50 days in Florida Itinerary

50 days in Florida Itinerary

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Route & dates

50 days in Florida Itinerary

Start: Fort Myers
Drive:  2​h 45​min
1
Miami Beach
— 4 nights
Drive:  2​h 45​min
2
Marathon
— 4 nights
bus:  1​h 15​min
3
Key West
— 6 nights
Fly:  4​h 30​min
4
West Palm Beach
— 4 nights
Drive:  3​h
5
Orlando
— 6 nights
Drive:  2​h
6
St. Augustine
— 5 nights
Drive:  2​h
7
Ocala
— 3 nights
Drive:  2​h 30​min
8
Sarasota
— 4 nights
Drive:  1​h 30​min
9
Clearwater
— 4 nights
Drive:  7​h
10
Panama City Beach
— 3 nights
Drive:  2​h 15​min
11
Pensacola
— 4 nights
Fly + bus:  8​h 15​min
End: Fort Myers

4
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.
Venture out of the city with trips to Aventura Mall (in Aventura), Dolphin Mall (in Miami) and Fairchild Tropical Botanic Garden (in Coral Gables). And it doesn't end there: kick back and relax at South Beach, take a stroll through Lincoln Road, take a tour by water with Boat Tours & Water Sports, and tour the water at your own pace with Miami Party Boat Rentals.

To see ratings, photos, where to stay, and other tourist information, read our Miami Beach online trip planner .

Fort Myers to Miami Beach is an approximately 3-hour car ride. You can also take a bus. In August, plan for daily highs up to 91°F, and evening lows to 78°F. Wrap up your sightseeing on the 4th (Sun) early enough to drive to Marathon.

Things to do in Miami Beach

Shopping Tours Outdoors

Side Trips

Miami, Coral Gables, Aventura Mall, Miami Party Boat Rentals
Highlights from your plan
Lincoln Road ©
Lincoln Road
South Beach ©
South Beach
Vizcaya Museum and Gardens ©
Vizcaya Museum and Gardens

4
nights
Marathon

A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
Explore Marathon's surroundings by going to Florida Keys Jet Ski Rentals (in Summerland Key) and Islamorada (Fishing Charters & Tours & Florida Keys Brewing Company). There's much more to do: kick back and relax at Bahia Honda State Park, identify plant and animal life at The Turtle Hospital, tour the pleasant surroundings at Sombrero Beach, and snap pictures at Seven Mile Bridge.

For reviews, traveler tips, where to stay, and tourist information, go to the Marathon trip itinerary planner .

Traveling by car from Miami Beach to Marathon takes 3 hours. Alternatively, you can take a bus; or do a combination of flight and bus. In September, plan for daily highs up to 90°F, and evening lows to 79°F. Finish your sightseeing early on the 8th (Thu) to allow enough time to take a bus to Key West.

Things to do in Marathon

Outdoors Parks Tours

Side Trips

Islamorada, Bahia Honda State Park, Florida Keys Jet Ski Rentals
Highlights from your plan
Fishing Charters & Tours
Bahia Honda State Park ©
Bahia Honda State Park
Florida Keys Jet Ski Rentals ©
Florida Keys Jet Ski Rentals

6
nights
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.
Spend the 10th (Sat) exploring nature at Dry Tortugas National Park. Next up on the itinerary: see the interesting displays at The Ernest Hemingway Home and Museum, discover the deep blue sea with Fun In The Sun Key West, look for all kinds of wild species at Key West Butterfly & Nature Conservatory, and find your balance on the water with some of the best stand-up paddleboarding in the area.

To see more things to do, ratings, maps, and other tourist information, refer to the Key West itinerary planning app .

Traveling by bus from Marathon to Key West takes 1.5 hours. Alternatively, you can drive. September in Key West sees daily highs of 88°F and lows of 80°F at night. Wrap up your sightseeing on the 14th (Wed) early enough to travel to West Palm Beach.

Things to do in Key West

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

4
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.
You'll find plenty of places to visit near West Palm Beach: Coral Cove Park (in Tequesta) and Panther Ridge Conservation Center (in Wellington). The adventure continues: get to know the resident critters at McCarthy's Wildlife Sanctuary, look for all kinds of wild species at Loggerhead Marinelife Center, indulge in some personalized pampering at The Spa at the Breakers Palm Beach, and see the interesting displays at Richard and Pat Johnson Palm Beach County Museum.

To find ratings, maps, traveler tips, and other tourist information, you can read our West Palm Beach trip itinerary builder tool .

Fly from Key West to West Palm Beach in 4.5 hours. Alternatively, you can do a combination of flight and train; or drive. September in West Palm Beach sees daily highs of 89°F and lows of 76°F at night. On the 18th (Sun), wrap the sightseeing up by early afternoon so you can drive to Orlando.

Things to do in West Palm Beach

Parks Beaches Outdoors

Side Trips

Loggerhead Marinelife Center, Coral Cove Park, Panther Ridge Conservation Center, The Spa at the Breakers Palm Beach, Jupiter Dog Beach
Highlights from your plan
McCarthy's Wildlife Sanctuary ©
McCarthy's Wildlife Sanctuary
Panther Ridge Conservation Center ©
Panther Ridge Conservation Center
Loggerhead Marinelife Center ©
Loggerhead Marinelife Center

6
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.
Pack the 19th (Mon) with family-friendly diversions at Discovery Cove. Pack the 20th (Tue) with family-friendly diversions at Universal's Islands of Adventure. Next up on the itinerary: find something for the whole family at Walt Disney World Resort, browse the different shops at Disney Springs, find your balance on the water with Paddleboard Orlando, and stop by The Mall at Millenia.

For maps, where to stay, ratings, and tourist information, you can read our Orlando trip planner .

Getting from West Palm Beach to Orlando by car takes about 3 hours. Other options: take a train; or take a bus. September in Orlando sees daily highs of 89°F and lows of 74°F at night. Wrap up your sightseeing on the 24th (Sat) to allow time to drive to St. Augustine.

Things to do in Orlando

Theme Parks Outdoors Parks

Side Trip

Charles Hosmer Morse Museum of American Art
Highlights from your plan
Walt Disney World Resort ©
Walt Disney World Resort
Universal Orlando Resort ©
Universal Orlando Resort
Universal's Islands of Adventure ©
Universal's Islands of Adventure

5
nights
St. Augustine

St. Augustine ©
SAINT AUGUSTINE | PONTE VEDRA on Florida's Historic Coast The Nation's oldest city (est. Venture out of the city with trips to Ormond Beach (St. Brendan Catholic Church & Andy Romano Beachfront Park). Spend the 27th (Tue) on the water with a fishing tour. There's still lots to do: brush up on your knowledge of spirits at St. Augustine Distillery, examine the collection at The Ximenez-Fatio House, gain insight at Flagler College, and look for all kinds of wild species at St. Augustine Wild Reserve.

To find reviews, more things to do, other places to visit, and 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. Expect a daytime high around 85°F in September, and nighttime lows around 73°F. Cap off your sightseeing on the 29th (Thu) early enough to go by car to Ocala.

Things to do in St. Augustine

Parks Outdoors Wildlife

Side Trip

Ormond Beach
Highlights from your plan
St. Augustine Wild Reserve ©
St. Augustine Wild Reserve
St. Augustine Distillery ©
St. Augustine Distillery

3
nights
Ocala

Ocala ©
Ocala is a city located in Northern Florida. You'll find plenty of places to visit near Ocala: Island Grove Winery (in Hawthorne), Butterfly Rainforest (in Gainesville) and Ichetucknee Springs State Park (in Fort White). The adventure continues: wander the wide-open spaces of Gypsy Gold Horse Farm, relax in the rural setting at Farm Tours of Ocala, play a few rounds at Candler Hills Golf Club, and take in nature's colorful creations at Sholom Park.

For ratings, where to stay, traveler tips, and more tourist information, refer to the Ocala tour itinerary planning tool .

You can drive from St. Augustine to Ocala in 2 hours. Alternatively, you can do a combination of bus and car; or take a bus. Expect a daytime high around 87°F in September, and nighttime lows around 70°F. Wrap up your sightseeing on the 2nd (Sun) to allow time to drive to Sarasota.

Things to do in Ocala

Parks Outdoors Wildlife

Side Trips

Island Grove Winery, Butterfly Rainforest, Ichetucknee Springs State Park
Highlights from your plan
Gypsy Gold Horse Farm ©
Gypsy Gold Horse Farm
Butterfly Rainforest ©
Butterfly Rainforest
Sholom Park ©
Sholom Park

4
nights
Sarasota

Sarasota ©
Sarasota is a city in Sarasota County on the southwestern coast of the U.S. You'll find plenty of places to visit near Sarasota: Nokomis Beach (in Nokomis) and Thrive Yoga and Fitness (in Bradenton). There's much more to do: glide peacefully along the water with Paradise Adventures Sarasota, join in the after-dark buzz at Siesta Key Wine Bar, kick back and relax at Siesta Beach, and do sightseeing at your own pace with Sarasota Paddleboard Company.

To find photos, ratings, where to stay, and other tourist information, go to the Sarasota online tour itinerary planner .

Traveling by car from Ocala to Sarasota takes 2.5 hours. Alternatively, you can take a bus. Traveling from Ocala in October, you can expect nighttime temperatures to be a bit warmer in Sarasota, with lows of 68°F. Wrap up your sightseeing on the 6th (Thu) early enough to drive to Clearwater.

Things to do in Sarasota

Outdoors Adventure Tours

Side Trips

Siesta Key, Nokomis Beach, Thrive Yoga and Fitness
Highlights from your plan
Sarasota National Cemetery ©
Sarasota National Cemetery
Siesta Beach ©
Siesta Beach
The Ringling ©
The Ringling

4
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.
Change things up with these side-trips from Clearwater: St. Pete Beach (Saint Pete Beach & JetLev at TradeWinds Island Resorts), Busch Gardens Tampa Bay (in Tampa) and St. Petersburg (Duncan McClellan Gallery & Speed Boat Adventures). The adventure continues: enjoy the sand and surf at Clearwater Beach, stop by Candy Kitchen, learn about winemaking at Murielle Winery, and take a leisurely stroll along John's Pass Village & Boardwalk.

To find photos, maps, ratings, and more tourist information, you can read our Clearwater travel route planning app .

Traveling by car from Sarasota to Clearwater takes 1.5 hours. Alternatively, you can take a bus. In October in Clearwater, expect temperatures between 85°F during the day and 71°F at night. Wrap up your sightseeing on the 10th (Mon) to allow time to drive to Panama City Beach.

Things to do in Clearwater

Outdoors Theme Parks Parks

Side Trips

Madeira Beach, St. Pete Beach, St. Petersburg, Busch Gardens Tampa Bay
Highlights from your plan
Duncan McClellan Gallery ©
Duncan McClellan Gallery
Busch Gardens Tampa Bay ©
Busch Gardens Tampa Bay
Clearwater Beach ©
Clearwater 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.
Change things up with a short trip to Beach Sand Sculptures in Seaside (about 48 minutes away). The adventure continues: get close to the beloved marine mammals with Water Planet, stop by Kilwin's Chocolate and Ice Cream, enjoy the sand and surf at Henderson Beach State Park, and discover the deep blue sea with a scuba or snorkeling tour.

To find photos, ratings, more things to do, and more tourist information, use the Panama City Beach trip planner.

Drive from Clearwater to Panama City Beach in 7 hours. Alternatively, you can do a combination of bus, flight, and car; or do a combination of bus and flight. Traveling from Clearwater in October, plan for slightly colder nights in Panama City Beach, with lows around 59°F. Finish up your sightseeing early on the 14th (Fri) so you can go by car to Pensacola.

Things to do in Panama City Beach

Outdoors Parks Beaches

Side Trips

Destin, LH Bead Gallery, Santa Rosa Beach, Beach Sand Sculptures
Highlights from your plan
Panama City Beach Winery ©
Panama City Beach Winery
Water Planet ©
Water Planet
Scuba & Snorkeling

4
nights
Pensacola

Pensacola ©
Surrounded on three sides by water, Pensacola offers access to white-sand beaches and emerald-green ocean unspoiled by large resorts.
Explore Pensacola's surroundings by going to Navarre (Navarre Beach & Island Style). There's lots more to do: learn about all things military at National Naval Aviation Museum, pause for some photo ops at Wall South, deepen your knowledge of military history at Pensacola Naval Air Station, and kick back and relax at Pensacola Beach.

To see photos, ratings, maps, and more tourist information, refer to the Pensacola trip maker site .

Drive from Panama City Beach to Pensacola in 2.5 hours. The time zone changes from Eastern Standard Time (EST) to Central Standard Time (CST), which is usually a -1 hour difference. Expect a daytime high around 82°F in October, and nighttime lows around 63°F. Wrap up your sightseeing on the 18th (Tue) early enough to travel back home.

Things to do in Pensacola

Parks Outdoors Beaches

Side Trips

Pensacola Beach, Navarre
Highlights from your plan
National Naval Aviation Museum ©
National Naval Aviation Museum
Navarre Beach ©
Navarre Beach
Gulf Islands National Seashore ©
Gulf Islands National Seashore

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