60 days in Florida Itinerary

60 days in Florida Itinerary

Created using Inspirock Florida visit planner

Make it your trip
Fly
1
Key West
— 11 nights
Drive
2
Marathon
— 7 nights
Drive
3
Islamorada
— 7 nights
Drive
4
Key Largo
— 8 nights
Drive
5
Miami
— 6 nights
Drive
6
St. Augustine
— 5 nights
Drive
7
Orlando
— 10 nights
Fly
8
Pensacola
— 5 nights
Fly

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Key West

— 11 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.
Spend the 4th (Mon) exploring nature at Dry Tortugas National Park. There's lots more to do: see the interesting displays at The Ernest Hemingway Home and Museum, tour the pleasant surroundings at Mallory Square, take an in-depth tour of Truman Little White House, and make a trip to Southernmost Point.

To find more things to do, traveler tips, where to stay, and other tourist information, go to the Key West trip itinerary builder.

Newark to Key West is an approximately 5-hour flight. You can also drive; or take a bus. Traveling from Newark in May, you will find days in Key West are somewhat warmer (85°F), and nights are warmer (77°F). Finish up your sightseeing early on the 12th (Tue) so you can go by car to Marathon.

Things to do in Key West

Museums · Parks · Historic Sites · Shopping

Marathon

— 7 nights

Heart of the Florida Keys

A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
Get out of town with these interesting Marathon side-trips: Sugarloaf Key (American Shoal Lighthouse & Key West Angling) and Sugarloaf Key Bat Tower (in Sugarloaf). There's still lots to do: kick back and relax at Bahia Honda State Park, examine the collection at Crane Point Museum & Nature Center, soothe aching muscles at some of the top local wellness centers, and snap pictures at Old Seven Mile Bridge.

To find other places to visit, maps, ratings, and more tourist information, read Marathon trip planner.

You can drive from Key West to Marathon in 1.5 hours. Alternatively, you can take a bus. May in Marathon sees daily highs of 88°F and lows of 77°F at night. Finish up your sightseeing early on the 19th (Tue) so you can go by car to Islamorada.

Things to do in Marathon

Parks · Wildlife · Outdoors · Beaches

Side Trips

Islamorada

— 7 nights

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.
Take a break from Islamorada with a short trip to 99 Mile Wilderness Waterway in Everglades National Park, about 3 hours away. And it doesn't end there: see what you can catch with a fishing tour, immerse yourself in nature at Lignumvitae Key Botanical State Park, get outside with Takedown Charters, and take an in-depth tour of History of Diving Museum.

For maps, photos, traveler tips, and other tourist information, use the Islamorada trip planning website.

You can drive from Marathon to Islamorada in an hour. Another option is to take a bus. In May in Islamorada, expect temperatures between 88°F during the day and 77°F at night. Cap off your sightseeing on the 26th (Tue) early enough to go by car to Key Largo.

Things to do in Islamorada

Outdoors · Parks · Wildlife · Tours

Side Trip

Key Largo

— 8 nights

Diving Capital of the World

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.
Get out of town with these interesting Key Largo side-trips: Everglades National Park (West Lake Trail, Mrazek Pond, &more). There's lots more to do: get a new perspective on things with Boat Tours & Water Sports, admire nature's wide array of creatures at Island Dolphin Care, take a tour of African Queen Canal Cruise, and admire the majestic nature at John Pennekamp Coral Reef State Park.

To find reviews, maps, and other tourist information, refer to the Key Largo trip website.

Key Largo is very close to Islamorada. Expect little chillier evenings in Key Largo when traveling from Islamorada in May, with lows around 72°F. Finish your sightseeing early on the 3rd (Wed) to allow enough time to drive to Miami.

Things to do in Key Largo

Parks · Wildlife · Nature · Outdoors

Side Trip

Miami

— 6 nights

Magic City

Florida’s mecca of fun in the sun, the lively tropical metropolis of Miami is one of the world’s top vacation spots.
Change things up with these side-trips from Miami: Everglades National Park (Shark Valley Visitor Center, Gumbo Limbo Trail, &more), Wiener Museum of Decorative Arts (WMODA) (in Dania Beach) and Hollywood (Boxroom Escape Games & JP Outfitters Inc.). There's lots more to do: stroll through South Beach, have fun at Lock & Load Miami, shop like a local with Aventura Mall, and admire the striking features of Art Deco Historic District.

To see other places to visit, maps, and more tourist information, go to the Miami day trip planning website.

You can drive from Key Largo to Miami in 1.5 hours. Another option is to take a bus. In June, plan for daily highs up to 89°F, and evening lows to 77°F. Wrap up your sightseeing on the 9th (Tue) early enough to drive to St. Augustine.

Things to do in Miami

Parks · Outdoors · Shopping · Museums

Side Trips

St. Augustine

— 5 nights
St. Change things up with these side-trips from St. Augustine: Andy Romano Beachfront Park (in Ormond Beach), Catty Shack Ranch Wildlife Sanctuary (in Jacksonville) and Mala Compra Mountain Bike Trail (in Palm Coast). There's much more to do: brush up on your knowledge of spirits at St. Augustine Distillery, tour the pleasant surroundings at St. Augustine Wild Reserve, enjoy the sea views from St. Augustine Lighthouse & Maritime Museum, Inc., and deepen your knowledge of military history at Fort Clinch State Park.

For ratings, where to stay, photos, and other tourist information, go to the St. Augustine online road trip planner.

You can drive from Miami to St. Augustine in 5 hours. Other options are to do a combination of flight and bus; or take a bus. In June, daytime highs in St. Augustine are 88°F, while nighttime lows are 73°F. Cap off your sightseeing on the 14th (Sun) early enough to go by car to Orlando.

Things to do in St. Augustine

Parks · Outdoors · Wildlife · Beaches

Side Trips

Orlando

— 10 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.
Venture out of the city with trips to Sacred Heart Catholic Church (in Tampa), Merritt Island (Space Shuttle Atlantis & NASA Kennedy Space Center Visitor Complex) and Scuba & Snorkeling (in Crystal River). And it doesn't end there: find something for the whole family at Walt Disney World Resort, make an unforgettable trip to Happily Ever After Fireworks, laugh and play at Disney’s Hollywood Studios, and make a splash at Discovery Cove.

To see ratings, other places to visit, where to stay, and more tourist information, read our Orlando holiday builder.

You can drive from St. Augustine to Orlando in 2 hours. Another option is to 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 24th (Wed) so you can fly to Pensacola.

Things to do in Orlando

Theme Parks · Museums · Childrens Museums · Fun & Games

Side Trips

Pensacola

— 5 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.
Change things up with these side-trips from Pensacola: Miramar Beach (Kitchenique & Waterfront Gifts and Art), Navarre Beach (in Navarre) and Santa Rosa Beach (in Santa Rosa Beach). There's much more to do: brush up on your military savvy at National Naval Aviation Museum, sample the fine beverages at Rollins Distillery, step off the mainland to explore Santa Rosa Island, and expand your understanding of the military at Pensacola Naval Air Station.

Take the guesswork out of planning a Pensacola vacation by using our trip itinerary maker.

Traveling by flight from Orlando to Pensacola takes 3.5 hours. Alternatively, you can drive; or take a bus. The time zone changes from Eastern Standard Time (EST) to Central Standard Time (CST), which is usually a -1 hour difference. In June in Pensacola, expect temperatures between 88°F during the day and 74°F at night. Wrap up your sightseeing on the 29th (Mon) early enough to fly back home.

Things to do in Pensacola

Parks · Outdoors · Beaches · Museums

Side Trips

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.