16 days in Florida Itinerary

16 days in Florida Itinerary

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Route & dates

16 days in Florida Itinerary

Start: Calgary
Fly:  11​h 15​min
1
Key West
— 2 nights
Fly:  2​h 45​min
2
Miami
— 4 nights
Drive:  4​h
3
Siesta Key
— 1 night
Drive:  4​h 15​min
4
St. Augustine
— 3 nights
Drive:  2​h
5
Orlando
— 4 nights
Fly:  9​h 15​min
End: Calgary

2
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.
We've included these beaches for you: Bahia Honda State Park and Sombrero Beach. Get in touch with nature at Key West Butterfly & Nature Conservatory and Fort Zachary Taylor. Change things up with a short trip to San Pablo Catholic Church in Marathon (about 1h 15 min away). Next up on the itinerary: see the interesting displays at The Ernest Hemingway Home and Museum, admire the natural beauty at Audubon House & Tropical Gardens, stroll the grounds of Key West Cemetery, and take in the architecture and atmosphere at Saint Mary Star of the Sea.

For maps, where to stay, other places to visit, and more tourist information, go to the Key West online holiday planner .

Calgary, Canada to Key West is an approximately 11.5-hour flight. You can also drive; or take a bus. The time zone changes from Mountain Standard Time to Eastern Standard Time, which is usually a 2 hour difference. Plan for much hotter temperatures traveling from Calgary in November, with highs in Key West at 32°C and lows at 26°C. Finish up your sightseeing early on the 9th (Fri) so you can travel to Miami.

Things to do in Key West

Parks Historic Sites Beaches

Side Trips

Marathon, Bahia Honda State Park
Highlights from your plan
The Ernest Hemingway Home and Museum ©
Bahia Honda State Park ©
Bahia Honda State Park

4
nights
Miami

Miami ©
Florida’s mecca of fun in the sun, the lively tropical metropolis of Miami is one of the world’s top vacation spots.
We've included these beaches for you: South Beach and Hollywood Beach. Lincoln Road and Bill Baggs Cape Florida State Park are good opportunities to explore the local culture. Get out of town with these interesting Miami side-trips: Everglades National Park (Shark Valley & Anhinga Trail). And it doesn't end there: admire the landmark architecture of Art Deco Historic District, do sightseeing your way with Art Deco Tours, kick back and relax at Haulover Beach Park, and appreciate the history behind Holocaust Memorial.

To find where to stay, maps, ratings, and more tourist information, read our Miami online sightseeing planner .

You can fly from Key West to Miami in 3 hours. Other options are to do a combination of flight and bus; or drive. November in Miami sees daily highs of 32°C and lows of 24°C at night. Finish your sightseeing early on the 13th (Tue) so you can drive to Siesta Key.

Things to do in Miami

Parks Outdoors Beaches

Side Trips

Miami Beach, Everglades National Park, Hollywood Beach, Bill Baggs Cape Florida State Park, Haulover Beach Park
Highlights from your plan
Shark Valley ©
Shark Valley
South Beach ©
South Beach
Lincoln Road ©
Lincoln Road

1
night
Siesta Key

Siesta Key ©
Siesta Key draws most of its visitors with soft, white-quartz sand beaches and translucent ocean water.
Start off your visit on the 14th (Wed): tour the pleasant surroundings at Crescent Beach, then enjoy the sand and surf at Siesta Beach, and then make a trip to Siesta Key Village.

To find maps, traveler tips, photos, and more tourist information, go to the Siesta Key trip itinerary planning app .

You can drive from Miami to Siesta Key in 4 hours. Alternatively, you can do a combination of tram, flight, and bus; or take a bus. Traveling from Miami in November, plan for a bit cooler nights in Siesta Key, with lows around 19°C. Cap off your sightseeing on the 14th (Wed) early enough to go by car to St. Augustine.

Things to do in Siesta Key

Beaches Parks Outdoors

Side Trip

Siesta Key Village
Highlights from your plan
Siesta Beach ©
Siesta Beach
Crescent Beach ©
Crescent Beach
Siesta Key Village ©
Siesta Key Village

3
nights
St. Augustine

St. Augustine ©
SAINT AUGUSTINE | PONTE VEDRA on Florida's Historic Coast The Nation's oldest city (est. Get outdoors at St. Augustine Beach and Sawgrass Country Club. Get some historical perspective at Bulow Plantation Ruins Historic State Park and St. Augustine Lighthouse & Maritime Museum. Venture out of the city with trips to Ormond Beach (Ormond Beach & Andy Romano Beachfront Park). There's still lots to do: appreciate the history behind Castillo de San Marcos and take an in-depth tour of The Oldest Store Museum.

To find photos, reviews, traveler tips, and other tourist information, you can read our St. Augustine online trip planner .

Drive from Siesta Key to St. Augustine in 4.5 hours. Alternatively, you can do a combination of bus and flight; or take a bus. While traveling from Siesta Key, expect a bit cooler days and about the same nights in St. Augustine, ranging from highs of 26°C to lows of 17°C. Wrap up your sightseeing on the 17th (Sat) early enough to drive to Orlando.

Things to do in St. Augustine

Beaches Parks Outdoors

Side Trips

Ormond Beach, Bulow Plantation Ruins Historic State Park, Sawgrass Country Club
Highlights from your plan
St. Augustine Beach ©
St. Augustine Beach
Ormond Beach ©
Ormond Beach

4
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.
Do some cultural sightseeing at Stetson Mansion and NASA Kennedy Space Center Visitor Complex. Pack the 19th (Mon) with family-friendly diversions at Walt Disney World Resort. Pack the 21st (Wed) with family-friendly diversions at Universal's Islands of Adventure. The adventure continues: make an unforgettable trip to Happily Ever After Fireworks, play a few rounds at Pirate's Cove Adventure Golf, and explore the world behind art at Charles Hosmer Morse Museum of American Art.

To find ratings, traveler tips, more things to do, and other tourist information, read Orlando tour builder tool .

Traveling by car from St. Augustine to Orlando takes 2 hours. Alternatively, you can take a bus. In November in Orlando, expect temperatures between 30°C during the day and 19°C at night. Cap off your sightseeing on the 21st (Wed) early enough to travel back home.

Things to do in Orlando

Theme Parks Museums Childrens Museums

Side Trips

Charles Hosmer Morse Museum of American Art, Stetson Mansion, NASA Kennedy Space Center Visitor Complex
Highlights from your plan
Stetson Mansion ©
Stetson Mansion
Happily Ever After Fireworks ©
Happily Ever After Fireworks

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