29 days in Florida Itinerary

29 days in Florida Itinerary

Created using Inspirock Florida trip planner

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Route & dates

Start: Toronto
+2
Fly + Tram + Bus:  6 h 30 min
1
Miami Beach
— 2 nights
Drive:  2 h
2
Islamorada
— 3 nights
Drive:  45 min
3
Marathon, Florida Keys
— 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
+3
Bus + Taxi + 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.
On the 21st (Sun), get a taste of the local shopping with Collins Avenue. Keep things going the next day: examine the collection at Vizcaya Museum and Gardens, then stroll around Lincoln Road, then kick back and relax at South Beach, and finally wander the streets of Espanola Way.

To find reviews, traveler tips, and more tourist information, you can read our Miami Beach trip site.

Toronto, Canada to Miami Beach is an approximately 6.5- hour combination of flight and bus. You can also do a combination of flight, train, and bus; or drive. Expect warmer temperatures when traveling from Toronto in January; daily highs in Miami Beach reach 29°C and lows reach 20°C. Wrap up your sightseeing on the 23rd (Tue) early enough to drive to Islamorada.

Things to do in Miami Beach

Shopping Neighborhoods Parks

Side Trips

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

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.
Museum-lovers will get to explore History of Diving Museum and Florida Keys History & Discovery Center. Step off the beaten path and head to Florida Keys Wild Bird Rehabilitation Center and African Queen Canal Cruise. There's lots more to do: cast your line with a fishing tour, take in the exciting artwork at Michelle Nicole Lowe Art Gallery, stop by Shell World Florida Keys, and get a taste of the local shopping with Old Road Gallery.

To find photos, more things to do, where to stay, and tourist information, go to the Islamorada tour builder tool.

Drive from Miami Beach to Islamorada in 2 hours. Alternatively, you can take a bus. In January, plan for daily highs up to 29°C, and evening lows to 22°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, Florida Keys

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 27th (Sat): kick back and relax at Bahia Honda State Park, then snap pictures at Seven Mile Bridge, and then look for all kinds of wild species at The Turtle Hospital. On your second day here, stroll through Sunset Park Beach, then enjoy the sand and surf at Sombrero Beach, and then examine the collection at Crane Point Museum & Nature Center.

For where to stay, maps, reviews, and other tourist information, refer to the Marathon trip itinerary planning site.

You can drive from Islamorada to Marathon in an hour. Alternatively, you can take a bus. In January, daily temperatures in Marathon can reach 29°C, while at night they dip to 22°C. Wrap up your sightseeing on the 29th (Mon) to allow time to take a bus to Key West.

Things to do in Marathon

Parks Outdoors Beaches

Side Trips

Sunset Park Beach, Bahia Honda State Park
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
Crane Point Museum & Nature Center ©
Crane Point Museum & Nature Center
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.
Discover out-of-the-way places like Dry Tortugas National Park and Stand-Up Paddleboarding. Shop till you drop at Alan S. Maltz Gallery and Rodriguez Cigar Factory. There's still lots to do: learn about all things military at U.S. Coast Guard Cutter Ingham Maritime Museum, see the interesting displays at Mel Fisher Maritime Heritage Museum, get a taste of the local shopping with 7 Artists & Friends Gallery, and learn more about the world around you at Florida Keys Eco-Discovery Center.

To see where to stay, other places to visit, ratings, and tourist information, go to the Key West itinerary planning site.

You can take a bus from Marathon to Key West in 1.5 hours. Alternatively, you can drive. In January in Key West, expect temperatures between 28°C during the day and 22°C at night. Finish your sightseeing early on the 2nd (Fri) so you can 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
U.S. Coast Guard Cutter Ingham Maritime Museum ©
The Ernest Hemingway Home and Museum ©
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.
For shopping fun, head to Sun Harvest Citrus or Finnimore's Cycle Shop. Discover out-of-the-way places like Bowman's Beach and Sanibel Island Farmer's Market. Step out of Sanibel Island with an excursion to Fort Myers Beach in Fort Myers Beach--about 34 minutes away. There's much more to do: enjoy the sand and surf at Captiva Beach, examine the collection at The Bailey-Matthews National Shell Museum, look for gifts at B Unique Boutique, and buy something for everyone on your list at Periwinkle Place.

For more things to do, photos, reviews, and more tourist information, you can read our Sanibel Island travel itinerary planner.

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, you can expect nighttime temperatures to be little chillier in Sanibel Island, with lows of 17°C. Finish your sightseeing early on the 5th (Mon) to allow enough time to drive to Naples.

Things to do in Sanibel Island

Outdoors Parks Beaches

Side Trips

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

4
nights
Naples

Naples ©
Head to Fifth Avenue South and Miromar Outlets between Naples & Fort Myersfor some retail therapy. You'll explore the less-touristy side of things at Lowdermilk Beach and Barefoot Beach Preserve. You'll find plenty of places to visit near Naples: Marco Island (South Marco Beach & Tigertail Beach).

For traveler tips, maps, other places to visit, and more tourist information, use the Naples road trip site.

Drive from Sanibel Island to Naples in 1.5 hours. In February, plan for daily highs up to 30°C, and evening lows to 18°C. Finish your sightseeing early on the 9th (Fri) to allow enough time to drive to Rotonda West.

Things to do in Naples

Outdoors Parks Beaches

Side Trips

Marco Island, Miromar Outlets between Naples & Fort Myers, Barefoot Beach Preserve
Highlights from your plan
Lowdermilk Beach ©
Lowdermilk Beach
Barefoot Beach Preserve ©
Barefoot Beach Preserve
Miromar Outlets between Naples & Fort Myers ©
Miromar Outlets between Naples & Fort Myers

1
night
Rotonda West

Rotonda West
Rotonda West is an unincorporated, deed-restricted community situated in west Charlotte County, Florida, United States. Kick off your visit on the 10th (Sat): tour the pleasant surroundings at Cape Haze Pioneer Trail Park.

To see photos, reviews, other places to visit, and more tourist information, refer to the Rotonda West trip planner.

You can drive from Naples to Rotonda West in 2 hours. While traveling from Naples, expect slightly colder days and about the same nights in Rotonda West, ranging from highs of 26°C to lows of 16°C. On the 10th (Sat), wrap the sightseeing up by early afternoon so you can travel to Orlando.

Things to do in Rotonda West

Trails Outdoors Parks

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.
Relax by the water at Beach at Daytona Beach and Cocoa Beach. Shop till you drop at Orlando Vineland Premium Outlets and World of Disney. You'll find plenty of places to visit near Orlando: Secrets of Cocoa Beach (in Cocoa Beach) and Stetson Mansion (in DeLand). Have a day of magic on the 13th (Tue) at Walt Disney World Resort. Next up on the itinerary: admire the masterpieces at Charles Hosmer Morse Museum of American Art, stop by The LEGO Store, and make an unforgettable trip to Happily Ever After Fireworks.

To see reviews, where to stay, other places to visit, and other tourist information, use the Orlando trip planner.

You can drive from Rotonda West to Orlando in 3 hours. In February, plan for daily highs up to 28°C, and evening lows 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 Outdoors

Side Trips

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

3
nights
St. Augustine

St. Augustine ©
St. Give yourself a bit of retail therapy at Claude's Chocolate and Market to Market. Step off the beaten path and head to St. Augustine Beach and Flagler College. There's lots more to do: see the interesting displays at Lightner Museum, stop by The Spice & Tea Exchange of St. Augustine, look for all kinds of wild species at St. Augustine Alligator Farm Zoological Park, and enjoy the sand and surf at Vilano Beach.

To see other places to visit, more things to do, and more tourist information, go to the St. Augustine travel itinerary planner.

Traveling by car from Orlando to St. Augustine takes 2 hours. Alternatively, you can take a bus. In February, St. Augustine is slightly colder than Orlando - with highs of 23°C and lows of 12°C. Finish up your sightseeing early on the 18th (Sun) so you can 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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