19 days in United States Itinerary
Created using Inspirock United States vacation planner
Start: Washington
Drive
1
Richmond
— 1 day
Fly
2
Charleston
— 2 nights
Drive
3
St. Augustine
— 1 day
Drive
4
Key Largo
— 3 nights
Drive
5
Islamorada
— 3 nights
Drive
6
Marathon
— 2 nights
Drive
7
Little Torch Key
— 1 night
Drive
8
Big Pine Key
— 3 nights
Drive
9
Key West
— 3 nights
End: Key West
Mon, May 10 - Fri, May 28
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Richmond — 1 day
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The River City
The capital city of Virginia, Richmond has diverse architecture, a large collection of monuments, and world-class museums that reveal the city's important role in American history.Start off your visit on the 10th (Mon): take in the history at Richmond National Battlefield Park, then do a tasting at Blue Bee Cider, and then contemplate the long history of Maggie L. Walker National Historic Site.
For more things to do, other places to visit, where to stay, and more tourist information, read our Richmond trip planner.
Washington to Richmond is an approximately 2-hour car ride. You can also drive. In May, plan for daily highs up to 78°F, and evening lows to 57°F. Finish up your sightseeing early on the 10th (Mon) so you can catch the flight to Charleston.
Highlights from your trip
Charleston — 2 nights
Many visitors describe their Charleston holiday as a warm embrace by an old, dear friend--who lived about 200 years ago.Kick off your visit on the 11th (Tue): get a new perspective on nature at The Charleston Museum, contemplate the long history of Joseph Manigault House, take in the spiritual surroundings of Kahal Kadosh Beth Elohim, then hit the best photo ops around with an inspiring photography tour, and finally admire the local landmark of Pineapple Fountain.
To find reviews, maps, where to stay, and more tourist information, go to the Charleston trip site.
You can fly from Richmond to Charleston in 5 hours. Alternatively, you can drive; or do a combination of train and car. Traveling from Richmond in May, expect somewhat warmer with lows of 64°F in Charleston. Finish your sightseeing early on the 12th (Wed) so you can drive to St. Augustine.
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St. Augustine — 1 day
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St. Start off your visit on the 12th (Wed): steep yourself in history at Villa Zorayda Museum, pause for some serene contemplation at Memorial Presbyterian Church, learn about all things military at Spanish Military Hospital Museum, then steep yourself in history at Pena-Peck House and Woman's Exchange of St Augustine, and finally see the interesting displays at The Ximenez-Fatio House.
To see maps, traveler tips, more things to do, and tourist information, you can read our St. Augustine road trip planning tool.
You can drive from Charleston to St. Augustine in 5 hours. Other options are to fly; or take a bus. May in St. Augustine sees daily highs of 83°F and lows of 67°F at night. Finish up your sightseeing early on the 12th (Wed) so you can catch the flight to Key Largo.
more
To see maps, traveler tips, more things to do, and tourist information, you can read our St. Augustine road trip planning tool.
You can drive from Charleston to St. Augustine in 5 hours. Other options are to fly; or take a bus. May in St. Augustine sees daily highs of 83°F and lows of 67°F at night. Finish up your sightseeing early on the 12th (Wed) so you can catch the flight to Key Largo.
Highlights from your trip
Key Largo — 3 nights
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Diving Capital of the World
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.You'll explore the less-touristy side of things at Anhinga Trail and Key Largo Baptist Church. The adventure continues: see the vivid underwater world at Spiegel Grove, identify plant and animal life at Florida Keys Wild Bird Rehabilitation Center, take in the architecture and atmosphere at Saint Justin Martyr Catholic Church, and discover the deep blue sea with Conch Republic Divers.
To find traveler tips, where to stay, reviews, and other tourist information, go to the Key Largo driving holiday planning app.
Getting from St. Augustine to Key Largo by flight takes about 3 hours. Other options: drive; or take a bus. May in Key Largo sees daily highs of 85°F and lows of 72°F at night. Wrap up your sightseeing on the 16th (Sun) to allow time to drive to Islamorada.
Side Trip
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Islamorada — 3 nights
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The Village of Islands
Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.Step off the beaten path and head to History of Diving Museum and Rain Barrel Village. Get some cultural insight at Pasta Pantaleo Signature Gallery and Old Road Gallery. There's much more to do: sample the tasty concoctions at Florida Keys Brewing Company, kick back and relax at Anne's Beach, soothe aching muscles at Island Flow Yoga, and see what you can catch with a fishing tour.
Quickly create a custom-made itinerary for Islamorada using our trip planner.
Islamorada is very close to Key Largo. In May in Islamorada, expect temperatures between 88°F during the day and 77°F at night. Finish up your sightseeing early on the 19th (Wed) so you can go by car to Marathon.
Highlights from your trip
Marathon — 2 nights
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Heart of the Florida Keys
A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.Start off your visit on the 19th (Wed): see what you can catch with a fishing tour, then tour the pleasant surroundings at Sunset Park Beach, then browse the exhibits of Shady Palm Art Gallery & Photography, and finally see the vivid underwater world at Sombrero Reef. Get ready for a full day of sightseeing on the next day: stroll through Sombrero Beach, look for all kinds of wild species at The Turtle Hospital, then look for all kinds of wild species at Crane Point Museum & Nature Center, and finally pause for some serene contemplation at San Pablo Catholic Church.
For more things to do, where to stay, ratings, and more tourist information, you can read our Marathon online route planner.
Drive from Islamorada to Marathon in an hour. Alternatively, you can take a bus. In May, plan for daily highs up to 88°F, and evening lows to 77°F. Wrap up your sightseeing on the 21st (Fri) to allow time to drive to Little Torch Key.
Side Trip
Highlights from your trip
Little Torch Key — 1 night
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Kick off your visit on the 21st (Fri): relax and rejuvenate at Angelic Moon Holistic Day Spa & APOTHECARY, then get a new perspective on things with High Tide Adventures, then visit a coastal fixture at American Shoal Lighthouse, and finally enjoy breathtaking views from Sugarloaf Key Bat Tower.
For where to stay, photos, traveler tips, and tourist information, refer to the Little Torch Key online trip itinerary builder.
Drive from Marathon to Little Torch Key in an hour. Alternatively, you can drive. In May, plan for daily highs up to 88°F, and evening lows to 77°F. Wrap up your sightseeing on the 22nd (Sat) to allow time to drive to Big Pine Key.
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For where to stay, photos, traveler tips, and tourist information, refer to the Little Torch Key online trip itinerary builder.
Drive from Marathon to Little Torch Key in an hour. Alternatively, you can drive. In May, plan for daily highs up to 88°F, and evening lows to 77°F. Wrap up your sightseeing on the 22nd (Sat) to allow time to drive to Big Pine Key.
Side Trips
Highlights from your trip
Big Pine Key — 3 nights
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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. Relax by the water at Bahia Honda State Park and Calusa Beach. Explore hidden gems such as Fishing Charters & Tours and Long Beach. There's lots more to do: look for all kinds of wild species at Blue Hole, view the masterpieces at Artists in Paradise Gallery, and relax and rejuvenate at A Caribbean Dream Salon & Day Spa.
For photos, other places to visit, more things to do, and tourist information, go to the Big Pine Key tour planner.
Big Pine Key is very close to Little Torch Key. In May in Big Pine Key, expect temperatures between 88°F during the day and 77°F at night. Cap off your sightseeing on the 25th (Tue) early enough to go by car to Key West.
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For photos, other places to visit, more things to do, and tourist information, go to the Big Pine Key tour planner.
Big Pine Key is very close to Little Torch Key. In May in Big Pine Key, expect temperatures between 88°F during the day and 77°F at night. Cap off your sightseeing on the 25th (Tue) early enough to go by car to Key West.
Highlights from your trip
Key West — 3 nights
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Conch Republic
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.Explore hidden gems such as U.S. Coast Guard Cutter Ingham Maritime Museum and St. Paul's Episcopal Church. Get some historical perspective at Saint Mary Star of the Sea and Key West Historic Seaport. The adventure continues: see the vivid underwater world at Vandenberg Wreck, explore the different monuments and memorials at Key West Cemetery, take in the pleasant sights at West Martello Tower, and identify plant and animal life at Key West Butterfly & Nature Conservatory.
To find where to stay, traveler tips, ratings, and more tourist information, use the Key West online tour planner.
Getting from Big Pine Key to Key West by car takes about an hour. Other options: take a shuttle; or take a bus. In May in Key West, expect temperatures between 85°F during the day and 77°F at night. You will have some time to spend on the 28th (Fri) before leaving for home.
Highlights from your trip
United States travel guide
More than the country of car-packed streets seen in TV shows and movies, the United States of America is a complex and diverse home to over 300 million people living in a wide range of landscapes and climates. From its big-city skyscrapers to its sprawling natural parks, the country's ''melting pot'' combines many ethnic groups that share a strong sense of national identity despite their cultural differences. A country of road trips and big blue skies, the United States harbors orderly cities filled with restaurants, parks, museums, and innumerable sightseeing opportunities, as well as pristine natural areas perfect for a holiday in the great outdoors. To see as much as you can of this diverse land quickly, drive over some of the more than 6 million km (4 million mi) of highways leading through deserts, mountain peaks, fertile fields, and giant urban centers.
