temperatures in Key West can reach 28°C, while at night they dip to 22°C. Finish up your sightseeing early on the 10th (Wed) so you can catch the flight to Sarasota.
Highlights from your trip
Sarasota — 3 nights

Sarasota is a city in Sarasota County on the southwestern coast of the U.S. state of Florida. Step out of the city life by going to Fishing Charters & Tours and Tampa Electric's Manatee Viewing Center. For shopping fun, head to St. Armands Circle or Fishermen's Village. You'll find plenty of places to visit near Sarasota: Duncan McClellan Gallery (in St. Petersburg) and Treasure Island Beach (in Treasure Island). There's more to do: look for all kinds of wild species at Myakka River State Park.
For ratings, other places to visit, and tourist information, you can read our Sarasota trip maker app.
Traveling by flight from Key West to Sarasota takes 3 hours. Alternatively, you can drive; or do a combination of ferry, taxi, and bus. Traveling from Key West in January, expect slightly colder with lows of 13°C in Sarasota. Finish your sightseeing early on the 13th (Sat) to allow enough time to drive to Naples.
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For ratings, other places to visit, and tourist information, you can read our Sarasota trip maker app.
Traveling by flight from Key West to Sarasota takes 3 hours. Alternatively, you can drive; or do a combination of ferry, taxi, and bus. Traveling from Key West in January, expect slightly colder with lows of 13°C in Sarasota. Finish your sightseeing early on the 13th (Sat) to allow enough time to drive to Naples.
Side Trips
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Naples — 4 nights

Step out of the city life by going to Lovers Key State Park and Corkscrew Swamp. Head to Miromar Outlets between Naples & Fort Myers and KAJ Galleryfor some retail therapy. Explore Naples' surroundings by going to Parasailing & Paragliding (in Fort Myers Beach), Edison and Ford Winter Estates (in Fort Myers) and 2 Islands Gallery (in Captiva Island).
To find ratings, traveler tips, other places to visit, and tourist information, go to the Naples trip itinerary builder.
You can drive from Sarasota to Naples in 2 hours. Alternatively, you can take a bus; or do a combination of taxi and bus. In January, plan for daily highs up to 28°C, and evening lows to 17°C. Finish your sightseeing early on the 17th (Wed) so you can drive to Marco Island.
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To find ratings, traveler tips, other places to visit, and tourist information, go to the Naples trip itinerary builder.
You can drive from Sarasota to Naples in 2 hours. Alternatively, you can take a bus; or do a combination of taxi and bus. In January, plan for daily highs up to 28°C, and evening lows to 17°C. Finish your sightseeing early on the 17th (Wed) so you can drive to Marco Island.
Side Trips
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Marco Island — 3 nights
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. You'll discover tucked-away gems like Waterskiing & Jetskiing and Spas. Get outdoors at Keewaydin Island and Island Bike Shop & Bicycle Rentals. Take a break from Marco Island with a short trip to Nature & Wildlife Tours in Ochopee, about 56 minutes away. And it doesn't end there: stroll through South Marco Beach, kick back and relax at Tigertail Beach, and look for gifts at Keep In Touch.
For ratings, where to stay, and tourist information, read Marco Island journey planner.
Marco Island is very close to Naples. Traveling from Naples in January, expect little chillier with lows of 13°C in Marco Island. Wrap up your sightseeing on the 20th (Sat) early enough to fly to Orlando.
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For ratings, where to stay, and tourist information, read Marco Island journey planner.
Marco Island is very close to Naples. Traveling from Naples in January, expect little chillier with lows of 13°C in Marco Island. Wrap up your sightseeing on the 20th (Sat) early enough to fly to Orlando.
Side Trip
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Orlando — 4 nights

Theme Park Capital of the World
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.Eschew the tourist crowds and head to Stetson Mansion and SKELETONS: Museum of Osteology. Get outdoors at Nature & Wildlife Tours and Beach at Daytona Beach. Explore the numerous day-trip ideas around Orlando: Ponce Inlet (Marine Science Center & Ponce de Leon Inlet Lighthouse & Museum). Have a day of magic on the 21st (Sun) at Walt Disney World Resort. The adventure continues: revel in the low prices at Orlando Vineland Premium Outlets, buy something for everyone on your list at The Florida Mall, and make an unforgettable trip to World of Disney.
To find more things to do and other tourist information, read our Orlando tour builder app.
Traveling by flight from Marco Island to Orlando takes 2.5 hours. Alternatively, you can drive; or do a combination of taxi, bus, and train. In January, daytime highs in Orlando are 25°C, while nighttime lows are 13°C. Finish your sightseeing early on the 24th (Wed) to allow enough time to drive to Crystal River.
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Crystal River — 2 nights
The Gem of the Nature Coast
The jewel of Florida's Nature Coast, Crystal River spreads around spring-fed Kings Bay, known for maintaining a constant 22 C (72 F) temperature all year long.Kick off your visit on the 25th (Thu): discover the deep blue sea with a scuba or snorkeling tour, take in the exciting artwork at Franklin Anderson Gallery, and then take in the exciting artwork at The Glass Garage. Get ready for a full day of sightseeing on the 26th (Fri): look for all kinds of wild species at Three Sisters Springs, then admire the majestic nature at Ellie Schiller Homosassa Springs Wildlife State Park, and then contemplate the waterfront views at Homosassa River.
To see reviews, more things to do, where to stay, and more tourist information, read our Crystal River trip planning site.
Traveling by car from Orlando to Crystal River takes 2 hours. Alternatively, you can do a combination of shuttle and taxi; or do a combination of bus and taxi. Traveling from Orlando in January, plan for little chillier nights in Crystal River, with lows around 8°C. Wrap up your sightseeing on the 26th (Fri) early enough to drive to St. Augustine.
Side Trips
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St. Augustine — 5 nights
St. Deepen your sense of the past at sights like Fort Clinch State Park and Old Jail Museum. Visiting Dolphin & Whale Watching and Fort Matanzas National Monument will get you outdoors. Change things up with a short trip to Fernandina Beach in Amelia Island (about 1h 25 min away). The adventure continues: kick back and relax at St. Augustine Beach, examine the collection at Lightner Museum, learn about winemaking at San Sebastian Winery, and take in the spiritual surroundings of National Shrine of Our Lady of La Leche at Mission Nombre de Dios.
To find ratings, where to stay, photos, and tourist information, use the St. Augustine trip itinerary builder.
Drive from Crystal River to St. Augustine in 3 hours. Alternatively, you can take a bus. In January in St. Augustine, expect temperatures between 21°C during the day and 11°C at night. Finish your sightseeing early on the 31st (Wed) so you can fly back home.
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To find ratings, where to stay, photos, and tourist information, use the St. Augustine trip itinerary builder.
Drive from Crystal River to St. Augustine in 3 hours. Alternatively, you can take a bus. In January in St. Augustine, expect temperatures between 21°C during the day and 11°C at night. Finish your sightseeing early on the 31st (Wed) so you can fly back home.
Side Trip
Highlights from your trip
Florida travel guide
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.