16 days in Florida Itinerary

16 days in Florida Itinerary

Created using Inspirock Florida route planner

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Route & dates

16 days in Florida Itinerary

Start: Toronto
Fly:  6​h 15​min
1
Sanibel Island
— 1 night
taxi + Fly:  3​h
2
Key West
— 3 nights
bus:  1​h 15​min
3
Marathon
— 2 nights
Drive:  45​min
4
Islamorada
— 1 night
+2
shuttle + Fly + Drive:  5​h 30​min
5
St. Augustine
— 3 nights
Drive:  2​h
6
Orlando
— 2 nights
Drive:  1​h 30​min
7
Tampa
— 3 nights
Fly:  6​h 15​min
End: Toronto

1
night
Sanibel Island

Sanibel Island ©
Take a trip to Sanibel Island if you like pretty sunsets and luxurious resorts.
To see traveler tips, reviews, ratings, and tourist information, you can read our Sanibel Island holiday planner .

Toronto, Canada to Sanibel Island is an approximately 6.5-hour flight. You can also do a combination of flight and bus; or drive. Expect warmer temperatures when traveling from Toronto in December; daily highs in Sanibel Island reach 31°C and lows reach 19°C. Finish up your sightseeing early on the 15th (Sun) so you can travel to Key West.

Things to do in Sanibel Island

Parks Beaches Museums

Side Trip

Edison and Ford Winter Estates
Highlights from your plan
Edison and Ford Winter Estates ©
Edison and Ford Winter Estates
Bowman's Beach ©
Bowman's Beach
Sanibel Island Farmer's Market ©
Sanibel Island Farmer's Market

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.
Let the collections at U.S. Coast Guard Cutter Ingham Maritime Museum and The Ernest Hemingway Home and Museum capture your imagination. Discover out-of-the-way places like Scuba & Snorkeling and Dry Tortugas National Park. There's lots more to do: see majestic marine mammals with a dolphin and whale watching tour, enjoy the sea views from Key West Lighthouse and Keeper's Quarters Museum, identify plant and animal life at Key West Butterfly & Nature Conservatory, and stroll the grounds of Key West Cemetery.

To find where to stay, maps, traveler tips, and more tourist information, read Key West tour planner.

Traveling by combination of taxi and flight from Sanibel Island to Key West takes 3 hours. Alternatively, you can ride a ferry; or drive. Traveling from Sanibel Island in December, plan for a bit warmer nights in Key West, with lows around 25°C. Cap off your sightseeing on the 18th (Wed) early enough to catcht the bus to Marathon.

Things to do in Key West

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

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.
Kick off your visit on the 19th (Thu): kick back and relax at Sombrero Beach, then look for all kinds of wild species at The Turtle Hospital, and then stroll through Bahia Honda State Park. On the 20th (Fri), you'll have a packed day of sightseeing: take a tour by water with Boat Tours & Water Sports, then identify plant and animal life at Dolphin Research Center, and then snap pictures at Seven Mile Bridge.

To find reviews, photos, traveler tips, and other tourist information, read Marathon visit website .

Traveling by bus from Key West to Marathon takes 1.5 hours. Alternatively, you can drive. In December, daytime highs in Marathon are 31°C, while nighttime lows are 25°C. Wrap up your sightseeing on the 20th (Fri) early enough to drive to Islamorada.

Things to do in Marathon

Parks Outdoors Wildlife

Side Trip

Bahia Honda State Park
Highlights from your plan
The Turtle Hospital ©
The Turtle Hospital
Dolphin Research Center ©
Dolphin Research Center
Fishing Charters & Tours

1
night
Islamorada

Islamorada ©
Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
Start off your visit on the 21st (Sat): take an in-depth tour of History of Diving Museum, identify plant and animal life at Florida Keys Wild Bird Rehabilitation Center, and then see what you can catch with a fishing tour.

Take the guesswork out of planning a Islamorada vacation by using our trip itinerary maker.

Drive from Marathon to Islamorada in an hour. Alternatively, you can take a bus. December in Islamorada sees daily highs of 31°C and lows of 25°C at night. Cap off your sightseeing on the 21st (Sat) early enough to travel to St. Augustine.

Things to do in Islamorada

Wildlife Tours Outdoors

Side Trip

Florida Keys Wild Bird Rehabilitation Center
Highlights from your plan
Fishing Charters & Tours
History of Diving Museum ©
History of Diving Museum

3
nights
St. Augustine

St. Augustine ©
SAINT AUGUSTINE | PONTE VEDRA on Florida's Historic Coast The Nation's oldest city (est. Explore hidden gems such as Vilano Beach and St. Augustine Beach. Deepen your sense of the past at sights like Cathedral Basilica of St. Augustine and Mission of Nombre de Dios. Spend the 23rd (Mon) exploring nature at Fort Matanzas National Monument. There's lots more to do: examine the collection at Lightner Museum, identify plant and animal life at St. Augustine Alligator Farm Zoological Park, view the masterpieces at High Tide Gallery Art & Gifts, and take in the architecture and atmosphere at Memorial Presbyterian Church.

To see reviews, maps, traveler tips, and other tourist information, read St. Augustine online trip itinerary planner .

Getting from Islamorada to St. Augustine by combination of shuttle, flight, and car takes about 5.5 hours. Other options: drive; or do a combination of shuttle, flight, and bus. Expect a bit cooler temperatures when traveling from Islamorada in December; daily highs in St. Augustine reach 24°C and lows reach 15°C. Finish your sightseeing early on the 24th (Tue) so you can drive to Orlando.

Things to do in St. Augustine

Parks Historic Sites Nature
Highlights from your plan
Cathedral Basilica of St. Augustine ©
St. Augustine Beach ©
St. Augustine Beach
Fort Matanzas National Monument ©
Fort Matanzas National Monument

2
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.
Kick off your visit on the 25th (Wed): get a sense of history and politics at City Hall, steep yourself in history at Stetson Mansion, and then take a stroll through International Drive. Here are some ideas for day two: take in the architecture and atmosphere at Basilica of the National Shrine of Mary, Queen of the Universe, then revel in the low prices at Orlando Vineland Premium Outlets, then stop by The LEGO Store Downtown Disney, and finally take in a show at Happily Ever After Fireworks.

To find photos, traveler tips, reviews, and tourist information, read Orlando trip planner .

Drive from St. Augustine to Orlando in 2 hours. Alternatively, you can take a bus. While traveling from St. Augustine, expect a bit warmer days and about the same nights in Orlando, ranging from highs of 29°C to lows of 17°C. Finish your sightseeing early on the 26th (Thu) so you can drive to Tampa.

Things to do in Orlando

Shopping Historic Sites Neighborhoods

Side Trip

Stetson Mansion
Highlights from your plan
Stetson Mansion ©
Stetson Mansion
International Drive ©
International Drive

3
nights
Tampa

Tampa ranks among the country's most livable cities, attracting newcomers with its growing economy and status as a major port on the Gulf of Mexico.
Step off the beaten path and head to Fishing Charters & Tours and Treasure Island Beach. Visiting Tampa Electric's Manatee Viewing Center and Saint Pete Beach will get you outdoors. Step out of Tampa with an excursion to Two Friend's Closet in St. Pete Beach--about 44 minutes away. There's more to do: get engrossed in the history at Henry B. Plant Museum and take in the views from Sunshine Skyway Bridge.

To find ratings and other tourist information, refer to the Tampa trip itinerary tool .

Getting from Orlando to Tampa by car takes about 1.5 hours. Other options: take a bus; or take a train. December in Tampa sees daily highs of 30°C and lows of 19°C at night. Finish up your sightseeing early on the 29th (Sun) so you can travel back home.

Things to do in Tampa

Outdoors Wildlife Tours

Side Trips

St. Pete Beach, Tampa Electric's Manatee Viewing Center, Treasure Island Beach
Highlights from your plan
Fishing Charters & Tours
Saint Pete Beach ©
Saint Pete Beach
Tampa Electric's Manatee Viewing Center ©