50 days in Florida Itinerary

50 days in Florida Itinerary

Created using Inspirock Florida Trip Planner

This plan was created by another user.  Make it your plan

Route & dates

50 days in Florida Itinerary

Start: San Juan, Puerto Rico
Fly:  4​h
1
Orlando
— 2 nights
Drive:  2​h 15​min
2
Tarpon Springs
— 3 nights
Drive:  1​h
3
St. Pete Beach
— 5 nights
Drive:  2​h 45​min
4
Naples
— 6 nights
ferry:  3​h
5
Key West
— 4 nights
bus:  1​h 15​min
6
Marathon
— 3 nights
Drive:  2​h 45​min
7
Miami Beach
— 6 nights
Drive:  1​h 30​min
8
West Palm Beach
— 3 nights
Drive:  2​h 30​min
9
Cocoa Beach
— 3 nights
Drive:  2​h 30​min
10
St. Augustine
— 4 nights
bus:  1​h
11
Daytona Beach
— 3 nights
Fly:  5​h 30​min
12
Panama City Beach
— 3 nights
Drive:  2​h 15​min
13
Pensacola
— 3 nights
Drive + Fly:  12​h 45​min
End: San Juan, Puerto Rico

2
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 a sense of the local culture at Charles Hosmer Morse Museum of American Art and Basilica of the National Shrine of Mary, Queen of the Universe. Visiting Discovery Cove and Makaio WaterSports will get you outdoors. When in Orlando, make a side trip to see Tenoroc Fish Management Area in Lakeland, approximately 1h 10 min away. There's more to do: get in on the family fun at Universal Orlando Resort.

For traveler tips, photos, maps, and other tourist information, refer to the Orlando online tour planner .

San Juan, Puerto Rico to Orlando is an approximately 4-hour flight. You can also do a combination of car and flight. Due to the time zone difference, you'll gain 1 hour traveling from San Juan to Orlando. July in Orlando sees daily highs of 38°C and lows of 28°C at night. Cap off your sightseeing on the 27th (Mon) early enough to go by car to Tarpon Springs.

Things to do in Orlando

Theme Parks Outdoors Parks

Side Trips

Charles Hosmer Morse Museum of American Art, Tenoroc Fish Management Area
Highlights from your plan

3
nights
Tarpon Springs

Tarpon Springs ©
With the highest percentage of Greek-Americans of any U.S.
You'll get in some beach time at Caladesi Island State Park and Fred Howard Park. Take a break from the city and head to Sunset Beach and Whitcomb Bayou. And it doesn't end there: kick back and relax at Anclote River Park, take in the waterfront activity at Tarpon Springs Sponge Docks, admire the masterpieces at Leepa-Rattner Museum of Art, and see what you can catch with Miss Virginia Deep Sea Fishing.

To see ratings, other places to visit, maps, and other tourist information, use the Tarpon Springs day trip planner .

You can drive from Orlando to Tarpon Springs in 2.5 hours. Another option is to do a combination of train and taxi. In July, daily temperatures in Tarpon Springs can reach 38°C, while at night they dip to 28°C. Wrap up your sightseeing on the 30th (Thu) early enough to drive to St. Pete Beach.

Things to do in Tarpon Springs

Parks Outdoors Beaches

Side Trips

Anclote River Park, Miss Virginia Deep Sea Fishing, Caladesi Island State Park
Highlights from your plan
Caladesi Island State Park ©
Caladesi Island State Park
Leepa-Rattner Museum of Art ©
Leepa-Rattner Museum of Art
Miss Virginia Deep Sea Fishing ©
Miss Virginia Deep Sea Fishing

5
nights
St. Pete Beach

St. Pete Beach ©
St. Deepen your sense of the past at sights like De Soto National Memorial and Pinellas County Heritage Village. Get outdoors at Island Ferry St. Pete Beach and Saint Pete Beach. Explore St. Pete Beach's surroundings by going to Siesta Beach (in Siesta Key), Honeymoon Island State Park (in Dunedin) and The Ringling (in Sarasota). There's much more to do: explore the world behind art at The Dali Museum, wander the streets of Pass-a-Grille, relax and rejuvenate at Body Works Salon & Spa, and stop by Candy Kitchen.

For where to stay, reviews, ratings, and tourist information, read our St. Pete Beach travel route planner .

Getting from Tarpon Springs to St. Pete Beach by car takes about an hour. Other options: take a bus. In July, daily temperatures in St. Pete Beach can reach 38°C, while at night they dip to 30°C. Finish your sightseeing early on the 4th (Tue) so you can drive to Naples.

Things to do in St. Pete Beach

Outdoors Parks Beaches

Side Trips

Candy Kitchen, Siesta Beach, Pinellas County Heritage Village, De Soto National Memorial, Honeymoon Island State Park
Highlights from your plan
De Soto National Memorial ©
De Soto National Memorial
Siesta Beach ©
Siesta Beach
The Dali Museum ©
The Dali Museum

6
nights
Naples

Naples ©
Naples is a city in Collier County, Florida, United States. Appreciate the collections at The Bailey-Matthews National Shell Museum and Collier Museum at Government Center. Get in touch with nature at Fort Myers Beach and Vanderbilt Beach. Explore the numerous day-trip ideas around Naples: Fort Myers Beach Public Library (in Fort Myers Beach), Port Sanibel Marina (in Fort Myers) and Little Hickory Beach Park (in Bonita Springs). There's still lots to do: look for all kinds of wild species at J.N. "Ding" Darling National Wildlife Refuge, stop by Toucan's World, stroll through Lowdermilk Beach, and enjoy the sand and surf at Tigertail Beach.

To see photos, ratings, and more tourist information, read Naples itinerary planner.

You can drive from St. Pete Beach to Naples in 3 hours. Another option is to take a bus. In August in Naples, expect temperatures between 38°C during the day and 28°C at night. Finish your sightseeing early on the 10th (Mon) to allow enough time to travel to Key West.

Things to do in Naples

Parks Outdoors Beaches

Side Trips

Fort Myers Beach, Marco Island, Sanibel Island, Port Sanibel Marina, Vanderbilt Beach
Highlights from your plan
Fort Myers Beach ©
Fort Myers Beach
Lowdermilk Beach ©
Lowdermilk Beach

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.
Escape the urban bustle at Fort Zachary Taylor and Sebago Key West. Let the collections at The Ernest Hemingway Home and Museum and Oldest House & Garden Museum capture your imagination. The adventure continues: explore the galleries of Truman Little White House, tour the pleasant surroundings at South Beach, admire the masterpieces at Fort East Martello Museum, and take in the waterfront at Mallory Square.

To find ratings, reviews, where to stay, and tourist information, refer to the Key West road trip planning website .

Ride a ferry from Naples to Key West in 3 hours. Alternatively, you can drive; or take a bus. In August in Key West, expect temperatures between 38°C during the day and 32°C at night. Finish your sightseeing early on the 14th (Fri) to allow enough time to take a bus to Marathon.

Things to do in Key West

Outdoors Parks Beaches
Highlights from your plan
The Ernest Hemingway Home and Museum ©
Truman Little White House ©
Truman Little White House
Fury Water Adventures Key West ©
Fury Water Adventures Key West

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.
Get outdoors at Bahia Honda State Park and Sunset Park Beach. You'll get in some beach time at Sombrero Beach and Anne's Beach. Explore Marathon's surroundings by going to Islamorada (History of Diving Museum & Lobster Trap Art Gift Shop and Gallery). Next up on the itinerary: take in the architecture and atmosphere at San Pablo Catholic Church, look for all kinds of wild species at Dolphin Research Center, and stroll through Coco Plum Beach.

To see where to stay, photos, ratings, and more tourist information, refer to the Marathon attractions planner .

You can take a bus from Key West to Marathon in 1.5 hours. Alternatively, you can drive. In August in Marathon, expect temperatures between 39°C during the day and 31°C at night. Finish up your sightseeing early on the 17th (Mon) so you can go by car to Miami Beach.

Things to do in Marathon

Parks Outdoors Beaches

Side Trips

Islamorada, Sunset Park Beach, Bahia Honda State Park
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
Sombrero Beach ©
Sombrero Beach
Sunset Park Beach ©
Sunset Park Beach

6
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.
Get a sense of the local culture at Art Deco Historic District and Bonnet House Museum and Gardens. Step out of the city life by going to South Beach and Hollywood Beach. Change things up with these side-trips from Miami Beach: Fort Lauderdale (Fort Lauderdale Beach Park, Stranahan House, & more), Fern Forest Nature Center (in Coconut Creek) and Divers Direct Fort Lauderdale (in Dania Beach). There's still lots to do: examine the collection at Vizcaya Museum and Gardens, walk around Lummus Park Beach, kick back and relax at Haulover Beach Park, and immerse yourself in nature at Bill Baggs Cape Florida State Park.

For where to stay, other places to visit, reviews, and other tourist information, go to the Miami Beach online journey planner .

Traveling by car from Marathon to Miami Beach takes 3 hours. Alternatively, you can take a bus; or do a combination of bus and flight. August in Miami Beach sees daily highs of 38°C and lows of 30°C at night. Cap off your sightseeing on the 23rd (Sun) early enough to go by car to West Palm Beach.

Things to do in Miami Beach

Parks Outdoors Beaches

Side Trips

Fort Lauderdale, Miami, Fern Forest Nature Center, Hollywood Beach, Divers Direct Fort Lauderdale
Highlights from your plan
Bill Baggs Cape Florida State Park ©
Bill Baggs Cape Florida State Park
South Beach ©
South Beach
Art Deco Historic District ©
Art Deco Historic District

3
nights
West Palm Beach

West Palm Beach ©
With a warm climate and sandy stretches, it's no surprise that West Palm Beach is a popular vacation spot.
Appreciate the collections at Henry Morrison Flagler Museum and Ann Norton Sculpture Gardens. Get in touch with nature at John D. MacArthur Beach State Park and Visit Palm Beach. Take a break from West Palm Beach with a short trip to Morikami Museum & Japanese Gardens in Delray Beach, about 36 minutes away. The adventure continues: admire the masterpieces at Norton Museum of Art, pause for some serene contemplation at Bethesda by the Sea, get interesting insight from Palm Beach Fishing Co., and get some fabulous bargains at Palm Beach Outlets.

To find where to stay, reviews, and other tourist information, go to the West Palm Beach day trip website .

Getting from Miami Beach to West Palm Beach by car takes about 1.5 hours. Other options: take a train; or take a bus. In August, plan for daily highs up to 38°C, and evening lows to 30°C. Finish your sightseeing early on the 26th (Wed) so you can drive to Cocoa Beach.

Things to do in West Palm Beach

Outdoors Museums Tours

Side Trips

Palm Beach, Morikami Museum & Japanese Gardens, John D. MacArthur Beach State Park
Highlights from your plan
John D. MacArthur Beach State Park ©
Henry Morrison Flagler Museum ©
Henry Morrison Flagler Museum
Norton Museum of Art ©
Norton Museum of Art

3
nights
Cocoa Beach

Cocoa Beach ©
Situated in one of Florida's busiest vacation areas, Cocoa Beach burst onto the world scene in the 1960s, when it became a popular setting for parades honoring the nation's "Apollo" astronauts.
Your itinerary includes some good beach time at Cocoa Beach and Paradise Beach & Park. Get outdoors at All Water Adventures and A1A Beach Rentals. Explore the numerous day-trip ideas around Cocoa Beach: NASA Kennedy Space Center Visitor Complex (in Merritt Island) and Sebastian Inlet State Park (in Melbourne). It doesn't end there: take a memorable tour with Nex Generation Surfing School and look for gifts at Secrets of Cocoa Beach.

To see ratings and more tourist information, read Cocoa Beach online itinerary planner .

Traveling by car from West Palm Beach to Cocoa Beach takes 2.5 hours. Alternatively, you can take a bus. In August, daily temperatures in Cocoa Beach can reach 36°C, while at night they dip to 30°C. Finish your sightseeing early on the 29th (Sat) to allow enough time to drive to St. Augustine.

Things to do in Cocoa Beach

Outdoors Parks Beaches

Side Trips

Melbourne, NASA Kennedy Space Center Visitor Complex, A1A Beach Rentals
Highlights from your plan
Sebastian Inlet State Park ©
Sebastian Inlet State Park
All Water Adventures ©
All Water Adventures

4
nights
St. Augustine

St. Augustine ©
SAINT AUGUSTINE | PONTE VEDRA on Florida's Historic Coast The Nation's oldest city (est. Visit St. Augustine Lighthouse & Maritime Museum, Inc. and The Oldest House Museum Complex for their historical value. Fort Matanzas National Monument and Spanish Military Hospital Museum are good opportunities to explore the local culture. Explore St. Augustine's surroundings by going to Jacksonville (Atlantic Beach & Kathryn Abbey Hanna Park). The adventure continues: enjoy the sand and surf at St. Augustine Beach, look for gifts at Old City Remedies, stroll through Vilano Beach, and examine the collection at Lightner Museum.

To find where to stay, ratings, traveler tips, and tourist information, read St. Augustine day trip planning tool .

Traveling by car from Cocoa Beach to St. Augustine takes 2.5 hours. Alternatively, you can do a combination of bus and car. Expect a daytime high around 37°C in August, and nighttime lows around 28°C. Wrap up your sightseeing on the 2nd (Wed) to allow time to take a bus to Daytona Beach.

Things to do in St. Augustine

Parks Outdoors Beaches

Side Trip

Jacksonville
Highlights from your plan
Kathryn Abbey Hanna Park ©
Kathryn Abbey Hanna Park
St. Augustine Beach ©
St. Augustine Beach

3
nights
Daytona Beach

Daytona Beach ©
The iconic seaside destination of Daytona Beach once supported sugar mill plantations, but now entertains up to 8 million visitors a year.
Ponce de Leon Inlet Lighthouse & Museum and St. Brendan Catholic Church are good opportunities to explore the local culture. Your itinerary includes some good beach time at Beach at Daytona Beach and Ormond Beach. There's still lots to do: browse the exhibits of The Casements, get engrossed in the history at Halifax Historical Museum, examine the collection at MOAS - Museum of Arts and Sciences, and kick back and relax at Lighthouse Point Park.

To find reviews, ratings, and other tourist information, you can read our Daytona Beach driving holiday app .

Getting from St. Augustine to Daytona Beach by bus takes about an hour. Other options: drive. In September, daytime highs in Daytona Beach are 36°C, while nighttime lows are 26°C. Finish your sightseeing early on the 5th (Sat) to allow enough time to travel to Panama City Beach.

Things to do in Daytona Beach

Parks Outdoors Beaches

Side Trips

Ormond Beach, Ponce Inlet
Highlights from your plan
Beach at Daytona Beach ©
Beach at Daytona Beach
Ormond Beach ©
Ormond Beach

3
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.
Get outdoors at Panama City Beach and Topsail Beach State Preserve. Visit St. Andrews State Park and Carillon Beach for some beach relaxation. There's much more to do: step off the mainland to explore Shell Island, get outside with Classic Rentals Inc., and look for gifts at Kilwin's Chocolate and Ice Cream.

For more things to do, where to stay, ratings, and other tourist information, go to the Panama City Beach online sightseeing planner .

You can fly from Daytona Beach to Panama City Beach in 5.5 hours. Alternatively, you can do a combination of shuttle and flight; or drive. Expect a daytime high around 37°C in September, and nighttime lows around 24°C. Finish your sightseeing early on the 8th (Tue) to allow enough time to drive to Pensacola.

Things to do in Panama City Beach

Parks Outdoors Beaches

Side Trips

Carillon Beach, Topsail Beach State Preserve
Highlights from your plan
St. Andrews State Park ©
St. Andrews State Park
Panama City Beach ©
Panama City Beach
Topsail Beach State Preserve ©
Topsail Beach State Preserve

3
nights
Pensacola

Pensacola ©
Surrounded on three sides by water, Pensacola offers access to white-sand beaches and emerald-green ocean unspoiled by large resorts.
Museum-lovers will get to explore National Naval Aviation Museum and Indian Temple Mound and Museum. Get in touch with nature at Navarre Beach and Pensacola Beach. When in Pensacola, make a side trip to see Camp Walton Schoolhouse in Fort Walton Beach, approximately 1h 05 min away. There's much more to do: kick back and relax at Johnson Beach, stop by Crabs, take in the waterfront at Pensacola Beach Gulf Pier, and shop like a local with Blue Morning Gallery.

Plan my trip to Pensacola with suggested itineraries provided by Inspirock.

You can drive from Panama City Beach to Pensacola in 2.5 hours. Due to the time zone difference, you'll gain 1 hour traveling from Panama City Beach to Pensacola. In September, plan for daily highs up to 36°C, and evening lows to 26°C. Wrap up your sightseeing on the 11th (Fri) to allow time to travel back home.

Things to do in Pensacola

Parks Outdoors Beaches

Side Trips

Fort Walton Beach, Pensacola Beach, Navarre Beach
Highlights from your plan
National Naval Aviation Museum ©
National Naval Aviation Museum
Navarre Beach ©
Navarre Beach
Pensacola Beach ©
Pensacola Beach

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