20 days in Florida Itinerary

20 days in Florida Itinerary

Created using Inspirock Florida trip planner
Make it your trip
Drive
1
Clearwater
— 1 night
Fly
2
Key Largo
— 3 nights
Drive
3
Marathon
— 2 nights
Drive
4
Key West
— 4 nights
Fly
5
Miami Beach
— 2 nights
Drive
6
St. Augustine
— 2 nights
Drive
7
Orlando
— 5 nights

S M T W T F S
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Clearwater — 1 night

Holding the record for most consecutive days of sunshine in a single year, Clearwater offers long sandy beaches and proximity to other major cities in the Tampa Bay area.
On the 18th (Fri), get up close to creatures of the deep with Little Toot Dolphin Adventure, do a tasting at Aspirations Winery, then stroll through Philippe Park, then explore the different monuments and memorials at Sylvan Abbey Funeral Home and Sylvan Abbey Cemetery, and finally contemplate the long history of Church of Scientology Information Center. Here are some ideas for day two: take in the spiritual surroundings of St. Nicholas Greek Orthodox Cathedral, take in the architecture and atmosphere at Sacred Heart Catholic Church, then do a tasting at Murielle Winery, and finally enjoy the sand and surf at Clearwater Beach.

Plan a Clearwater trip in moments using our itinerary builder.

Orlando to Clearwater is an approximately 2-hour car ride. You can also do a combination of train and taxi; or take a bus. In February, plan for daily highs up to 74°F, and evening lows to 57°F. Finish up your sightseeing early on the 19th (Sat) so you can catch the flight to Key Largo.
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Outdoors · Parks · Beaches · Historic Sites
Side Trips

Key Largo — 3 nights

The northernmost island of the Florida Keys, Key Largo provides stunning scenery, a number of watersports opportunities, and plenty of areas to relax on vacation.
Step out of Key Largo to go to Everglades National Park and see Anhinga Trail, which is approximately 56 minutes away. There's lots more to do: identify plant and animal life at Florida Keys Wild Bird Rehabilitation Center, pause for some serene contemplation at Key Largo Baptist Church, see the vivid underwater world at Spiegel Grove, and see some colorful creatures with a scuba or snorkeling tour.

To see ratings, where to stay, other places to visit, and tourist information, read our Key Largo trip planner.

Traveling by flight from Clearwater to Key Largo takes 3 hours. Alternatively, you can drive; or do a combination of taxi, train, and bus. February in Key Largo sees daily highs of 78°F and lows of 62°F at night. Cap off your sightseeing on the 22nd (Tue) early enough to go by car to Marathon.
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Wildlife · Outdoors · Tours · Parks
Side Trip

Marathon — 2 nights

A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
Start off your visit on the 23rd (Wed): examine the collection at Crane Point Museum & Nature Center, identify plant and animal life at National Key Deer Refuge, and then kick back and relax at Bahia Honda State Park. Get ready for a full day of sightseeing on the next day: soothe aching muscles at some of the top local wellness centers, then take in the architecture and atmosphere at San Pablo Catholic Church, then identify plant and animal life at The Turtle Hospital, and finally get answers to all your questions at Pigeon Key.

For traveler tips, maps, other places to visit, and tourist information, use the Marathon online itinerary builder.

Traveling by car from Key Largo to Marathon takes 1.5 hours. Alternatively, you can take a bus. Plan for a bit warmer nights when traveling from Key Largo in February since evenings lows in Marathon dip to 68°F. Finish your sightseeing early on the 24th (Thu) to allow enough time to drive to Key West.
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Parks · Wildlife · Outdoors · Beaches
Side Trip

Key West — 4 nights

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.
Visit Truman Little White House and Saint Mary Star of the Sea for their historical value. Next up on the itinerary: contemplate the long history of Curry Mansion Inn, enjoy the sand and surf at Fort Zachary Taylor, look for all kinds of wild species at Key West Butterfly & Nature Conservatory, and stroll the grounds of Key West Cemetery.

To see more things to do, photos, other places to visit, and other tourist information, read Key West travel route website.

Drive from Marathon to Key West in 1.5 hours. Alternatively, you can take a bus. In February, daytime highs in Key West are 78°F, while nighttime lows are 68°F. Wrap up your sightseeing on the 28th (Mon) early enough to fly to Miami Beach.
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Historic Sites · Outdoors · Wildlife · Tours

Miami Beach — 2 nights

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 1st (Tue), wander the streets of Art Deco Historic District, then wander the streets of Lincoln Road, and then wander the streets of Collins Avenue. Get ready for a full day of sightseeing on the 2nd (Wed): wander the streets of Espanola Way, get the lay of the land with Art Deco Tours, then take in the architecture and atmosphere at Saint Francis de Sales Catholic Church, and finally have fun at Lock & Load Miami.

To find photos, more things to do, ratings, and tourist information, refer to the Miami Beach holiday maker website.

You can fly from Key West to Miami Beach in 2.5 hours. Other options are to drive; or take a bus. In February, daily temperatures in Miami Beach can reach 79°F, while at night they dip to 65°F. Cap off your sightseeing on the 2nd (Wed) early enough to go by car to St. Augustine.
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Neighborhoods · Shopping · Historic Sites · Nightlife
Side Trip

St. Augustine — 2 nights

St. On the 3rd (Thu), brush up on your knowledge of spirits at St. Augustine Distillery, steep yourself in history at The St. Augustine Historical Society, meet the residents at St. Augustine Wild Reserve, then pause for some serene contemplation at Cathedral Basilica of St. Augustine, and finally contemplate the long history of Pena-Peck House and Woman's Exchange of St Augustine. On the next day, pause for some serene contemplation at Grace United Methodist Church, visit a coastal fixture at St. Augustine Lighthouse & Maritime Museum, Inc., explore the different monuments and memorials at Saint Augustine National Cemetery, then get a new perspective on things with Red Boat Water Tours, and finally stroll the grounds of Tolomato Cemetery.

For maps, reviews, traveler tips, and more tourist information, read our St. Augustine trip itinerary builder site.

Getting from Miami Beach to St. Augustine by car takes about 5.5 hours. Other options: do a combination of flight and bus; or take a bus. Expect a bit cooler temperatures when traveling from Miami Beach in March; daily highs in St. Augustine reach 71°F and lows reach 54°F. Finish up your sightseeing early on the 4th (Fri) so you can go by car to Orlando.
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Historic Sites · Zoos & Aquariums · Outdoors · Breweries & Distilleries

Orlando — 5 nights

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.
Your inner history buff will appreciate Stetson Mansion and First United Methodist Church. Take a break from Orlando with a short trip to St. Barnabas Episcopal Church in DeLand, about 50 minutes away. Have a day of magic on the 5th (Sat) at Disney's Animal Kingdom Theme Park. Pack the 8th (Tue) with family-friendly diversions at Universal Orlando Resort. It doesn't end there: discover the magic at Walt Disney World Resort and cool off at Discovery Cove.

Inspirock's itinerary builder makes planning a Orlando trip simple and quick.

Drive from St. Augustine to Orlando in 2 hours. Alternatively, you can take a bus. When traveling from St. Augustine in March, plan for somewhat warmer days and about the same nights in Orlando: temperatures range from 78°F by day to 58°F at night. Wrap up your sightseeing on the 9th (Wed) to allow time to travel back home.
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Theme Parks · Historic Sites
Side Trip

Florida travel guide

4.3
Disney Parks & Activities · Beaches · Theme Parks
The Sunshine State
The “Sunshine State,” Florida became a favorite winter destination for the affluent crowd over a century ago. Today, the state attracts visitors from around the world with its golden beaches and modern theme parks. You can spend your entire vacation enjoying the state's highly developed seaside areas, but remember that some of Florida's best-kept secrets are in secluded locations. Visit the big cities and their comfortable resorts offering top-notch dining and nightlife, but leave some time to see the peninsula's swampy landscape, filled with wild creatures and native plants. Farther away from the tourist-packed urban areas, the untamed wetlands of Florida offer a selection of things to do, such as kayaking, boat rides, and numerous other outdoor activities.
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