27 days in Florida Itinerary

27 days in Florida Itinerary

Created using Inspirock Florida route planner

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Route & dates

27 days in Florida Itinerary

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

14
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.
Get in touch with nature at Disney's Animal Kingdom and Stand-Up Paddleboarding. Visit Stetson Mansion and Cape Canavarel National Cemetery for their historical value. Get out of town with these interesting Orlando side-trips: Scuba & Snorkeling (in Crystal River), Fishing Charters & Tours (in Port Canaveral) and Brevard County Erna Nixon Park (in Melbourne). Have a day of magic on the 12th (Tue) at Walt Disney World Resort. Pack the 14th (Thu) with family-friendly diversions at Universal Orlando Resort. There's still lots to do: get in on the family fun at Universal's Islands of Adventure, discover the magic at Happily Ever After Fireworks, pause for some serene contemplation at St. Barnabas Episcopal Church, and admire nature's wide array of creatures at SeaWorld Orlando.

To see maps, traveler tips, ratings, and tourist information, go to the Orlando attractions planner .

New York City to Orlando is an approximately 6-hour flight. You can also do a combination of bus and flight; or drive. In February, Orlando is much hotter than New York City - with highs of 75°F and lows of 56°F. Finish your sightseeing early on the 26th (Tue) to allow enough time to drive to Miami Beach.

Things to do in Orlando

Theme Parks Wildlife Parks

Side Trips

Crystal River, DeLand, Fishing Charters & Tours, Hidden Waters Preserve, Oakland Nature Preserve
Highlights from your plan
Stetson Mansion ©
Stetson Mansion
Scuba & Snorkeling
Disney's Animal Kingdom ©
Disney's Animal Kingdom

3
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.
Step out of the city life by going to Shark Valley and South Beach. Visit Art Deco Historic District and Barnacle State Historic Site for their historical value. And it doesn't end there: buy something for everyone on your list at Lincoln Road, wander the streets of Espanola Way, get a taste of the local shopping with Ocean Drive, and make a trip to Bayside Marketplace.

To see where to stay, photos, reviews, and tourist information, refer to the Miami Beach online trip itinerary planner .

You can drive from Orlando to Miami Beach in 4 hours. Alternatively, you can take a bus; or take a train. Expect a bit warmer evenings in Miami Beach when traveling from Orlando in February, with lows around 65°F. Wrap up your sightseeing on the 1st (Fri) to allow time to drive to Key Largo.

Things to do in Miami Beach

Neighborhoods Shopping Parks

Side Trips

Miami, Shark Valley Visitor Center
Highlights from your plan
Shark Valley Visitor Center ©
Shark Valley Visitor Center
Art Deco Historic District ©
Art Deco Historic District
South Beach ©
South Beach

2
nights
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 2nd (Sat): explore and take pictures at African Queen Canal Cruise and then see what you can catch with a fishing tour. Keep things going the next day: don't miss a visit to Coral Castle, then stop by Robert Is Here, and then identify plant and animal life at Anhinga Trail.

To find maps, ratings, where to stay, and tourist information, refer to the Key Largo tour itinerary planning site .

You can drive from Miami Beach to Key Largo in 1.5 hours. Another option is to take a bus. In March, plan for daily highs up to 79°F, and evening lows to 63°F. Cap off your sightseeing on the 3rd (Sun) early enough to go by car to Marathon.

Things to do in Key Largo

Wildlife Outdoors Tours

Side Trips

Homestead, Anhinga Trail, Fishing Charters & Tours
Highlights from your plan
Fishing Charters & Tours
Anhinga Trail ©
Anhinga Trail
Coral Castle ©
Coral Castle

2
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.
Start off your visit on the 4th (Mon): kick back and relax at Bahia Honda State Park and then look for all kinds of wild species at The Turtle Hospital. Here are some ideas for day two: pause for some serene contemplation at San Pablo Catholic Church, then identify plant and animal life at Crane Point Museum & Nature Center, and then see what you can catch with a fishing tour.

For ratings, other places to visit, where to stay, and more tourist information, you can read our Marathon online trip maker .

Traveling by car from Key Largo to Marathon takes 1.5 hours. Alternatively, you can take a bus; or do a combination of taxi and bus. Expect somewhat warmer evenings in Marathon when traveling from Key Largo in March, with lows around 69°F. Finish your sightseeing early on the 5th (Tue) to allow enough time to take a bus to Key West.

Things to do in Marathon

Outdoors Wildlife Parks

Side Trip

Bahia Honda State Park
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
The Turtle Hospital ©
The Turtle Hospital
Crane Point Museum & Nature Center ©

4
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.
Visit Audubon House & Tropical Gardens and Truman Little White House for their historical value. Step out of the city life by going to Key West Butterfly & Nature Conservatory and Parasailing & Paragliding. Spend the 9th (Sat) exploring nature at Dry Tortugas National Park. There's still lots to do: admire the majestic nature at Fort Zachary Taylor, explore the different monuments and memorials at Key West Cemetery, see the interesting displays at The Ernest Hemingway Home and Museum, and take in the architecture and atmosphere at Saint Mary Star of the Sea.

Inspirock's itinerary builder makes planning a Key West trip simple and quick.

Getting from Marathon to Key West by bus takes about 1.5 hours. Other options: drive. In March, daytime highs in Key West are 79°F, while nighttime lows are 69°F. Finish up your sightseeing early on the 9th (Sat) so you can travel back home.

Things to do in Key West

Parks Outdoors Historic Sites
Highlights from your plan
Fishing Charters & Tours
Dry Tortugas National Park ©
Dry Tortugas National Park

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