29 days in Florida Itinerary

29 days in Florida Itinerary

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Route & dates

29 days in Florida Itinerary

Start: Toronto
Fly:  6​h 30​min
1
Miami Beach
— 2 nights
Drive:  2​h
2
Islamorada
— 3 nights
Drive:  45​min
3
Marathon
— 3 nights
bus:  1​h 15​min
4
Key West
— 4 nights
Fly + taxi:  2​h 45​min
5
Sanibel Island
— 3 nights
Drive:  1​h 15​min
6
Naples
— 4 nights
Drive:  2​h
7
Rotonda West
— 1 night
Drive:  3​h 15​min
8
Orlando
— 5 nights
Drive:  2​h
9
St. Augustine
— 3 nights
bus + Fly:  7​h 30​min
End: Toronto

2
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.
Start off your visit on the 21st (Sun): take a stroll through Collins Avenue. Keep things going the next day: see the interesting displays at Vizcaya Museum & Gardens, wander the streets of Lincoln Road, then kick back and relax at South Beach, and finally shop like a local with Espanola Way.

To see other places to visit, traveler tips, ratings, and more tourist information, refer to the Miami Beach day trip planning site .

Toronto, Canada to Miami Beach is an approximately 6.5-hour combination of flight, tram, and bus. You can also drive; or take a bus. Expect much hotter temperatures when traveling from Toronto in January; daily highs in Miami Beach reach 29°C and lows reach 19°C. Cap off your sightseeing on the 23rd (Tue) early enough to go by car to Islamorada.

Things to do in Miami Beach

Shopping Neighborhoods Parks

Side Trips

Vizcaya Museum and Gardens, E Las Olas Blvd, Aventura Mall
Highlights from your plan
Aventura Mall ©
Aventura Mall
Vizcaya Museum and Gardens ©
Vizcaya Museum and Gardens
Collins Avenue ©
Collins Avenue

3
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 Shell World. Museum-lovers will get to explore History of Diving Museum and Michelle Nicole Lowe Art Gallery. There's lots more to do: look for gifts at Petals With Pizzazz, examine the collection at Florida Keys History & Discovery Center, view the masterpieces at Lobster Trap Art Gift Shop and Gallery, and identify plant and animal life at Florida Keys Wild Bird Rehabilitation Center.

To find photos, other places to visit, traveler tips, and other tourist information, use the Islamorada trip planner .

Getting from Miami Beach to Islamorada by car takes about 2 hours. Other options: do a combination of bus and shuttle; or take a bus. In January, plan for daily highs up to 28°C, and evening lows to 20°C. Wrap up your sightseeing on the 26th (Fri) early enough to drive to Marathon.

Things to do in Islamorada

Shopping Museums Wildlife

Side Trip

Key Largo
Highlights from your plan
Old Road Gallery ©
Old Road Gallery
History of Diving Museum ©
History of Diving Museum
African Queen Canal Cruise ©
African Queen Canal Cruise

3
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 27th (Sat), tour the pleasant surroundings at Bahia Honda State Park, take in the views from Seven Mile Bridge, and then look for all kinds of wild species at The Turtle Hospital. Here are some ideas for day two: enjoy the sand and surf at Sunset Park Beach, then stroll through Sombrero Beach, and then look for all kinds of wild species at Crane Point Museum & Nature Center.

Discover how to plan a Marathon trip in just a few steps with Inspirock's itinerary builder.

Getting from Islamorada to Marathon by car takes about an hour. Other options: take a shuttle; or take a bus. In January, plan for daily highs up to 28°C, and evening lows to 21°C. Finish your sightseeing early on the 29th (Mon) so you can drive to Key West.

Things to do in Marathon

Parks Outdoors Beaches

Side Trips

Bahia Honda State Park, Sunset Park Beach
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
Sombrero Beach ©
Sombrero Beach
Sunset Park Beach ©
Sunset Park Beach

4
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.
Step off the beaten path and head to Dry Tortugas National Park and Key West Lighthouse and Keeper's Quarters Museum. Museum-lovers will appreciate The Ernest Hemingway Home and Museum and Florida Keys Eco-Discovery Center. The adventure continues: see the interesting displays at Mel Fisher Maritime Museum, glide peacefully along the water with some of the best stand-up paddleboarding in the area, take an in-depth tour of Key West Firehouse Museum, and stop by Peppers Of Key West.

To find maps, where to stay, more things to do, and tourist information, go to the Key West itinerary builder site .

You can drive from Marathon to Key West in 1.5 hours. Alternatively, you can take a bus. Expect a daytime high around 28°C in January, and nighttime lows around 22°C. Wrap up your sightseeing on the 2nd (Fri) early enough to travel to Sanibel Island.

Things to do in Key West

Museums Parks Shopping
Highlights from your plan
Dry Tortugas National Park ©
Dry Tortugas National Park
The Ernest Hemingway Home and Museum ©

3
nights
Sanibel Island

Sanibel Island ©
Take a trip to Sanibel Island if you like pretty sunsets and luxurious resorts.
Step off the beaten path and head to Bowman's Beach and The Bailey-Matthews National Shell Museum. Shop till you drop at Sanibel Island Farmer's Market and Bailey's General Store. Explore the numerous day-trip ideas around Sanibel Island: Sun Harvest Citrus (in Fort Myers) and Fort Myers Beach (in Fort Myers Beach).

To find where to stay, more things to do, ratings, and other tourist information, go to the Sanibel Island trip planner.

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. Traveling from Key West in February, plan for little chillier nights in Sanibel Island, with lows around 16°C. Wrap up your sightseeing on the 5th (Mon) early enough to drive to Naples.

Things to do in Sanibel Island

Parks Outdoors Beaches

Side Trips

Sun Harvest Citrus, Captiva Beach, Fort Myers Beach
Highlights from your plan
Bowman's Beach ©
Bowman's Beach
Captiva Beach ©
Captiva Beach

4
nights
Naples

Naples ©
Naples is a city in Collier County, Florida, United States. Relax by the water at Barefoot Beach Preserve and South Marco Beach. Explore hidden gems such as Fifth Avenue South and Waterside Shops. Venture out of the city with trips to Tigertail Beach (in Marco Island) and Miromar Outlets (in Estero). The adventure continues: kick back and relax at Lowdermilk Beach, take a stroll through Third Street South, view the masterpieces at Naples Art Association, and look for gifts at Toucan's World.

To see traveler tips, other places to visit, ratings, and more tourist information, go to the Naples vacation app .

Getting from Sanibel Island to Naples by car takes about 1.5 hours. In February, daily temperatures in Naples can reach 29°C, while at night they dip to 17°C. Finish your sightseeing early on the 9th (Fri) to allow enough time to travel to Rotonda West.

Things to do in Naples

Outdoors Parks Beaches

Side Trips

Marco Island, Miromar Outlets, Barefoot Beach Preserve
Highlights from your plan
Barefoot Beach Preserve ©
Barefoot Beach Preserve
Lowdermilk Beach ©
Lowdermilk Beach
South Marco Beach ©
South Marco Beach

1
night
Rotonda West

Rotonda West
Kick off your visit on the 10th (Sat): explore the landscape on two wheels at Cape Haze Pioneer Trail Park.

To find ratings, reviews, photos, and tourist information, read our Rotonda West travel site .

Traveling by car from Naples to Rotonda West takes 2 hours. Expect a daytime high around 26°C in February, and nighttime lows around 15°C. On the 10th (Sat), wrap the sightseeing up by early afternoon so you can travel to Orlando.

Things to do in Rotonda West

Parks Outdoors Trails

5
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.
Give yourself a bit of retail therapy at Orlando Vineland Premium Outlets and Secrets of Cocoa Beach. Explore hidden gems such as Beach at Daytona Beach and The LEGO Store. Get out of town with these interesting Orlando side-trips: Cocoa Beach (in Cocoa Beach) and Stetson Mansion (in DeLand). Pack the 13th (Tue) with family-friendly diversions at Walt Disney World Resort. There's lots more to do: look for gifts at World of Disney, explore the world behind art at The Charles Hosmer Morse Museum of American Art, and make an unforgettable trip to Happily Ever After Fireworks.

For ratings, other places to visit, where to stay, and other tourist information, read Orlando tour itinerary planner .

Getting from Rotonda West to Orlando by car takes about 3 hours. In February, daily temperatures in Orlando can reach 27°C, while at night they dip to 15°C. Wrap up your sightseeing on the 15th (Thu) to allow time to drive to St. Augustine.

Things to do in Orlando

Theme Parks Shopping Parks

Side Trips

Cocoa Beach, Stetson Mansion, Beach at Daytona Beach, Charles Hosmer Morse Museum of American Art
Highlights from your plan
Walt Disney World Resort ©
Walt Disney World Resort
Beach at Daytona Beach ©
Beach at Daytona Beach
Cocoa Beach ©
Cocoa Beach

3
nights
St. Augustine

St. Augustine ©
SAINT AUGUSTINE | PONTE VEDRA on Florida's Historic Coast The Nation's oldest city (est. Appreciate the collections at Lightner Museum and High Tide Gallery. Do your shopping at Claude's Chocolate and Spice & Tea Exchange of St. Augustine. There's lots more to do: kick back and relax at St. Augustine Beach, see the interesting displays at St. Augustine Pirate & Treasure Museum, admire all the interesting features of Flagler College, and make a trip to St. George Street.

Discover how to plan a St. Augustine trip in just a few steps with Inspirock's itinerary builder.

Traveling by car from Orlando to St. Augustine takes 2 hours. Alternatively, you can take a bus. In February, St. Augustine is a bit cooler than Orlando - with highs of 22°C and lows of 11°C. Wrap up your sightseeing on the 18th (Sun) to allow time to travel back home.

Things to do in St. Augustine

Parks Museums Outdoors
Highlights from your plan
St. Augustine Beach ©
St. Augustine Beach
Vilano Beach ©
Vilano Beach
Lightner Museum ©
Lightner Museum

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