50 days in Florida Itinerary

50 days in Florida Itinerary

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Route & dates

50 days in Florida Itinerary

Start: Orlando
1
Orlando
— 8 nights
Drive:  2​h
2
St. Augustine
— 6 nights
Drive:  5​h 30​min
3
Panama City Beach
— 4 nights
taxi + Fly:  6​h 15​min
4
Key West
— 8 nights
Fly + foot:  2​h 45​min
5
Miami
— 6 nights
Drive:  2​h 15​min
6
Naples
— 5 nights
Drive:  2​h
7
Sarasota
— 6 nights
Drive:  1​h 15​min
8
Clearwater
— 6 nights
Drive:  2​h
End: Orlando

8
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.
Relax by the water at Ponce de Leon Inlet Lighthouse & Museum and Cocoa Beach. Head to Disney Springs and The Mall at Milleniafor some retail therapy. Explore the numerous day-trip ideas around Orlando: Boxelder (in Sanford), Stetson Mansion (in DeLand) and NASA Kennedy Space Center Visitor Complex (in Titusville). Pack the 3rd (Thu) with family-friendly diversions at Walt Disney World Resort. Pack the 8th (Tue) with family-friendly diversions at Universal's Islands of Adventure. And it doesn't end there: discover the magic at Happily Ever After Fireworks, admire the masterpieces at Charles Hosmer Morse Museum of American Art, get some fabulous bargains at Orlando Premium Outlets - Vineland Avenue, and get in on the family fun at Magic Kingdom Park.

To see maps, more things to do, other places to visit, and other tourist information, read our Orlando online trip builder .

Use the Route module to find travel options from your starting location to Orlando. May in Orlando sees daily highs of 88°F and lows of 69°F at night. Finish your sightseeing early on the 11th (Fri) so you can drive to St. Augustine.

Things to do in Orlando

#Theme Parks, #Shopping, #Museums

Side Trips

Cocoa Beach, NASA Kennedy Space Center Visitor Complex, Stetson Mansion, Charles Hosmer Morse Museum of American Art, Ponce de Leon Inlet Lighthouse & Museum
Highlights from your plan
Walt Disney World Resort ©
Walt Disney World Resort
Stetson Mansion ©
Stetson Mansion

6
nights
St. Augustine

St. Augustine ©
SAINT AUGUSTINE | PONTE VEDRA on Florida's Historic Coast The Nation's oldest city (est. Popular historic sites such as Castillo de San Marcos and Memorial Presbyterian Church are in your itinerary. Let the collections at The Ximenez-Fatio House and St. Augustine Pirate & Treasure Museum capture your imagination. Get out of town with these interesting St. Augustine side-trips: Daytona Beach (Beach at Daytona Beach & Ocean Walk Village) and Ormond Beach (in Ormond Beach). Spend the 16th (Wed) exploring nature at Fort Matanzas National Monument. The adventure continues: enjoy the sand and surf at St. Augustine Beach, stop by Pop N Off, steep yourself in history at The Old Senator Tree, and sample the fine beverages at St. Augustine Distillery.

To see photos, other places to visit, ratings, and other tourist information, refer to the St. Augustine trip planner .

You can drive from Orlando to St. Augustine in 2 hours. Alternatively, you can take a bus. While traveling from Orlando, expect little chillier days and about the same nights in St. Augustine, ranging from highs of 82°F to lows of 67°F. Finish your sightseeing early on the 17th (Thu) to allow enough time to drive to Panama City Beach.

Things to do in St. Augustine

#Parks, #Historic Sites, #Beaches

Side Trips

Daytona Beach, Ormond Beach
Highlights from your plan
St. Augustine Beach ©
St. Augustine Beach
Ormond Beach ©
Ormond Beach
Castillo de San Marcos ©
Castillo de San Marcos

4
nights
Panama City Beach

Panama City Beach ©
Boasting 43 km (27 mi) of white sandy beaches and plenty of sunshine, Panama City Beach is an ideal choice for a relaxing holiday.
You'll get in some beach time at Navarre Beach and Santa Rosa Beach. Do some cultural sightseeing at Panama City Beach Winery and Eden Gardens State Park. Step out of Panama City Beach to go to Fort Walton Beach and see Air Force Armament Museum, which is approximately 1h 25 min away. There's lots more to do: take advantage of the amenities at Panama City Beach, see majestic marine mammals with a dolphin and whale watching tour, admire the majestic nature at St. Andrews State Park, and meet the residents at Gulf World Marine Park.

To see ratings, maps, and other tourist information, you can read our Panama City Beach trip itinerary planning app .

Traveling by car from St. Augustine to Panama City Beach takes 5.5 hours. Alternatively, you can do a combination of bus and taxi; or do a combination of bus, flight, and taxi. In May, daily temperatures in Panama City Beach can reach 85°F, while at night they dip to 63°F. Wrap up your sightseeing by early afternoon on the 21st (Mon) to allow enough time to travel to Key West.

Things to do in Panama City Beach

#Parks, #Outdoors, #Beaches

Side Trips

Navarre Beach, Air Force Armament Museum, Santa Rosa Beach, Eden Gardens State Park
Highlights from your plan
Panama City Beach Winery ©
Panama City Beach Winery
Navarre Beach ©
Navarre Beach
Santa Rosa Beach ©
Santa Rosa Beach

8
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 Truman Little White House and Curry Mansion for their historical value. Head to Uva Wine Shop & Bar and Sunset Celebrationfor plenty of shopping. Spend the 25th (Fri) airborne with a parasailing or paragliding tour. Spend the 27th (Sun) exploring nature at Dry Tortugas National Park. The adventure continues: examine the collection at The Ernest Hemingway Home and Museum, explore the different monuments and memorials at Key West Cemetery, take a tour by water with Boat Tours & Water Sports, and admire the natural beauty at Audubon House & Tropical Gardens.

For other places to visit, ratings, traveler tips, and more tourist information, read Key West day trip planning app .

You can do a combination of taxi and flight from Panama City Beach to Key West in 6.5 hours. Alternatively, you can do a combination of taxi and flight; or drive. Traveling from Panama City Beach in May, you can expect nighttime temperatures to be somewhat warmer in Key West, with lows of 77°F. Finish up your sightseeing early on the 29th (Tue) so you can travel to Miami.

Things to do in Key West

#Outdoors, #Parks, #Tours
Highlights from your plan
The Ernest Hemingway Home and Museum ©
Truman Little White House ©
Truman Little White House
Fort Zachary Taylor ©
Fort Zachary Taylor

6
nights
Miami

Miami ©
Florida’s mecca of fun in the sun, the lively tropical metropolis of Miami is one of the world’s top vacation spots.
Deepen your sense of the past at sights like Lincoln Road and Barnacle State Historic Site. You'll explore and learn at Vizcaya Museum and Gardens and Wynwood Walls. Explore Miami's surroundings by going to Fort Lauderdale Beach (in Fort Lauderdale), Hollywood Beach (in Hollywood) and Sawgrass Mills (in Sunrise). There's lots more to do: enjoy the sand and surf at South Beach, wander the streets of Espanola Way, get to know the fascinating history of Art Deco Historic District, and get a taste of the local shopping with Ocean Drive.

For ratings, traveler tips, photos, and other tourist information, read our Miami trip itinerary builder .

Do a combination of flight and tram from Key West to Miami in 3 hours. Alternatively, you can drive; or take a bus. In May in Miami, expect temperatures between 87°F during the day and 74°F at night. Cap off your sightseeing on the 4th (Mon) early enough to go by car to Naples.

Things to do in Miami

#Shopping, #Parks, #Beaches

Side Trips

Miami Beach, Hollywood Beach, Sawgrass Mills, Aventura Mall, Haulover Beach Park
Highlights from your plan
Lincoln Road ©
Lincoln Road
Art Deco Historic District ©
Art Deco Historic District
South Beach ©
South Beach

5
nights
Naples

Naples ©
Naples is a city in Collier County, Florida, United States. For shopping fun, head to Miromar Outlets or Tin City. Satisfy your inner culture vulture at The Revs Institute and Edison & Ford Winter Estates. Explore the numerous day-trip ideas around Naples: Fort Myers Beach (in Fort Myers Beach), Barefoot Beach Preserve (in Bonita Springs) and Fort Myers (Sun Harvest Citrus & Norman Love Confections). There's lots more to do: enjoy the sand and surf at Tigertail Beach, make a trip to Waterside Shops, listen to music at Artis-Naples, and wander the streets of Fifth Avenue South.

For ratings, more things to do, and tourist information, go to the Naples trip maker tool .

You can drive from Miami to Naples in 2.5 hours. Alternatively, you can take a bus. In June in Naples, expect temperatures between 89°F during the day and 75°F at night. Cap off your sightseeing on the 9th (Sat) early enough to go by car to Sarasota.

Things to do in Naples

#Parks, #Shopping, #Outdoors

Side Trips

Fort Myers, Marco Island, Fort Myers Beach, Barefoot Beach Preserve, Miromar Outlets
Highlights from your plan
The Revs Institute ©
The Revs Institute
Barefoot Beach Preserve ©
Barefoot Beach Preserve
Fort Myers Beach ©
Fort Myers Beach

6
nights
Sarasota

Sarasota ©
Sarasota is a city in Sarasota County on the southwestern coast of the U.S. Sarasota National Cemetery and The Ringling are good opportunities to explore the local culture. Get some historical perspective at Marie Selby Botanical Gardens and Ca d'Zan Mansion. Venture out of the city with trips to Venice (Venice Beach & Caspersen Beach), LEGOLAND Florida Resort (in Winter Haven) and De Soto National Memorial (in Bradenton). There's lots more to do: kick back and relax at Siesta Beach, make a trip to St. Armands Circle, revel in the low prices at Ellenton Premium Outlets, and tour the pleasant surroundings at Turtle Beach.

Use Inspirock's suggestions to plan your Sarasota trip and find the best activities and attractions for your vacation.

Getting from Naples to Sarasota by car takes about 2 hours. Other options: take a bus. June in Sarasota sees daily highs of 89°F and lows of 74°F at night. Wrap up your sightseeing on the 15th (Fri) to allow time to drive to Clearwater.

Things to do in Sarasota

#Parks, #Outdoors, #Beaches

Side Trips

Siesta Key, Venice, De Soto National Memorial, Legoland Florida Resort, Ellenton Premium Outlets
Highlights from your plan
Sarasota National Cemetery ©
Sarasota National Cemetery
Siesta Beach ©
Siesta Beach
Crescent Beach ©
Crescent Beach

6
nights
Clearwater

Clearwater ©
Holding the record for most consecutive days of sunshine in a single year, Clearwater offers long sandy beaches and proximity to other major cities in the Tampa Bay area.
Satisfy your inner culture vulture at Philippe Park and The Dali Museum. You'll get in some beach time at Clearwater Beach and Honeymoon Island State Park. Explore Clearwater's surroundings by going to Treasure Island Beach (in Treasure Island), Tampa (Ybor City & Busch Gardens) and Madeira Beach (John's Pass Village and Boardwalk & Madeira Beach). Next up on the itinerary: kick back and relax at Saint Pete Beach, wander the streets of Pass-a-Grille, look for gifts at Michele Tuegel Contemporary, and don't miss a visit to Clay and Paper Gallery of Art.

To see other places to visit, maps, traveler tips, and other tourist information, go to the Clearwater trip planner .

Drive from Sarasota to Clearwater in 1.5 hours. Alternatively, you can take a bus. In June, plan for daily highs up to 89°F, and evening lows to 75°F. Cap off your sightseeing on the 21st (Thu) early enough to go by car back home.

Things to do in Clearwater

#Parks, #Outdoors, #Beaches

Side Trips

Madeira Beach, St. Petersburg, St. Pete Beach, Dunedin, Tampa
Highlights from your plan
Philippe Park ©
Philippe Park
Clearwater Beach ©
Clearwater Beach
Saint Pete Beach ©
Saint Pete Beach

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