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.
Popular historic sites such as Lincoln Road and The Barnacle Historic State Park are in your itinerary. Shop till you drop at Aventura Mall and Collins Avenue. Step out of Miami Beach to go to Hollywood and see Hollywood Beach, which is approximately 48 minutes away. Next up on the itinerary: get to know the fascinating history of Art Deco Historic District, enjoy the sand and surf at South Beach, stroll through Matheson Hammock Park, and admire the landmark architecture of Art Deco Tours.

For ratings, other places to visit, maps, and tourist information, read Miami Beach attractions 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. Traveling from Boracay to Miami Beach, you'll gain 13 hours due to the time zone difference. Expect little chillier evenings in Miami Beach when traveling from Boracay in May, with lows around 27°C. Finish up your sightseeing early on the 5th (Sat) so you can travel to Everglades National Park.

Things to do in Miami Beach

Parks Beaches Outdoors

Side Trips

Miami, Bal Harbour, Aventura Mall, Hollywood Beach
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.
Visiting Shark Valley and Shark River Slough will get you outdoors. Spend the 8th (Tue) exploring nature at Everglades National Park. There's still lots to do: look for all kinds of wild species at Anhinga Trail and stroll through Gumbo Limbo Trail.

To see ratings, photos, reviews, and more tourist information, read Everglades National Park holiday planner .

Traveling by bus from Miami Beach to Everglades National Park takes 3.5 hours. In May, daytime highs in Everglades National Park are 36°C, while nighttime lows are 28°C. Wrap up your sightseeing on the 9th (Wed) early enough to take a 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. On the 9th (Wed), tour the pleasant surroundings at Bahia Honda State Park.

To find reviews, more things to do, ratings, and more tourist information, go to the Big Pine Key trip planner .

Traveling by bus from Everglades National Park to Big Pine Key takes 5 hours. In May, daytime highs in Big Pine Key are 36°C, while nighttime lows are 28°C. Cap off your sightseeing on the 10th (Thu) early enough to go by car 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.
For shopping fun, head to Uva Wine Shop & Bar or Diamonds International. Get some cultural insight at The Ernest Hemingway Home and Museum and Amsterdam's Curry Mansion Inn. Spend the 13th (Sun) airborne with a parasailing or paragliding tour. And it doesn't end there: immerse yourself in nature at Fort Zachary Taylor, take in the waterfront at Mallory Square, stroll the grounds of Key West Cemetery, and take in nature's colorful creations at Audubon House & Tropical Gardens.

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

You can drive from Big Pine Key to Key West in an hour. Other options are to take a shuttle; or take a bus. May in Key West sees daily highs of 34°C and lows of 29°C at night. Wrap up 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 ©
Truman Little White House ©
Truman Little White House

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.
Get outdoors at Clearwater Beach and Parasailing & Paragliding. Get a sense of the local culture at Philippe Park and Aspirations Winery. Go for a jaunt from Clearwater to St. Pete Beach to see Saint Pete Beach about 46 minutes away. The adventure continues: step off the mainland to explore Caladesi Island State Park and kick back and relax at Sunset Beach.

To find other places to visit, photos, reviews, and other tourist information, you can read our Clearwater attractions planning tool .

You can 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. Plan for little chillier nights when traveling from Key West in May since evenings lows in Clearwater dip to 24°C. Finish your sightseeing early on the 18th (Fri) to allow enough time to drive 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): kick back and relax at Crescent Beach and then kick back and relax at Siesta Beach. On your second day here, kick back and relax at Venice Beach, enjoy the sand and surf at Nokomis Beach, and then enjoy the sand and surf at Turtle Beach.

To see where to stay, reviews, more things to do, and other tourist information, read Siesta Key trip builder site .

You can drive from Clearwater to Siesta Key in 1.5 hours. Alternatively, you can take a bus. In May, daily temperatures in Siesta Key can reach 36°C, while at night they dip to 23°C. 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.
NASA Kennedy Space Center Visitor Complex and The Charles Hosmer Morse Museum of American Art will appeal to museum buffs. Pack the 20th (Sun) with family-friendly diversions at Walt Disney World Resort. Have a day of magic on the 24th (Thu) at Magic Kingdom Park. Next up on the itinerary: discover the magic at Happily Ever After Fireworks, get in on the family fun at Universal Orlando Resort, admire nature's wide array of creatures at SeaWorld Orlando, and stop by The LEGO Store.

For traveler tips, more things to do, maps, and more tourist information, use the Orlando online trip builder .

Drive from Siesta Key to Orlando in 2.5 hours. Alternatively, you can do a combination of bus and train; or take a bus. Expect a daytime high around 36°C in May, and nighttime lows around 24°C. Finish your sightseeing early on the 25th (Fri) to allow enough time 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

4
nights
St. Augustine

St. Augustine ©
SAINT AUGUSTINE | PONTE VEDRA on Florida's Historic Coast The Nation's oldest city (est. Relax by the water at Andy Romano Beachfront Park and Sawgrass Country Club. Step out of the city life by going to Ormond Beach and Jacksonville Beach. Spend the 29th (Tue) exploring nature at Fort Matanzas National Monument. There's much more to do: kick back and relax at St. Augustine Beach, take in the exciting artwork at High Tide Gallery, and contemplate the long history of Castillo de San Marcos.

For traveler tips, more things to do, maps, and tourist information, you can read our St. Augustine vacation planner .

Getting from Orlando to St. Augustine by car takes about 2 hours. Other options: take a bus. When traveling from Orlando in May, plan for little chillier days and about the same nights in St. Augustine: temperatures range from 32°C by day to 22°C at night. 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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