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The morning summer sun cast its vibrant glow across the road as we whooshed past the retro-style roadside store in South Carolina, hoping to make it to South Florida before the sun dipped into the horizon. Then my husband saw the sign for fresh-baked pies—apple, cherry, pecan, peach, sweet potato and blueberry. My hands grabbed the steering wheel with determination, and I made a quick U-turn.

Roadside store in South Carolina
The Carolina Cider Co. roadside shop in South Carolina.

I was taking those pies home, or as many as our sedan could carry, even if they were jammed in amid the multiple pillows and blankets, empty fast food paper bags, and shiny-new GoPro. Buying a homemade pie in a Low Country store packed to the gills with jams, jellies, cider, grits and the like would be a time-honored way to end a road trip. It was a U.S. East Coast road trip that had taken us through the wide, open spaces of the Deep South to the decidedly more frantic Northeast landscape—hopscotching from one historic era to another. One day we’d be touring Boston’s Granary Burying Ground, where some of the American Revolution’s greats are buried, and a few days later we’d gain a better comprehension of the enormity of the Civil War while walking through historic Charleston and coming face-to-face with the Old Slave Mart, an antebellum slave auction facility.

We’d hopped on I-95 nine days earlier, driving from Miami to Boston, where we vacationed for three days. We were headed back to the tip of the Southeast U.S. again and stopping at the Carolina Cider Co. roadside shop was going to be the culmination to the more than weeklong road trip. During the 3,000-mile roundtrip journey, we’d eaten pizza in New York City’s Union Square; ate lunch alongside centuries-old Spanish ghosts; drove through pastoral towns, as well as noise-polluted metropolises; seen some of the country’s most revered landmarks; and slept in five different cities bursting with history, enjoying a few of the East Coast’s coolest, most restful and top-notch accommodations.

Lunch with Pedro’s Ghost
Spanish admiral Pedro Menendez de Aviles founded St. Augustine, a city in northeastern Florida, in 1565. Four-hundred-plus years later, this destination, the oldest continuously occupied settlement of European origin in the United States, is still going strong, with pirate ships sailing the Inlet, and a charming historic center where multi-colored flowers and lush greenery embrace centuries-old wooden homes and schoolhouses still echo with the sounds of lessons harking back to the 1700s.

StAugustine Old Town
Strolling through St. Augustine’s Old Town.

In this destination—our first stop as we made our way north from Miami—old forts welcome new tourists, and great places for lunch are around every corner. Our recommendation: O.C. White’s, located in the historic Worth building across from the City Marina. Choose from a long list of menu items, including crab gouda-stuffed Portobello sandwich, fried calamari and golden fried shrimp—seafood is king here—and then walk off the meal with a stroll through the Old Town. It’s a distinctly unique place on the Florida map, where chasing ghosts, climbing forts and ziplining over crocodiles are all in a day’s fun. After a bite to eat and some time travel through town, we headed north to Savannah, where we would spend the evening.

It All Started with Anne
Savannah, Georgia’s first city, has survived many heart-stopping events since it was first “discovered” by General James Oglethorpe back in 1733—he was sailing on the ship Anne and landed on a bluff high along the Savannah River. The rest, like they say, is history, with Savannah considered one of the Southeast’s most beautiful cities—so stunning, in fact, it was spared during the Civil War. Today, its famous squares, oak trees dripping with Spanish moss, stylish architecture, artsy vibe and sometimes infamous history draw millions of visitors a year.

Bohemian Hotel Savannah Riverfront
Bohemian Hotel Savannah Riverfront.

We first set eyes on the city under a nighttime downpour, with what seemed to be buckets of water hitting the windshield. And then we saw light—at least the twinkly lights from our home for the evening, the Bohemian Hotel Savannah Riverfront, a Kessler property that’s part of the Autograph Collection.

The rain was still coming down hard as we pulled into the hotel’s driveway, but we were greeted right at our car and escorted quickly into the lobby—no worries about the luggage, someone would grab those. The sexy, inviting interior, with brick walls, mood lighting, snug leather seats and reclaimed oak floors, made us feel instantly cozy. During the brief check-in, our eyes immediately darted to the original art pieces found throughout the lobby—daringly unique for a hotel, but this is a Kessler property, after all. The guestrooms are just as welcoming, with unique features such as seashell-encrusted light fixtures, and touches of velvet, brass and leather. These are fabulous spaces with unique artwork and some with floor-to-ceiling windows that look out over the Historic District.

Given that the weather didn’t let down, we knew we wouldn’t be able to explore the city that night, but we would make the most of our evening with dinner at this fashionable Savannah address. The kids ordered in, and my husband and I went straight to the onsite Rocks on the River, where we ordered a Bohemian Hunt Board (cheese, olives and plenty of meat to go around), fried green tomatoes, truffle fries and crab cake.

Strolling through Savannah’s historic area.

The hotel is located is one of the city’s most iconic tourist areas. It’s on the city’s riverfront, or River Street, home to one-time cotton houses that have been restored to house boutiques, restaurants, and galleries. While strolling along the street the following morning, we peeked into the Savannah Candy Kitchen, where visitors can watch saltwater taffy being pulled and stretched on a 100-year-old machine. Before heading over to the candy store—where we took a few too many bites of the decadent pecan praline—we feasted on a Southern-style breakfast at Goose Feathers Cafe. Highly recommend the eggs Benedict, Savannah-style on a homemade croissant (it’s a long line so recommend clients get there early).

Breakfast is a must at Savannah’s Goose Feathers Cafe.

Having only a couple of hours for some morning exploration, we hopped in the car and drove through Savannah’s historic center, gazing at the squares, well-dressed with monuments and monumental trees, and lined with marvelously chic mansions. While clients are driving through the city tell them to take time to stop at the gothic Cathedral of St. John the Baptist, with its beautiful stained glass windows and definitely circle 30-acre Forsythe Park, with its gorgeous fountain built back in 1858. If visitors have more time in town, plan for a detour to the Bonaventure Cemetery, once home to the famous “Bird Girl” statue, which is now located at the Telfair Museum of Art, housing the oldest art museum in the South.

Savannah church
Cathedral of St. John the Baptist in Savannah.

A Quirky Stay
The scent of mouthwatering cuisine greeted us when we stepped into the Quirk Hotel in Richmond, Virginia. Luckily, we arrived at this Destination Hotels property, our home for the evening, just in time for dinner. The hotel’s Maple & Pine Restaurant is located smack-center in the open-style lobby, and its menu is highly decadent and creative. Our favorites were the seared duck breast with ginger-date puree, roasted spaghetti squash, and Tokyo turnips, as well as the sage fettuccine with heirloom squash, poached egg and country ham. There’s also its to-die-for dessert menu, featuring items like local apple crisp with cheddar cheese ice cream.

Art piece at Quirk Hotel.

While we dined on these delights we noticed a long line waiting to enter the elevator, and being that it wasn’t check-in or check-out time, we enquired what all the fuss was about. Apparently, the hotel’s Q Rooftop Bar is one of the city’s most happening spots, although by the time we finished dinner—we’d arrived at the hotel pretty late because on the way from Savannah to Richmond, my husband insisted we stop at South of the Border in South Carolina (won’t go into much detail on this one, but imagine a Mexico-themed roadside area known for its fireworks shop; and it’s South of the Border, well, because it’s just a hair south of North Carolina)—it was too late to hang out and enjoy the city views from the rooftop.

Quirk Hotel, besides having plenty of history (it’s a 1916 building that housed the J.B. Mosby and Co. dry goods store) offers a quirky style and fabulous art pieces—think portraits of black cats holding an octopus, or stylish, contemporary abstract paintings—and is located in one of the city’s trendiest neighborhoods. It’s a west downtown Richmond neighborhood that has recently become the hub of the city’s arts and creative scene. There are galleries everywhere, including the hotel’s gallery, as well as cafes and it’s near some of the city’s most important landmarks.

Public art in Richmond, Virginia.

The following morning we woke up to a lazy Sunday, and found a fabulous hipster diner, Pearly’s Delicatessen Restaurant, for breakfast that’s located about two to three blocks from the hotel. Along the way, we feasted our eyes on some cool art pieces, including a giant metal sculpture of a policeman’s head protruding from the side of the Richmond Police Department headquarters building. At Pearly’s, we got drunk on cinnamon babka french toast, matzoh brei, and Benny Goodman, no not his music, rather two potato latkes topped with smoked salmon, poached eggs, dill hollandaise and salmon roe.

It was a quiet morning, so we took the opportunity to take a stroll through this very hip neighborhood, and then headed to the White House of the Confederacy in the historic Court End neighborhood. We had to head out of town early, but our next visit to this cool, laid-back, progressive city will take us to the American Civil War Center, and we hope to walk in Lincoln’s footsteps—did you know he visited the city 10 days before he was assassinated? And lest you forget, literary aficionados, this city is also home to the Edgar Allan Poe Museum in Downtown Richmond.

We jumped in the car and headed north, way north to Boston, but before that we had to make another “pit stop” in New York City for pizza, of course (yes, it’s silly—pizza in NYC, but my husband really likes his NYC-style pizza…he’s a romantic, what can I say). Next stop: My sister’s house in Boston.

Sam Adams grave in Boston
Samuel Adams grave at the Granary Burying Ground.

I’ll skip the stay in Boston as it was a family visit, but suffice it to say, it’s Boston, so it’s got a lot going on, and for families wanting to dive into American history, a visit to this New England town is unbeatable. Take a walk along the city’s famed Freedom Trail, have lunch in Quincy Market, and top it off with an Italian pastry and espresso in the North End. It might be evident, but a day trip to Salem is a must on the itinerary; beyond its famous Witch Trials history, this city is just lovely (and Hawthorne fans will get a kick out of it, too). Tip: If you’re in Boston for July 4th celebrations and you’d rather skip the famous Boston Pops celebration, there are areas along the river where spectators get amazing views (crowded, but not overly crowded).

Take a detour to Breezing Along the U.S. East Coast Part 2 here.