31 days in Florida Itinerary

31 days in Florida Itinerary

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Route & dates

31 days in Florida Itinerary

Start: Boracay
+2
ferry + foot + Fly:  31​h
1
Miami Beach
— 3 nights
bus:  3​h 30​min
2
Everglades National Park
— 4 nights
bus:  4​h 45​min
3
Big Pine Key
— 1 night
bus:  45​min
4
Key West
— 5 nights
+2
Fly + foot + bus:  3​h
5
Clearwater
— 3 nights
Drive:  1​h 30​min
6
Siesta Key
— 2 nights
Drive:  2​h 30​min
7
Orlando
— 5 nights
Drive:  2​h
8
St. Augustine
— 4 nights
+3
bus + Fly + foot + ferry:  33​h
End: Boracay

3
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.
Satisfy your inner culture vulture at Lincoln Road and Art Deco Historic District. Do your shopping at Aventura Mall and Bayside Marketplace. The adventure continues: kick back and relax at South Beach, tour the pleasant surroundings at Haulover Beach Park, wander the streets of Collins Avenue, and get to know the fascinating history of Art Deco Tours.

To find photos, maps, and more tourist information, refer to the Miami Beach trip maker site .

Boracay, Philippines to Miami Beach is an approximately 31-hour combination of ferry, bus, flight, and tram. You can also do a combination of ferry, flight, tram, and bus. Due to the time zone difference, you'll gain 13 hours traveling from Boracay to Miami Beach. Traveling from Boracay in May, plan for slightly colder nights in Miami Beach, with lows around 27°C. Wrap up your sightseeing by early afternoon on the 5th (Sat) to allow time for travel to Everglades National Park.

Things to do in Miami Beach

Parks Shopping Neighborhoods

Side Trips

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

4
nights
Everglades National Park

Everglades National Park ©
A vast expanse of pristine wetlands, Everglades National Park holds the distinction of being the largest tropical wilderness in the U.S.
Take a break from the city and head to Shark Valley and Shark River Slough. Spend the 8th (Tue) exploring nature at Everglades National Park. It doesn't end there: identify plant and animal life at Anhinga Trail and stroll through Gumbo Limbo Trail.

To see other places to visit, maps, ratings, and tourist information, read our Everglades National Park road trip site .

You can take a bus from Miami Beach to Everglades National Park in 3.5 hours. In May, daily temperatures in Everglades National Park can reach 36°C, while at night they dip to 28°C. Finish up your sightseeing early on the 9th (Wed) so you can catcht the bus to Big Pine Key.

Things to do in Everglades National Park

Parks Nature Outdoors

Side Trip

Everglades National Park
Highlights from your plan
Shark Valley Visitor Center ©
Shark Valley Visitor Center
Gumbo Limbo Trail ©
Gumbo Limbo Trail
Anhinga Trail ©
Anhinga Trail

1
night
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 9th (Wed): admire the majestic nature at Bahia Honda State Park.

To find photos, other places to visit, ratings, and more tourist information, go to the Big Pine Key trip itinerary maker tool .

Getting from Everglades National Park to Big Pine Key by bus takes about 5 hours. Expect a daytime high around 36°C in May, and nighttime lows around 28°C. Wrap up your sightseeing on the 10th (Thu) to allow time to drive to Key West.

Things to do in Big Pine Key

Parks Beaches Outdoors
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park

5
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.
Take a break from the city and head to Fort Zachary Taylor and Key West Butterfly & Nature Conservatory. Visit Truman Little White House and Key West Cemetery for their historical value. Spend the 13th (Sun) exploring nature at Dry Tortugas National Park. Spend the 14th (Mon) airborne with a parasailing or paragliding tour. There's lots more to do: see the interesting displays at The Ernest Hemingway Home and Museum, contemplate the long history of Amsterdam's Curry Mansion Inn, look for gifts at De La Gallery, and take in nature's colorful creations at Oldest House & Garden Museum.

To find reviews, photos, other places to visit, and more tourist information, go to the Key West sightseeing planning app .

Traveling by car from Big Pine Key to Key West takes an hour. Alternatively, you can take a shuttle; or take a bus. In May, daytime highs in Key West are 34°C, while nighttime lows are 29°C. Cap off your sightseeing on the 15th (Tue) early enough to travel to Clearwater.

Things to do in Key West

Outdoors Tours Adventure
Highlights from your plan
The Ernest Hemingway Home and Museum ©
Dry Tortugas National Park ©
Dry Tortugas National Park

3
nights
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.
Visit Clearwater Beach and Sunset Beach for some beach relaxation. Satisfy your inner culture vulture at Philippe Park and Aspirations Winery. You'll find plenty of places to visit near Clearwater: Parasailing & Paragliding (in Madeira Beach) and Saint Pete Beach (in St. Pete Beach). Next up on the itinerary: enjoy the sand and surf at Caladesi Island State Park.

For maps, traveler tips, photos, and more tourist information, use the Clearwater sightseeing planner .

Do a combination of flight and taxi from Key West to Clearwater in 3 hours. Alternatively, you can drive; or do a combination of ferry, taxi, and bus. Traveling from Key West in May, you can expect nighttime temperatures to be slightly colder in Clearwater, with lows of 24°C. Cap off your sightseeing on the 18th (Fri) early enough to go by car to Siesta Key.

Things to do in Clearwater

Parks Outdoors Beaches

Side Trips

Philippe Park, Parasailing & Paragliding, Sunset Beach, Caladesi Island State Park, Saint Pete Beach
Highlights from your plan
Parasailing & Paragliding
Clearwater Beach ©
Clearwater Beach
Saint Pete Beach ©
Saint Pete Beach

2
nights
Siesta Key

Siesta Key ©
Siesta Key draws most of its visitors with soft, white-quartz sand beaches and translucent ocean water.
Kick off your visit on the 18th (Fri): tour the pleasant surroundings at Crescent Beach and then kick back and relax at Siesta Beach. On your second day here, tour the pleasant surroundings at Venice Beach, then tour the pleasant surroundings at Nokomis Beach, and then kick back and relax at Turtle Beach.

For reviews, maps, other places to visit, and more tourist information, go to the Siesta Key trip planner .

Traveling by car from Clearwater to Siesta Key takes 1.5 hours. Alternatively, you can take a bus. In May in Siesta Key, expect temperatures between 36°C during the day and 23°C at night. Finish your sightseeing early on the 20th (Sun) to allow enough time to drive to Orlando.

Things to do in Siesta Key

Parks Beaches Outdoors

Side Trips

Venice Beach, Nokomis Beach
Highlights from your plan
Siesta Beach ©
Siesta Beach
Crescent Beach ©
Crescent Beach
Nokomis Beach ©
Nokomis Beach

5
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.
Your cultural itinerary includes sights like NASA Kennedy Space Center Visitor Complex and The Charles Hosmer Morse Museum of American Art. Pack the 20th (Sun) with family-friendly diversions at Walt Disney World Resort. Pack the 22nd (Tue) with family-friendly diversions at Universal's Islands of Adventure. There's still lots to do: make an unforgettable trip to Happily Ever After Fireworks, get in on the family fun at Magic Kingdom Park, meet the residents at SeaWorld Orlando, and stop by The LEGO Store.

To find traveler tips, ratings, more things to do, and more tourist information, read Orlando travel itinerary planner.

Traveling by car from Siesta Key to Orlando takes 2.5 hours. Alternatively, you can do a combination of bus and train; or take a bus. May in Orlando sees daily highs of 36°C and lows of 24°C at night. Wrap up your sightseeing on the 25th (Fri) early enough to drive to St. Augustine.

Things to do in Orlando

Theme Parks Museums Childrens Museums

Side Trips

Charles Hosmer Morse Museum of American Art, NASA Kennedy Space Center Visitor Complex
Highlights from your plan
Walt Disney World Resort ©
Walt Disney World Resort
Happily Ever After Fireworks ©
Happily Ever After Fireworks

4
nights
St. Augustine

St. Augustine ©
SAINT AUGUSTINE | PONTE VEDRA on Florida's Historic Coast The Nation's oldest city (est. Castillo de San Marcos and Fort Matanzas National Monument are good opportunities to explore the local culture. Get outdoors at Andy Romano Beachfront Park and Sawgrass Country Club. Get out of town with these interesting St. Augustine side-trips: Jacksonville Beach (in Jacksonville Beach) and Ormond Beach (in Ormond Beach). There's more to do: kick back and relax at St. Augustine Beach and view the masterpieces at High Tide Gallery.

To see ratings, traveler tips, where to stay, and more tourist information, use the St. Augustine attractions app .

Traveling by car from Orlando to St. Augustine takes 2 hours. Alternatively, you can take a bus. When traveling from Orlando in May, plan for little chillier days in St. Augustine, with highs around 32°C, while nights are about the same with lows around 22°C. Wrap up your sightseeing on the 29th (Tue) to allow time to travel back home.

Things to do in St. Augustine

Parks Beaches Outdoors

Side Trips

Ormond Beach, Jacksonville Beach, Sawgrass Country Club
Highlights from your plan
Ormond Beach ©
Ormond Beach
St. Augustine Beach ©
St. Augustine Beach
Fort Matanzas National Monument ©
Fort Matanzas National Monument

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