59 days in Florida Itinerary

59 days in Florida Itinerary

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Route & dates

59 days in Florida Itinerary

Orlando
Drive:  2​h
St. Augustine
— 5 nights
Drive:  5​h 30​min
Panama City Beach
— 5 nights
+2
taxi + Fly + taxi:  5​h 30​min
Sanibel Island
— 7 nights
Drive:  1​h 15​min
Naples
— 5 nights
Drive:  30​min
Marco Island
— 4 nights
Drive:  3​h 30​min
Islamorada
— 6 nights
Drive:  45​min
Marathon
— 6 nights
Drive:  1​h 15​min
Key West
— 7 nights
Fly + taxi:  3​h
St. Pete Beach
— 3 nights
Drive:  2​h
Crystal River
— 5 nights
Drive:  1​h 45​min
Orlando
— 5 nights
Orlando

5
days
St. Augustine

St. Augustine ©
SAINT AUGUSTINE | PONTE VEDRA on Florida's Historic Coast The Nation's oldest city (est. Your cultural itinerary includes sights like Fort Matanzas National Monument and The Lightner Museum. You'll discover tucked-away gems like St. Augustine Beach and St. Augustine Distillery. Change things up with a short trip to Ormond Beach in Ormond Beach (about 1h 15 min away). There's much more to do: look for all kinds of wild species at St. Augustine Alligator Farm Zoological Park, wander the streets of Old City, examine the collection at St. Augustine Pirate & Treasure Museum, and learn about winemaking at San Sebastian Winery.

To find photos, where to stay, reviews, and tourist information, read our St. Augustine route site .

Orlando to St. Augustine is an approximately 2-hour car ride. You can also take a bus. Traveling from Orlando in March, expect St. Augustine to be a bit cooler, temps between 72°F and 54°F. On the 14th (Wed), wrap the sightseeing up by early afternoon so you can drive to Panama City Beach.

Things to do in St. Augustine

#Parks, #Historic Sites, #Outdoors

Side Trip

Ormond Beach
Highlights from your plan
St. Augustine Beach ©
St. Augustine Beach
Ormond Beach ©
Ormond Beach

4
days
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.
Escape the urban bustle at Henderson Beach State Park and Camp Helen State Park. You'll explore the less-touristy side of things at Navarre Beach and St. Andrews State Park. Change things up with these side-trips from Panama City Beach: Grayton Beach State Park (in Grayton Beach), Santa Rosa Beach (in Santa Rosa Beach) and Dolphin & Whale Watching (in Destin). There's still lots to do: browse the different shops at Pier Park, learn about winemaking at Panama City Beach Winery, and admire nature's wide array of creatures at Gulf World Marine Park.

To find where to stay, reviews, and other tourist information, read Panama City Beach day trip planning site .

You can drive from St. Augustine to Panama City Beach in 5.5 hours. Other options are to do a combination of bus and taxi; or do a combination of bus, flight, and taxi. In March in Panama City Beach, expect temperatures between 73°F during the day and 50°F at night. Wrap up your sightseeing by early afternoon on the 19th (Mon) to allow enough time to travel to Sanibel Island.

Things to do in Panama City Beach

#Parks, #Outdoors, #Beaches

Side Trips

Destin, Grayton Beach State Park, Santa Rosa Beach, Navarre Beach, Camp Helen State Park
Highlights from your plan
Panama City Beach Winery ©
Panama City Beach Winery
Henderson Beach State Park ©
Henderson Beach State Park
Dolphin & Whale Watching

6
days
Sanibel Island

Sanibel Island ©
Take a trip to Sanibel Island if you like pretty sunsets and luxurious resorts.
Step off the beaten path and head to Bowman's Beach and Dolphin & Whale Watching. Get some cultural insight at Edison & Ford Winter Estates and The Bailey-Matthews National Shell Museum. Venture out of the city with trips to Six Mile Cypress Slough Preserve (in Fort Myers) and Fort Myers Beach (Parasailing & Paragliding, Fort Myers Beach, & more).

To plan Sanibel Island vacation without wasting time, ask Inspirock to design an itinerary.

Traveling by combination of taxi and flight from Panama City Beach to Sanibel Island takes 5.5 hours. Alternatively, you can drive; or do a combination of taxi and bus. Plan for somewhat warmer temperatures traveling from Panama City Beach in March, with highs in Sanibel Island at 82°F and lows at 60°F. Wrap up your sightseeing on the 26th (Mon) to allow time to drive to Naples.

Things to do in Sanibel Island

#Parks, #Outdoors, #Beaches

Side Trips

Fort Myers Beach, Fort Myers, Captiva Beach
Highlights from your plan
Fort Myers Beach ©
Fort Myers Beach
Bowman's Beach ©
Bowman's Beach
Captiva Beach ©
Captiva Beach

5
days
Naples

Naples ©
Naples is a city in Collier County, Florida, United States. Visit Barefoot Beach Preserve and Clam Pass Park for some beach relaxation. Shop till you drop at Fifth Avenue South and Toucan's World. Explore the numerous day-trip ideas around Naples: Bonita Springs Public Beach (in Bonita Springs) and Miromar Outlets (in Estero). There's much more to do: look for all kinds of wild species at Audubon Corkscrew Swamp Sanctuary, kick back and relax at Vanderbilt Beach, stroll through Lowdermilk Beach, and take in nature's colorful creations at Naples Botanical Garden.

To see reviews, maps, ratings, and tourist information, go to the Naples road trip planning tool .

You can drive from Sanibel Island to Naples in 1.5 hours. Alternatively, you can do a combination of taxi and bus. In March in Naples, expect temperatures between 80°F during the day and 61°F at night. Finish up your sightseeing early on the 31st (Sat) so you can go by car to Marco Island.

Things to do in Naples

#Parks, #Outdoors, #Beaches

Side Trips

Bonita Springs, Miromar Outlets, Vanderbilt Beach
Highlights from your plan
Audubon Corkscrew Swamp Sanctuary ©
Audubon Corkscrew Swamp Sanctuary
Barefoot Beach Preserve ©
Barefoot Beach Preserve
Bonita Springs Public Beach ©
Bonita Springs Public Beach

5
days
Marco Island

Marco Island is a city in Collier County, Florida, United States, located on an island by the same name in the Gulf of Mexico off the coast of Southwest Florida. Step out of the city life by going to Nature & Wildlife Tours and South Marco Beach. You'll visit kid-friendly attractions like Tigertail Beach and Cape Romano. Step out of Marco Island with an excursion to Speed Boats Tours in Everglades City--about 36 minutes away. There's still lots to do: get some thrills out on the water with a waterskiing or jet-skiing adventure, look for gifts at Island Trends, enjoy the sand and surf at Keewaydin Island, and see what you can catch with a fishing tour.

To find traveler tips, more things to do, reviews, and tourist information, read our Marco Island trip itinerary builder site .

Marco Island is just a stone's throw from Naples. March in Marco Island sees daily highs of 81°F and lows of 62°F at night. Wrap up your sightseeing on the 4th (Wed) early enough to drive to Islamorada.

Things to do in Marco Island

#Outdoors, #Tours, #Parks

Side Trip

Everglades City
Highlights from your plan
Waterskiing & Jetskiing
Nature & Wildlife Tours
Tigertail Beach ©
Tigertail Beach

6
days
Islamorada

Islamorada ©
Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
Get in touch with nature at Florida Keys Wild Bird Rehabilitation Center and Anne's Beach. Eschew the tourist crowds and head to Robbie's of Islamorada and A Lil' Tail Charters. There's still lots to do: glide through the air with a parasailing or paragliding tour, look for gifts at Ocean Gardens, get interesting insight from Spray Watersports, and take in the exciting artwork at Old Road Gallery.

To see reviews, more things to do, ratings, and more tourist information, read our Islamorada trip itinerary builder .

Traveling by car from Marco Island to Islamorada takes 3.5 hours. Alternatively, you can do a combination of taxi and bus; or do a combination of taxi, bus, and flight. Plan for somewhat warmer nights when traveling from Marco Island in April since evenings lows in Islamorada dip to 73°F. Wrap up your sightseeing on the 10th (Tue) to allow time to drive to Marathon.

Things to do in Islamorada

#Outdoors, #Tours, #Adventure

Side Trips

Key Largo, Florida Keys Wild Bird Rehabilitation Center
Highlights from your plan
Anne's Beach ©
Anne's Beach

6
days
Marathon

Marathon ©
A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
Your itinerary includes some good beach time at Sombrero Beach and Bahia Honda State Park. Get outdoors at Dolphin Research Center and Scuba & Snorkeling. Change things up with a short trip to National Key Deer Refuge in Big Pine Key (about 36 minutes away). And it doesn't end there: identify plant and animal life at The Turtle Hospital, tour the water at your own pace with All Aboard Boat Rentals, get a new perspective on things with Boat Tours & Water Sports, and paddle through the water with a kayaking and canoeing tour.

To see ratings, traveler tips, reviews, and tourist information, use the Marathon trip site .

Drive from Islamorada to Marathon in an hour. Alternatively, you can take a bus. In April, plan for daily highs up to 86°F, and evening lows to 75°F. Finish your sightseeing early on the 16th (Mon) to allow enough time to drive to Key West.

Things to do in Marathon

#Outdoors, #Parks, #Tours

Side Trips

Big Pine Key, Sunset Park Beach
Highlights from your plan
The Turtle Hospital ©
The Turtle Hospital
Bahia Honda State Park ©
Bahia Honda State Park
Dolphin Research Center ©
Dolphin Research Center

7
days
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.
You'll visit kid-friendly attractions like Dolphin & Whale Watching and Scuba & Snorkeling. Step off the beaten path and head to Dry Tortugas National Park and Florida Keys Eco-Discovery Center. And it doesn't end there: glide peacefully along the water with some of the best stand-up paddleboarding in the area, visit a coastal fixture at Key West Lighthouse and Keeper's Quarters Museum, admire the majestic nature at Fort Zachary Taylor, and steep yourself in history at Key West Garden Club.

For photos, traveler tips, other places to visit, and more tourist information, you can read our Key West itinerary builder app .

You can drive from Marathon to Key West in 1.5 hours. Alternatively, you can take a bus. In April, plan for daily highs up to 82°F, and evening lows to 74°F. Wrap up your sightseeing on the 23rd (Mon) to allow time to travel to St. Pete Beach.

Things to do in Key West

#Outdoors, #Tours, #Parks
Highlights from your plan
Dry Tortugas National Park ©
Dry Tortugas National Park
Scuba & Snorkeling
Dolphin & Whale Watching

3
days
St. Pete Beach

St. Pete Beach ©
St. Relax by the water at Treasure Island Beach and Saint Pete Beach. You'll explore the less-touristy side of things at Caspersen Beach and Myakka River State Park. You'll find plenty of places to visit near St. Pete Beach: Venice Beach (in Venice) and Crescent Beach (in Siesta Key). The adventure continues: look for gifts at John's Pass Village and Boardwalk.

For where to stay, other places to visit, and other tourist information, refer to the St. Pete Beach trip itinerary maker app .

Do a combination of flight and taxi from Key West to St. Pete Beach in 3 hours. Alternatively, you can do a combination of ferry, taxi, and bus; or drive. Traveling from Key West in April, St. Pete Beach is a bit cooler at night with lows of 67°F. Finish up your sightseeing early on the 26th (Thu) so you can go by car to Crystal River.

Things to do in St. Pete Beach

#Parks, #Outdoors, #Beaches

Side Trips

Venice, Crescent Beach, Treasure Island Beach, Myakka River State Park, John's Pass Village and Boardwalk
Highlights from your plan
Saint Pete Beach ©
Saint Pete Beach
Caspersen Beach ©
Caspersen Beach
Crescent Beach ©
Crescent Beach

4
days
Crystal River

The jewel of Florida's Nature Coast, Crystal River spreads around spring-fed Kings Bay, known for maintaining a constant 22 C (72 F) temperature all year long.
Step off the beaten path and head to Ellie Schiller Homosassa Springs Wildlife State Park and Lower Suwannee National Wildlife Refuge. Take a break from the city and head to Stand-Up Paddleboarding and Scuba & Snorkeling. Get out of town with these interesting Crystal River side-trips: Cedar Key (Cedar Key Railroad Trestle Nature Trail & Cedar Keys National Wildlife Refuge). There's still lots to do: explore the activities along Three Sisters Springs, identify plant and animal life at Alpaca Magic USA, look for gifts at The Glass Garage, and take a memorable tour with Tours.

To find photos, ratings, and more tourist information, go to the Crystal River tour itinerary planner.

Drive from St. Pete Beach to Crystal River in 2 hours. Alternatively, you can take a bus. Traveling from St. Pete Beach in April, Crystal River is a bit cooler at night with lows of 59°F. Wrap up your sightseeing on the 1st (Tue) early enough to drive to Orlando.

Things to do in Crystal River

#Wildlife, #Parks, #Outdoors

Side Trips

Homosassa, Cedar Key, Ellie Schiller Homosassa Springs Wildlife State Park
Highlights from your plan
Scuba & Snorkeling
Stand-Up Paddleboarding
Cedar Keys National Wildlife Refuge ©

6
days
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 Cocoa Beach and Beach at Daytona Beach. Your cultural itinerary includes sights like Ponce de Leon Inlet Lighthouse & Museum and Dunlawton Sugar Mill Gardens. Explore Orlando's surroundings by going to Stetson Mansion (in DeLand), Boxelder (in Sanford) and Cocoa Beach (The Florida Key Lime Pie Company & Ron Jon Surf Shop). There's still lots to do: make an unforgettable trip to World of Disney, stroll through Brevard Zoo, take a stroll through Old Town, and don't miss a visit to International Drive.

To see more things to do, maps, photos, and other tourist information, go to the Orlando online trip builder .

Traveling by car from Crystal River to Orlando takes 2 hours. Alternatively, you can take a bus; or do a combination of bus and train. In May, plan for daily highs up to 88°F, and evening lows to 69°F. Finish your sightseeing early on the 6th (Sun) so you can travel back home.

Things to do in Orlando

#Shopping, #Parks, #Outdoors

Side Trips

Cocoa Beach, Stetson Mansion, Brevard Zoo, Dunlawton Sugar Mill Gardens, Boxelder
Highlights from your plan
Beach at Daytona Beach ©
Beach at Daytona Beach
Cocoa Beach ©
Cocoa Beach
World of Disney ©
World of Disney

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