Although Kim and I have paused our cross-country roadtrip to winter in Savannah, we haven’t stopped exploring the U.S. While in the South, we want to do our best to learn about the region. Plus, we’ve scheduled upcoming trips to New York City and southern Florida.

Most of our trips are close to “home”. We’ve darted down to Orlando a couple of times (a five-hour drive) to visit friends, but that’s about the farthest we want to drive. (That means Atlanta is within reach should we decide to visit.) For the most part, we’re trying to stay within two or three hours of Savannah. That’s okay. There are a couple of great cities nearby.

In fact, you can create a worthwhile roadtrip by starting in Charleston, South Carolina and working your way down to St. Augustine, Florida. We didn’t do this all in one go, but we’ve seen this stretch in pieces during the past couple of months. Let me tell you about it.


Two hours north of Savannah is Charleston — a sister city of sorts. Charleston was founded in 1670 by English colonists. Today it features stately old homes, plentiful shopping, and lots of restaurants. Plus, there’s plenty to do nearby.

I spent far too much time researching where to stay in Charleston. A lot of the downtown hotels are expensive because they put you in the heart of the city. At first, I thought it’d be best to save money by staying on the outskirts, but then I realized parking is costly too. In the end, I opted to book two nights at The Governor’s House Inn, a bed and breakfast (with free parking) in the former governor’s mansion. It wasn’t cheap, but it didn’t blow our budget either. Plus, the place was amazing. The rooms (and the entire house) are gorgeous, and nearly everything we wanted to see was within walking distance.

[Christmas at the Governor's House]
We loved the Governor’s House. We’d stay there again.

While in Charleston, Kim and I spent most our afternoons and evenings walking King Street and Meeting Street. This historic downtown area is less charming than it probably once was; it’s become a massive outdoor shopping center with stores like Victoria’s Secret and Anthropologie on every corner. But there are also plenty of amazing restaurants all over the place too, and that’s what we were after. Turns out Charleston has the best food scene we’ve encountered since leaving Portland. (We still think our hometown has the best restaurants in the U.S. We’re biased!)

As always, we asked locals for their recommendations. We couldn’t try every place, of course, but we did visit:

  • The Rooftop at the Vendue, a standard bar at the top of a hotel. The food and drinks were meh, but the sunset view of the city was stunning.
  • Burwell’s, which had delicious drinks and an interesting (and tasty!) meat presentation. Your server brings you raw meat and a hot stone. You cook your own food. Sounds odd, but it was awesome.
  • Husk, a trendy place with a companion bar next door. This place is crowded, so get there early (or make reservations). Husk’s upscale southern food was yummy, but the service was iffy.

While afternoons and evenings were devoted to food and drink, our mornings were spent visiting sites outside the city. We drove out to see the famous Angel Oak, for example:

The Angel Oak
The massive Angel Oak is a Charleston landmark.

We spent three hours exploring Middleton Place, a former plantation (and home to the oldest landscaped gardens in the U.S.). We paid to take a tour of the grounds by horse and carriage, which added to the experience. (We actually wanted to visit the well-preserved Drayton Hall but balked at the price.)

On a previous visit to Charleston, we’d already driven through Sullivan’s Island and Isle of Palms (not much to see). We also enjoyed a short morning at Folly Beach, south of town, where we had a great breakfast at the Lost Dog Cafe.

[Middleton Place]
Except for the alligator, we thought the mill pond at Middleton was beautiful.


Savannah isn’t quite as old as Charleston. It was founded in 1733 (also by English settlers). What sets it apart, however, is that most of the historic buildings survived General Sherman’s march to the sea during the Civil War. (Or, as people call it down here, the War Between the States.)

During our time in Savannah, we haven’t played tourist as much as you might expect. Yes, we’ve done some — and I’ll get to those experiences in a moment — but mostly Kim and I have been focused on work. That’s a good thing. But at the same time, we need to be sure we visit a few more places before we leave here at the end of March.

Most of our touring was done at the beginning of November, when Kim’s brother Doug flew out to visit for a couple of days. While he was here, we took a walking tour of Savannah’s historic downtown, strolled the beaches of Tybee Island, boarded a riverboat, and sampled some of Savannah’s restaurants. (Savannah’s food scene isn’t on par with Charleston but it’s still very good compared to most of the U.S.)

Doug and J.D.
Doing the tourist thing with Kim’s brother, Doug.

Kim and I agree that the walking tour of downtown Savannah was the highlight of Doug’s visit. (The tour was free, but everyone tipped the guide, of course.) The walking tour allowed us to get up-close and personal with some of the city’s most interesting buildings and stories. Plus, the slower pace allowed our group to ask about the things that interested us most.

[Savannah Walking Tour]
It’s easy and fun to tour downtown Savannah by foot…

The riverboat cruise was less exciting. Savannah’s waterfront just isn’t that big (or interesting). Plus, this is one of the country’s largest working ports, so there’s mostly commercial traffic along the river, which means lots of factories and warehouses, etc. Don’t get me wrong. The tour was fun, but it seemed expensive for what we got. (This has been a common theme on our trip: Boat tours don’t offer much bang for the buck. The one notable exception is the river-based Chicago architecture tour, which was awesome.)

As you wander downtown Savannah, there are plenty of restaurants to sample. Some of our favorites include:

  • Rocks on the Roof, a rooftop bar similar to the one we visited in Charleston (but with more seating). Again, the food and drinks aren’t great but the views of the river and downtown are worth the visit.
  • Jazz’d, a basement tapas bar with live jazz and blues. Kim and I have been here twice, and we’ll be back. The food and drinks are good and reasonably priced.
  • Treylor Park, a kitschy bar that serves fancified white-trash food like peanut butter and jelly wings, chicken pancake tacos, sloppy joes, and bacon brownies. We loved the food here — but then all three of us had a good buzz on by the time we sat down.
  • The Olde Pink House is a Savannah landmark, a sprawling restaurant in an old pink mansion. The food is good, no question, but the prices are high because this is such a popular place with tourists.

One place we have not tried yet is Mrs. Wilke’s Dining Room, which serves southern food family-style. It’s only open for lunch on weekdays, which makes it tough for us to get to. Plus, rumor has it the place has lines. Locals love it just as much as visitors.

Warning: Savannah has a reputation for crime. I wish I could say this reputation were undeserved, but it’s not. For such a small city, there are an alarming number of shootings. The tourist areas are generally safe. Generally. As always, be sensible when you visit. Be aware of your surroundings. Don’t do anything dumb.

The interesting thing about Savannah is the city isn’t just the city. The downtown is what most visitors come for, but there’s plenty more besides. Because this is one of the oldest colonized areas in the country, you can drive in any direction and come to someplace interesting.

Kim and I live on Whitemarsh Island, which is midway between downtown and another popular location, Tybee Island. Tybee offers sandy beaches and a funky vibe. (Locals talk about “Tybee time”, which is fluid and flexible. They also point out that the place has a reputation as a part spot — as much for the residents as the tourists.) To us, this beach isn’t much — but neither was the beach in Atlantic City. Maybe we’re spoiled by the beaches on the West Coast?

[Fort Pulaski]
Between downtown and Tybee is Fort Pulaski National Monument

That said, we do have some favorite restaurants on Tybee. In fact, we’ve begun doing more date nights there than in town.

The very first place we ate in Savannah was Sundae Cafe, and it’s still one of of our favorites. The bartender is awesome. The same folks run 80 East Gastropub, which isn’t quite as good (although I’m fond of the buffalo chicken mac and cheese). I think our favorite, though, is the Tybee Island Fish Camp, a tiny place (six tables and a bar!) with rich, delicious foods and terrific drinks. (Will, the bartender, recently won the bartending competition at the Savannah Food & Wine Festival.)

Note: The only place where we’re regulars in Savannah? Basil’s, a Mediterranean place known for its beer and pizza. Not a lot of people like Basil’s and we’re not sure why. We always sit at the bar (and in the same spot at the bar) and have a great time chatting with the staff. Plus, the beer and pizza are both different and delicious. Maybe it helps that Basil’s is just a five-minute drive from our condo.

St. Augustine

The final city on our tour is also the smallest. And the oldest. In fact, St. Augustine is the oldest continuously inhabited European settlement in the United States. (Yes, that’s a lot of qualifications. That’s because other sites in Virginia and New Mexico claim slightly different “oldest” bragging rights.) St. Augustine was founded by the Spanish in 1565. There’s a lot of history to explore in this town.

The best way to get a feel for the place is to buy a pass for one of the several trolley rides that wind through the narrow streets. The tour guides point out landmarks and talk about the town’s history. When you’ve finished the loop, you can go back and explore the sites that piqued your interest.

We were fortunate to spend one evening with Allie O, who publishes Simply St. Augustine, a blog designed to help visitors make the most of their trip. She and her husband know all of the best places to eat and drink and visit.

For instance, we never would have known about Odd Birds if Allie hadn’t showed us. This tiny hole-in-the-wall bar offers craft cocktails and small bites. It’s a tight fit, but well worth a short wait. Allie also introduced us to The Floridian, a local favorite.

On our own, Kim and I found The Tini Martini Bar, which doesn’t get great reviews. We liked it, however, especially our bartender. The only place in town where we’ve eaten twice is Taberna del Caballo. Again, this place doesn’t get good reviews (they’re awful, in fact), but we found the staff friendly, the food good, and the atmosphere very much like a Spanish inn.

[St. Augustine Distillery]
Touring the distillery. Ready for samples!

We didn’t just eat food while we were in St. Augustine. We also drank! We joined our friends Toni and David for a tour of the St. Augustine Distillery, which recently set up shop in the city’s old ice house. The tour was fun, the samples fine, and the food in the restaurant upstairs delicious.

It’s important to note that St. Augustine is very touristy. It’s packed with people like us, even in the winter. That means prices for lodging are high, especially near the historic downtown area. Kim and I found a fun solution. When we stay in St. Augustine, which we’ve already done twice, we opt to stay a few miles north of town at the Magic Beach Motel. This motel is quaint (and reeks of bleach) but it’s cheap. Because we spend so much on food when we’re in town, a cheap place to stay is the best option.

[Magic Beach Motel]
The Magic Beach Motel isn’t for everyone, but it’s perfect for us.

Final Thoughts

As with many cities, it’s the downtowns in these old settlements that hold the most charm. Outside the historic city centers, you could be anywhere in Middle America. (Well, anywhere in the South, I guess. The Spanish moss hanging from the trees is unique to this region, as is the predominance of brick buildings and the racial diversity.)

Locals in Charleston and Savannah aren’t that fond of the downtown areas because they’re crowded with tourists. (St. Augustine, especially, feels like one giant tourist trap. A fun tourist trap, but still a tourist trap.) Natives find it frustrating, so they don’t venture into the city center except for work, food, and beer. I get it. But for visitors, these three cities offer a peek at this country’s history, a vibrant restaurant scene, and architecture you can’t find anywhere else.

The Old Sheldon Church
The ruins of the Old Sheldon Church between Charleston and Savannah.

Based on what I know now, I think a fantastic 10-14 day itinerary could be built around Charleston, Savannah, and St. Augustine. Here’s how I’d do it:

  • Days 1-3: Fly into Charleston. Spend two nights exploring the area, including evenings dining downtown. Rent a car.
  • Days 3-5: Drive to Beaufort via Highway 17, stopping along the way to visit the church ruins and other points of interest. Spend two nights, using this as a base to explore Hilton Head Island.
  • Days 5-8: Make the short drive to Savannah, where you’ll spend three nights. Wander downtown. Visit Tybee Island for an afternoon and have dinner at one of its great restaurants.
  • Days 8-10: Slowly make your way down Highway 17, entering the marshes, swamps, and sloughs of Georgia’s Sea Islands. Take time to explore St. Simons Island and Jekyll Island.
  • Days 10-12: Bypass Jacksonville for St. Augustine. (Use either Highway 17 or I-95, as you see fit.) Spend two nights here. See the city by trolley. There’s lots to see and do. And eat.
  • Days 12-13: Finally, scoot down to Kennedy Space Center, about 120 miles south of St. Augustine. (Kim and I haven’t done this yet; we’ll visit the Space Coast when we drive back from Miami in March.)
  • Days 13-14: Zip back to Charleston and spend one last night enjoying the city.

During our time on the road, Kim and I have designed a handful of great roadtrips that we’d happily recommend to others. This is one of them. It’s an excellent way to see the Old South and get a taste for what the culture is like here. Interested in making this journey? Want more info? Ask!

Warning: Drivers in the South suck. Not kidding. Orlando drivers are consistently ranked the worst in the nation by a variety of measures, and their bad habits seem to bleed over into Savannah. (And Atlanta, according to one long-time resident I spoke with.) Pedestrians, especially, need to be careful. Kim and I have had multiple close calls in which clueless drivers have come within inches of mowing us over — while we’re in the crosswalk with the signal. Traffic on I-95 (and most other highways) travels not at 5mph over the limit, but at 10-15. Or more! On Savannah’s surface streets, there are two speeds: full and stopped. When the light goes green, drivers accelerate rapidly. They rush to the next light, braking abruptly when they reach it. Collective fuel efficiency here must be abysmal.

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It’s been more than a month now since Kim and I began to feel road-weary. To add to the fatigue, we spent a week in Charlotte, North Carolina for Fincon, the annual conference for all things financial. Then we spent a week driving all over the Southeast in the Mini Cooper, searching for a place to live.

Note: To add to our desire to settle, I’ve begun working in earnest on my new personal-finance site, Money Boss; meanwhile, Kim has been exploring the possibility of opening an online store.

On the Road Again

Last Monday morning, we piled all of our stuff into the Mini Cooper and drove south out of Charlotte. Initially, we were aiming for Jacksonville, Florida. Our idea was to explore the Sunshine State to see if we could find someplace to stay for the winter. (Yes, we’re well aware that many people have the same idea every year.)

Staying true to our motto as a couple — “go with the flow” — we changed course midstream. While stopped for lunch, I browsed for rentals on Craigslist. For some reason (I can’t remember why), I started with Myrtle Beach, South Carolina.

“There are a lot of cheap places in Myrtle Beach,” I told Kim. “I don’t know anything about the city, but maybe we should start our search there instead of Jacksonville.”

“Sounds good,” she said, and so we veered east. As we drove, we continued to research. “I’m not sure there’s much for us to do in Myrtle Beach,” Kim said. “What about Charleston instead?”

“Charleston works,” I said, and we altered our path once more. Kim, who is a Priceline ninja, snagged a cheap hotel room as we drove, and by late afternoon we were exploring the city.

We liked Charleston just fine. It has some funky neighborhoods and interesting restaurants. Plus it’s filled with history (Fort Sumter!) and close to the beach. Still, it didn’t feel like home to us. In the morning, we drove south toward Georgia. We spent a couple of hours in and around Hilton Head, South Carolina before crossing the state line to visit Savannah.

Savannah! Now here was a city we loved.

Savannah, Georgia

First, Savannah’s setting is strange and wonderful. It’s lush. It’s swampy. It’s flat. The area is heavily forested, and there’s lots of Spanish moss hanging from branches, both in town and outside of it. The trees are filled with noisy birds whose songs and cries are completely unfamiliar to me. Plus, there are tons of turtles in the area. (I like turtles.)

But we loved more than just the city’s setting. Because Savannah is one of the few southern cities to have not been destroyed during the Civil War, there are many old buildings in the area. Plus, large parts have a sort of “seventies” feel that always appeals to me. There’s also a vibrant culture of diverse people in the city, which is something that our home in Portland lacks. The historic district is peppered with parks squares (much like London) and good restaurants and funky shops.

“I could live here,” Kim said. I agreed. (One downside? Except for downtown, Savannah is pedestrian-hostile. There are no sidewalks, cars don’t stop for pedestrians in crosswalks, etc. For a walker like me, this isn’t a good thing.)

Orlando, Florida

Our next stop was Orlando, where our friend Toni Anderson lives. “You should come down here and check it out,” she’d told us at Fincon. “My husband’s parents might even have a room where you could stay for a few weeks.”

We met Toni’s in-laws for lunch and then stayed the night at their house. There company was terrific and the room was perfect — but Orlando didn’t match our vibe. Maybe because we didn’t see enough of it, the place reminded us of any other sprawling, generic medium-sized U.S. city. It could have been Sacramento or Indianapolis or Spokane.

“I keep thinking about Savannah,” I told Kim.

“Me too,” she said. “Cindy and David are great, but I don’t want to live in Orlando. I want to live in Savannah.”

“Let’s go back!” I said. And so we did.

Downtown Savannah

As I sat behind the wheel for six hours, Kim browsed Craigslist and called property managers. We soon realized that our budget — $1000 per month for a six-month rental — wasn’t realistic. Places downtown were renting for at least three times that amount. Even on the outskirts, people were asking for $2000 in rent.

The first place we visited had an ideal location at the edge of the historic city center. It was surrounded by restaurants and shops and park and was only a few blocks from the river. The unit itself was a 500-square-foot loft with hardwood floors and quality fixtures. The downsides? It felt crowded with so much furniture in so little space. Plus, it was a little expensive ($1750 per month). My biggest complaint, however, was the mold we saw everywhere. “I know it’s humid in Savannah, but I’m worried that much mold will screw with my allergies,” I said.

We were tempted to take the place without looking at anything else. We filled out the rental application and paid our $40.

“How soon could we move in?” Kim asked.

“You could move in tomorrow, if you wanted,” the agent told us.

“That’s tempting,” Kim said, laughing. “But we should probably go look at least one more place.”

In the Suburbs

The second place we saw was completely different, a condo between the city of Savannah and nearby Tybee Island. The home was twice as big as the first place and much more modern. It didn’t have as much character, but it provided a number of other advantages:

  • Free parking (for the Mini Cooper, not the motorhome).
  • A community pool and hot tub. (We love hot tubs!)
  • A fitness center just outside the front door. (Seriously, a thirty second walk from door to door.)
  • Perhaps best of all, two bathtubs in the unit.

Plus, the unit would only cost $1325 per month (plus utilities).

“What do you think?” Kim asked after our tour of the condo. “Should we start a list of pros and cons?”

“I’ll be honest,” I said. “I love the place downtown and it’d be a lot of fun to live there, but it doesn’t match our goals for the next six months. We want to work. We want to eat right. We want to exercise. In town, there’d be too many temptations and distractions. Out here, we still have access to that stuff when we want it, but there’s a twenty minute barrier between us and bad behavior.”

“That’s true,” Kim said. “Plus, out here there’d be no excuses with the exercise. We’d have a gym outside our front door.”

“Exactly,” I said.

“And I’ll be honest too,” said Kim. “My heart sunk when I saw there wasn’t a bathtub in the apartment downtown. Here we’d have two bathtubs — one for you and one for me. Not to mention the community hot tub and pool.”

“See,” I said. “I don’t think we need to make a list of pros and cons. I think the choice is obvious. We can save $400 per month by living out here, and we’ll be better able to do the things we want to do. Let’s take it.”

Home Sweet Home

So, there you go. Kim and I will spend the next six months as residents of Savannah, Georgia. We plan to spend most of our time exercising and working, but we’ll make some weekend trips to Florida and the Carolinas and possibly even New Orleans. For me, it’ll be fun to live somewhere other than Oregon for a while. I’ve lived my entire life within a 25-mile radius of the town where I grew up. Now I can experience something different.

As you can guess, this means Far Away Places will be on hiatus for a while. In a week or two, I’ll publish a stats breakdown of our first six months on the road. Plus, I’ll post updates here whenever we take jaunts outside Savannah. But until the end of March, I’ll be focusing my attention on two places: writing about radical personal finance at Money Boss and writing about personal development at my personal site.

So, until the spring: Be well, my friends!


A Slight Change of Plans

September 5, 2015

“I’m going to be honest with you,” Kim said the other day. “I’m tired. I love our life on the road, but I’m ready to take a break. I want to pick a place and stay put for a while.” I could tell she was reluctant to say this. Our year-long RV trip is a […]

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Niagara Falls and Northwestern New York

August 31, 2015

After two weeks in Ohio, Kim and I were pleased to move on to new territory. We leaped across the northwest corner of Pennsylvania and set up camp near Niagara Falls, New York. Kim had never visited New York before this trip. And although I’d been to New York City a couple of times, I […]

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Roller Coasters and Rock and Roll in Cleveland, Ohio

August 26, 2015

After a few days exploring West Virginia, Kim and I drove north to Cleveland, Ohio, on the shore of Lake Erie. Kim and I passed an entire week in and around Cleveland. There was lots we wanted to do — but mostly we stayed home. Why? A couple of reasons: First, lately we’ve both been […]

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Wandering through West Virginia

August 19, 2015

Between southern Ohio and northern Ohio, Kim and I found the time to spend a couple of nights in wonderful West Virginia. Seriously, this state is gorgeous. It’s easy to see why John Denver called it “almost heaven”. At the start of this trip, we were blown away by the beauty of Arizona. Since then, […]

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Finding Time for Friends (Old and New)

August 15, 2015

For me, one of the joys of visiting the Midwest was finding time to connect with friends, both old and new. I’ve mentioned some of these folks already. After our engine replacement in South Dakota, for instance, we drove to St. Cloud, Minnesota where I had dinner with two of my favorite people, Aimee and […]

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One Week in Indiana’s Amish Country

August 11, 2015

After two weeks touring the Great Lakes and the Great North Woods, Kim and I drove south to Shipshewana, Indiana to visit Amish country. Before we looked around, however, we took a couple of days to decompress. As I’ve mentioned before, there are three types of days on this trip: travel days, touring days, and […]

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Making Our Way Around Lake Michigan

August 6, 2015

After a week on the shores of Lake Superior, Kim and I made our way to another great lake, Lake Michigan. There, over the course of a couple of weeks, we made our way almost completely around this vast body of water. We started our tour of Lake Michigan in the small town of Oostburg, […]

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On the Shores of Lake Superior

July 24, 2015

After nine days of unplanned rest in Plankinton, South Dakota, Kim and I resumed our year-long RV trip around the United States. We drove slowly at first, unwilling to put too much stress on the motorhome’s new engine. With each passing hour, however, our confidence grew. By the end of the day, Bigfoot was humming […]

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