15 days in Florida Itinerary

15 days in Florida Itinerary

Created using Inspirock Florida holiday planner

Make it your trip
Fly to Destin-Fort Walton Beach Airport, Drive to Pensacola
1
Pensacola
— 2 nights
Fly
2
Miami Beach
— 2 nights
Drive
3
Islamorada
— 1 night
Drive
4
Key West
— 4 nights
Fly
5
Orlando
— 5 nights
Fly

S M T W T F S
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Pensacola

— 2 nights

Western Gate to the Sunshine State

Surrounded on three sides by water, Pensacola offers access to white-sand beaches and emerald-green ocean unspoiled by large resorts.
Kick off your visit on the 19th (Sun): enjoy the sand and surf at Pensacola Beach, discover the deep blue sea with Jolly Sailing and Dolphin Cruises, and then step off the mainland to explore Gulf Islands. On your second day here, learn about all things military at National Naval Aviation Museum, deepen your knowledge of military history at Pensacola Naval Air Station, and then enjoy the sand and surf at Navarre Beach.

Plan my day in Pensacola using traveler tips and tourist information provided by Inspirock.

Vancouver, Canada to Pensacola is an approximately 13.5-hour combination of flight and car. You can also fly; or drive; or do a combination of train, bus, and taxi. Traveling from Vancouver to Pensacola, you'll lose 2 hours due to the time zone difference. Traveling from Vancouver in September, expect nights in Pensacola to be a bit warmer, around 26°C, while days are much hotter, around 36°C. Wrap up your sightseeing on the 20th (Mon) to allow time to fly to Miami Beach.

Things to do in Pensacola

Outdoors · Parks · Beaches · Wildlife

Side Trips

Miami Beach

— 2 nights

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 21st (Tue): immerse yourself in nature at Oleta River State Park, then don't miss a visit to Collins Avenue, and then indulge in some culinary diversions at a local gastronomic tour. On the 22nd (Wed), you'll have a packed day of sightseeing: kick back and relax at South Beach, stop by Art Deco Historic District, then browse the different shops at Lincoln Road, then contemplate the long history of Freedom Tower at Miami Dade College, and finally zoom along the surf with a waterskiing or jet-skiing adventure.

For reviews, maps, more things to do, and other tourist information, you can read our Miami Beach online tour builder.

You can fly from Pensacola to Miami Beach in 3.5 hours. Alternatively, you can drive; or take a bus. The time zone difference when traveling from Pensacola to Miami Beach is 1 hour. In September, plan for daily highs up to 38°C, and evening lows to 29°C. Finish your sightseeing early on the 22nd (Wed) so you can drive to Islamorada.

Things to do in Miami Beach

Parks · Neighborhoods · Tours · Historic Sites

Side Trips

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 23rd (Thu): stop by The Mystical Mermaid, then soothe aching muscles at Island Flow Yoga, then cast your line with a fishing tour, and finally indulge your thirst for a good beer at Florida Keys Brewing Company.

To see reviews, ratings, photos, and more tourist information, read Islamorada trip itinerary website.

You can drive from Miami Beach to Islamorada in 2 hours. Alternatively, you can do a combination of bus and shuttle; or take a bus. In September, daytime highs in Islamorada are 38°C, while nighttime lows are 30°C. Finish your sightseeing early on the 23rd (Thu) to allow enough time to drive to Key West.

Things to do in Islamorada

Outdoors · Wildlife · Tours · Breweries & Distilleries

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.
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, stop by Peppers of Key West, contemplate the long history of Curry Mansion Inn, and don't miss a visit to Duval Street.

For photos, traveler tips, other places to visit, and other tourist information, read our Key West trip itinerary builder website.

Traveling by car from Islamorada to Key West takes 2 hours. Alternatively, you can take a bus. In September in Key West, expect temperatures between 36°C during the day and 31°C at night. Finish your sightseeing early on the 27th (Mon) to allow enough time to fly to Orlando.

Things to do in Key West

Museums · Parks · Shopping · Historic Sites

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.
Pack the 29th (Wed) with family-friendly diversions at Universal Orlando Resort. Pack the 30th (Thu) with family-friendly diversions at Universal's Islands of Adventure. The adventure continues: discover the magic at Walt Disney World Resort, find something for the whole family at SeaWorld, and make a splash at Discovery Cove.

For reviews, traveler tips, maps, and tourist information, go to the Orlando day trip planner.

You can fly from Key West to Orlando in 3 hours. Other options are to drive; or take a bus. Expect a bit cooler evenings in Orlando when traveling from Key West in September, with lows around 27°C. Cap off your sightseeing on the 2nd (Sat) early enough to catch the flight back home.

Things to do in Orlando

Theme Parks

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.