30 days in Florida Itinerary

30 days in Florida Itinerary

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Route & dates

30 days in Florida Itinerary

Start: New York City
+3
bus + Fly + taxi + bus:  5​h 45​min
1
St. Augustine
— 3 nights
Drive:  2​h
2
Orlando
— 5 nights
Drive:  2​h
3
Clearwater
— 4 nights
Drive:  1​h 15​min
4
Sarasota
— 2 nights
Drive:  2​h
5
Naples
— 3 nights
ferry:  2​h 45​min
6
Key West
— 4 nights
Fly:  2​h 30​min
7
Miami
— 3 nights
train:  1​h 30​min
8
Everglades National Park
— 3 nights
train:  3​h 30​min
9
West Palm Beach
— 2 nights
Fly:  5​h
End: New York City

3
nights
St. Augustine

St. Augustine ©
SAINT AUGUSTINE | PONTE VEDRA on Florida's Historic Coast The Nation's oldest city (est. On the 1st (Tue), contemplate the long history of The Old Senator Tree and then sample the fine beverages at St. Augustine Distillery. Here are some ideas for day two: admire all the interesting features of Flagler College, pause for some photo ops at Castillo de San Marcos, then identify plant and animal life at St. Augustine Wild Reserve, and finally take in the architecture and atmosphere at Memorial Presbyterian Church.

For maps, ratings, photos, and other tourist information, read our St. Augustine trip itinerary maker .

New York City to St. Augustine is an approximately 6-hour combination of train and flight. You can also do a combination of flight and bus; or drive. In May, St. Augustine is a bit warmer than New York City - with highs of 82°F and lows of 67°F. Wrap up your sightseeing on the 4th (Fri) to allow time to drive to Orlando.

Things to do in St. Augustine

Wildlife Parks Historic Sites
Highlights from your plan
Flagler College ©
Flagler College

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.
Pack the 4th (Fri) with family-friendly diversions at Walt Disney World Resort. Plan for a day of cool, family-friendly fun on the 9th (Wed) at Discovery Cove. There's still lots to do: get in on the family fun at Universal's Islands of Adventure, discover the magic at Magic Kingdom Park, take in a show at Happily Ever After Fireworks, and admire nature's wide array of creatures at SeaWorld Orlando.

For ratings, photos, and other tourist information, refer to the Orlando trip planner .

Getting from St. Augustine to Orlando by car takes about 2 hours. Other options: take a bus. When traveling from St. Augustine in May, plan for a bit warmer days in Orlando, with highs around 88°F, while nights are about the same with lows around 69°F. Wrap up your sightseeing on the 9th (Wed) to allow time to drive to Clearwater.

Things to do in Orlando

Theme Parks Parks Beaches
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

4
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.
Change things up with these side-trips from Clearwater: Saint Pete Beach (in St. Pete Beach), Busch Gardens Tampa Bay (in Tampa) and Parasailing & Paragliding (in Madeira Beach). There's much more to do: kick back and relax at Clearwater Beach, learn about winemaking at Aspirations Winery, contemplate the long history of Philippe Park, and explore and take pictures at Spectrum Field.

You can plan Clearwater trip in no time by asking Inspirock to help create your itinerary.

You can drive from Orlando to Clearwater in 2 hours. Other options are to do a combination of train and bus; or take a bus. Expect a daytime high around 87°F in May, and nighttime lows around 70°F. Wrap up your sightseeing on the 13th (Sun) to allow time to drive to Sarasota.

Things to do in Clearwater

Parks Outdoors Beaches

Side Trips

Philippe Park, Parasailing & Paragliding, Saint Pete Beach, Busch Gardens Tampa Bay
Highlights from your plan
Parasailing & Paragliding
Busch Gardens Tampa Bay ©
Busch Gardens Tampa Bay
Clearwater Beach ©
Clearwater Beach

2
nights
Sarasota

Sarasota ©
Sarasota is a city in Sarasota County on the southwestern coast of the U.S. When in Sarasota, make a side trip to see Venice Beach in Venice, approximately 32 minutes away. And it doesn't end there: enjoy the sand and surf at Siesta Beach, admire all the interesting features of Ed Smith Stadium, tour the pleasant surroundings at Crescent Beach, and explore the world behind art at The Ringling.

Inspirock's itinerary builder makes planning a Sarasota trip simple and quick.

Getting from Clearwater to Sarasota by car takes about 1.5 hours. Other options: take a bus. In May, daily temperatures in Sarasota can reach 87°F, while at night they dip to 68°F. Finish up your sightseeing early on the 15th (Tue) so you can go by car to Naples.

Things to do in Sarasota

Outdoors Parks Beaches

Side Trips

Siesta Key, Venice Beach
Highlights from your plan
Sarasota National Cemetery ©
Sarasota National Cemetery
Kayaking & Canoeing
Siesta Beach ©
Siesta Beach

3
nights
Naples

Naples is a city in Collier County, Florida, United States. Explore Naples' surroundings by going to Fort Myers Beach (in Fort Myers Beach) and Marco Island (Parasailing & Paragliding & Waterskiing & Jetskiing). There's much more to do: see the interesting displays at The Revs Institute, take in nature's colorful creations at Naples Botanical Garden, and take a leisurely stroll along Naples Pier.

For more things to do, traveler tips, reviews, and tourist information, read Naples trip planner.

You can drive from Sarasota to Naples in 2 hours. Another option is to take a bus. In May, plan for daily highs up to 88°F, and evening lows to 70°F. Wrap up your sightseeing by early afternoon on the 18th (Fri) to allow enough time to travel to Key West.

Things to do in Naples

Outdoors Parks Tours

Side Trips

Marco Island, Fort Myers Beach
Highlights from your plan
Waterskiing & Jetskiing
Parasailing & Paragliding
Revs Institute ©
Revs Institute

4
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 22nd (Tue) airborne with a parasailing or paragliding tour. There's much more to do: see the interesting displays at The Ernest Hemingway Home and Museum, find your balance on the water with some of the best stand-up paddleboarding in the area, tour the pleasant surroundings at Mallory Square, and get engrossed in the history at Truman Little White House.

To see traveler tips, reviews, ratings, and tourist information, you can read our Key West online travel route builder .

You can do a combination of taxi and flight from Naples to Key West in 3 hours. Alternatively, you can do a combination of taxi and ferry; or drive. Traveling from Naples in May, you can expect nighttime temperatures to be somewhat warmer in Key West, with lows of 77°F. Wrap up your sightseeing on the 22nd (Tue) early enough to travel to Miami.

Things to do in Key West

Tours Outdoors Adventure
Highlights from your plan
Kayaking & Canoeing
The Ernest Hemingway Home and Museum ©

3
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.
Miami is known for shopping, museums, zoos & aquariums, fun & games, and nightlife. Your plan includes some of its best attractions: take in nature's colorful creations at Fairchild Tropical Botanic Garden, buy something for everyone on your list at Bayside Marketplace, steep yourself in history at Freedom Tower, and enjoy some diversion at Lock & Load Miami: Machine Gun Experience & Range.

To find more things to do, reviews, other places to visit, and more tourist information, use the Miami trip planner .

Traveling by combination of flight and tram from Key West to Miami takes 2.5 hours. Alternatively, you can drive; or take a shuttle. In May, plan for daily highs up to 87°F, and evening lows to 74°F. Finish up your sightseeing early on the 25th (Fri) so you can catcht the bus to Everglades National Park.

Things to do in Miami

Parks Shopping Historic Sites

Side Trips

Miami Beach, Aventura Mall, Fairchild Tropical Botanic Garden, Oleta River State Park
Highlights from your plan
Fairchild Tropical Botanic Garden ©
Fairchild Tropical Botanic Garden
South Beach ©
South Beach
Lincoln Road ©
Lincoln Road

3
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.
Everglades National Park is known for wildlife, trails, nature, and adventure. Your plan includes some of its best attractions: admire the verdant scenery at Shark Valley, hike along Anhinga Trail, explore the activities along Shark River Slough, and stroll through Gumbo Limbo Trail.

For traveler tips, more things to do, and more tourist information, refer to the Everglades National Park trip maker tool .

You can take a bus from Miami to Everglades National Park in 1.5 hours. In May in Everglades National Park, expect temperatures between 87°F during the day and 76°F at night. Wrap up your sightseeing by early afternoon on the 28th (Mon) to allow enough time to take a bus to West Palm Beach.

Things to do in Everglades National Park

Parks Trails Outdoors
Highlights from your plan
Shark Valley Visitor Center ©
Shark Valley Visitor Center
Gumbo Limbo Trail ©
Gumbo Limbo Trail
Anhinga Trail ©
Anhinga Trail

2
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.
On the 29th (Tue), identify plant and animal life at Panther Ridge Conservation Center, then meet the residents at McCarthy's Wildlife Sanctuary, and then take a stroll through Worth Avenue. On your second day here, identify plant and animal life at Loggerhead Marinelife Center, admire nature's wide array of creatures at Palm Beach Zoo & Conservation Society, and then identify plant and animal life at Wakodahatchee Wetlands.

For maps, reviews, traveler tips, and more tourist information, read West Palm Beach itinerary planner .

You can take a bus from Everglades National Park to West Palm Beach in 3.5 hours. Alternatively, you can do a combination of bus and train; or take a bus. In May, daily temperatures in West Palm Beach can reach 86°F, while at night they dip to 72°F. Cap off your sightseeing on the 30th (Wed) early enough to travel back home.

Things to do in West Palm Beach

Parks Wildlife Zoos & Aquariums

Side Trips

Panther Ridge Conservation Center, Wakodahatchee Wetlands, Worth Avenue, Loggerhead Marinelife Center
Highlights from your plan
McCarthy's Wildlife Sanctuary ©
McCarthy's Wildlife Sanctuary
Panther Ridge Conservation Center ©
Panther Ridge Conservation Center
Wakodahatchee Wetlands ©
Wakodahatchee Wetlands

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