19 days in Florida & Houston Itinerary

19 days in Florida & Houston Itinerary

Created using Inspirock United States journey planner

Make it your trip
Fly
1
St. Petersburg
— 1 night
Drive
2
Orlando
— 3 nights
Drive
3
St. Augustine
— 2 nights
Drive
4
Merritt Island
— 1 night
Fly
5
Miami
— 3 nights
Drive
6
Marathon
— 1 night
Drive
7
Key West
— 4 nights
Fly
8
Houston
— 3 nights
Fly

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St. Petersburg

— 1 night

Florida's Sunshine City

Located on a peninsula between Tampa Bay and the Gulf of Mexico, St.
Kick off your visit on the 21st (Mon): view the masterpieces at Morean Art Center, explore the world behind art at James Museum of Western & Wildlife Art, then explore the world behind art at The Dali Museum, and finally shop like a local with Craftsman House Gallery. Get ready for a full day of sightseeing on the next day: admire the masterpieces at Imagine Museum, see the interesting displays at Duncan McClellan Gallery, and then get engrossed in the history at The Ringling.

For other places to visit, ratings, where to stay, and tourist information, refer to the St. Petersburg road trip website.

Chicago to St. Petersburg is an approximately 4-hour flight. You can also drive; or take a bus. The time zone changes from Central Standard Time to Eastern Standard Time, which is usually a 1 hour difference. Traveling from Chicago in December, things will get much warmer in St. Petersburg: highs are around 74°F and lows about 63°F. Finish your sightseeing early on the 22nd (Tue) to allow enough time to drive to Orlando.

Things to do in St. Petersburg

Museums · Shopping

Side Trip

Orlando

— 3 nights

Theme Park Capital of the World

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.
Appreciate the collections at Charles Hosmer Morse Museum of American Art and Jeanine Taylor Folk Art. Go for a jaunt from Orlando to DeLand to see Stetson Mansion about 50 minutes away. Have a day of magic on the 24th (Thu) at Walt Disney World Resort. There's still lots to do: find something for the whole family at Universal Orlando Resort and take in the exciting artwork at Timothy's Gallery.

To see where to stay, traveler tips, reviews, and tourist information, read our Orlando day trip tool.

Drive from St. Petersburg to Orlando in 2 hours. Alternatively, you can do a combination of bus and train; or take a bus. In December, daily temperatures in Orlando can reach 77°F, while at night they dip to 59°F. Wrap up your sightseeing on the 25th (Fri) to allow time to drive to St. Augustine.

Things to do in Orlando

Theme Parks · Museums · Shopping · Historic Sites

Side Trips

St. Augustine

— 2 nights
St. On the 26th (Sat), get engrossed in the history at Medieval Torture Museum, enjoy the sea views from St. Augustine Lighthouse & Maritime Museum, Inc., take in the exciting artwork at High Tide Gallery Art & Gifts, examine the collection at The Ximenez-Fatio House, then appreciate the history behind Castillo de San Marcos National Monument, and finally explore the different monuments and memorials at Tolomato Cemetery. On the 27th (Sun), you'll have a packed day of sightseeing: see the interesting displays at St. Augustine Pirate & Treasure Museum, then take in the spiritual surroundings of St. Photios Greek Orthodox National Shrine, then examine the collection at Lightner Museum, and finally sample the fine beverages at St. Augustine Distillery.

To find ratings, traveler tips, maps, and tourist information, read St. Augustine trip builder app.

Traveling by car from Orlando to St. Augustine takes 2 hours. Alternatively, you can take a bus. Traveling from Orlando in December, expect nights in St. Augustine to be about the same, around 55°F, while days are little chillier, around 70°F. Cap off your sightseeing on the 27th (Sun) early enough to go by car to Merritt Island.

Things to do in St. Augustine

Museums · Historic Sites · Breweries & Distilleries · Shopping

Merritt Island

— 1 night
Start off your visit on the 28th (Mon): examine the collection at Parker Brothers Concepts, then see the sky in a new way at NASA Kennedy Space Center Visitor Complex, then get curious at Space Shuttle Atlantis, and finally take an unforgettable tour with Cocoa Beach Helicopters.

For ratings, maps, reviews, and more tourist information, you can read our Merritt Island day trip tool.

Traveling by car from St. Augustine to Merritt Island takes 2.5 hours. Alternatively, you can do a combination of bus and car; or do a combination of bus and taxi. Plan for a bit warmer nights when traveling from St. Augustine in December since evenings lows in Merritt Island dip to 64°F. Cap off your sightseeing on the 28th (Mon) early enough to catch the flight to Miami.

Things to do in Merritt Island

Museums · Childrens Museums · Tours

Side Trip

Miami

— 3 nights

Magic City

Florida’s mecca of fun in the sun, the lively tropical metropolis of Miami is one of the world’s top vacation spots.
Let the collections at Vizcaya Museum and Gardens and Wynwood Walls capture your imagination. Step out of Miami to go to Everglades National Park and see Shark Valley Visitor Center, which is approximately 1 hour away. There's still lots to do: view the masterpieces at Art Basel, appreciate the extensive heritage of Art Deco Historic District, admire the natural beauty at Fairchild Tropical Botanic Garden, and explore the world behind art at The Wolfsonian - Florida International University.

To find ratings, photos, where to stay, and more tourist information, refer to the Miami trip maker app.

You can fly from Merritt Island to Miami in 3 hours. Alternatively, you can drive; or do a combination of taxi and bus. While traveling from Merritt Island, expect somewhat warmer days and about the same nights in Miami, ranging from highs of 81°F to lows of 68°F. Finish your sightseeing early on the 31st (Thu) so you can drive to Marathon.

Things to do in Miami

Museums · Parks · Shopping · Nature

Side Trips

Marathon

— 1 night

Heart of the Florida Keys

A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
On the 1st (Fri), see the world from above with Ultimate HeliTours, head outdoors with Z Flight Watersports, then browse the exhibits of Shady Palm Art Gallery & Photography, then see the interesting displays at Crane Point Museum & Nature Center, and finally pause for some serene contemplation at San Pablo Catholic Church.

To see where to stay, other places to visit, and other tourist information, read our Marathon day trip tool.

You can drive from Miami to Marathon in 2.5 hours. Other options are to do a combination of flight and bus; or take a bus. Expect a daytime high around 80°F in December, and nighttime lows around 71°F. Cap off your sightseeing on the 1st (Fri) early enough to go by car to Key West.

Things to do in Marathon

Museums · Outdoors · Tours · Historic Sites

Key West

— 4 nights

Conch Republic

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.
You'll explore and learn at The Ernest Hemingway Home and Museum and 7 Artists & Friends Gallery. Truman Little White House and Key West Shipwreck Museum will appeal to history buffs. There's lots more to do: enjoy the sea views from Key West Lighthouse and Keeper's Quarters Museum, see the interesting displays at Mel Fisher Maritime Heritage Museum, take an in-depth tour of Key West Museum of Art & History at the Custom House, and stroll the grounds of Key West Cemetery.

For where to stay, other places to visit, reviews, and more tourist information, you can read our Key West trip maker.

Drive from Marathon to Key West in 1.5 hours. Alternatively, you can take a bus. In January, daily temperatures in Key West can reach 76°F, while at night they dip to 66°F. Finish up your sightseeing early on the 5th (Tue) so you can catch the flight to Houston.

Things to do in Key West

Museums · Historic Sites · Outdoors · Tours

Houston

— 3 nights

Bayou City

Although urban sprawl remains synonymous with Houston, most of the city's tourist attractions lie within the relatively small downtown area, surrounded by diverse neighborhoods housing the nation's biggest African-American, Asian-American, and Latino communities.
Appreciate the collections at Space Center Houston and Houston Museum District. Venture out of the city with trips to Dickinson Historical Society Depot Museum (in Dickinson) and That Escape Place (in Spring). Next up on the itinerary: stroll through Cockrell Butterfly Center, contemplate the long history of Bayou Bend Collection and Gardens, examine the collection at Asia Society Texas Center, and explore the world behind art at The Menil Collection.

For reviews, maps, and tourist information, read Houston driving holiday app.

Fly from Key West to Houston in 6 hours. Alternatively, you can drive; or take a bus. The time zone difference moving from Eastern Standard Time (EST) to Central Standard Time (CST) is minus 1 hour. Traveling from Key West in January, expect nights in Houston to be cooler, around 46°F, while days are slightly colder, around 63°F. Wrap up your sightseeing on the 8th (Fri) early enough to fly back home.

Things to do in Houston

Museums · Parks · Historic Sites · Fun & Games

Side Trips

Florida travel guide

4.4
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.