19 days in United States Itinerary

19 days in United States Itinerary

Created using Inspirock United States vacation planner

Make it your trip
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

S M T W T F S
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Richmond

— 1 day

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. 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.

Things to do in Richmond

Historic Sites · Wineries

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, steep yourself in history at Joseph Manigault House, then take in the spiritual surroundings of Kahal Kadosh Beth Elohim, then capture your vacation like a pro with an inspiring photography tour, and finally admire the local landmark of Pineapple Fountain.

To find more things to do, ratings, traveler tips, and tourist information, read our Charleston road trip planning website.

Fly from Richmond to Charleston in 5 hours. Alternatively, you can drive; or do a combination of train and car. Expect somewhat warmer evenings in Charleston when traveling from Richmond in May, with lows around 64°F. Finish up your sightseeing early on the 12th (Wed) so you can go by car to St. Augustine.

Things to do in Charleston

Historic Sites · Museums · Tours

St. Augustine

— 1 day
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.

Things to do in St. Augustine

Historic Sites · Museums

Key Largo

— 3 nights

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 Florida Keys Wild Bird Rehabilitation Center. Your inner history buff will appreciate Key Largo Baptist Church and Saint Justin Martyr Catholic Church. There's lots more to do: explore the gorgeous colors at Spiegel Grove, identify plant and animal life at North Dry Rocks, discover the deep blue sea with Conch Republic Divers, and stroll through Harry Harris Park.

To see reviews, maps, photos, and more tourist information, read Key Largo trip tool.

Fly from St. Augustine to Key Largo in 3 hours. Alternatively, you can drive; or take a bus. Expect a daytime high around 85°F in May, and nighttime lows around 72°F. Cap off your sightseeing on the 16th (Sun) early enough to go by car to Islamorada.

Things to do in Key Largo

Parks · Wildlife · Outdoors · Historic Sites

Side Trip

Islamorada

— 3 nights

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 Florida Keys Brewing Company. Get some cultural insight at Rain Barrel Village and Lobster Trap Art Gift Shop and Gallery. There's much more to do: cast your line with a fishing tour, view the masterpieces at Old Road Gallery, appreciate the extensive heritage of Indian Key State Historic Site, and indulge your thirst for a good beer at Islamorada Brewery & Distillery.

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.

Things to do in Islamorada

Museums · Shopping · Outdoors · Historic Sites

Marathon

— 2 nights

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 get a taste of the local shopping with 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.

Things to do in Marathon

Parks · Wildlife · Outdoors · Beaches

Side Trip

Little Torch Key

— 1 night
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. 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.

Things to do in Little Torch Key

Wildlife · Historic Sites · Outdoors · Spas

Side Trips

Big Pine Key

— 3 nights
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 A Caribbean Dream Salon & Day Spa. There's much more to do: kick back and relax at Long Beach, view the masterpieces at Artists in Paradise Gallery, and look for all kinds of wild species at Blue Hole.

To see traveler tips, ratings, reviews, and tourist information, go to the Big Pine Key trip planner.

Big Pine Key is just a stone's throw from Little Torch Key. In May, plan for daily highs up to 88°F, and evening lows to 77°F. Finish your sightseeing early on the 25th (Tue) so you can drive to Key West.

Things to do in Big Pine Key

Parks · Outdoors · Wildlife · Beaches

Key West

— 3 nights

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.
Deepen your sense of the past at sights like Saint Mary Star of the Sea and Key West Lighthouse and Keeper's Quarters Museum. Get some cultural insight at The Ernest Hemingway Home and Museum and Key West Historic Seaport. And it doesn't end there: look for all kinds of wild species at Vandenberg Wreck, take in the pleasant sights at Key West Garden Club, stroll through West Martello Tower, and pause for some serene contemplation at St. Paul's Episcopal Church.

For ratings, more things to do, photos, and more tourist information, refer to the Key West travel tool.

Traveling by car from Big Pine Key to Key West takes an hour. Alternatively, you can take a shuttle; or take a bus. In May, daytime highs in Key West are 85°F, while nighttime lows are 77°F. On the 28th (Fri), you'll have the morning to explore before heading back home.

Things to do in Key West

Historic Sites · Parks · Museums · Wildlife

United States travel guide

4.5
Specialty Museums · Beaches · Historic Sites
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.