49 days in Florida Itinerary

49 days in Florida Itinerary

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Route & dates

49 days in Florida Itinerary

Start: Sydney
Fly:  25​h
1
Orlando
— 7 nights
Drive:  2​h
2
St. Augustine
— 6 nights
Drive + Fly:  5​h 45​min
3
Key West
— 6 nights
bus:  45​min
4
Big Pine Key
— 3 nights
bus:  30​min
5
Marathon
— 6 nights
Drive:  45​min
6
Islamorada
— 6 nights
Drive:  45​min
7
Key Largo
— 6 nights
Drive:  1​h 30​min
8
Miami Beach
— 5 nights
+2
bus + tram + Fly:  24​h
End: Sydney

7
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.
Take a break from the city and head to Discovery Cove and Disney's Animal Kingdom. Get some historical perspective at Stetson Mansion and St. Barnabas Episcopal Church. Take a break from Orlando with a short trip to Gallery On First in Sanford, about 38 minutes away. Have a day of magic on the 20th (Wed) at Walt Disney World Resort. Pack the 22nd (Fri) with family-friendly diversions at Universal's Islands of Adventure. Next up on the itinerary: get in on the family fun at Universal Orlando Resort, admire nature's wide array of creatures at SeaWorld Orlando, admire the masterpieces at Charles Hosmer Morse Museum of American Art, and stop by The LEGO Store Downtown Disney.

Plan trip to Orlando with our itinerary maker to find out where to go and what to do.

Sydney, Australia to Orlando is an approximately 25-hour flight. You can also do a combination of bus and flight; or do a combination of train and flight. Due to the time zone difference, you'll gain 15 hours traveling from Sydney to Orlando. Expect a daytime high around 30°C in November, and nighttime lows around 19°C. Wrap up your sightseeing on the 24th (Sun) to allow time to drive to St. Augustine.

Things to do in Orlando

Theme Parks Parks Beaches

Side Trips

DeLand, Charles Hosmer Morse Museum of American Art, Gallery On First
Highlights from your plan
Universal Orlando Resort ©
Universal Orlando Resort
Walt Disney World Resort ©
Walt Disney World Resort
Discovery Cove ©
Discovery Cove

6
nights
St. Augustine

St. Augustine ©
SAINT AUGUSTINE | PONTE VEDRA on Florida's Historic Coast The Nation's oldest city (est. Your itinerary includes some good beach time at Andy Romano Beachfront Park and St. Augustine Beach. Visit St. Augustine Lighthouse & Maritime Museum, Inc. and Cathedral Basilica of St. Augustine for their historical value. You'll find plenty of places to visit near St. Augustine: Bulow Plantation Ruins Historic State Park (in Bunnell), Gainesville (Carson Springs Wildlife Conservation Foundation & Butterfly Rainforest) and Single Vision Inc. (in Melrose). Spend the 28th (Thu) exploring nature at Fort Matanzas National Monument. There's lots more to do: identify plant and animal life at St. Augustine Wild Reserve, contemplate in the serene atmosphere at St. Photios Greek Orthodox National Shrine, admire the majestic nature at Marjorie Kinnan Rawlings Historic State Park, and examine the collection at The Ximenez-Fatio House.

To see reviews, more things to do, ratings, and tourist information, you can read our St. Augustine holiday maker site .

Getting from Orlando to St. Augustine by car takes about 2 hours. Other options: take a bus. While traveling from Orlando, expect slightly colder days and about the same nights in St. Augustine, ranging from highs of 26°C to lows of 17°C. Finish your sightseeing early on the 30th (Sat) so you can travel to Key West.

Things to do in St. Augustine

Parks Historic Sites Nature

Side Trips

Gainesville, Marjorie Kinnan Rawlings Historic State Park, Andy Romano Beachfront Park, Bulow Plantation Ruins Historic State Park, Single Vision Inc.
Highlights from your plan

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.
Popular historic sites such as Truman Little White House and Fort Zachary Taylor are in your itinerary. Head to Alan S. Maltz Gallery and KEPart Studio-Galleryfor some retail therapy. Spend the 4th (Wed) exploring nature at Dry Tortugas National Park. And it doesn't end there: examine the collection at The Ernest Hemingway Home and Museum, visit a coastal fixture at Key West Lighthouse and Keeper's Quarters Museum, stroll the grounds of Key West Cemetery, and tour the water at your own pace with Fun In The Sun Key West.

For maps, reviews, ratings, and more tourist information, read Key West online tour planner .

Do a combination of car and flight from St. Augustine to Key West in 6 hours. Alternatively, you can do a combination of bus and flight; or drive. Expect a bit warmer temperatures when traveling from St. Augustine in December; daily highs in Key West reach 30°C and lows reach 25°C. Finish up your sightseeing early on the 7th (Sat) so you can catcht the bus to Big Pine Key.

Things to do in Key West

Outdoors Tours Historic Sites
Highlights from your plan
The Ernest Hemingway Home and Museum ©
Dry Tortugas National Park ©
Dry Tortugas National Park

3
nights
Big Pine Key

Big Pine Key ©
Big Pine Key is a census-designated place and unincorporated community in Monroe County, Florida, United States, on an island of the same name in the Florida Keys. Get outdoors at Bahia Honda State Park and National Key Deer Refuge. Visit Calusa Beach and Long Beach for some beach relaxation. And it doesn't end there: take in the exciting artwork at Artists in Paradise Gallery, paddle through the water with a kayaking and canoeing tour, stop by Out of the Blue Gallery, and look for all kinds of wild species at Blue Hole.

To see maps, ratings, where to stay, and tourist information, use the Big Pine Key online trip itinerary maker .

You can take a bus from Key West to Big Pine Key in an hour. Alternatively, you can drive. In December, plan for daily highs up to 31°C, and evening lows to 25°C. Wrap up your sightseeing on the 10th (Tue) to allow time to take a bus to Marathon.

Things to do in Big Pine Key

Parks Outdoors Beaches
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
Stand-Up Paddleboarding
Blue Hole ©
Blue Hole

6
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.
Attractions like Pigeon Key Foundation and The Turtle Hospital make great kid-friendly stops. Visiting Crane Point Museum & Nature Center and Marathon Garden Club will get you outdoors. Next up on the itinerary: pause for some serene contemplation at San Pablo Catholic Church, look for all kinds of wild species at Dolphin Research Center, add some adventure to your tour with a kayaking and canoeing tour, and kick back and relax at Sunset Park Beach.

To find photos, other places to visit, where to stay, and more tourist information, go to the Marathon day trip planning site .

Marathon is very close to Big Pine Key. In December in Marathon, expect temperatures between 31°C during the day and 25°C at night. Finish your sightseeing early on the 16th (Mon) to allow enough time to drive to Islamorada.

Things to do in Marathon

Outdoors Parks Wildlife

Side Trip

Sunset Park Beach
Highlights from your plan
San Pablo Catholic Church ©
San Pablo Catholic Church
Pigeon Key Foundation ©
Pigeon Key Foundation
Sombrero Beach ©
Sombrero Beach

6
nights
Islamorada

Islamorada ©
Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
Do your shopping at Old Road Gallery and Bella Sol Fragrance Bar and Gifts. Escape the urban bustle at Robbie's of Islamorada and Bayside Boat Rentals. And it doesn't end there: steep yourself in history at Indian Key State Historic Site, immerse yourself in nature at Lignumvitae Key Botanical State Park, head outdoors with A Lil' Tail Charters, and view the masterpieces at Gallery Morada.

For maps, reviews, other places to visit, and more tourist information, go to the Islamorada trip planner .

Drive from Marathon to Islamorada in an hour. Alternatively, you can take a bus. In December in Islamorada, expect temperatures between 31°C during the day and 25°C at night. Finish your sightseeing early on the 22nd (Sun) to allow enough time to drive to Key Largo.

Things to do in Islamorada

Outdoors Tours Wildlife
Highlights from your plan
Robbie's of Islamorada ©
Robbie's of Islamorada
Spray Watersports ©
Spray Watersports
Lignumvitae Key Botanical State Park ©

6
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.
Do some cultural sightseeing at Coral Castle and Key Largo Baptist Church. Kids will appreciate attractions like Florida Keys Wild Bird Rehabilitation Center and Spiegel Grove. When in Key Largo, make a side trip to see Anhinga Trail in Everglades National Park, approximately 48 minutes away. Spend the 27th (Fri) peacefully gliding across the water with some of the best stand-up paddleboarding in the area. There's much more to do: discover the deep blue sea with a scuba or snorkeling tour, identify plant and animal life at Molasses Reef, explore the gorgeous colors at Key Largo Undersea Park, and pause for some serene contemplation at Saint Justin Martyr Catholic Church.

To see where to stay, ratings, reviews, and other tourist information, read Key Largo trip itinerary planner.

Drive from Islamorada to Key Largo in an hour. Alternatively, you can do a combination of bus and taxi. Traveling from Islamorada in December, plan for little chillier nights in Key Largo, with lows around 22°C. Finish your sightseeing early on the 28th (Sat) to allow enough time to drive to Miami Beach.

Things to do in Key Largo

Wildlife Outdoors Parks

Side Trips

Anhinga Trail, Coral Castle
Highlights from your plan
Key Largo Fishing Adventures ©
Key Largo Fishing Adventures
Scuba & Snorkeling

5
nights
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.
Family-friendly places like Lincoln Road and South Beach will thrill your kids. Head to Collins Avenue and Aventura Mallfor plenty of shopping. Venture out of the city with trips to Dolphin Mall (in Miami) and Shark Valley (in Everglades National Park). The adventure continues: appreciate the extensive heritage of Art Deco Historic District, take a stroll through Espanola Way, make a trip to Bayside Marketplace, and examine the collection at Vizcaya Museum and Gardens.

For photos, traveler tips, more things to do, and other tourist information, read our Miami Beach travel website .

Drive from Key Largo to Miami Beach in 1.5 hours. Alternatively, you can take a bus; or do a combination of taxi and bus. In December, daily temperatures in Miami Beach can reach 32°C, while at night they dip to 23°C. Wrap up your sightseeing by early afternoon on the 2nd (Thu) to allow enough time to travel back home.

Things to do in Miami Beach

Shopping Neighborhoods Historic Sites

Side Trips

Miami, Aventura Mall, St. Raymond Catholic Church, Shark Valley
Highlights from your plan
Lincoln Road ©
Lincoln Road
South Beach ©
South Beach
Art Deco Historic District ©
Art Deco Historic District

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