27 days in United States Itinerary

27 days in United States Itinerary

Created using Inspirock Florida trip itinerary builder

Plan created by another user. Make it yours
1
Islamorada
— 1 night
2
Key West
— 3 nights
3
Big Pine Key
— 2 nights
4
Marathon
— 2 nights
5
Marco Island
— 3 nights
6
Naples
— 2 nights
7
Key Largo
— 3 nights
8
Sanibel Island
— 3 nights
9
St. Augustine
— 3 nights
10
Crystal River
— 3 nights

1
night
Islamorada

Islamorada ©
Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
On the 6th (Mon), see the vivid underwater world at Alligator Reef Light House, get to know the fascinating history of Indian Key State Historic Site, and then indulge your thirst for a good beer at Islamorada Brewery & Distillery.

To see where to stay, photos, and more tourist information, go to the Islamorada holiday builder website.

London, UK to Islamorada is an approximately 15-hour flight. The time zone difference moving from Greenwich Mean Time to Eastern Standard Time is minus 5 hours. In May, Islamorada is much hotter than London - with highs of 36°C and lows of 29°C. Wrap up your sightseeing on the 6th (Mon) to allow time to drive to Key West.

Things to do in Islamorada

Historic Sites · Wildlife · Parks
Highlights from your plan
Indian Key State Historic Site ©
Indian Key State Historic Site
Alligator Reef Light House ©
Alligator Reef Light House
Islamorada Brewery & Distillery ©
Islamorada Brewery & Distillery

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.
Get some historical perspective at St. Paul's Episcopal Church and Key West Cemetery. Step out of the city life by going to Stand-Up Paddleboarding and Vandenberg Wreck. There's much more to do: pause for some serene contemplation at Saint Mary Star of the Sea, steep yourself in history at Key West Garden Club, stop by Isle Cook Key West, and paddle through the water with a kayaking and canoeing tour.

Discover how to plan a Key West trip in just a few steps with Inspirock's itinerary builder.

Traveling by car from Islamorada to Key West takes 2 hours. Alternatively, you can take a bus. In May in Key West, expect temperatures between 34°C during the day and 29°C at night. Finish up your sightseeing early on the 9th (Thu) so you can go by car to Big Pine Key.

Things to do in Key West

Parks · Tours · Outdoors
Highlights from your plan
Stand-Up Paddleboarding
Vandenberg Wreck ©
Vandenberg Wreck
Kayaking & Canoeing

2
nights
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 10th (Fri): tour the pleasant surroundings at Bahia Honda State Park and then get a new perspective on things with Boat Tours & Water Sports. Keep things going the next day: hunt for treasures at The Big Pine Key Flea Market, take in the exciting artwork at Artists in Paradise Gallery, and then stop by Out of the Blue Gallery.

For more things to do, photos, maps, and tourist information, go to the Big Pine Key tour itinerary builder tool.

Drive from Key West to Big Pine Key in an hour. Alternatively, you can take a bus. In May in Big Pine Key, expect temperatures between 36°C during the day and 29°C at night. Wrap up your sightseeing on the 11th (Sat) early enough to drive to Marathon.

Things to do in Big Pine Key

Outdoors · Wildlife · Tours
Highlights from your plan
Fishing Charters & Tours
Bahia Honda State Park ©
Bahia Honda State Park
Artists in Paradise Gallery ©
Artists in Paradise Gallery

2
nights
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 12th (Sun): add some adventure to your tour with a kayaking and canoeing tour, examine the collection at Crane Point Museum & Nature Center, and then get all the information you need at Pigeon Key Foundation. Here are some ideas for day two: pause for some serene contemplation at San Pablo Catholic Church, then enjoy the sand and surf at Sunset Park Beach, and then see what you can catch with a fishing tour.

To find other places to visit, traveler tips, more things to do, and more tourist information, refer to the Marathon vacation builder site.

Marathon is very close to Big Pine Key. In May, daytime highs in Marathon are 36°C, while nighttime lows are 29°C. Finish up your sightseeing early on the 13th (Mon) so you can go by car to Marco Island.

Things to do in Marathon

Outdoors · Tours · Wildlife

Side Trip

Key Colony Beach
Highlights from your plan
Fishing Charters & Tours
Kayaking & Canoeing
Crane Point Museum & Nature Center ©
Crane Point Museum & Nature Center

3
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. On the 14th (Tue), steep yourself in history at Smallwood Store, kick back and relax at Keewaydin Island, and then contemplate the waterfront views at Capri Paddlecraft Park. Keep things going the next day: relax and rejuvenate at some of the top local wellness centers, don't miss a visit to Marco Island Center for the Arts, and then see what you can catch with a fishing tour.

To see traveler tips, other places to visit, and other tourist information, read Marco Island trip itinerary website.

Getting from Marathon to Marco Island by car takes about 4 hours. Other options: fly; or do a combination of bus and ferry. Traveling from Marathon in May, you can expect nighttime temperatures to be a bit cooler in Marco Island, with lows of 24°C. Wrap up your sightseeing by early afternoon on the 16th (Thu) to allow enough time to drive to Naples.

Things to do in Marco Island

Outdoors · Parks · Beaches

Side Trips

Smallwood Store, Fishing Charters & Tours
Highlights from your plan
Fishing Charters & Tours
Keewaydin Island ©
Keewaydin Island
Cape Romano ©
Cape Romano

2
nights
Naples

Naples ©
On the 16th (Thu), look for gifts at Island Trends and then enjoy the sand and surf at Vanderbilt Beach. Get ready for a full day of sightseeing on the 17th (Fri): look for all kinds of wild species at Big Cypress National Preserve and then cast your line with a fishing tour.

To find traveler tips, photos, more things to do, and more tourist information, go to the Naples day trip planning app.

Traveling by car from Marco Island to Naples takes an hour. In May, plan for daily highs up to 36°C, and evening lows to 24°C. Wrap up your sightseeing on the 18th (Sat) early enough to drive to Key Largo.

Things to do in Naples

Wildlife · Outdoors · Tours

Side Trips

Fishing Charters & Tours, Big Cypress National Preserve, Vanderbilt Beach, Waterskiing & Jetskiing
Highlights from your plan
Big Cypress National Preserve ©
Big Cypress National Preserve
Fishing Charters & Tours
Waterskiing & Jetskiing

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.
On the 19th (Sun), look for all kinds of wild species at North Dry Rocks, then see the vivid underwater world at Grecian Rocks, and then pause for some serene contemplation at Key Largo Baptist Church. On the 20th (Mon), you'll have a packed day of sightseeing: step aboard USCG Duane, admire nature's wide array of creatures at Island Dolphin Care, get close to the beloved marine mammals with Dolphins Plus Marine Mammal Responder, then look for gifts at Sandal Kingdom, and finally take in the architecture and atmosphere at Saint Justin Martyr Catholic Church.

For ratings, where to stay, and tourist information, go to the Key Largo online trip itinerary builder.

Traveling by car from Naples to Key Largo takes 3 hours. Alternatively, you can take a bus. In May in Key Largo, expect temperatures between 34°C during the day and 26°C at night. On the 21st (Tue), wrap the sightseeing up by early afternoon so you can drive to Sanibel Island.

Things to do in Key Largo

Wildlife · Parks · Tours
Highlights from your plan
Grecian Rocks ©
Grecian Rocks
Dolphins Plus Marine Mammal Responder ©
Dolphins Plus Marine Mammal Responder
Shark Diving

3
nights
Sanibel Island

Sanibel Island ©
Take a trip to Sanibel Island if you like pretty sunsets and luxurious resorts.
Here are some ideas for day two: see majestic marine mammals with a dolphin and whale watching tour, walk around Pond Apple Park, and then enjoy the sand and surf at Gulfside Beach.

For ratings, where to stay, reviews, and other tourist information, refer to the Sanibel Island online trip planner.

Getting from Key Largo to Sanibel Island by car takes about 4 hours. Other options: do a combination of bus and taxi; or do a combination of bus and taxi. In May, daytime highs in Sanibel Island are 38°C, while nighttime lows are 24°C. Wrap up your sightseeing by early afternoon on the 24th (Fri) to allow enough time to drive to St. Augustine.

Things to do in Sanibel Island

Wildlife · Parks · Outdoors
Highlights from your plan
Sanibel Captiva Conservation Foundation ©
Sanibel Captiva Conservation Foundation
Gulfside Beach ©
Gulfside Beach
Sanibel Historical Museum and Village ©
Sanibel Historical Museum and Village

3
nights
St. Augustine

St. On the 25th (Sat), enjoy the sand and surf at Jacksonville Beach, then get up close to creatures of the deep with a dolphin and whale watching tour, and then contemplate the long history of Old St. Augustine Village. Get ready for a full day of sightseeing on the next day: take in the architecture and atmosphere at Memorial Presbyterian Church, then contemplate the long history of Colonial Quarter, then take in the history at Mission of Nombre de Dios, and finally kick back and relax at Vilano Beach.

For traveler tips, photos, other places to visit, and more tourist information, use the St. Augustine trip planner.

Traveling by car from Sanibel Island to St. Augustine takes 6 hours. Alternatively, you can do a combination of flight, train, and bus; or do a combination of taxi, bus, and flight. When traveling from Sanibel Island in May, plan for a bit cooler days in St. Augustine, with highs around 33°C, while nights are about the same with lows around 22°C. Wrap up your sightseeing by early afternoon on the 27th (Mon) to allow time for the car ride to Crystal River.

Things to do in St. Augustine

Outdoors · Parks · Beaches

Side Trips

Jacksonville Beach, Crescent Beach Public Beach
Highlights from your plan
Dolphin & Whale Watching
Vilano Beach ©
Vilano Beach
Jacksonville Beach ©
Jacksonville Beach

3
nights
Crystal River

The jewel of Florida's Nature Coast, Crystal River spreads around spring-fed Kings Bay, known for maintaining a constant 22 C (72 F) temperature all year long.
Start off your visit on the 27th (Mon): pause for some photo ops at Old Homosassa Veteran's Memorial. Here are some ideas for day two: add some adventure to your tour with a kayaking and canoeing tour and then tee off at Nancy Lopez Legacy Golf & Country Club.

For maps, photos, other places to visit, and more tourist information, you can read our Crystal River trip planning website.

Traveling by car from St. Augustine to Crystal River takes 3 hours. Alternatively, you can take a bus. Plan for slightly colder nights when traveling from St. Augustine in May since evenings lows in Crystal River dip to 19°C. On the 30th (Thu), you'll travel back home.

Things to do in Crystal River

Outdoors · Tours · Wildlife

Side Trips

Nancy Lopez Legacy Golf & Country Club, Kayaking & Canoeing, Old Homosassa Veteran's Memorial
Highlights from your plan
Kayaking & Canoeing
Crystal River National Wildlife Refuge ©
Crystal River National Wildlife Refuge
Fishing Charters & Tours

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