29 days in Florida Itinerary

29 days in Florida Itinerary

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Route & dates

29 days in Florida Itinerary

Start: Washington DC
Fly + bus:  4​h 15​min
1
West Palm Beach
— 3 nights
Drive:  3​h
2
Orlando
— 6 nights
Drive:  4​h
3
Miami Beach
— 2 nights
Drive:  1​h 30​min
4
Key Largo
— 3 nights
Drive:  45​min
5
Islamorada
— 4 nights
Drive:  45​min
6
Marathon
— 3 nights
bus:  30​min
7
Big Pine Key
— 2 nights
bus:  45​min
8
Key West
— 5 nights
Fly:  5​h
End: Washington DC

3
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.
You'll get in some beach time at John D. MacArthur Beach State Park and Lake Worth Beach. Get in touch with nature at Peanut Island Park and Lion Country Safari. When in West Palm Beach, make a side trip to see Wakodahatchee Wetlands in Delray Beach, approximately 34 minutes away. There's lots more to do: look for all kinds of wild species at Loggerhead Marinelife Center, buy something for everyone on your list at CityPlace, grab your bike and head to On Your Mark Performance Center, and wander the streets of Worth Avenue.

To see photos, where to stay, more things to do, and other tourist information, read West Palm Beach online trip planner .

Washington DC to West Palm Beach is an approximately 4.5-hour combination of flight and bus. You can also do a combination of train, flight, and bus; or drive. Plan for warmer temperatures traveling from Washington DC in February, with highs in West Palm Beach at 78°F and lows at 62°F. Wrap up your sightseeing on the 18th (Mon) to allow time to drive to Orlando.

Things to do in West Palm Beach

Parks Outdoors Beaches

Side Trips

Palm Beach, Wakodahatchee Wetlands, Lake Worth Beach, Lion Country Safari, Peanut Island Park
Highlights from your plan
John D. MacArthur Beach State Park ©
John D. MacArthur Beach State Park
Peanut Island Park ©
Peanut Island Park
Loggerhead Marinelife Center ©
Loggerhead Marinelife Center

6
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.
Relax by the water at Ormond Beach and Lighthouse Point Park. Take a break from the city and head to Disney's Animal Kingdom and Beach at Daytona Beach. Venture out of the city with trips to Blue Spring State Park (in Orange City), Cocoa Beach (in Cocoa Beach) and Celebration Farmers Market (in Celebration). Pack the 20th (Wed) with family-friendly diversions at Walt Disney World Resort. Next up on the itinerary: make an unforgettable trip to Happily Ever After Fireworks, revel in the low prices at Orlando Premium Outlets - Vineland Avenue, look for gifts at The LEGO Store Downtown Disney, and find something for the whole family at SeaWorld Orlando.

For reviews, other places to visit, photos, and tourist information, use the Orlando road trip planner .

Traveling by car from West Palm Beach to Orlando takes 3 hours. Alternatively, you can take a bus; or take a train. Traveling from West Palm Beach in February, expect little chillier with lows of 56°F in Orlando. Wrap up your sightseeing on the 24th (Sun) early enough to drive to Miami Beach.

Things to do in Orlando

Theme Parks Parks Outdoors

Side Trips

Cocoa Beach, Celebration Farmers Market, Lighthouse Point Park, Beach at Daytona Beach, Ormond Beach
Highlights from your plan
Walt Disney World Resort ©
Walt Disney World Resort
SeaWorld Orlando ©
SeaWorld Orlando
Disney's Animal Kingdom ©
Disney's Animal Kingdom

2
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.
Kick off your visit on the 25th (Mon): make a trip to Collins Avenue, take a stroll through Lincoln Road, then appreciate the extensive heritage of Art Deco Historic District, and finally kick back and relax at South Beach. Keep things going the next day: get a taste of the local shopping with Bayside Marketplace and then get a taste of the local shopping with Ocean Drive.

To find maps, where to stay, ratings, and tourist information, refer to the Miami Beach online attractions planner .

You can drive from Orlando to Miami Beach in 4 hours. Other options are to take a bus; or do a combination of train and bus. Plan for somewhat warmer nights when traveling from Orlando in February since evenings lows in Miami Beach dip to 65°F. Finish your sightseeing early on the 26th (Tue) so you can drive to Key Largo.

Things to do in Miami Beach

Shopping Neighborhoods Parks

Side Trip

Bayside Marketplace
Highlights from your plan
Lincoln Road ©
Lincoln Road
South Beach ©
South Beach
Bayside Marketplace ©
Bayside Marketplace

3
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.
Family-friendly places like Florida Keys Wild Bird Rehabilitation Center and Scuba & Snorkeling will thrill your kids. Get in touch with nature at Anhinga Trail and Molasses Reef. There's still lots to do: admire the majestic nature at John Pennekamp Coral Reef State Park, glide through the air with a parasailing or paragliding tour, stop by Robert Is Here, and take in the architecture and atmosphere at Key Largo Baptist Church.

For more things to do, ratings, and more tourist information, refer to the Key Largo trip itinerary builder website .

Traveling by car from Miami Beach to Key Largo takes 1.5 hours. Alternatively, you can take a bus; or do a combination of bus and taxi. In February, daily temperatures in Key Largo can reach 78°F, while at night they dip to 62°F. Finish your sightseeing early on the 1st (Fri) so you can drive to Islamorada.

Things to do in Key Largo

Parks Wildlife Outdoors

Side Trips

Anhinga Trail, Robert Is Here
Highlights from your plan
Scuba & Snorkeling
Molasses Reef ©
Molasses Reef

4
nights
Islamorada

Islamorada ©
Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
Bring the kids along to Anne's Beach and Parasailing & Paragliding. Escape the urban bustle at Robbie's of Islamorada and Lignumvitae Key Botanical State Park. There's lots more to do: get outside with A Lil' Tail Charters, take a memorable tour with Spray Watersports, look for gifts at Bella Sol Fragrance Bar and Gifts, and sample the tasty concoctions at Florida Keys Brewing Company.

To see reviews, other places to visit, photos, and tourist information, read our Islamorada trip itinerary planner .

Traveling by car from Key Largo to Islamorada takes an hour. Alternatively, you can do a combination of taxi and bus. Traveling from Key Largo in March, plan for somewhat warmer nights in Islamorada, with lows around 69°F. Cap off your sightseeing on the 5th (Tue) early enough to go by car to Marathon.

Things to do in Islamorada

Outdoors Tours Parks
Highlights from your plan
Robbie's of Islamorada ©
Robbie's of Islamorada
Anne's Beach ©
Anne's Beach
Spray Watersports ©
Spray Watersports

3
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.
Family-friendly places like Sombrero Beach and Crane Point Museum & Nature Center will thrill your kids. Get outdoors at Pigeon Key Foundation and The Turtle Hospital. There's lots more to do: identify plant and animal life at Dolphin Research Center, see what you can catch with a fishing tour, discover the deep blue sea with a scuba or snorkeling tour, and look for gifts at Bayshore Clothing.

For traveler tips, maps, photos, and tourist information, use the Marathon trip app .

You can drive from Islamorada to Marathon in an hour. Another option is to take a bus. In March, plan for daily highs up to 81°F, and evening lows to 69°F. Finish your sightseeing early on the 8th (Fri) so you can take a bus to Big Pine Key.

Things to do in Marathon

Wildlife Parks Outdoors
Highlights from your plan
Dolphin Research Center ©
Dolphin Research Center
Sombrero Beach ©
Sombrero Beach
Crane Point Museum & Nature Center ©

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. On the 9th (Sat), stop by Out of the Blue Gallery, glide peacefully along the water with some of the best stand-up paddleboarding in the area, and then admire the majestic nature at Bahia Honda State Park. Keep things going the next day: take in the exciting artwork at Artists in Paradise Gallery, then look for all kinds of wild species at Blue Hole, and then identify plant and animal life at National Key Deer Refuge.

To find where to stay, more things to do, ratings, and tourist information, refer to the Big Pine Key holiday planner .

Big Pine Key is just a stone's throw from Marathon. In March in Big Pine Key, expect temperatures between 81°F during the day and 69°F at night. Finish up your sightseeing early on the 10th (Sun) so you can catcht the bus to Key West.

Things to do in Big Pine Key

Parks Outdoors Wildlife
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
Blue Hole ©
Blue Hole
Stand-Up Paddleboarding

5
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.
Head to Uva Wine Shop & Bar and Key West Potteryfor some retail therapy. Kids will appreciate attractions like Key West Butterfly & Nature Conservatory and Dolphin & Whale Watching. Spend the 13th (Wed) exploring nature at Dry Tortugas National Park. The adventure continues: admire the majestic nature at Fort Zachary Taylor, glide through the air with a parasailing or paragliding tour, explore the different monuments and memorials at Key West Cemetery, and explore and take pictures at Mallory Square.

For reviews, traveler tips, photos, and more tourist information, use the Key West attractions planner.

Traveling by bus from Big Pine Key to Key West takes an hour. Alternatively, you can drive. In March, plan for daily highs up to 79°F, and evening lows to 69°F. Wrap up your sightseeing on the 15th (Fri) early enough to travel back home.

Things to do in Key West

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

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