28 days in Florida Itinerary

28 days in Florida Itinerary

Created using Inspirock Florida trip planner

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Route & dates

28 days in Florida Itinerary

Start: New Orleans
Fly:  4​h 15​min
1
Miami Beach
— 3 nights
Drive:  1​h 30​min
2
Key Largo
— 3 nights
Drive:  45​min
3
Islamorada
— 3 nights
Drive:  45​min
4
Marathon
— 4 nights
Drive:  30​min
5
Big Pine Key
— 2 nights
bus:  45​min
6
Key West
— 5 nights
ferry:  2​h 30​min
7
Marco Island
— 2 nights
Drive:  4​h 15​min
8
Orlando
— 5 nights
Fly:  4​h 15​min
End: New Orleans

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.
Do your shopping at Lincoln Road and Espanola Way. Do some cultural sightseeing at Collins Avenue and The Wolfsonian - Florida International University. When in Miami Beach, make a side trip to see Shark Valley in Everglades National Park, approximately 1h 10 min away. There's lots more to do: tour the pleasant surroundings at South Beach, admire the landmark architecture of Art Deco Historic District, shop like a local with Ocean Drive, and get a new perspective on things with Boat Tours & Water Sports.

For traveler tips, where to stay, more things to do, and other tourist information, read our Miami Beach trip app .

New Orleans to Miami Beach is an approximately 4.5-hour flight. You can also do a combination of flight and bus; or drive. Traveling from New Orleans to Miami Beach, you'll lose 1 hour due to the time zone difference. When traveling from New Orleans in May, plan for a bit warmer days and about the same nights in Miami Beach: temperatures range from 87°F by day to 74°F at night. Finish your sightseeing early on the 26th (Sun) to allow enough time to drive to Key Largo.

Things to do in Miami Beach

Neighborhoods Shopping Outdoors

Side Trips

Shark Valley Visitor Center, Waterskiing & Jetskiing
Highlights from your plan
Lincoln Road ©
Lincoln Road
Shark Valley Visitor Center ©
Shark Valley Visitor Center
South Beach ©
South Beach

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.
Step out of the city life by going to Florida Keys Wild Bird Rehabilitation Center and Anhinga Trail. Change things up with these side-trips from Key Largo: Homestead (Everglades Alligator Farm & Coral Castle). There's lots more to do: discover the deep blue sea with a scuba or snorkeling tour, stop by Robert Is Here, enjoy the sand and surf at Harry Harris Park, and immerse yourself in nature at John Pennekamp Coral Reef State Park.

For where to stay, maps, reviews, and other tourist information, go to the Key Largo trip itinerary builder site .

You can drive from Miami Beach to Key Largo in 1.5 hours. Alternatively, you can take a bus. Expect a daytime high around 85°F in May, and nighttime lows around 72°F. Finish your sightseeing early on the 29th (Wed) so you can drive to Islamorada.

Things to do in Key Largo

Parks Outdoors Wildlife

Side Trips

Homestead, Anhinga Trail
Highlights from your plan
Anhinga Trail ©
Anhinga Trail
Scuba & Snorkeling

3
nights
Islamorada

Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
Shop till you drop at Old Road Gallery and Zero Dress Code Boutique. Step out of the city life by going to Fishing Charters & Tours and Alligator Reef Light House. Next up on the itinerary: see some colorful creatures with a scuba or snorkeling tour, glide through the air with a parasailing or paragliding tour, glide peacefully along the water with some of the best stand-up paddleboarding in the area, and indulge your thirst for a good beer at Islamorada Beer Company.

To find photos, more things to do, ratings, and tourist information, refer to the Islamorada trip planner .

Drive from Key Largo to Islamorada in an hour. Alternatively, you can do a combination of taxi and bus. May in Islamorada sees daily highs of 88°F and lows of 77°F at night. Wrap up your sightseeing on the 1st (Sat) early enough to drive to Marathon.

Things to do in Islamorada

Outdoors Tours Wildlife
Highlights from your plan
Fishing Charters & Tours
Scuba & Snorkeling
Alligator Reef Light House ©
Alligator Reef Light House

4
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.
San Pablo Catholic Church and Shady Palm Art Gallery & Photography are good opportunities to explore the local culture. Get outdoors at Pigeon Key Foundation and Crane Point Museum & Nature Center. The adventure continues: identify plant and animal life at The Turtle Hospital, see the vivid underwater world at Sombrero Reef, add some adventure to your tour with a kayaking and canoeing tour, and stop by Christina's Consignment Boutique.

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

You can drive from Islamorada to Marathon in an hour. Alternatively, you can take a bus. In June, daily temperatures in Marathon can reach 90°F, while at night they dip to 79°F. Wrap up your sightseeing on the 5th (Wed) to allow time to take a bus to Big Pine Key.

Things to do in Marathon

Wildlife Outdoors Parks

Side Trip

Sunset Park Beach
Highlights from your plan
Crane Point Museum & Nature Center ©
The Turtle Hospital ©
The Turtle Hospital
Dolphin Research Center ©
Dolphin Research 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 6th (Thu), look for gifts at Out of the Blue Gallery, admire the majestic nature at Bahia Honda State Park, and then find your balance on the water with some of the best stand-up paddleboarding in the area. Get ready for a full day of sightseeing on the next day: identify plant and animal life at National Key Deer Refuge and then cast your line with a fishing tour.

To find more things to do, ratings, photos, and tourist information, read our Big Pine Key day trip planner.

Big Pine Key is just a stone's throw from Marathon. Expect a daytime high around 90°F in June, and nighttime lows around 79°F. Wrap up your sightseeing on the 7th (Fri) early enough to take a bus to Key West.

Things to do in Big Pine Key

Outdoors Wildlife Parks
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
National Key Deer Refuge ©
National Key Deer Refuge
Fishing Charters & Tours

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.
The Ernest Hemingway Home and Museum and 7 Artists & Friends are good opportunities to explore the local culture. Get outdoors at Key West Butterfly & Nature Conservatory and Fishing Charters & Tours. Spend the 10th (Mon) exploring nature at Dry Tortugas National Park. There's lots more to do: get up close to creatures of the deep with a dolphin and whale watching tour, glide peacefully along the water with some of the best stand-up paddleboarding in the area, glide through the air with a parasailing or paragliding tour, and view the masterpieces at Alan S. Maltz Gallery.

To see reviews, ratings, and other tourist information, refer to the Key West trip planner.

You can take a bus from Big Pine Key to Key West in an hour. Alternatively, you can drive. In June, daily temperatures in Key West can reach 88°F, while at night they dip to 79°F. Finish your sightseeing early on the 12th (Wed) to allow enough time to ride a ferry to Marco Island.

Things to do in Key West

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

2
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. Kick off your visit on the 13th (Thu): get a new perspective on things with Boat Tours & Water Sports, then get a new perspective on things with Boat Tours & Water Sports, and then paddle through the water with a kayaking and canoeing tour. On the 14th (Fri), you'll have a packed day of sightseeing: see what you can catch with a fishing tour, then see majestic marine mammals with a dolphin and whale watching tour, and then look for gifts at Keep In Touch.

For ratings, where to stay, other places to visit, and other tourist information, you can read our Marco Island trip itinerary planning app .

Traveling by ferry from Key West to Marco Island takes 2.5 hours. Alternatively, you can drive. Traveling from Key West in June, you can expect nighttime temperatures to be slightly colder in Marco Island, with lows of 74°F. Finish your sightseeing early on the 14th (Fri) so you can drive to Orlando.

Things to do in Marco Island

Outdoors Tours Adventure
Highlights from your plan
Dolphin & Whale Watching
Waterskiing & Jetskiing
Stand-Up Paddleboarding

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 19th (Wed) with family-friendly diversions at Discovery Cove. Pack the 16th (Sun) with family-friendly diversions at Universal Orlando Resort. And it doesn't end there: discover the magic at Walt Disney World Resort, get in on the family fun at Universal's Islands of Adventure, laugh and play at Happily Ever After Fireworks, and look for gifts at MacroBaby.

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

Traveling by car from Marco Island to Orlando takes 4.5 hours. Alternatively, you can do a combination of bus and flight; or take a bus. June in Orlando sees daily highs of 91°F and lows of 73°F at night. Finish up your sightseeing early on the 19th (Wed) so you can travel back home.

Things to do in Orlando

Theme Parks Parks Beaches
Highlights from your plan
Universal Orlando Resort ©
Universal Orlando Resort
Walt Disney World Resort ©
Walt Disney World Resort
Discovery Cove ©
Discovery Cove

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