18 days in Florida Itinerary

18 days in Florida Itinerary

Created using Inspirock Florida vacation planner

Make it your trip
Fly
1
Key Largo
— 1 day
Drive
2
Islamorada
— 1 night
Drive
3
Marathon
— 2 nights
Drive
4
Key West
— 2 nights
Ferry to Marco Island, FL, Taxi to Naples
5
Naples
— 2 nights
Fly
6
St. Augustine
— 5 nights
Drive
7
Orlando
— 5 nights
Fly

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Key Largo

— 1 day

Diving Capital of the World

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.
Start off your visit on the 17th (Fri): take in the architecture and atmosphere at Saint Justin Martyr Catholic Church, observe the fascinating underwater world at Island Dolphin Care, and then stroll through Florida Keys Wild Bird Rehabilitation Center.

To find ratings, photos, other places to visit, and tourist information, you can read our Key Largo trip itinerary website.

San Francisco to Key Largo is an approximately 7-hour flight. You can also drive; or do a combination of train and bus. The time zone changes from Pacific Standard Time (PST) to Eastern Standard Time (EST), which is usually a 3 hour difference. Traveling from San Francisco in December, you will find days in Key Largo are somewhat warmer (79°F), and nights are warmer (66°F). Wrap up your sightseeing on the 17th (Fri) early enough to drive to Islamorada.

Things to do in Key Largo

Historic Sites · Parks · Wildlife · Zoos & Aquariums

Islamorada

— 1 night

The Village of Islands

Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
Kick off your visit on the 17th (Fri): relax and rejuvenate at Island Flow Yoga.

To find reviews, ratings, where to stay, and other tourist information, you can read our Islamorada online attractions planner.

Islamorada is very close to Key Largo. In December, plan for daily highs up to 80°F, and evening lows to 71°F. Finish up your sightseeing early on the 18th (Sat) so you can go by car to Marathon.

Things to do in Islamorada

Outdoors · Shopping · Spas · Adventure

Marathon

— 2 nights

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.
Keep things going the next day: immerse yourself in nature at Curry Hammock State Park, get close to the beloved marine mammals with Dolphin Connection, enjoy the sand and surf at Sombrero Beach, then examine the collection at Crane Point Museum & Nature Center, and finally take in the architecture and atmosphere at San Pablo Catholic Church.

To see where to stay, photos, ratings, and more tourist information, go to the Marathon trip itinerary site.

Traveling by car from Islamorada to Marathon takes an hour. Alternatively, you can take a bus. Expect a daytime high around 80°F in December, and nighttime lows around 71°F. Wrap up your sightseeing on the 20th (Mon) early enough to drive to Key West.

Things to do in Marathon

Parks · Outdoors · Wildlife · Beaches

Side Trips

Key West

— 2 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.
Start off your visit on the 20th (Mon): relax and rejuvenate at some of the best spas. Here are some ideas for day two: explore the world behind art at Key West Museum of Art & History at the Custom House, observe the fascinating underwater world at Florida Keys Eco-Discovery Center, learn about all things military at U.S. Coast Guard Cutter Ingham Maritime Museum, then pause for some serene contemplation at St. Paul's Episcopal Church, and finally make a trip to Key West Historic Seaport.

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

Traveling by car from Marathon to Key West takes 1.5 hours. Alternatively, you can take a bus. In December in Key West, expect temperatures between 79°F during the day and 71°F at night. Cap off your sightseeing on the 22nd (Wed) early enough to travel to Naples.

Things to do in Key West

Historic Sites · Museums · Parks · Wildlife

Naples

— 2 nights
On the 23rd (Thu), see the interesting displays at Revs Institute, take in nature's colorful creations at Naples Botanical Garden, then glide peacefully along the water with some of the best stand-up paddleboarding in the area, and finally take in the waterfront at Naples Pier. Keep things going the next day: tour the pleasant surroundings at Gordon River Greenway and then admire all the interesting features of Naples Historical Society.

Make your Naples itinerary with Inspirock to find out what to see and where to go.

You can do a combination of ferry and taxi from Key West to Naples in 4 hours. Other options are to drive; or take a bus. Traveling from Key West in December, Naples is slightly colder at night with lows of 63°F. Finish up your sightseeing early on the 24th (Fri) so you can catch the flight to St. Augustine.

Things to do in Naples

Tours · Parks · Adventure · Outdoors

St. Augustine

— 5 nights
St. Discover out-of-the-way places like Medieval Torture Museum and Fernandina Beach. Change things up with these side-trips from St. Augustine: Flagler Beach Municipal Pier (in Flagler Beach), Jacksonville (Kingsley Plantation & The Cummer Museum of Art and Gardens) and Princess Place Preserve (in Palm Coast). There's lots more to do: examine the collection at The Ximenez-Fatio House, contemplate the long history of Old St. Augustine Village, get outside with Outdoor Activities, and gain insight at Flagler College.

To find reviews, traveler tips, ratings, and tourist information, refer to the St. Augustine online trip itinerary maker.

You can fly from Naples to St. Augustine in 3.5 hours. Alternatively, you can drive; or take a bus. In December, St. Augustine is little chillier than Naples - with highs of 70°F and lows of 55°F. Wrap up your sightseeing on the 29th (Wed) early enough to drive to Orlando.

Things to do in St. Augustine

Historic Sites · Museums · Parks · Tours

Side Trips

Orlando

— 5 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.
Step off the beaten path and head to Stetson Mansion and Tree of Life. Explore Orlando's surroundings by going to Tampa Electric's Manatee Viewing Center (in Apollo Beach), Largo (Florida Botanical Gardens & Largo Central Park) and Blue Spring State Park (in Orange City). Next up on the itinerary: discover the magic at Walt Disney World Resort, see the world from above with a helicopter tour, pause for some serene contemplation at Basilica of the National Shrine of Mary, Queen of the Universe, and experience the excitement of ICON Park.

For traveler tips, reviews, and other tourist information, read Orlando trip builder site.

You can drive from St. Augustine to Orlando in 2 hours. Another option is to take a bus. Expect a bit warmer weather when traveling from St. Augustine in December: highs in Orlando hover around 77°F, while lows dip to 59°F. Cap off your sightseeing on the 3rd (Mon) early enough to catch the flight back home.

Things to do in Orlando

Theme Parks · Parks · Childrens Museums · Museums

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.