15 days in Florida Itinerary

15 days in Florida Itinerary

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Route & dates

15 days in Florida Itinerary

Start: Philadelphia
Fly:  4​h 45​min
1
Key West
— 3 nights
Bus:  45​min
2
Big Pine Key, Florida Keys
— 1 night
Drive:  30​min
3
Marathon, Florida Keys
— 1 night
Drive:  2​h 45​min
4
Miami Beach
— 2 nights
Fly + Drive:  4​h 45​min
5
St. Augustine
— 2 nights
Drive:  2​h
6
Orlando
— 3 nights
Fly + Drive:  4​h 45​min
7
Pensacola
— 2 nights
Fly:  5​h 30​min
End: Philadelphia

3
nights
Key West

Key West ©
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.
Your cultural itinerary includes sights like The Ernest Hemingway Home and Museum and Mel Fisher Maritime Heritage Museum. Let the collections at Alan S. Maltz Gallery and Truman Little White House capture your imagination. The adventure continues: admire the majestic nature at Fort Zachary Taylor, take an in-depth tour of Key West Firehouse Museum, stroll the grounds of Key West Cemetery, and take a tour by water with Boat Tours & Water Sports.

To see traveler tips, reviews, and tourist information, read our Key West trip itinerary builder tool .

Philadelphia to Key West is an approximately 5-hour flight. You can also do a combination of train and flight; or drive. Traveling from Philadelphia in June, expect a bit warmer with lows of 79°F in Key West. Wrap up your sightseeing on the 6th (Thu) early enough to take a bus to Big Pine Key.

Things to do in Key West

Museums Outdoors Tours
Highlights from your plan
The Ernest Hemingway Home and Museum ©
Truman Little White House ©
Truman Little White House
Alan S. Maltz Gallery ©
Alan S. Maltz Gallery

1
night
Big Pine Key, Florida Keys

Big Pine Key ©
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. Kick off your visit on the 7th (Fri): get a taste of the local shopping with Artists in Paradise Gallery, kick back and relax at Calusa Beach, and then admire the majestic nature at Bahia Honda State Park.

To see photos, where to stay, ratings, and more tourist information, you can read our Big Pine Key attractions planning app .

You can take a bus from Key West to Big Pine Key in an hour. Alternatively, you can drive. In June, daily temperatures in Big Pine Key can reach 90°F, while at night they dip to 79°F. Finish up your sightseeing early on the 7th (Fri) so you can catcht the bus to Marathon.

Things to do in Big Pine Key

Beaches Outdoors Parks
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
Artists in Paradise Gallery ©
Artists in Paradise Gallery

1
night
Marathon, Florida Keys

Marathon ©
A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
Kick off your visit on the 8th (Sat): relax and rejuvenate at some of the top local wellness centers, tour the pleasant surroundings at Sunset Park Beach, then take in the architecture and atmosphere at San Pablo Catholic Church, and finally tour the pleasant surroundings at Sombrero Beach.

For photos, reviews, traveler tips, and more tourist information, you can read our Marathon road trip planner.

Marathon is just a short distance from Big Pine Key. In June, daily temperatures in Marathon can reach 90°F, while at night they dip to 79°F. Finish your sightseeing early on the 8th (Sat) so you can drive to Miami Beach.

Things to do in Marathon

Beaches Outdoors Parks

Side Trip

Sunset Park Beach
Highlights from your plan
Sombrero Beach ©
Sombrero Beach
Sunset Park Beach ©
Sunset Park Beach
San Pablo Catholic Church ©
San Pablo Catholic Church

2
nights
Miami Beach

Miami Beach ©
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 9th (Sun), make a trip to Collins Avenue, appreciate the extensive heritage of Art Deco Historic District, then admire the masterpieces at The Wolfsonian - Florida International University, and finally stroll through South Beach. Get ready for a full day of sightseeing on the next day: enjoy the sand and surf at 12th Street Beach, then examine the collection at Vizcaya Museum and Gardens, and then wander the streets of Lincoln Road.

To see ratings, other places to visit, more things to do, and more tourist information, refer to the Miami Beach tour planner.

Getting from Marathon to Miami Beach by car takes about 3 hours. Other options: take a bus; or do a combination of bus and flight. In June in Miami Beach, expect temperatures between 89°F during the day and 77°F at night. Finish your sightseeing early on the 10th (Mon) to allow enough time to travel to St. Augustine.

Things to do in Miami Beach

Parks Neighborhoods Beaches

Side Trip

Vizcaya Museum and Gardens
Highlights from your plan
South Beach ©
South Beach
Lincoln Road ©
Lincoln Road
Vizcaya Museum and Gardens ©
Vizcaya Museum and Gardens

2
nights
St. Augustine

St. Augustine ©
SAINT AUGUSTINE | PONTE VEDRA on Florida's Historic Coast The Nation's oldest city (est. Kick off your visit on the 11th (Tue): enjoy the sand and surf at Crescent Beach Public Beach, enjoy the sand and surf at Frank Butler County Park West, and then brush up on your knowledge of spirits at St. Augustine Distillery. On your second day here, enjoy the sand and surf at St. Augustine Beach, visit a coastal fixture at St. Augustine Lighthouse & Maritime Museum, Inc., then examine the collection at The Ximenez-Fatio House, and finally see the interesting displays at St. Augustine Pirate & Treasure Museum.

To see other places to visit, traveler tips, maps, and tourist information, read St. Augustine trip itinerary builder .

Traveling by combination of flight and car from Miami Beach to St. Augustine takes 5 hours. Alternatively, you can drive; or take a bus. In June, daytime highs in St. Augustine are 88°F, while nighttime lows are 73°F. Finish your sightseeing early on the 12th (Wed) to allow enough time to drive to Orlando.

Things to do in St. Augustine

Beaches Outdoors Parks

Side Trip

Crescent Beach Public Beach
Highlights from your plan
St. Augustine Beach ©
St. Augustine Beach
The Ximenez-Fatio House ©
The Ximenez-Fatio House

3
nights
Orlando

Orlando ©
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 13th (Thu) with family-friendly diversions at Discovery Cove. Pack the 15th (Sat) with family-friendly diversions at Universal Orlando Resort. There's still lots to do: get in on the family fun at Walt Disney World Resort.

Before you visit Orlando, use our trip planner to discover what you can do and see there.

Drive from St. Augustine to Orlando in 2 hours. Alternatively, you can take a bus. In June, daily temperatures in Orlando can reach 91°F, while at night they dip to 73°F. Finish your sightseeing early on the 15th (Sat) to allow enough time to travel to Pensacola.

Things to do in Orlando

Theme Parks Beaches Outdoors
Highlights from your plan
Discovery Cove ©
Discovery Cove
Walt Disney World Resort ©
Walt Disney World Resort
Universal Orlando Resort ©
Universal Orlando Resort

2
nights
Pensacola

Pensacola ©
Surrounded on three sides by water, Pensacola offers access to white-sand beaches and emerald-green ocean unspoiled by large resorts.
Start off your visit on the 16th (Sun): stroll through Gulf Islands National Seashore and then enjoy the sand and surf at Navarre Beach. Keep things going the next day: see the interesting displays at National Naval Aviation Museum and then enjoy the sea views from Pensacola Lighthouse and Museum.

For reviews, photos, and tourist information, read our Pensacola online route planner .

Traveling by combination of flight and car from Orlando to Pensacola takes 5 hours. Alternatively, you can fly; or drive. The time zone changes from Eastern Standard Time (EST) to Central Standard Time (CST), which is usually a -1 hour difference. In June, daily temperatures in Pensacola can reach 88°F, while at night they dip to 74°F. Wrap up your sightseeing on the 17th (Mon) to allow time to travel back home.

Things to do in Pensacola

Beaches Outdoors Parks

Side Trips

Navarre Beach, Gulf Islands National Seashore
Highlights from your plan
National Naval Aviation Museum ©
National Naval Aviation Museum
Navarre Beach ©
Navarre Beach
Gulf Islands National Seashore ©
Gulf Islands National Seashore

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