19 days in Florida Itinerary

19 days in Florida Itinerary

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Route & dates

19 days in Florida Itinerary

Start: Toronto
Fly + shuttle:  8​h 15​min
1
Islamorada
— 3 nights
Drive:  45​min
2
Marathon
— 2 nights
bus:  1​h 15​min
3
Key West
— 3 nights
Fly + taxi:  3​h
4
Sanibel Island
— 3 nights
Drive:  1​h 15​min
5
Naples
— 2 nights
Drive:  3​h 45​min
6
Orlando
— 2 nights
Drive:  2​h
7
St. Augustine
— 3 nights
bus + Fly:  7​h 30​min
End: Toronto

3
nights
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 29th (Mon): sample the tasty concoctions at Islamorada Beer Company Brewery and Tasting Room. On the 30th (Tue), you'll have a packed day of sightseeing: get a new perspective on things with Boat Tours & Water Sports, then stop by Petals With Pizzazz, then get a taste of the local shopping with Old Road Gallery, and finally look for all kinds of wild species at Florida Keys Wild Bird Rehabilitation Center.

For other places to visit, photos, maps, and other tourist information, read Islamorada driving holiday site .

Toronto, Canada to Islamorada is an approximately 8.5-hour combination of flight and shuttle. You can also do a combination of bus, flight, and shuttle; or drive. Traveling from Toronto in January, expect Islamorada to be much hotter, temps between 28°C and 20°C. Wrap up your sightseeing on the 1st (Thu) to allow time to drive to Marathon.

Things to do in Islamorada

#Tours, #Outdoors, #Shopping

Side Trip

Florida Keys Wild Bird Rehabilitation Center
Highlights from your plan
Fishing Charters & Tours
Indian Key State Historic Site ©
Indian Key State Historic Site
Old Road Gallery ©
Old Road Gallery

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 1st (Thu), immerse yourself in nature at Bahia Honda State Park, then take in the views from Seven Mile Bridge, and then look for all kinds of wild species at The Turtle Hospital. Get ready for a full day of sightseeing on the next day: stop by The Tackle Box, then enjoy the sand and surf at Sombrero Beach, and then take a memorable tour with Tours.

For other places to visit, photos, traveler tips, and other tourist information, you can read our Marathon trip itinerary maker .

Traveling by car from Islamorada to Marathon takes an hour. Alternatively, you can take a bus. Expect a daytime high around 30°C in February, and nighttime lows around 22°C. Finish your sightseeing early on the 3rd (Sat) so you can drive to Key West.

Things to do in Marathon

#Outdoors, #Parks, #Beaches

Side Trip

Bahia Honda State Park
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
Sombrero Beach ©
Sombrero Beach
The Tackle Box ©
The Tackle Box

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.
Do some cultural sightseeing at Key West Lighthouse and Keeper's Quarters Museum and The Basilica School of Saint Mary Star of the Sea. Deepen your sense of the past at sights like Key West Cemetery and Key West Garden Club. Spend the 4th (Sun) exploring nature at Dry Tortugas National Park. Next up on the itinerary: look for gifts at Uva Wine Shop & Bar, see the interesting displays at Mel Fisher Maritime Museum, browse the different shops at Marcial de Gomar Emeralds International, and soothe aching muscles at some of the top local wellness centers.

To find traveler tips, more things to do, and other tourist information, refer to the Key West road trip planner.

Getting from Marathon to Key West by car takes about 1.5 hours. Other options: take a bus. In February, plan for daily highs up to 29°C, and evening lows to 23°C. Finish your sightseeing early on the 6th (Tue) so you can travel to Sanibel Island.

Things to do in Key West

#Shopping, #Parks, #Historic Sites
Highlights from your plan
Uva Wine Shop & Bar ©
Uva Wine Shop & Bar
Key West Cemetery ©
Key West Cemetery

3
nights
Sanibel Island

Sanibel Island ©
Take a trip to Sanibel Island if you like pretty sunsets and luxurious resorts.
Deepen your sense of the past at sights like Edison and Ford Winter Estates and Sanibel Island Lighthouse. Do your shopping at Sanibel Island Farmer's Market and B Unique Boutique. Change things up with a short trip to Fort Myers Beach in Fort Myers Beach (about 34 minutes away).

To find photos, maps, more things to do, and other tourist information, refer to the Sanibel Island road trip planning site .

You can do a combination of flight and taxi from Key West to Sanibel Island in 3 hours. Alternatively, you can do a combination of ferry and taxi; or drive. Plan for a bit cooler nights when traveling from Key West in February since evenings lows in Sanibel Island dip to 16°C. Finish up your sightseeing early on the 9th (Fri) so you can go by car to Naples.

Things to do in Sanibel Island

#Parks, #Beaches, #Outdoors

Side Trips

Fort Myers Beach, Captiva Beach, Edison & Ford Winter Estates
Highlights from your plan
Bowman's Beach ©
Bowman's Beach
Fort Myers Beach ©
Fort Myers Beach
Captiva Beach ©
Captiva Beach

2
nights
Naples

Naples ©
Naples is a city in Collier County, Florida, United States. On the 10th (Sat), take in nature's colorful creations at Naples Botanical Garden, kick back and relax at Lowdermilk Beach, and then wander the streets of Fifth Avenue South. Get ready for a full day of sightseeing on the next day: get a taste of the local shopping with Third Street South.

For other places to visit, ratings, maps, and more tourist information, you can read our Naples trip planner .

Drive from Sanibel Island to Naples in 1.5 hours. Alternatively, you can do a combination of taxi and bus. In February, plan for daily highs up to 29°C, and evening lows to 17°C. Wrap up your sightseeing by early afternoon on the 11th (Sun) to allow enough time to drive to Orlando.

Things to do in Naples

#Neighborhoods, #Shopping, #Parks
Highlights from your plan
Fifth Avenue South ©
Fifth Avenue South
Third Street South ©
Third Street South
Naples Botanical Garden ©
Naples Botanical Garden

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 12th (Mon): stop by The LEGO Store, then get some fabulous bargains at Orlando Vineland Premium Outlets, and then wander the streets of International Drive. Get ready for a full day of sightseeing on the 13th (Tue): steep yourself in history at Stetson Mansion and then browse the different shops at The Florida Mall.

For other places to visit and other tourist information, use the Orlando planning app .

Getting from Naples to Orlando by car takes about 4 hours. Other options: do a combination of bus and flight; or do a combination of bus and train. In February in Orlando, expect temperatures between 27°C during the day and 15°C at night. Finish up your sightseeing early on the 13th (Tue) so you can go by car to St. Augustine.

Things to do in Orlando

#Shopping, #Neighborhoods, #Historic Sites

Side Trip

Stetson Mansion
Highlights from your plan
Stetson Mansion ©
Stetson Mansion
The Florida Mall ©
The Florida Mall

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 Cathedral Basilica of St. Augustine. Get some cultural insight at Fort Matanzas National Monument and Lightner Museum. And it doesn't end there: sample the fine beverages at St. Augustine Distillery, examine the collection at St. Augustine Pirate & Treasure Museum, and admire all the interesting features of Flagler College.

To see reviews, ratings, more things to do, and tourist information, read St. Augustine trip planner.

Traveling by car from Orlando to St. Augustine takes 2 hours. Alternatively, you can take a bus. In February, St. Augustine is little chillier than Orlando - with highs of 22°C and lows of 11°C. Cap off your sightseeing on the 16th (Fri) early enough to travel back home.

Things to do in St. Augustine

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

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