29 days in United States Itinerary

29 days in United States Itinerary

Created using Inspirock Florida itinerary planner

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Route & dates

29 days in United States Itinerary

Start: Toronto
Fly:  8​h 30​min
1
Key West
— 5 nights
bus:  45​min
2
Big Pine Key
— 2 nights
Drive:  1​h 15​min
3
Islamorada
— 4 nights
Drive:  2​h
4
Miami Beach
— 5 nights
Drive:  4​h 15​min
5
Bradenton
— 3 nights
Drive:  2​h 15​min
6
Orlando
— 5 nights
Drive:  1​h
7
Daytona Beach
— 4 nights
shuttle + Fly:  7​h 15​min
End: Toronto

5
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.
Spend the 8th (Wed) exploring nature at Dry Tortugas National Park. There's lots more to do: examine the collection at The Ernest Hemingway Home and Museum, find your balance on the water with some of the best stand-up paddleboarding in the area, contemplate the long history of Curry Mansion, and don't miss a visit to Duval Street.

For other places to visit, where to stay, reviews, and other tourist information, use the Key West day trip planner.

Toronto, Canada to Key West is an approximately 8.5-hour flight. You can also do a combination of bus and flight; or drive. Prepare for much warmer weather when traveling from Toronto in January: high temperatures in Key West hover around 28°C and lows are around 22°C. Cap off your sightseeing on the 11th (Sat) early enough to catcht the bus to Big Pine Key.

Things to do in Key West

Tours Outdoors Parks
Highlights from your plan
Alan S. Maltz Gallery ©
Alan S. Maltz Gallery
The Ernest Hemingway Home and Museum ©

2
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. On the 12th (Sun), identify plant and animal life at National Key Deer Refuge, immerse yourself in nature at Bahia Honda State Park, and then snap pictures at Seven Mile Bridge. Get ready for a full day of sightseeing on the 13th (Mon): get all the information you need at Pigeon Key Foundation, then pause for some serene contemplation at San Pablo Catholic Church, then identify plant and animal life at Crane Point Museum & Nature Center, and finally kick back and relax at Sombrero Beach.

For maps, reviews, and other tourist information, refer to the Big Pine Key travel route planning app .

You can take a bus from Key West to Big Pine Key in an hour. Alternatively, you can drive. In January, daytime highs in Big Pine Key are 29°C, while nighttime lows are 22°C. Cap off your sightseeing on the 13th (Mon) early enough to go by car to Islamorada.

Things to do in Big Pine Key

Parks Beaches Outdoors

Side Trip

Marathon
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
National Key Deer Refuge ©
National Key Deer Refuge
Crane Point Museum & Nature Center ©

4
nights
Islamorada

Islamorada ©
Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
Change things up with these side-trips from Islamorada: Everglades National Park (Nine Mile Pond Canoe Trail & 99 Mile Wilderness Waterway) and Key Largo Chamber of Commerce and Florida Keys Visitor Center (in Key Largo). And it doesn't end there: look for all kinds of wild species at Florida Keys Wild Bird Rehabilitation Center, observe the fascinating underwater world at Dolphins Plus Marine Mammal Responder, sample the tasty concoctions at Islamorada Beer Company, and get outside with Contagious Charters.

Use Inspirock's suggestions to plan your Islamorada trip and find the best activities and attractions for your vacation.

Traveling by car from Big Pine Key to Islamorada takes 1.5 hours. Alternatively, you can take a bus. In January in Islamorada, expect temperatures between 29°C during the day and 22°C at night. Wrap up your sightseeing on the 17th (Fri) to allow time to drive to Miami Beach.

Things to do in Islamorada

Parks Outdoors Wildlife

Side Trips

Key Largo, Everglades National Park
Highlights from your plan
Island Dolphin Care ©
Island Dolphin Care
Fishing Charters & Tours

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.
Change things up with these side-trips from Miami Beach: Wiener Museum of Decorative Arts (WMODA) (in Dania Beach), Everglades National Park (Shark Valley Visitor Center, Osceola panthers, & more) and Fairchild Tropical Botanic Garden (in Coral Gables). And it doesn't end there: tour the pleasant surroundings at South Beach, get to know the fascinating history of Lincoln Road, identify plant and animal life at Panther Ridge Conservation Center, and shop like a local with Village of Merrick Park.

To find ratings, reviews, maps, and more tourist information, refer to the Miami Beach day trip tool .

You can drive from Islamorada to Miami Beach in 2 hours. Another option is to take a bus. In January in Miami Beach, expect temperatures between 29°C during the day and 20°C at night. Cap off your sightseeing on the 22nd (Wed) early enough to go by car to Bradenton.

Things to do in Miami Beach

Parks Outdoors Trails

Side Trips

Coral Gables, Everglades National Park, Miami, Wiener Museum of Decorative Arts (WMODA), Panther Ridge Conservation Center
Highlights from your plan
Panther Ridge Conservation Center ©
Panther Ridge Conservation Center
Shark Valley Visitor Center ©
Shark Valley Visitor Center
Fairchild Tropical Botanic Garden ©
Fairchild Tropical Botanic Garden

3
nights
Bradenton

Bradenton boasts a handful of historical buildings, but its real claim to fame is as the home of Tropicana Products and its quirky culture.
Change things up with these side-trips from Bradenton: Sarasota (Stand-Up Paddleboarding & Sarasota National Cemetery), Fishing Charters & Tours (in Punta Gorda) and St. Petersburg (Duncan McClellan Gallery & The Dali Museum). Next up on the itinerary: sample the fine beverages at Siesta Key Rum, identify plant and animal life at Robinson Nature Preserve, and explore the world behind art at The Ringling.

Plan my day in Bradenton using traveler tips and tourist information provided by Inspirock.

Traveling by car from Miami Beach to Bradenton takes 4.5 hours. Alternatively, you can take a bus. Expect slightly colder temperatures when traveling from Miami Beach in January; daily highs in Bradenton reach 26°C and lows reach 13°C. Cap off your sightseeing on the 25th (Sat) early enough to go by car to Orlando.

Things to do in Bradenton

Tours Outdoors Wildlife

Side Trips

Sarasota, St. Petersburg, Fishing Charters & Tours
Highlights from your plan
Stand-Up Paddleboarding
Siesta Key Rum ©
Siesta Key Rum
Sarasota National Cemetery ©
Sarasota National Cemetery

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.
Orlando is known for theme parks, nightlife, fun & games, shopping, and museums. Your plan includes some of its best attractions: make an unforgettable trip to Walt Disney World Resort, laugh and play at Happily Ever After Fireworks, find something for the whole family at Universal Orlando Resort, and have some family-friendly fun at Nomadic.

To find photos, reviews, more things to do, and other tourist information, refer to the Orlando tour itinerary planner .

Traveling by car from Bradenton to Orlando takes 2.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. In January, daily temperatures in Orlando can reach 25°C, while at night they dip to 13°C. Finish your sightseeing early on the 30th (Thu) to allow enough time to drive to Daytona Beach.

Things to do in Orlando

Theme Parks Fun & Games Parks

Side Trip

Charles Hosmer Morse Museum of American Art
Highlights from your plan
Walt Disney World Resort ©
Walt Disney World Resort
Universal Orlando Resort ©
Universal Orlando Resort
Universal's Islands of Adventure ©
Universal's Islands of Adventure

4
nights
Daytona Beach

Daytona Beach ©
The iconic seaside destination of Daytona Beach once supported sugar mill plantations, but now entertains up to 8 million visitors a year.
Change things up with these side-trips from Daytona Beach: St. Augustine (The Ximenez-Fatio House, St. Augustine Distillery, & more), Jacksonville (Room Escape Games & Veterans Memorial Wall) and Canaveral National Seashore (in Titusville). There's lots more to do: admire the landmark architecture of Stetson Mansion, gain insight at Stetson University, join the crowd at Daytona International Speedway, and brush up on your military savvy at Veterans Museum & Education Center.

To find photos, where to stay, other places to visit, and tourist information, use the Daytona Beach day trip planner.

You can drive from Orlando to Daytona Beach in an hour. Alternatively, you can take a bus. In January, daytime highs in Daytona Beach are 24°C, while nighttime lows are 11°C. Wrap up your sightseeing on the 3rd (Mon) early enough to travel back home.

Things to do in Daytona Beach

Historic Sites Parks Wildlife

Side Trips

St. Augustine, Jacksonville, DeLand, Palms Up Pottery Studio and Gallery, Canaveral National Seashore
Highlights from your plan
Stetson Mansion ©
Stetson Mansion
Canaveral National Seashore ©
Canaveral National Seashore
Stetson University ©
Stetson University

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