22 days in Florida Itinerary

22 days in Florida Itinerary

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Route & dates

22 days in Florida Itinerary

Start: Boston
+2
bus + Fly + bus:  6​h 15​min
1
Siesta Key
— 1 night
Drive:  2​h 30​min
2
Orlando
— 4 nights
Drive:  2​h
3
St. Augustine
— 4 nights
Drive + Fly:  6​h
4
Key West
— 4 nights
bus:  1​h 15​min
5
Marathon
— 3 nights
Drive:  2​h 45​min
6
Miami Beach
— 4 nights
+3
bus + tram + Fly + bus:  5​h 45​min
End: Boston

1
night
Siesta Key

Siesta Key ©
Siesta Key draws most of its visitors with soft, white-quartz sand beaches and translucent ocean water.
Kick off your visit on the 17th (Mon): stroll through Venice Beach.

For photos, traveler tips, ratings, and more tourist information, go to the Siesta Key day trip planning tool .

Boston to Siesta Key is an approximately 6.5-hour combination of bus and flight. You can also drive; or take a bus. In December, Siesta Key is much hotter than Boston - with highs of 78°F and lows of 59°F. Finish your sightseeing early on the 18th (Tue) to allow enough time to drive to Orlando.

Things to do in Siesta Key

#Beaches, #Parks, #Outdoors

Side Trips

Siesta Key Village, Venice Beach
Highlights from your plan
Siesta Beach ©
Siesta Beach
Crescent Beach ©
Crescent Beach
Venice Beach ©
Venice 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.
Get some cultural insight at Stetson Mansion and Charles Hosmer Morse Museum of American Art. Pack the 20th (Thu) with family-friendly diversions at Walt Disney World Resort. Pack the 21st (Fri) with family-friendly diversions at Universal's Islands of Adventure. Next up on the itinerary: discover the magic at Happily Ever After Fireworks, find something for the whole family at Universal Orlando Resort, and test your problem-solving skills at popular escape rooms.

To find photos, traveler tips, other places to visit, and tourist information, you can read our Orlando trip planning website .

Traveling by car from Siesta Key to Orlando takes 2.5 hours. Alternatively, you can take a bus. In December, daytime highs in Orlando are 77°F, while nighttime lows are 59°F. Cap off your sightseeing on the 22nd (Sat) early enough to go by car to St. Augustine.

Things to do in Orlando

#Theme Parks, #Historic Sites, #Fun & Games

Side Trips

Charles Hosmer Morse Museum of American Art, Stetson Mansion
Highlights from your plan
Stetson Mansion ©
Stetson Mansion
Happily Ever After Fireworks ©
Happily Ever After Fireworks

4
nights
St. Augustine

St. Augustine ©
SAINT AUGUSTINE | PONTE VEDRA on Florida's Historic Coast The Nation's oldest city (est. Escape the urban bustle at St. Augustine Beach and Ormond Beach. Do some cultural sightseeing at Castillo de San Marcos and St. Augustine Lighthouse & Maritime Museum. Explore St. Augustine's surroundings by going to Andy Romano Beachfront Park (in Ormond Beach), Bulow Plantation Ruins Historic State Park (in Bunnell) and Sawgrass Country Club (in Ponte Vedra Beach). The adventure continues: tour the pleasant surroundings at Jacksonville Beach, tour the water at your own pace with Red Boat Water Tours, LLC, and pause for some serene contemplation at Memorial Presbyterian Church.

For ratings, other places to visit, where to stay, and more tourist information, use the St. Augustine trip planner .

You can drive from Orlando to St. Augustine in 2 hours. Another option is to take a bus. Traveling from Orlando in December, expect nights in St. Augustine to be about the same, around 55°F, while days are slightly colder, around 70°F. Finish up your sightseeing early on the 26th (Wed) so you can travel to Key West.

Things to do in St. Augustine

#Outdoors, #Beaches, #Parks

Side Trips

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

4
nights
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.
Deepen your sense of the past at sights like Fort Zachary Taylor and Key West Cemetery. Get a sense of the local culture at The Ernest Hemingway Home and Museum and Saint Mary Star of the Sea. There's lots more to do: identify plant and animal life at Key West Butterfly & Nature Conservatory, tour the water at your own pace with Fun In The Sun Key West, explore the galleries of Truman Little White House, and take a leisurely stroll along Mallory Square.

To find maps, traveler tips, more things to do, and other tourist information, read our Key West trip planner .

Do a combination of car and flight from St. Augustine to Key West in 6 hours. Alternatively, you can do a combination of bus and flight; or drive. Expect a bit warmer temperatures when traveling from St. Augustine in December; daily highs in Key West reach 79°F and lows reach 71°F. Finish your sightseeing early on the 31st (Mon) to allow enough time to take a bus to Marathon.

Things to do in Key West

#Outdoors, #Tours, #Adventure
Highlights from your plan
Stand-Up Paddleboarding
Fort Zachary Taylor ©
Fort Zachary Taylor

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.
You'll enjoy a bit of beach vacationing at Bahia Honda State Park and Sombrero Beach. Step out of the city life by going to Gumbo Limbo Trail and Pineland Trail. Explore the numerous day-trip ideas around Marathon: Everglades National Park (Anhinga Trail & Long Pine Key). It doesn't end there: enjoy the sand and surf at Anne's Beach and take in the architecture and atmosphere at San Pablo Catholic Church.

For maps, ratings, where to stay, and other tourist information, refer to the Marathon trip itinerary planner .

Traveling by bus from Key West to Marathon takes 1.5 hours. Alternatively, you can drive. In December, daytime highs in Marathon are 80°F, while nighttime lows are 71°F. Finish your sightseeing early on the 3rd (Thu) to allow enough time to drive to Miami Beach.

Things to do in Marathon

#Parks, #Outdoors, #Beaches

Side Trips

Everglades National Park, Bahia Honda State Park, Anne's Beach
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
Gumbo Limbo Trail ©
Gumbo Limbo Trail
Sombrero Beach ©
Sombrero Beach

4
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.
Popular historic sites such as Art Deco Historic District and Bill Baggs Cape Florida State Park are in your itinerary. Relax by the water at South Beach and Fort Lauderdale Beach. When in Miami Beach, make a side trip to see Hollywood Beach in Hollywood, approximately 48 minutes away. The adventure continues: take a stroll through Lincoln Road, get a taste of the local shopping with Collins Avenue, make a trip to Port of Miami, and get to know the fascinating history of Art Deco Tours.

For ratings, photos, and other tourist information, read Miami Beach trip itinerary builder website .

You can drive from Marathon to Miami Beach in 3 hours. Alternatively, you can take a bus; or do a combination of bus, flight, and tram. In January, plan for daily highs up to 77°F, and evening lows to 63°F. Wrap up your sightseeing on the 7th (Mon) to allow time to travel back home.

Things to do in Miami Beach

#Parks, #Beaches, #Outdoors

Side Trips

Key Biscayne, Haulover Beach Park, Hollywood Beach, Fort Lauderdale Beach, Port of Miami
Highlights from your plan
Art Deco Tours ©
Art Deco Tours
South Beach ©
South Beach
Lincoln Road ©
Lincoln Road

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