The Ultimate Guide to a Road Trip from Florida to New York

The Ultimate Guide to a Road Trip from Florida to New York

Road Trips in the USA have always been a thing to me. It probably started after reading Jack Kerouac’s iconic book On the Road and falling in love with films such as Almost Famous, Elizabethtown and Little Miss Sunshine.

There is something magical and unique about getting in a car, choosing the perfect playlists and letting the tarmac behind us. California would be the obvious first option, but what about exploring some iconic American cities? If you love history, this is the perfect path for you!

And how ow long would it take? 3 days? A week? It’s up to you. It’s a long one, but google maps say we can make it in 23 hours.

I would prefer to take my time and enjoy the best of the drive through the States. So, take your time and enjoy my guide of the best 10 cities to visit on your road trip from Florida to New York.

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1-Miami | Florida

I’ve no doubt Florida is fun! And of course, you can be tempted to visit Orlando and indulge in Walt Disney World and hundreds of miles of stunning beaches can inspire you to see more of this beautiful part of South Eastern in the U.S state?

But I would start in Miami to check all flavours and colours of Cuban food, heritage and architecture, as well as pop to Key West to pay a visit to the Ernest Hemingway Home and Museum.

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2-Savannah |Georgia

I have no doubts that I would spend more than one day in Savannah. This coastal city is home to beautiful parks and stunning red-brick architecture. Have a stroll the River Street and don’t forget to visit the cathedral of St. John The Baptist – also known as “The Sistine of the South.

If time is not a probably, lost yourself on the sandy beaches of Tybee Island, only 20 minutes from Savannah downtown. A boat trip to Cumberland Island is also highly recommended.

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3-Charleston | South Carolina

When I was young, I used to associate Charleston only with its eponymous dance moves. But this iconic port city in South Carolina is a popular tourist destination that has certainly much more to offer.

Its historic market is a must-see spot. Placed in the heart of the town, it’s the number one most visited attraction.

Charleston is a city to explore walking around. And it doesn’t matter if the tour is for haunted, historic, gastronomic or plantation spots. Go walking. But don’t forget to visit its stunning harbour and check out its well-preserved building and the Charleston Museum – which is known as America’s first museum founded back in 1773.

PS- If you have some spare time, I would also recommend you pop to the historic Wilmington in South Carolina as well. So much to see, I know!

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4- Williamsburg | Virginia

When reaching Williamsburg, you can’t miss the American Revolution Museum in Yorktown- it’s the largest living-history museum in the World. The city is the home of the Declaration of Independence and Colonial Williamsburg is also the place to be if you want some indulgence yourself in the 18th– century history of America.

Plus, the Jamestowne Rediscovery and its archaeological sites can be worth it to be visited, if you want to investigate the history of the American people a bit further.

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5- Washington | DC

It doesn’t matter how many days you’re saving for this road trip, it’s a fact that you should spend more than two days in Washington to have a gist of the city and its numerous sights.

From International Spy Museum to Lincoln Memorial to Smithsonian National Museum of Natural History. Yep, there is so much to be experienced. It’s true. But as life is made of choices, try to do your best and check whatever fist your schedule and taste.

The Arlington National Cemetery is a must-see stop with all famous presidential graveyards. And if you’re a foodie, Georgetown food tours can be a great way of trying the best of local food.

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6- Baltimore | Maryland

Here’s one of the most exciting stops on this long road trip. You need to make the most of its diverse and contradictory city. Baltimore is a true gem and some areas of the city boost creativity.

So, what to see and do in Baltimore? I would start visiting the stunning Peabody Library – without a doubt, one of the most beautiful libraries in the world. Take some time to contemplate its stack rooms that contain five tiers of ornamental cast-iron balconies. It’s guaranteed there is nothing more beautiful in the city.

Here is a 360 virtual tour of Peabody Library.

Explore the street art of Baltimore visiting the murals spread in different parts of the city. There are online detailed maps of where to see it, but if you’re in a hurry, try the graffiti alley in States North Art and Entertainment district.

Let’s talk about food? Waterside Fell’s Point is the hipster part of Baltimore. The melting pot of foodies with its trendy pub and bars. Not to mention that it’s where most immigrants coming from Eastern Europe, Mexico, Central America and even Ireland ended up living. Can you imagine more diverse gastronomy?

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7- Lancaster | Pennsylvania

Most known for having the largest Amish settlements, Lancaster is another point of interest for those who want to understand their culture. Visit the Amish Village and Farm and House to get an authentic close-up of their lifestyle and culture.

Another spot not to be missed in this beautiful city is the Central Market – the oldest, continuously, running public farmer’s market in the country. It’s a beautiful terracotta building that deserves to be explored.

Have a ride on an authentic steam train of Strasbourg Rail Road to end up your visit to Lancaster in style.

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8- New York | New York

It’s the end of the road trip and it’s time to think about what to do and see in New York. But that’s probably the most challenging part of this trip as well. You can spend life in New York and won’t see a fraction of it.

So, why not enjoy a stroll in Manhattan and choose one of its iconic buildings to check the city from above. Empire State Building? One World Trade Centre? It’s up to you.

I would recommend you to explore Greenwich Village shops, cafes, bookshops and restaurants as well,  and check the Transit Museum in Brooklyn as well. And of course, walk through Brooklyn bridge.

You know, New York can be the end and also the start of any journey.

Check out more things to do in New York here.

Featured Image | Photo by Hugo Kemmel on Unsplash

*This is a collaborative post. 

Simone Ribeiro
Hi! I'm Simone, a citizen of Britain, where I live for over a decade, and of Brazil, where I was born. Midlands Traveller is where I combine my passion for travelling, business and an Eco-friendly lifestyle.