A Solo Road-Tripper Takes His New Girlfriend from Miami to New York (and Doesn't Drive Her Crazy)

Shawn Sachs, partner at Sunshine Sachs, has been going on road trips every holiday season for the past 6 years. This year he has a girlfriend (Laney Crowell, who creates online content at Estée Lauder), so for the first time he has a co-pilot. Read about their recent 1,955-mile adventure from Miami to New York and make sure to check out their photos on their Instagram feeds for more pictures from their trip, @sachsel and @laneycrowell.

We probably stopped three to four times per drive. Finding interesting places to pull off, either for a view or coffee, like at this country store in Front Royal, Virginia, is the key. (All photos courtesy of Laney Crowell and Shawn Sachs)

Day 1: Miami to Amelia Island

It’s Saturday afternoon, and we’ve just arrived in Miami. We had spent the week in Little Cayman Island soaking in the sunshine and relaxing. Now part two of our vacation is starting: a weeklong road trip from Miami to New York City. Shawn has been doing road trips over Christmas and New Years for the past six years, this year he has a co-pilot.

It takes us three flights, two hour-long layovers, and one temporarily lost Global Entry Card to get to our car in the Miami airport Park and Fly. We are picking up our Audi TDI Q7 — the car is perfect. The drive ahead of us isn’t short. Our first stop is Amelia Island, about five hours north. About an hour out, Shawn is so tired driving that we blast the music and have a dance party in the car to keep us awake. He won’t admit it but it definitely involved a lot of Taylor Swift. We get to the Ritz Carlton around 12 a.m. and are asleep by 12:05 a.m.

Day 2: Amelia Island to Savannah

Hour 5: are we there yet?!”

We wake up to the town covered in the most beautiful, thick, white fog. Amelia Island is just north of Jacksonville near the Georgia border. The white beach and the heavy mist are perfect for a morning walk and coffee before heading out to Big Talbot State Park.

Part of the idea behind the road trip is to just get up and go, with as little planning as possible. So when an incredibly nice state ranger immediately notices our lack of planning and directs us to The Ribault Club and Kingsley Plantation on Fort George Island, we head there. We find The Ribault Club at the end of a long sandy road, covered by oak trees dripping in Spanish moss. It was founded in 1928 for the affluent and you can easily imagine women and men walking around with parasols and bowties. I think Shawn might have imagined it more with guns and cigars —but you get the idea. Just a little farther down is Kingsley Plantation. The oldest plantation in Florida, it is a very interesting piece of history that’s not to be missed. It was moving, powerful, and sobering all at once. You go to a place like this and you begin to understand how intertwined slavery is with our country’s history. This plantation does its best to be honest about its past, and it’s something we will never forget.

As the saying goes, when in Rome (or as the case may be, Amelia Island, Florida)…. We stocked up on oranges, but the boiled peanuts are delicious too.

On the way to downtown Amelia we stop at Driftwood Beach, which is something out of Lord of the Rings (or so Shawn says). Miles upon miles of black sand beach covered in driftwood the size of trees. If we had more time, we would have done the mile walk down to the beach instead of just looking at it from the bluff.

On the way to lunch we go flying past a sign that requires a U-Turn: “BOILED PEANUTS & FRESH CITRUS.” Nothing beats a Florida orange – the juice pours through our fingers as we munch from the back of the car. The real test is the boiled peanuts; neither of us has ever tried them. The guy tells us they are 1 quart for $4. Problem is, we really only want a couple of peanuts, so we compromise on a half-quart for $2. He judged and gives us the “you aren’t from around here” look.

Fort Clinch is definitely worth a stop when driving through Florida. It was so well preserved.

Shawn wants to check out Fort Clinch. To be honest I am ready to get to Savannah, but we all know about boys and forts. The stop is actually great. Fort Clinch boasts the longest pier on the East Coast and is one of the most well-preserved 19th century forts in the country. It costs $2 to enter.

Just two hours and 119 miles away, Savannah lies ahead of us. Upon arrival we go straight to our hotel: The Forsyth Park Inn, a tiny bed and breakfast. Since it feels like the right thing to do, we pour ourselves some wine and relax in two white wooden rocking chairs. We rock and sip and sip and rock while we watch the park evolve from dusk to night. Shawn, with a big smile on his face, states, “I did good.” Yes honey. Nice job.

Fast food restaurants in the South have rocking chairs out front — true story. God bless Cracker Barrel.

Dinner is a short drive away at Elizabeth on 37th. Having won more awards than anyone can count, including Top 25 Restaurants in the U.S. by Food and Wine and Top 10 Dreamy Dining Destinations in America, we have high expectations. It doesn’t disappoint. The restaurant is located in an old 1900s Southern Mansion complete with fireplaces, antique furniture, and an armada of oil paintings. Shawn has the oysters prepared two ways, and I pick the homemade mozzarella and tomato salad to start. For our entrees we order the grouper and red snapper specials and then share the triple chocolate fudge cake for dessert.

Day 3: Savannah

We are so anxious to explore Savannah that we barely stay for the hot breakfast at the hotel. Out of the hotel and towards the water we go, stopping every few feet to read the next historical marker or admire a new house. Shawn is really into his camera, so we are also stopping every few feet to take a picture. Strung together these pictures could make a movie.

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Just before getting to the water we pick up sweetened cortaditos at The Coffee Fox (and a couple of sweatshirts from the J.Crew sale rack since we were undeniably underdressed for the rainy weather). Neither of us is really down with taking an organized tour, but one of those horse carriages went by and we couldn’t resist. We jump on a carriage tour to learn more about the city and all its mysterious lore. Our guide Sam and her horse Flint are great. Yes, a carriage ride looks cheesy, but the tour guides are super-informative and move at a nice slow speed so you don’t miss anything. Although at times it would be nicer if it weren’t so cold. Or, rainy. Poor Flint.

Best road trip car I’ve ever had. Audi Q7 Diesel. Comfort, space and great milage.

We heard that Savannah is a bit of a party town on top of being so historic, so we decide to do a little bar hopping. The Tavern at the Old Pink House is situated in Savannah’s only 18th century mansion. The rest burned down — the city has had a lot of tragedy. Some say that’s why it’s haunted. Upstairs is fine dining, but we head downstairs for spicy margaritas, blackened oysters and live music. Afterward we walk to Bernie’s Oyster House on River Street for some down and dirty seafood. Not that raw seafood should be dirty, but Shawn assures me he has eaten here before and that it was totally fine. The oysters were fresh and I had my first crayfish. Regardless we drank a little whisky just to be safe.

From the water to the hotel, it’s about a 20-minute walk through all the squares. Past the monuments and mansions, I could swear something was lurking in the shadows (or maybe that was just Shawn climbing on benches to get a good picture). A hearse drives by packed with people on a haunted house tour. In Forsyth Park we stand next to the fountain for a bit, admiring the beauty and pretending we are characters in Midnight in the Garden of Good and Evil.

Day 4: Savannah to Charleston

First rule of road tripping: when you see a sign for BBQ and a long line, pull over.

Shawn let me sleep in and offered to pick up breakfast. He loves to get up early and take pictures and I like to sleep to a normal hour. This is the perfect compromise. Collin’s Quarter is a few blocks from our hotel and serves Toby’s Estate Coffee, avocado toast, and delicious muesli. We set up a picnic in the hotel room and got to packing. It’s great to have two nights in a city so it doesn’t feel like you’re constantly packing and unpacking. It’s one small request I made before we started this adventure.

On the way out of town we stop by Bonaventure Cemetery. Not the oldest cemetery in Savannah, but definitely the most famous. “Part natural cathedral, part sculpture garden,” the place is almost overwhelming. On the way back to the freeway we saw people standing outside Randy’s Bar-B-Q, so naturally we stop. For some reason Shawn tells me I’m the best girlfriend ever (#bestgirlfriendever). Do other girls not eat BBQ at 11 a.m.?

Bonaventure cemetery could double at a sculpture garden. People say it’s haunted. Mostly Shawn.

Halfway to Charleston we drive through Beaufort for a little break. We get pulled pork and southern egg rolls (the filling was pork and potatoes). Yes, we are eating BBQ again. The town is quaint, but it’s rainy and cold and we want to get to Charleston so we don’t stay for long.

We arrive in Charleston at 4 p.m. and check in to Belmond Charleston Place hotel. After dinner and bunch of cocktails, Shawn wants more drinks. I want more dessert. I win. We go to The Peninsula Grill for their incredibly famous coconut cake. We, make that I, stumble back to the hotel tipsy and full.

Day 5: Charleston (New Year’s Eve)

Once again, Shawn lets me sleep in while he wanders around taking photos. It’s becoming a routine that I’m perfectly fine with. I get in a short run and then we meet up at Black Tap Coffee for breakfast. We stumble upon Kahal Kadosh Beth Elohim — the second oldest Synagogue in the country. We wander on through College of Charleston; founded in 1770 it’s exactly what you would want a southern college to look like. Think Gone with the Wind meets Hope Floats.

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Our favorite part of the day was our walk down to the water. We follow King Street all the way, admiring the houses, each one more unique than the last. Lunch is at Gigi’s Brasserie, where we chat up a distinguished-looking man next to us. He seems to be especially knowledgeable about the oysters he is eating, so we know he is our guy. When we ask him what we should do and see in the city. We figure he is going suggest we visit an old plantation or one of the city’s oldest homes. Instead he tells us that the best activity in Charleston is “drinking and eating, and then drinking and eating again.” I think Shawn and I were both feeling a little guilty about our excessive gluttony, so we take this as validation, and after our oysters we head to Husk for more eating and drinking.

You can’t go to Charleston without going to Husk. Problem is, the reviews we had heard from friends were incredibly mixed. Some hated it, others loved it. We compromise and go to the Husk Bar for cocktails (I get the Garden Party and Shawn gets another Manhattan, apparently his drink of choice on this trip). We top it off with a cheese, apple and pecan plate.

After that, it’s all kind of a blur, being that it is New Year’s and all.

Day 6: Charleston to Durham

Up early (despite a strong argument by me to stay in bed due to a splitting headache) we immediately head to see Angel Oak tree. It’s an Oak Tree that is somewhere between 400 and 1,200 years old. Sadly, the people in charge of the tree were allowed to sleep in (unlike me) and it was closed for the holiday.

We ask one of the locals if there is anything on the drive from Charleston to Durham, N.C. “Strip clubs and fireworks,” they say. One of us was thrilled. I’ll let you guess who. I do a little research and find Brown’s BBQ, for which I receive my 2nd Best Girlfriend Ever Badge. What is it with men and pork? Brown’s was on just about everyone’s list of best BBQ in South Carolina, boasting a spicy vinegar base and great sides. It is an hour detour, but we decide to go for it.

We went an hour (or two) out of our way to get to Brown’s BBQ. The fried chicken made it worth the extra time in the car. Not to mention the hushpuppies.

Brown’s is full of men dressed head to toe in camo fresh from hunting. Regardless of how out of place we are, we pile our plates up high with ribs, pulled pork, fried chicken, sweet potatoes, coleslaw, and hush puppies. To be honest my eyes are a little bigger than my stomach, but it is worth it. Best buffet either of us have ever been to.

We arrive in Durham around 5 p.m. and check into The King’s Daughter’s Hotel. Dinner is at a pizza joint called Lilly’s, which served possibly one of the best pizzas we’ve ever had.

Day 7: Durham to Washington

In the name of accurate blogging, I have to disclose that Shawn hugged me this morning and whispered lovingly in my ear that I smelled like pepperoni. True story.

Eventually we make it to Chapel Hill to tour the college. I have to admit, it made me a little nostalgic. The still-decorated dorms, big bars, store after store filled with light blue UNC paraphernalia, and the palpable energy left over from last semester make me wish I could go back in time for a weekend or two. If you go to Chapel Hill, make sure to stop in Sutton’s Drug Store, a retro spot that has a diner tucked in the back, and then take a spin through Sunrise Biscuit Kitchen drive-through for a biscuit with strawberry jam.

Touring University of North Carolina was so cool. Go Heels. We’d only ever seen their packed basketball games on TV, so we were pretty blown away by the amazing architecture and history.

The reason why we are in the Chapel Hill-Raleigh-Durham triangle is so I can go on a cigarette factory tour (originally we were headed to Charlotte). Apparently cigarette tours are illegal, so the closest we can get is the Duke Homestead and Tobacco Museum. It is small and focused on the history of the crop, not the details I am hoping to hear about the industry. At the very, very end they said, “Oh yeah, and cigarettes have caused some controversy. “Some controversy? Talk about a one-sided rewrite. We walked through quickly (Shawn actually ran) and head to the Tobacco Historic District in search of more information. That turns out to be a renovated factory full of offices — beautifully done, but not exactly educational.

Knowing it’s our next-to-last day before heading back to New York, we are dragging our heels a bit. Yes, we’ve been on the road for two weeks, but we’re having the best time. I had been worried that we would be on each other’s nerves at this point, but it’s actually the opposite. We’re in synch in a way I didn’t know possible, walking in step and even holding hands while driving. I know it’s going to be a not-so-fun transition going back to the real world. Shawn says I’m just going to miss all the pork products. Boys…

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On the way to the Inn at Little Washington we have lunch at Horseshoe Restaurant in South Hill, Virginia. We walk in and are greeted by Joyce, the friendliest waitress of all time: “Hi ya’ll! Sit whereva you like.” I try to order a salad with chicken, but she wasn’t about to let that happen “Suga’ you can have a salad anywhere, you should get the BLT special and don’t forget about our famous brown sugar pie.” I comply and get the bacon, fried green tomato, and pimento cheese sandwich. Shawn gets the bison bacon cheddar cheeseburger. We share the pie. Not sure you will ever find yourself in South Hill, but if you do, visit Joyce.

One of the best things we ate on the trip. A piece of brown sugar pie in at the Horseshoe Restaurant on the way from Durham to Little Washington.

About an hour later Shawn picks out a battlefield to explore. Petersburg National Battlefield is a big open field. Quiet and serene with a scattering of old cannons. While we walk through the small museum, we’re struck by the huge differences, and yet strikingly sad similarities of war between then and now. I’m reading American Sniper right now, so it all feels particularly poignant. I grab the brochures so we can read more in the car. It’s striking to see how much the cloud of the Civil War still hangs over where we have been on our drive. We have seen a fair share of Confederate flags, battlefields, statues, and monuments honoring the fallen soldiers of the Confederate Army.

Around 6 p.m. we arrive at The Inn at Little Washington between Sperryville and Flint Hill, tucked in the Shenandoah National Park. It’s hard to find words to describe this hotel. It’s been ranked one of the best for food and service for over 35 years (Julia Child had her 90th birthday dinner here). I feel like I’m in Downton Abbey with all of the antiques and layers of wallpaper. Our room has a separate living room and a ginormous bathroom punctuated by a huge soaking tub, which I immediately jump in to. Shawn makes up for getting me early.

Day 8: The Inn at Little Washington

Skyline drive was closed this day because of bad weather,so we didn’t get to see the view. But the drive up was breathtaking. Like a car ad.

Shawn and I both get up early to do our morning routine. Shawn grabs his camera and goes exploring to take pictures of the area — he promises that he will add working out to his morning routine after all this eating. He drives up to Skyline Drive — which is closed due to the weather. I don my running clothes and go for a jog to the neighboring town. We meet back up at the Inn for breakfast.

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The house breakfast is a selection of four fresh juices, cashew granola, homemade muffins, croissants, and jams. The yogurt is so unbelievable, Shawn asks about it. We’re told that it’s Greek yogurt mixed with mascarpone cheese and honey. Naturally we wish we didn’t know that, but we still have seconds. Shawn is still puzzled by the fact they gave us four juices and a choice of eight jams.

Hands down the most romantic hotel we’ve ever been to. Shawn got major points for booking us a room here.

The afternoon is the laziest we’ve ever had. Since breakfast was so big we snack on a little cheese and wine while hanging out on the couch in our living room and watching The Wire on our laptop. I finish my book and then take a nap. I should mention that there isn’t any phone reception at the Inn, which is a surprise blessing. We were truly relaxed, a million miles away from New York and work. Sadly, we are actually only one day away. Tears.

Dinner is at 8:45 p.m. We go over early for a cocktail on their velvet couch. Rumor has it the wait staff has a rating system for folks having dinner so they can better serve. It has put us on our best behavior. Dinner is a four-course meal that leaves us speechless. We started with foie gras prepared two ways and oyster shooters with sorbet. Next are scallops and sweet potatoes. I have sweetbreads and homemade pappardelle and Shawn has pheasant and then filet mignon of tuna. When they come for our dessert order you can have one or the sample of seven different desserts. We chose the seven. How many deadly sins are there?

Day 9: The Inn at Little Washington to New York City

Up early we get coffee to go (and more of the cheese-filled yogurt) and then pile in the car. It’s about five hours back to the city. The drive is easy and quick and we get back to the city with enough time to come to terms with the fact that the trip is over. The thing about road trips is that you see so much, you do so much, and it feels much longer than it actually was. Savannah seems like a month ago.

To be honest I wasn’t sure about this trip. I mean, the flight is only 2.5 hours from Miami to New York City. This was Shawn’s thing and I didn’t want him to miss out on something he loves so much. That said, seeing the country, learning about our history firsthand, and yes eating a lot of BBQ, made me really proud and interested in spending more time traveling around the USA.

Can’t wait till next year’s drive. As long as it also involves some green juice.

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