39 days in Florida Itinerary

39 days in Florida Itinerary

Created using Inspirock Florida trip planner

Plan created by another user. Make it yours
1
Pensacola Beach
— 2 nights
2
Marco Island
— 3 nights
3
Key West
— 6 nights
4
Big Pine Key
— 2 nights
5
Marathon
— 5 nights
6
Islamorada
— 3 nights
7
Key Largo
— 4 nights
8
Miami
— 5 nights
9
Orlando
— 7 nights

2
nights
Pensacola Beach

Pensacola Beach ©
Pensacola Beach is an unincorporated community located on Santa Rosa Island, a barrier island, in Escambia County, Florida, United States. Kick off your visit on the 23rd (Thu): take in the waterfront at Pensacola Beach Gulf Pier. Get ready for a full day of sightseeing on the 24th (Fri): contemplate the long history of Fort Pickens Area and then enjoy the sand and surf at Gulf Islands National Seashore.

For reviews, photos, and other tourist information, read Pensacola Beach trip maker website.

Little Rock to Pensacola Beach is an approximately 6.5-hour flight. You can also drive; or do a combination of bus, train, and taxi. Traveling from Little Rock in May, you can expect nighttime temperatures to be somewhat warmer in Pensacola Beach, with lows of 66°F. Finish your sightseeing early on the 25th (Sat) to allow enough time to travel to Marco Island.

Things to do in Pensacola Beach

Parks · Beaches · Outdoors

Side Trip

Navarre Beach
Highlights from your plan
Navarre Beach ©
Navarre Beach
Gulf Islands National Seashore ©
Gulf Islands National Seashore
Pensacola Beach ©
Pensacola Beach

3
nights
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. Go for a jaunt from Marco Island to Everglades City to see Speed Boats Tours about 38 minutes away. Next up on the itinerary: get interesting insight from Tours, get a new perspective on things with Boat Tours & Water Sports, see what you can catch with a fishing tour, and walk around Frank E. Mackle Park.

For other places to visit, traveler tips, where to stay, and tourist information, you can read our Marco Island day trip app.

Traveling by flight from Pensacola Beach to Marco Island takes 7.5 hours. Alternatively, you can drive; or do a combination of taxi and bus. You'll lose 1 hour traveling from Pensacola Beach to Marco Island due to the time zone difference. In May, plan for daily highs up to 88°F, and evening lows to 69°F. Finish up your sightseeing early on the 29th (Wed) so you can catch the ferry to Key West.

Things to do in Marco Island

Outdoors · Tours · Wildlife

Side Trip

Speed Boats Tours
Highlights from your plan
Dolphin & Whale Watching
Waterskiing & Jetskiing
Stand-Up Paddleboarding

6
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.
Spend the 2nd (Sun) exploring nature at Dry Tortugas National Park. And it doesn't end there: examine the collection at The Ernest Hemingway Home and Museum, get up close to creatures of the deep with a dolphin and whale watching tour, get interesting insight from Tours, and get a new perspective on things with Boat Tours & Water Sports.

To find photos, maps, reviews, and tourist information, you can read our Key West trip itinerary planner.

Traveling by ferry from Marco Island to Key West takes 3.5 hours. Alternatively, you can drive. Plan for somewhat warmer nights when traveling from Marco Island in May since evenings lows in Key West dip to 77°F. Wrap up your sightseeing on the 4th (Tue) to allow time to drive to Big Pine Key.

Things to do in Key West

Outdoors · Tours · Parks
Highlights from your plan
Alan S. Maltz Gallery ©
Alan S. Maltz Gallery
Key West Butterfly & Nature Conservatory ©
Key West Butterfly & Nature Conservatory
Parasailing & Paragliding

2
nights
Big Pine Key

Big Pine Key ©
Big Pine Key is a census-designated place and unincorporated community in Monroe County, Florida, United States, on an island of the same name in the Florida Keys. Kick off your visit on the 5th (Wed): look for all kinds of wild species at National Key Deer Refuge and then stroll through Bahia Honda State Park. On your second day here, get interesting insight from Tours and then identify plant and animal life at Blue Hole.

For where to stay, maps, more things to do, and tourist information, go to the Big Pine Key trip planner.

Traveling by car from Key West to Big Pine Key takes an hour. Alternatively, you can take a bus. In June, plan for daily highs up to 90°F, and evening lows to 79°F. Cap off your sightseeing on the 6th (Thu) early enough to go by car to Marathon.

Things to do in Big Pine Key

Parks · Wildlife · Outdoors
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
National Key Deer Refuge ©
National Key Deer Refuge
Scuba & Snorkeling

5
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.
Marathon is known for wildlife, beaches, and adventure. Your plan includes some of its best attractions: get answers to all your questions at Pigeon Key Foundation, see what you can catch with a fishing tour, stroll through Sombrero Beach, and see the interesting displays at Crane Point Museum & Nature Center.

To see where to stay, maps, photos, and more tourist information, you can read our Marathon planning tool.

Marathon is very close to Big Pine Key. June in Marathon sees daily highs of 90°F and lows of 79°F at night. Finish up your sightseeing early on the 11th (Tue) so you can go by car to Islamorada.

Things to do in Marathon

Parks · Wildlife · Outdoors

Side Trip

Sunset Park Beach
Highlights from your plan
Sombrero Beach ©
Sombrero Beach
The Turtle Hospital ©
The Turtle Hospital
Pigeon Key Foundation ©
Pigeon Key Foundation

3
nights
Islamorada

Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
Islamorada is known for wildlife, adventure, and museums. Your plan includes some of its best attractions: see what you can catch with a fishing tour, indulge your thirst for a good beer at Islamorada Brewery & Distillery, enjoy the sand and surf at Anne's Beach, and get engrossed in the history at History of Diving Museum.

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

Drive from Marathon to Islamorada in an hour. Alternatively, you can take a bus. June in Islamorada sees daily highs of 90°F and lows of 79°F at night. Wrap up your sightseeing by early afternoon on the 14th (Fri) to allow enough time to drive to Key Largo.

Things to do in Islamorada

Outdoors · Tours · Wildlife
Highlights from your plan
Fishing Charters & Tours
Scuba & Snorkeling
Parasailing & Paragliding

4
nights
Key Largo

Key Largo ©
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.
Explore the numerous day-trip ideas around Key Largo: Homestead (Everglades Alligator Farm & Coral Castle) and Anhinga Trail (in Everglades National Park). Next up on the itinerary: see some colorful creatures with a scuba or snorkeling tour, identify plant and animal life at Florida Keys Wild Bird Rehabilitation Center, step aboard USCG Duane, and admire nature's wide array of creatures at Island Dolphin Care.

To find other places to visit, photos, reviews, and more tourist information, use the Key Largo tour itinerary maker tool.

Key Largo is just a stone's throw from Islamorada. In June, plan for daily highs up to 88°F, and evening lows to 75°F. Wrap up your sightseeing on the 18th (Tue) early enough to drive to Miami.

Things to do in Key Largo

Parks · Wildlife · Outdoors

Side Trips

Homestead, Anhinga Trail
Highlights from your plan
Island Dolphin Care ©
Island Dolphin Care
Scuba & Snorkeling
Dolphins Plus Marine Mammal Responder ©
Dolphins Plus Marine Mammal Responder

5
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.
Explore Miami's surroundings by going to Everglades National Park (Shark Valley Visitor Center & Gumbo Limbo Trail), iFLY Indoor Skydiving - Fort Lauderdale (in Davie) and Palm Beach Zoo & Conservation Society (in West Palm Beach). There's much more to do: kick back and relax at South Beach, buy something for everyone on your list at Bayside Marketplace, look for all kinds of wild species at Loggerhead Marinelife Center, and view the masterpieces at Britto Central.

For where to stay, more things to do, ratings, and other tourist information, go to the Miami travel site.

You can drive from Key Largo to Miami in 1.5 hours. Alternatively, you can take a bus. In June in Miami, expect temperatures between 89°F during the day and 77°F at night. Finish your sightseeing early on the 23rd (Sun) so you can travel to Orlando.

Things to do in Miami

Parks · Outdoors · Trails

Side Trips

Miami Beach, Everglades National Park, JP Outfitters Inc., Loggerhead Marinelife Center, iFLY Indoor Skydiving - Fort Lauderdale
Highlights from your plan
Lock & Load Miami ©
Lock & Load Miami
Shark Valley Visitor Center ©
Shark Valley Visitor Center
Gumbo Limbo Trail ©
Gumbo Limbo Trail

7
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 26th (Wed) with family-friendly diversions at Universal Orlando Resort. Have a day of magic on the 30th (Sun) at Walt Disney World Resort. There's much more to do: find something for the whole family at Universal's Islands of Adventure, laugh and play at Happily Ever After Fireworks, make an unforgettable trip to Magic Kingdom Park, and get your game on at Nomadic.

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

Getting from Miami to Orlando by flight takes about 3.5 hours. Other options: drive; or take a bus. In June, daily temperatures in Orlando can reach 91°F, while at night they dip to 73°F. Finish up your sightseeing early on the 30th (Sun) so you can travel back home.

Things to do in Orlando

Theme Parks · Fun & Games · Nightlife
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

Similar plans

7 days in Florida BY A USER FROM UNITED STATES June, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, fast-paced, popular sights Preferences: June, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife Attraction style: Popular sights Pace: Fast-paced 8 days in Florida BY A USER FROM UNITED STATES June, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, fast-paced, hidden gems Preferences: June, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife Attraction style: Hidden gems Pace: Fast-paced 7 days in Florida BY A USER FROM UNITED STATES June, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems Preferences: June, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife Attraction style: Popular & hidden gems Pace: Medium 7 days in Florida BY A USER FROM UNITED STATES November, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, wildlife, popular & hidden gems Preferences: November, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, wildlife Attraction style: Popular & hidden gems Pace: Medium 20 days in Florida BY A USER FROM PHILIPPINES July, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular sights Preferences: July, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife Attraction style: Popular sights Pace: Medium 7 days in Florida BY A USER FROM UNITED STATES June, culture, outdoors, relaxing, romantic, beaches, historic sites, shopping, popular & hidden gems Preferences: June, culture, outdoors, relaxing, romantic, beaches, historic sites, shopping Attraction style: Popular & hidden gems Pace: Medium 15 days in Florida BY A USER FROM CANADA July, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, popular sights Preferences: July, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife Attraction style: Popular sights Pace: Medium 5 days in Florida BY A USER FROM UNITED STATES November, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, popular sights Preferences: November, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife Attraction style: Popular sights Pace: Medium 6 days in Florida BY A USER FROM UNITED STATES June, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, wildlife, popular sights Preferences: June, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, wildlife Attraction style: Popular sights Pace: Medium 22 days in Florida BY A USER FROM UNITED STATES February, culture, outdoors, relaxing, historic sites, museums, shopping, wildlife, popular & hidden gems Preferences: February, culture, outdoors, relaxing, historic sites, museums, shopping, wildlife Attraction style: Popular & hidden gems Pace: Medium 6 days in Florida BY A USER FROM UNITED STATES June, culture, outdoors, relaxing, beaches, historic sites, museums, wildlife, popular & hidden gems Preferences: June, culture, outdoors, relaxing, beaches, historic sites, museums, wildlife Attraction style: Popular & hidden gems Pace: Medium
See more plans