31 days in Florida Itinerary
Created using Inspirock Florida travel planner
Start: New York City
Fly
1
St. Augustine
— 3 nights
Drive
2
Orlando
— 5 nights
Drive
3
Siesta Key
— 2 nights
Fly
4
Key West
— 5 nights
Drive
5
Big Pine Key
— 2 nights
Drive
6
Islamorada
— 5 nights
Drive
7
Miami Beach
— 4 nights
Fly to Tallahassee, Drive to Panama City Beach
8
Panama City Beach
— 4 nights
Fly
End: New York City
Mon, May 1 - Wed, May 31
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View full calendar
St. Augustine — 3 nights
©
We've included these beaches for you: St. Augustine Beach and Ormond Beach. Venture out of the city with trips to TPC at Sawgrass Stadium Course (in Ponte Vedra Beach) and Andy Romano Beachfront Park (in Ormond Beach).
To find more things to do, reviews, maps, and more tourist information, refer to the St. Augustine trip itinerary app.
New York City to St. Augustine is an approximately 4-hour flight. You can also drive; or take a bus. Prepare for a bit warmer weather when traveling from New York City in May: high temperatures in St. Augustine hover around 83°F and lows are around 67°F. Finish up your sightseeing early on the 4th (Thu) so you can go by car to Orlando.
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To find more things to do, reviews, maps, and more tourist information, refer to the St. Augustine trip itinerary app.
New York City to St. Augustine is an approximately 4-hour flight. You can also drive; or take a bus. Prepare for a bit warmer weather when traveling from New York City in May: high temperatures in St. Augustine hover around 83°F and lows are around 67°F. Finish up your sightseeing early on the 4th (Thu) so you can go by car to Orlando.
Side Trips
Highlights from your trip
Orlando — 5 nights
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Theme Park Capital of the World
Have a day of magic on the 5th (Fri) at Walt Disney World Resort. Pack the 7th (Sun) with family-friendly diversions at Universal's Islands of Adventure. There's lots more to do: find something for the whole family at Universal Orlando Resort, look for gifts at MacroBaby, explore the world behind art at Museum Of Illusions Orlando, and make a splash at Discovery Cove.
For traveler tips, other places to visit, photos, and more tourist information, read our Orlando day trip site.
You can drive from St. Augustine to Orlando in 2 hours. Alternatively, you can drive; or take a bus. In May, daily temperatures in Orlando can reach 88°F, while at night they dip to 69°F. Finish your sightseeing early on the 9th (Tue) so you can drive to Siesta Key.
more
For traveler tips, other places to visit, photos, and more tourist information, read our Orlando day trip site.
You can drive from St. Augustine to Orlando in 2 hours. Alternatively, you can drive; or take a bus. In May, daily temperatures in Orlando can reach 88°F, while at night they dip to 69°F. Finish your sightseeing early on the 9th (Tue) so you can drive to Siesta Key.
Highlights from your trip
Siesta Key — 2 nights
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Start off your visit on the 10th (Wed): stroll through North Jetty Beach, enjoy the sand and surf at Turtle Beach, then walk around Siesta Beach, and finally look for gifts at The Spice & Tea Exchange. On the next day, indulge your taste buds at Siesta Key Rum, tour the pleasant surroundings at St. Pete Beach, then explore the world behind art at Duncan McClellan Gallery, and finally relax and rejuvenate at Nava Yoga Studio.
For maps, other places to visit, reviews, and more tourist information, read Siesta Key trip itinerary planner.
Traveling by car from Orlando to Siesta Key takes 2.5 hours. Alternatively, you can drive; or take a bus; or do a combination of train and bus. In May, daily temperatures in Siesta Key can reach 87°F, while at night they dip to 68°F. Wrap up your sightseeing on the 11th (Thu) early enough to fly to Key West.
more
For maps, other places to visit, reviews, and more tourist information, read Siesta Key trip itinerary planner.
Traveling by car from Orlando to Siesta Key takes 2.5 hours. Alternatively, you can drive; or take a bus; or do a combination of train and bus. In May, daily temperatures in Siesta Key can reach 87°F, while at night they dip to 68°F. Wrap up your sightseeing on the 11th (Thu) early enough to fly to Key West.
Side Trips
Highlights from your trip
Key West — 5 nights
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Conch Republic
Head to Sunset Celebration and Guild Hall Galleryfor some retail therapy. We've included these beaches for you: Fort Zachary Taylor and Higgs Beach. And it doesn't end there: see the interesting displays at The Ernest Hemingway Home and Museum, steep yourself in history at Truman Little White House, relax and rejuvenate at some of the best spas, and take in the waterfront at Mallory Square.
Quickly create a custom-made itinerary for Key West using our trip planner.
Traveling by flight from Siesta Key to Key West takes 3 hours. Alternatively, you can drive; or do a combination of bus, taxi, and ferry. Traveling from Siesta Key in May, Key West is somewhat warmer at night with lows of 77°F. Finish your sightseeing early on the 16th (Tue) so you can drive to Big Pine Key.
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Quickly create a custom-made itinerary for Key West using our trip planner.
Traveling by flight from Siesta Key to Key West takes 3 hours. Alternatively, you can drive; or do a combination of bus, taxi, and ferry. Traveling from Siesta Key in May, Key West is somewhat warmer at night with lows of 77°F. Finish your sightseeing early on the 16th (Tue) so you can drive to Big Pine Key.
Highlights from your trip
Big Pine Key — 2 nights
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Start off your visit on the 17th (Wed): kick back and relax at Long Beach, kick back and relax at Bahia Honda State Park, and then tour the pleasant surroundings at Calusa Beach. Keep things going the next day: stop by Out of the Blue Gallery, indulge in some personalized pampering at SpaTerre at Little Palm Island Resort, and then take in the exciting artwork at Artists in Paradise Gallery.
Make your Big Pine Key itinerary with Inspirock to find out what to see and where to go.
Traveling by car from Key West to Big Pine Key takes an hour. Alternatively, you can take a shuttle; or take a bus. In May, daytime highs in Big Pine Key are 88°F, while nighttime lows are 77°F. Finish your sightseeing early on the 18th (Thu) so you can drive to Islamorada.
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Make your Big Pine Key itinerary with Inspirock to find out what to see and where to go.
Traveling by car from Key West to Big Pine Key takes an hour. Alternatively, you can take a shuttle; or take a bus. In May, daytime highs in Big Pine Key are 88°F, while nighttime lows are 77°F. Finish your sightseeing early on the 18th (Thu) so you can drive to Islamorada.
Side Trip
Highlights from your trip
Islamorada — 5 nights
©
The Village of Islands
Give yourself a bit of retail therapy at Zero Dress Code Boutique and Old Road Gallery. You'll enjoy a bit of beach vacationing at Sombrero Beach and Anne's Beach. Change things up with these side-trips from Islamorada: Marathon (Shady Palm Art Gallery & Photography & Spas & Wellness) and Sunset Park Beach (in Key Colony Beach). There's lots more to do: indulge your thirst for a good beer at Florida Keys Brewing Company, take in the exciting artwork at Pasta Pantaleo Signature Gallery, shop like a local with Lobster Trap Art Gift Shop and Gallery, and head outdoors with Outdoor Activities.
To find ratings, reviews, maps, and other tourist information, go to the Islamorada trip app.
Drive from Big Pine Key to Islamorada in 1.5 hours. Alternatively, you can take a bus. In May, daytime highs in Islamorada are 88°F, while nighttime lows are 77°F. Finish your sightseeing early on the 23rd (Tue) so you can drive to Miami Beach.
more
To find ratings, reviews, maps, and other tourist information, go to the Islamorada trip app.
Drive from Big Pine Key to Islamorada in 1.5 hours. Alternatively, you can take a bus. In May, daytime highs in Islamorada are 88°F, while nighttime lows are 77°F. Finish your sightseeing early on the 23rd (Tue) so you can drive to Miami Beach.
Side Trips
Highlights from your trip
Miami Beach — 4 nights
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The World's Playground
Do your shopping at Lincoln Road and Ocean Drive. Relax by the water at Fort Lauderdale Beach and Hollywood Beach. Explore the numerous day-trip ideas around Miami Beach: Aventura Mall (in Aventura) and Dolphin Mall (in Miami). There's still lots to do: wander the streets of Collins Avenue, appreciate the extensive heritage of Art Deco Historic District, browse the different shops at Bayside Marketplace, and look for gifts at Bachi Jewels.
To see traveler tips, where to stay, more things to do, and other tourist information, read Miami Beach day trip site.
You can drive from Islamorada to Miami Beach in 2 hours. Alternatively, you can do a combination of shuttle and bus; or take a bus. In May, daytime highs in Miami Beach are 87°F, while nighttime lows are 74°F. Finish your sightseeing early on the 27th (Sat) to allow enough time to travel to Panama City Beach.
more
To see traveler tips, where to stay, more things to do, and other tourist information, read Miami Beach day trip site.
You can drive from Islamorada to Miami Beach in 2 hours. Alternatively, you can do a combination of shuttle and bus; or take a bus. In May, daytime highs in Miami Beach are 87°F, while nighttime lows are 74°F. Finish your sightseeing early on the 27th (Sat) to allow enough time to travel to Panama City Beach.
Side Trips
Highlights from your trip
Panama City Beach — 4 nights
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World's Most Beautiful Beaches
Head to Adonia and 30A Farmers Marketfor some retail therapy. We've included these beaches for you: Navarre Beach and St. Andrews State Park. Explore the numerous day-trip ideas around Panama City Beach: Santa Rosa Beach (Blue Mountain Beach & Santa Rosa Beach), Rollins Distillery (in Gulf Breeze) and Emerald Coast Wine Cellars (in Miramar Beach). The adventure continues: do a tasting at Panama City Beach Winery, get outside with Huntress Charter Fishing, kick back and relax at Henderson Beach State Park, and head off the coast to Okaloosa Island.
To find other places to visit, reviews, photos, and tourist information, use the Panama City Beach trip itinerary app.
You can do a combination of flight and car from Miami Beach to Panama City Beach in 5.5 hours. Another option is to drive. Traveling from Miami Beach in May, Panama City Beach is a bit cooler at night with lows of 62°F. Wrap up your sightseeing on the 31st (Wed) to allow time to fly back home.
more
To find other places to visit, reviews, photos, and tourist information, use the Panama City Beach trip itinerary app.
You can do a combination of flight and car from Miami Beach to Panama City Beach in 5.5 hours. Another option is to drive. Traveling from Miami Beach in May, Panama City Beach is a bit cooler at night with lows of 62°F. Wrap up your sightseeing on the 31st (Wed) to allow time to fly back home.
Side Trips
Highlights from your trip
Florida travel guide
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.
