21 days in Florida Itinerary

21 days in Florida Itinerary

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Route & dates

21 days in Florida Itinerary

Start: New York City
Fly:  6​h
1
Orlando
— 4 nights
Drive:  2​h
2
St. Augustine
— 2 nights
Drive + Fly:  4​h 45​min
3
Miami Beach
— 2 nights
Drive:  1​h 30​min
4
Key Largo
— 2 nights
Drive:  45​min
5
Islamorada
— 2 nights
Drive:  45​min
6
Marathon
— 3 nights
bus:  1​h 15​min
7
Key West
— 5 nights
Fly + bus:  6​h
End: New York City

4
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.
Step out of Orlando with an excursion to Corpus Christi Catholic Church in Celebration--about 38 minutes away. Pack the 8th (Wed) with family-friendly diversions at Discovery Cove. Have a day of magic on the 9th (Thu) at Walt Disney World Resort. Next up on the itinerary: get in on the family fun at Universal Orlando Resort, make an unforgettable trip to Disney's Animal Kingdom, and laugh and play at Happily Ever After Fireworks.

For more things to do, where to stay, other places to visit, and more tourist information, you can read our Orlando day trip planning website .

New York City to Orlando is an approximately 6-hour flight. You can also do a combination of bus and flight; or drive. Traveling from New York City in May, things will get a bit warmer in Orlando: highs are around 88°F and lows about 69°F. Finish up your sightseeing early on the 11th (Sat) so you can go by car to St. Augustine.

Things to do in Orlando

Theme Parks Parks Beaches

Side Trip

Corpus Christi Catholic Church
Highlights from your plan
Discovery Cove ©
Discovery Cove
Disney's Animal Kingdom ©
Disney's Animal Kingdom
Happily Ever After Fireworks ©
Happily Ever After Fireworks

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 12th (Sun): brush up on your knowledge of spirits at St. Augustine Distillery, then enjoy the sand and surf at St. Augustine Beach, and then visit a coastal fixture at St. Augustine Lighthouse & Maritime Museum, Inc.. Get ready for a full day of sightseeing on the 13th (Mon): take in the architecture and atmosphere at Grace United Methodist Church, take in the history at Mission of Nombre de Dios, then look for all kinds of wild species at St. Augustine Wild Reserve, and finally take in the architecture and atmosphere at Memorial Presbyterian Church.

Ask Inspirock to suggest an itinerary and make planning a trip to St. Augustine fast, fun, and easy.

Traveling by car from Orlando to St. Augustine takes 2 hours. Alternatively, you can take a bus. Expect slightly colder weather when traveling from Orlando in May: highs in St. Augustine hover around 83°F, while lows dip to 67°F. Finish your sightseeing early on the 13th (Mon) so you can travel to Miami Beach.

Things to do in St. Augustine

Historic Sites Parks Beaches
Highlights from your plan
St. Augustine Beach ©
St. Augustine Beach
Mission of Nombre de Dios ©
Mission of Nombre de Dios

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.
Start off your visit on the 14th (Tue): stroll through South Beach, then get to know the fascinating history of Art Deco Historic District, and then wander the streets of Lincoln Road. On the next day, explore and take pictures at Art Deco Tours, then see the interesting displays at Vizcaya Museum and Gardens, and then admire the striking features of Freedom Tower.

Planning Miami Beach trip won't be overwheling when you use's Insprock itinerary maker.

Traveling by combination of car and flight from St. Augustine to Miami Beach takes 5 hours. Alternatively, you can drive; or take a bus. Expect a bit warmer evenings in Miami Beach when traveling from St. Augustine in May, with lows around 74°F. Finish your sightseeing early on the 15th (Wed) to allow enough time to drive to Key Largo.

Things to do in Miami Beach

Historic Sites Parks Neighborhoods

Side Trip

Miami
Highlights from your plan
Lincoln Road ©
Lincoln Road
South Beach ©
South Beach
Art Deco Historic District ©
Art Deco Historic District

2
nights
Key Largo

Key Largo ©
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 16th (Thu): discover the deep blue sea with a scuba or snorkeling tour, pause for some serene contemplation at Saint Justin Martyr Catholic Church, and then take in the architecture and atmosphere at Key Largo Baptist Church. Get ready for a full day of sightseeing on the 17th (Fri): identify plant and animal life at Florida Keys Wild Bird Rehabilitation Center, look for all kinds of wild species at Molasses Reef, and then see the vivid underwater world at Spiegel Grove.

To find traveler tips, maps, more things to do, and more tourist information, read our Key Largo road trip planning site .

Drive from Miami Beach to Key Largo in 1.5 hours. Alternatively, you can take a bus. In May, daily temperatures in Key Largo can reach 85°F, while at night they dip to 72°F. Wrap up your sightseeing on the 17th (Fri) early enough to drive to Islamorada.

Things to do in Key Largo

Wildlife Parks Outdoors
Highlights from your plan
Scuba & Snorkeling
Spiegel Grove ©
Spiegel Grove

2
nights
Islamorada

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 18th (Sat): shop like a local with Old Road Gallery, then see the vivid underwater world at Alligator Reef Light House, then contemplate the long history of Indian Key State Historic Site, and finally sample the tasty concoctions at Islamorada Beer Company Brewery and Tasting Room. Keep things going the next day: see what you can catch with a fishing tour and then sample the tasty concoctions at Florida Keys Brewing Company.

To find where to stay, maps, traveler tips, and more tourist information, you can read our Islamorada online trip builder .

You can drive from Key Largo to Islamorada in an hour. Alternatively, you can do a combination of taxi and bus. In May, daily temperatures in Islamorada can reach 88°F, while at night they dip to 77°F. Finish up your sightseeing early on the 19th (Sun) so you can go by car to Marathon.

Things to do in Islamorada

Wildlife Outdoors Tours
Highlights from your plan
Fishing Charters & Tours
Alligator Reef Light House ©
Alligator Reef Light House
Indian Key State Historic Site ©
Indian Key State Historic Site

3
nights
Marathon

Marathon ©
A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
Relax by the water at Bahia Honda State Park and Sombrero Beach. Take a break from Marathon with a short trip to National Key Deer Refuge in Big Pine Key, about 34 minutes away. Next up on the itinerary: take in the architecture and atmosphere at San Pablo Catholic Church, look for all kinds of wild species at The Turtle Hospital, get answers to all your questions at Pigeon Key Foundation, and take in the views from Seven Mile Bridge.

For maps, other places to visit, photos, and more tourist information, use the Marathon trip maker website .

Getting from Islamorada to Marathon by car takes about an hour. Other options: take a bus. Expect a daytime high around 88°F in May, and nighttime lows around 77°F. Wrap up your sightseeing on the 22nd (Wed) early enough to take a bus to Key West.

Things to do in Marathon

Parks Wildlife Beaches

Side Trip

Big Pine Key
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
The Turtle Hospital ©
The Turtle Hospital
Dolphin Research Center ©
Dolphin Research Center

5
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.
Appreciate the collections at The Ernest Hemingway Home and Museum and Truman Little White House. Audubon House & Tropical Gardens and Key West Cemetery will appeal to history buffs. There's lots more to do: identify plant and animal life at Key West Butterfly & Nature Conservatory, steep yourself in history at Curry Mansion, pause for some serene contemplation at Saint Mary Star of the Sea, and visit a coastal fixture at Key West Lighthouse and Keeper's Quarters Museum.

To see where to stay, other places to visit, maps, and more tourist information, go to the Key West trip itinerary builder site .

Traveling by bus from Marathon to Key West takes 1.5 hours. Alternatively, you can drive. In May, plan for daily highs up to 85°F, and evening lows to 77°F. Cap off your sightseeing on the 27th (Mon) early enough to travel back home.

Things to do in Key West

Outdoors Historic Sites Tours
Highlights from your plan
The Ernest Hemingway Home and Museum ©
Dolphin & Whale Watching

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