14 days in Florida Itinerary

14 days in Florida Itinerary

Created using Inspirock Florida tour itinerary builder

This plan was created by another user.  Make it your plan

Route & dates

14 days in Florida Itinerary

Start: Boston
Fly:  5​h 30​min
1
Miami
— 2 nights
Drive:  1​h 15​min
2
Key Largo
— 2 nights
Drive:  1​h 15​min
3
Marathon
— 1 night
Drive:  30​min
4
Big Pine Key
— 1 night
bus:  45​min
5
Key West
— 3 nights
6
Orlando
— 4 nights
Fly:  5​h
End: Boston

2
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.
Kick off your visit on the 1st (Fri): stroll through South Beach. Get ready for a full day of sightseeing on the 2nd (Sat): admire the masterpieces at Lowe Art Museum, then look for all kinds of wild species at Shark Valley Visitor Center, and then enjoy some diversion at Lock & Load Miami.

To see other places to visit, reviews, and more tourist information, go to the Miami holiday builder website .

Boston to Miami is an approximately 5.5-hour flight. You can also do a combination of flight and bus; or drive. Traveling from Boston in May, you will find days in Miami are somewhat warmer (87°F), and nights are much hotter (74°F). Wrap up your sightseeing on the 3rd (Sun) early enough to drive to Key Largo.

Things to do in Miami

Parks Outdoors Trails

Side Trips

Miami Beach, Everglades National Park, Lowe Art Museum
Find places to stay May 1 — 3:
Highlights from your plan
Lock & Load Miami ©
Lock & Load Miami
Shark Valley Visitor Center ©
Shark Valley Visitor Center
Gumbo Limbo Trail ©
Gumbo Limbo Trail

2
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.
On the 4th (Mon), meet the residents at Dolphins Plus Marine Mammal Responder, observe the fascinating underwater world at Island Dolphin Care, and then see what you can catch with a fishing tour. Get ready for a full day of sightseeing on the 5th (Tue): identify plant and animal life at Anhinga Trail, take a tour by water with Boat Tours & Water Sports, and then identify plant and animal life at Florida Keys Wild Bird Rehabilitation Center.

To see ratings, more things to do, other places to visit, and tourist information, read our Key Largo online vacation planner .

Traveling by car from Miami to Key Largo takes 1.5 hours. Alternatively, you can take a bus. In May, daytime highs in Key Largo are 85°F, while nighttime lows are 72°F. Finish your sightseeing early on the 5th (Tue) to allow enough time to drive to Marathon.

Things to do in Key Largo

Wildlife Outdoors Tours

Side Trips

Fishing Charters & Tours, Anhinga Trail
Find places to stay May 3 — 5:
Highlights from your plan
Island Dolphin Care ©
Island Dolphin Care
Dolphins Plus Marine Mammal Responder ©

1
night
Marathon

Marathon ©
A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
Kick off your visit on the 6th (Wed): look for all kinds of wild species at Pigeon Key Foundation, then identify plant and animal life at The Turtle Hospital, then look for all kinds of wild species at Crane Point Museum & Nature Center, and finally tour the pleasant surroundings at Sombrero Beach.

For more things to do, traveler tips, reviews, and more tourist information, read Marathon trip app .

Getting from Key Largo to Marathon by car takes about 1.5 hours. Other options: take a bus. In May, daily temperatures in Marathon can reach 88°F, while at night they dip to 77°F. Finish up your sightseeing early on the 6th (Wed) so you can go by car to Big Pine Key.

Things to do in Marathon

Parks Wildlife Beaches
Find places to stay May 5 — 6:
Highlights from your plan
Sombrero Beach ©
Sombrero Beach
Crane Point Museum & Nature Center ©
The Turtle Hospital ©
The Turtle Hospital

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. Start off your visit on the 7th (Thu): identify plant and animal life at National Key Deer Refuge, look for gifts at Out of the Blue Gallery, and then immerse yourself in nature at Bahia Honda State Park.

For photos, reviews, and other tourist information, read Big Pine Key trip itinerary maker website .

Big Pine Key is just a stone's throw from Marathon. May in Big Pine Key sees daily highs of 88°F and lows of 77°F at night. Wrap up your sightseeing on the 7th (Thu) to allow time to take a bus to Key West.

Things to do in Big Pine Key

Parks Beaches Nature
Find places to stay May 6 — 7:
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
National Key Deer Refuge ©
National Key Deer Refuge

3
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 10th (Sun) exploring nature at Dry Tortugas National Park. There's lots more to do: look for all kinds of wild species at Key West Butterfly & Nature Conservatory, fly like a bird with a parasailing or paragliding tour, get interesting insight from Tours, and cast your line with a fishing tour.

To see other places to visit, more things to do, where to stay, and tourist information, go to the Key West travel route planner .

Take a bus from Big Pine Key to Key West in an hour. Alternatively, you can drive. In May, daytime highs in Key West are 85°F, while nighttime lows are 77°F. Cap off your sightseeing on the 10th (Sun) early enough to travel to Orlando.

Things to do in Key West

Tours Outdoors Wildlife
Find places to stay May 7 — 10:
Highlights from your plan
Dolphin & Whale Watching
Parasailing & Paragliding

4
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.
You'll visit kid-friendly attractions like Universal Orlando Resort and Universal's Islands of Adventure. There's lots more to do: find something for the whole family at Walt Disney World Resort, test your team's savvy at The Escape Game Orlando, have some family-friendly fun at 7D Dark Ride Adventure, and make an unforgettable trip to Avatar Flight of Passage.

Planning Orlando trip won't be overwheling when you use's Insprock itinerary maker.

Traveling by flight from Key West to Orlando takes 4.5 hours. Alternatively, you can drive; or take a bus. Traveling from Key West in May, Orlando is slightly colder at night with lows of 69°F. Cap off your sightseeing on the 14th (Thu) early enough to travel back home.

Things to do in Orlando

Theme Parks Fun & Games Museums

Side Trip

Charles Hosmer Morse Museum of American Art
Find places to stay May 10 — 14:
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

Similar Plans

15 days in United States BY A USER FROM UNITED KINGDOM September, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems PREFERENCES: September, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 18 days in Florida BY A USER FROM AUSTRALIA January, culture, outdoors, relaxing, romantic, beaches, historic sites, hidden gems PREFERENCES: January, culture, outdoors, relaxing, romantic, beaches, historic sites ATTRACTION STYLE: Hidden gems PACE: Medium 19 days in Florida BY A USER FROM AUSTRALIA January, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems PREFERENCES: January, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 16 days in West Coast, Florida & Turks and Caicos BY A USER FROM ARGENTINA October, culture, outdoors, relaxing, romantic, beaches, historic sites, slow & easy, popular & hidden gems PREFERENCES: October, culture, outdoors, relaxing, romantic, beaches, historic sites ATTRACTION STYLE: Popular & hidden gems PACE: Slow & easy 32 days in Florida BY A USER FROM UNITED STATES July, culture, outdoors, relaxing, beaches, historic sites, museums, wildlife, slow & easy, popular & hidden gems PREFERENCES: July, culture, outdoors, relaxing, beaches, historic sites, museums, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Slow & easy 19 days in Florida BY A USER FROM GERMANY October, culture, outdoors, romantic, beaches, historic sites, shopping, wildlife, popular sights PREFERENCES: October, culture, outdoors, romantic, beaches, historic sites, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 39 days in Florida BY A USER FROM PUERTO RICO July, kids, culture, outdoors, relaxing, beaches, historic sites, museums, wildlife, popular & hidden gems PREFERENCES: July, kids, culture, outdoors, relaxing, beaches, historic sites, museums, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 28 days in Florida & New York City BY A USER FROM KUWAIT August, kids, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, fast-paced, popular sights PREFERENCES: August, kids, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Fast-paced 15 days in Florida BY A USER FROM UNITED KINGDOM April, teens, culture, relaxing, beaches, wildlife, popular sights PREFERENCES: April, teens, culture, relaxing, beaches, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 15 days in Florida BY A USER FROM UNITED KINGDOM April, culture, outdoors, shopping, popular sights PREFERENCES: April, culture, outdoors, shopping ATTRACTION STYLE: Popular sights PACE: Medium 21 days in Florida BY A USER FROM ARGENTINA October, outdoors, relaxing, romantic, beaches, shopping, popular & hidden gems PREFERENCES: October, outdoors, relaxing, romantic, beaches, shopping ATTRACTION STYLE: Popular & hidden gems PACE: Medium 21 days in Florida BY A USER FROM ARGENTINA October, relaxing, romantic, beaches, shopping, slow & easy, hidden gems PREFERENCES: October, relaxing, romantic, beaches, shopping ATTRACTION STYLE: Hidden gems PACE: Slow & easy
View more plans