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Top 10 Places to Stop On Your Boston-to-Miami Road Trip

A road trip from Boston, Massachusetts driving along the Atlantic Coast to Miami, or even beyond, to Florida’s southern tip at Key West, can be the trip of a lifetime, by stopping in some of its best destinations along the way. There are multiple fabulous stops for spending a few hours, a day or overnight.You may even want to venture off the main route to do some exploring too, with lots of great detours and scenic byways, hidden beaches, tranquil country roads, vintage diners and more.

Newport, Rhode Island The Breakers, Newport, Rhode Island
Credit: The Breakers, Newport, Rhode Island by Bigstock.com

Newport, Rhode Island

Newport is just an hour-and-a-half’s drive from Boston, but it’s well worth a stop. Not only does it offer a thriving foodie scene, including fresh-from-the-ocean seafood at Bowen’s wharf, but it’s world-renowned for its mansions, remnants of the over-the-top luxurious lifestyles of America’s wealthiest industrialists in the 19th and early 20th centuries. The Breakers is one of the most truly amazing of them all, a Renaissance-style “summer cottage” that was commissioned in 1893 by railroad tycoon Cornelius Vanderbilt II, and inspired by the palaces of northern Italy. It features Italian marble, ornate gold ceilings, French antique furnishings and fixtures, diamonds, rubies and other precious gems encrusted in the walls. If you only have time to see one, it should really be this.

New York City, New York New York City skyline
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New York City, New York

Driving so close to New York City, you won’t want to miss the chance to stretch your legs and enjoy at least some of what the Big Apple offers. You can see a different side of it by walking the 1.5-mile path along the High Line, an elevated walking park that was built atop an unused section of the New York Central Railroad. Or, for the quintessential New York experience, head to Central Park for a stroll, enjoying some great people watching and all sorts of performers along the way.

Philadelphia, Pennsylvania Philadelphia
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Philadelphia, Pennsylvania

In the City of Brotherly Love, you can walk the 35 square blocks of the Old City, lined with buildings from the 18th and 19th centuries, many of which have hosted significant historical events through the years. While gazing at the historical buildings is a must for history enthusiasts, there are lots of places where you’ll want to go in and do a little exploring too, like Independence Hall, the very place where the Founding Fathers of America met to debate and eventually sign both the Declaration of Independence and the Constitution. Paying homage to the famously cracked Liberty Bell, located at the Independence National Historical Park, is also a must.

Washington, DC Washington, DC
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Washington, DC

In the nation’s capital, you can get one of the best crash courses on U.S. history there is, from the National Portrait Gallery with its hall of presidents to one of the latest, the National Museum of African American History and Culture. The Smithsonian Institution is the world’s largest museum complex, made up of 19 separate museums and galleries and entrance to most is free. It houses more than 137 million objects,including the Hope Diamond, the Wright brothers’ 1903 Flyer, and the original Star-Spangled Banner.

Cape Hatteras National Seashore, North Carolina Cape Hatteras National Seashore Bodie Lighthouse
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Cape Hatteras National Seashore, North Carolina

The stunning North Carolina coast is another ideal place to stretch your legs, particularly the Pea Island National Wildlife Refuge along Cape Hatteras National Seashore. A bird watcher’s paradise, you can check out the birds while walking the 13 miles of shore, or just relax and enjoy the scenery.

Charleston, South Carolina Charletson
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Charleston, South Carolina

The charming, historic cobblestone streets of Charleston are great for exploring on foot, but you can also tour the historic district the old-fashioned way, on a horse and buggy, passing magnificent mansions and a number of area landmarks, with something interesting around just about every corner. Sampling the Low Country cuisine is really a must, so you may want to plan to have dinner here to dine on this delicious fare that has influences ranging from English and French to African, introduced by the slaves who were brought here in the past.

Savannah, Georgia Savannah, Georgia
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Savannah, Georgia

Savannah is often considered the “crown jewel” of Georgia, and it’s surely one of the state’s most alluring towns, with its moody Spanish moss and cobblestone streets. Enjoy a quiet stroll under the spectacular canopy of greenery, pop into the unique boutiques, and take in one of the top attractions like River Street and the Davenport House Museums. Before continuing on your journey, you may want to treat yourself at the famously delicious Leopold’s Ice Cream.

St. Augustine, Florida Cathedral of St. Augustine
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St. Augustine, Florida

Your road trip can also bring you to the oldest continuously occupied European settlement in North America: St. Augustine, founded by the Spanish in 1565. Many historic buildings still stand and can be visited today, like the Castillo de San Marcos, built in 1672, the historic city gate and the Plaza de la Constitucion.

Miami Miami Beach Boardwalk
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Head to Miami’s South Beach Art Deco District to discover the world’s largest concentration of 1920s and 1930s historic architecture with many impressive buildings that have been impeccably preserved. The beach is right across the street, so you’ll be able to take advantage of all of that sunshine with a snooze on the soft sand or by spending time in the warm water. While you could end your journey here, it’s well worth driving a bit father to get to the nation’s southernmost point, Key West.

Key West

Key West

Key West is synonymous with fun, from wild times on Duval Street with its legendary bars and eateries to all types of water sports, jaw-dropping sunsets and fascinating museums like the Shipwrecker’s Treasure Museum, the Key West Lighthouse Museum and the Ernest Hemingway House and Museum. But if there’s one thing you absolutely must do, it’s to take a sunset sailing cruise, taking in those spectacular views while sipping a cocktail or two.

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