14 days in Florida Itinerary

14 days in Florida Itinerary

Created using Inspirock Florida sightseeing planner

Make it your trip
Fly
1
Miami Beach
— 1 night
Drive
2
Key Largo
— 2 nights
Drive
3
Islamorada
— 2 nights
Drive
4
Big Pine Key
— 1 night
Drive
5
Key West
— 3 nights
Fly
6
Orlando
— 4 nights
Fly

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Miami Beach

— 1 night

The World's Playground

Separated by water from the neighboring city of Miami, Miami Beach sits on a barrier island between Biscayne Bay and the Atlantic Ocean.
Kick off your visit on the 27th (Fri): explore the world behind art at The Wolfsonian - Florida International University, appreciate the extensive heritage of Art Deco Historic District, and then kick back and relax at South Beach. On the next day, take in the architecture and atmosphere at St Patrick Catholic Church, explore the world behind art at Wiener Museum of Decorative Arts (WMODA), then enjoy some diversion at Lock & Load Miami, and finally wander the streets of Lincoln Road.

To see ratings, reviews, more things to do, and tourist information, read our Miami Beach trip planner.

New York City to Miami Beach is an approximately 5-hour flight. You can also drive; or take a bus. Traveling from New York City in November, expect Miami Beach to be much hotter, temps between 82°F and 70°F. Cap off your sightseeing on the 28th (Sat) early enough to go by car to Key Largo.

Things to do in Miami Beach

Historic Sites · Neighborhoods · Parks · Museums

Side Trips

Key Largo

— 2 nights

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.
On the 29th (Sun), push the limits with Jetpack Water Flights, then head outdoors with Capt. Sterling's Everglades Eco-Tours, then glide peacefully along the water with PADDLE! The Florida Keys, and finally tour the pleasant surroundings at Florida Keys Wild Bird Rehabilitation Center. Get ready for a full day of sightseeing on the next day: get up close and personal with brilliant marine life at Island Dolphin Care, bet on your favorite at Homestead Miami Speedway, and then step aboard USCG Duane.

For photos, traveler tips, maps, and tourist information, read our Key Largo road trip planning website.

Drive from Miami Beach to Key Largo in 1.5 hours. Alternatively, you can take a bus; or take a bus. In November, daytime highs in Key Largo are 81°F, while nighttime lows are 68°F. Finish your sightseeing early on the 30th (Mon) to allow enough time to drive to Islamorada.

Things to do in Key Largo

Outdoors · Tours · Wildlife · Adventure

Side Trip

Islamorada

— 2 nights

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 1st (Tue): look for gifts at Bella Sol Fragrance Bar and Gifts, soothe aching muscles at Island Flow Yoga, then see what you can catch with a fishing tour, and finally sample the tasty concoctions at Florida Keys Brewing Company. On the 2nd (Wed), you'll have a packed day of sightseeing: see the top attractions with Ultimate HeliTours, stroll through The Turtle Hospital, examine the collection at Crane Point Museum & Nature Center, then enjoy the sand and surf at Sombrero Beach, and finally indulge your thirst for a good beer at Islamorada Brewery & Distillery.

To find other places to visit, traveler tips, more things to do, and tourist information, go to the Islamorada online travel route planner.

Islamorada is just a short distance from Key Largo. In November in Islamorada, expect temperatures between 82°F during the day and 72°F at night. Finish your sightseeing early on the 2nd (Wed) so you can drive to Big Pine Key.

Things to do in Islamorada

Wildlife · Parks · Outdoors · Breweries & Distilleries

Side Trip

Big Pine Key

— 1 night
Big Pine Key is a census-designated place and unincorporated community in Monroe County, Florida, United States, on an island of the same name in the Florida Keys. Start off your visit on the 3rd (Thu): kick back and relax at Bahia Honda State Park, then take the plunge with Skydive Key West, and then get a new perspective on things with Florida Keys Kayaks and Eco Tours.

To find other places to visit, where to stay, traveler tips, and other tourist information, refer to the Big Pine Key route builder site.

Drive from Islamorada to Big Pine Key in 1.5 hours. Alternatively, you can take a bus. In December, daytime highs in Big Pine Key are 80°F, while nighttime lows are 71°F. Cap off your sightseeing on the 3rd (Thu) early enough to go by car to Key West.

Things to do in Big Pine Key

Outdoors · Beaches · Parks · Adventure

Side Trips

Key West

— 3 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.
Key West is known for museums, adventure, and wildlife. Your trip includes some of its best attractions: see the interesting displays at The Ernest Hemingway Home and Museum, get a taste of the local shopping with 7 Artists & Friends Gallery, tour the pleasant surroundings at Key West Butterfly & Nature Conservatory, and admire the natural beauty at Audubon House & Tropical Gardens.

Start your trip to Key West by creating a personalized itinerary on Inspirock.

Traveling by car from Big Pine Key to Key West takes an hour. Alternatively, you can take a shuttle; or take a bus. December in Key West sees daily highs of 79°F and lows of 71°F at night. Cap off your sightseeing on the 6th (Sun) early enough to catch the flight to Orlando.

Things to do in Key West

Wildlife · Museums · Outdoors · Tours

Orlando

— 4 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.
Have a day of magic on the 7th (Mon) at Walt Disney World Resort. Pack the 10th (Thu) with family-friendly diversions at Universal Orlando Resort. The adventure continues: get in on the family fun at Universal's Islands of Adventure and admire the masterpieces at Charles Hosmer Morse Museum of American Art.

To see photos, where to stay, ratings, and other tourist information, refer to the Orlando road trip site.

Traveling by flight from Key West to Orlando takes 3 hours. Alternatively, you can drive; or take a bus. Plan for little chillier nights when traveling from Key West in December since evenings lows in Orlando dip to 59°F. Finish your sightseeing early on the 10th (Thu) so you can fly back home.

Things to do in Orlando

Theme Parks · Museums

Side Trip

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.