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500 days on the road: Tops & Flops of the last 100 days

500 days on the road: Tops & Flops of the last 100 days

Last Updated on April 13, 2021

While we were finishing up our five-week, 5,000 miles (8,000km) road trip last week, we used the long hours in the car to reflect on the last 100 days, which we spent in sunny Lisbon, in Canada, where we traveled in Ontario and Quebec, and finally road tripping along the East Coast and through the South of the U.S.

Lisbon to Toronto

north america road tripHere are the Tops and Flops of our last 100 days:

**Top Travel Moments

Beach days in Cascais, Lisbon

One of the best things about the Portuguese capital is the miles and miles of beaches that surround the city and the best part about that is how easy it is to get to these beautiful beaches. The popular beach town of Cascais is an easy 40 minute train ride along the coast (sit on the left of the train for the best views!). There are beaches all along the way to stop at, but we really loved arriving in Cascais, walking up and down the promenade and lazily laying on the sunny Atlantic shores. The town itself is well worth exploring too, with beautiful tiled houses, and plenty of narrow alleys to get lost in. Because we knew that this would probably be our last chance to be a beach bum for the next three months, we made a few train trips out to Cascais, and we discovered several great restaurants of all budget ranges and cuisines.

Read more: 33 Things we love about Lisbon

reflections cascaisCycling through Ottawa

We love renting bikes in almost every city we visit, but what we loved about Ottawa was just how easy it is to cycle in, through and around this Canada’s capital city. Ottawa has over 200 miles of perfectly-maintained cycle paths that can take you from the city center to lakes or farmland within 30 minutes. Our day saw us spend over seven hours on our Ottawa rental bikes exploring and enjoying Ottawa.

Ottawa parliament sunsetNYC2NOLA Great American Road Trip Highlight: Labor Day weekend in Savannah

Our Great American Road trip from New York to New Orleans brought us to Savannah for Labor Day weekend. Our long weekend there was as relaxing as it was active and a major highlight on our road trip! We were very lucky to be able to party hearty at the Craft Brew Fest at the Westin Savannah. We tasted tons of domestic and international craft brews, bellied up to one of the best Sunday brunch spreads we have ever had, and slept in the most comfortable hotel bed since leaving our Ottawa housesit in early August.

african beers at savannah craft brew festNYC2NOLA Great American Road Trip Highlight: New Orleans

Finding the right way to express just how much we enjoyed New Orleans is still a difficult task, as we were just so surprised at the incredible layers of this fine southern city. Of course we knew that New Orleans was much more than Bourbon Street, but had no idea how fantastic this city is – from the Garden District and Magazine Street to Treme, the sculpture garden in City Park and of course the entire deliciously charming French Quarter.

new orleans louisiana picturesArriving to Chicago in time for my birthday

Our 500th day of travel sees us reaching Chicago just in time for my birthday. This is the first time I have been home to celebrate my birthday since 2003, and only the second time since 1998, so it means a lot to be able to spend time with friends and family while we gear up for the next major leg of our travels. One of my bestest besties from back when phones still had cords threw me a birthday bash with my closest friends and I couldn’t have asked for more. After such a long time on the road, it really warms your heart and eases your soul to be surrounded by your friends.

Favorite Places in the last 100 days


We decided to head to Lisbon on a whim back in May, and the city quickly eclipsed almost all other European cities for us. It’s hard to describe the feeling of sunny freedom we felt here, but it was also the cultural diversity, rich history, tiled houses and exotic-sounding language that sits just outside of our Spanish-speaking reach.

lisbon pictures portugal


The largest city in French-speaking Canada, Montreal is a healthy balance between all that is good about Europe and all that we love about North America. Montreal is a cycling city, easy to explore by bike, the food is delicious, and the culture incorporates the laid-back coffeehouse culture we love so much abut Europe.

montreal canada

Charleston, SC & Savannah, GA

Putting both these small southern cities on our itinerary put us smack in the center of a long-standing rival between Charleston and Savannah. Which do you like better, nearly everyone asked. What do you prefer about Charleston? Don’t you just love Savannah, it has so much more to offer than Charleston, and so on. So, rather than put our foot in it either way, we’re choosing both cities as some of our favorites in the last 100 days – and there is no compromise being made here as we truly loved both! Savannah is quirky, mystic while Charleston oozes that classic southern charm.

charleston & savannah

New York, New York

Anytime and always, we love New York. This time around we spent most of our time in Manhattan exploring the quintessential New York stops: The Statue of Liberty, Ellis Island and a trip on Top of the Rock. We padded the pavement north, south, east and west through Central Park early one morning as well as taking long night strolls through Greenwich Village, Times Square and along 5th Avenue. We also explored some areas that we hadn’t been to before, including parts of Brooklyn, Coney Island and the Little Odessa area around Brighton Beach and are already looking forward to our next visit to the Big Apple!

new york new york

Most disappointing places

Atlanta, Georgia

Maybe we built it up too much and were too excited about spending time in Atlanta, but it turns out – we don’t really understand the city at all. We relate Atlanta to hip hop and R&B, but couldn’t find a trace of promotion around this aspect of the city. Sure, we experienced Buckhead, Vinnings, drove past the Governor’s Mansion and we loved the only-in-Atlanta experiences like the CNN studio tour and the World of Coca Cola, but felt no connection at all with the city. Its expansive, suburban set-up was difficult to navigate without a car, and each trip in the car must be destination based – you have to know where you want to go, you never just happen to pass a great bar or restaurant from the six-lane highways and jump off.

CNN studio tour atlanta

Interstate Highways

We traveled over 3,000 miles from NYC to NOLA, and over 5,000 miles on our Canadian and our U.S. road trips combined, so while we wanted to do a lot of back roads driving, much of the time was spent on Eisenhower’s interstate highway system to get from point A to point B. Some of the drives were breathtaking – especially from Washington, DC to Asheville, but otherwise highway life is an unhealthy, uninspired blend of the same fast-food and budget hotel chains. Finding anything fresh or creative on the interstate is like needle hunting in a haystack.

american interstates highways


Blues, Soul, Elvis…Memphis has a rich music history, but we had a hard time finding much of anything left. Beale Street, once the beating heart of the blues, now seems like a cheap commercialization of its past, and the downtown area lacks charm. But it is the rust on signs and bridges, falling down signs and city center office buildings sitting completely empty that made us so sad.

memphis beale street


Don’t get us wrong – Toronto is a very cool city. Great food, creative street art, very plenty to do, but we didn’t feel the charm of Montreal or Quebec, the ease of Ottawa, and because we had expected to adore the city, we ended up feeling disappointed by Toronto – which doesn’t mean we didn’t like the city, though!

toronto canada

Best food moments

Indian Food in Lisbon

Goa, India was a territory of Portugal until the mid-20th century – a happy discovery for us as we dined at Indian restaurant after Indian restaurant throughout our three weeks in Lisbon. While seafood fans can eat like absolute kings in this port city, vegetarians could have a much harder time finding veggie dining options, but the dozens of affordable, quality Indian restaurants really save the day.

lisbon indian food

La Grande-mere Poule breakfast cafe – Montreal

Cute as a button from the outside, this breakfast cafe offers up hearty but healthy plates of pipping hot pancakes, french toast and enough egg dishes for an entire summer of breakfasts in this fine francophone city.

breakfast montreal

Eggplant Parmesan pizza in New York

We have a must-eat dish in many cities we visit often. In Leon, Nicaragua, we would make a beeline for Desayunazo’s gallo pinto, in Germany it’s pretzel rolls, and in New York City it’s eggplant Parmesan sandwiches…until now. Rarely do vegetarians get to cram an entire baguette of heavy, meaty, saucy Italian deliciousness into their mouths, so eggplant parm sandwiches really used to hit the spot. Until this time. We found this great place off Wall Street that puts thin slices of eggplant Parmesan on pizza. Not eggplant cubes or anything we’ve had infinite times in infinite places. We mean an entire layer of thinly breaded eggplant parm slices on top of delicious New York style pizza with cheese and sauce on top. We now have a favorite New York food, ladies and gentlemen.

eggplant pizza

Mary Mac’s Tea Room – Atlanta, Georgia

If you’re looking for down-home southern cooking with a smile and you happen to be in Atlanta – make sure to eat in one of the six tea rooms at Mary Mac’s. The menu is about as traditional as southern cookin’ can get – drink Mint Julip or Peach Iced Tea to wash down Chicken and Dumplin’s, Crawfish, fried green tomatoes, mac-n-cheese, broccoli-cheese souffle or fried breaded okra. For dessert, we sampled the banana pudding and peach cobbler.

Mary Macs tea room vegetable platter

Travel recommendations


We did not spend one cent on accommodation throughout our time in Canada. This was primarily accomplished through our five-week housesit outside of Ottawa, but in the last 100 days we’ve also really gotten involved with couchsurfing (finally!). We were hosted in Toronto, Montreal and Quebec, and couldn’t be more pleased with how it went, having met interesting locals who gave us tips and showed us around town in a way we never could have otherwise seen those two cities. Not only does couchsurfing save us a lot of money on accommodation, but we also appreciate getting to know areas outside of the downtown hotel areas and getting insider tips from people who live in the towns we visit. is one of the booking websites that offers great mystery deals, whereby if you give up your right to know exactly which hotel you will stay in until after booking, you can choose an approximate area of the city and how many stars the hotel has, and get up to a 60% discount on rooms. We used Hotwire quite a lot on our U.S. road trip, as the site has great deals in many cities allowing us to remain within our comfortable budget range, but stay in hotels that would normally be out of reach for us. We were never disappointed, and stayed in some great hotels thanks to Hotwire in the last 100 days.

Worst travel moments

Movie tour in Savannah

Savannah is famous for both the book and the film version of Midnight in the Garden of Good and Evil, as well as the setting for much of Forest Gump, so we thought a movie tour would be an interesting addition in our touring of this city. We were excited to watch the film clips as the bus went from location to location. Unfortunately, and for the first time ever, we actually recommend our readers NOT to take part in something – avoid the Savannah movie tours. The information was shallow, not knowledgable, there was little passion involved on the part of the guide, and at one point, he offered for everyone to get off the bus and eat ice cream at a well-known ice-cream parlor (aka tourist trap). This was the only tour we had to book a day in advance for, but don’t waste your time or money – these tours are not worth it!

Laptop burn-out

Over 500 days ago we purchased our little Asus Netbooks and loved them as family until one day, Dani’s netbook crashed. Luckily Dani is good at backing up and so didn’t lose everything, but she did lose loads of recent documents and downloads, and we had a heck of time transfering data and getting back up and running on a new computer (a brand-new Apple Macbook Air). The second netbook is on its last leg and also about to crash as well, so we are on the hunt for a new laptop for the next big stop on our trip – Asia!

Dani with her Asus Netbook

Travel mishaps

No Map, No Hotel Room in Boston

Luckily, we have no major mishaps to report in the last 100 days, but we have to admit to one mishap which should not have happened to the well-traveled globetrotting people we claim to be. It was a long, hot drive from Quebec City, across the border (with some hassle to get Dani back into the U.S. which caused a two-hour delay) and into Boston. When we arrived in the dark of night, we were focused only on making it to a bar to meet Adventurous Kate before she left for Europe. We had booked no room in Boston, had no map of the city, and didn’t leave the bar til around 11pm. We headed over to the hostel which was conveniently just around the corner from the bar where we had met, but was completely booked.

We were so ridiculously relaxed about the whole ordeal until it was 2:30am, we had driven for over three hours, couldn’t find an affordable hotel or motel that didn’t have roaches, and, without really saying it out loud, had decided that checking into a hotel wasn’t really worth it anymore, since we had planned an early start on the next day. So we headed over to Cambridge because we knew that sleeping in the car would be safer in Good Will Hunting’s academic stomping grounds. Yes, we slept in the car off of a quiet little side street just around the corner from Harvard University. Oops…

harvard book store in cambridgeIf you enjoyed that, check out more of our Tops and Flops:

Our Tops and Flops of 400 days of travel: Panama, Germany, Italy, Spain
Our Tops and Flops of 300 days of travel: Guatemala, Honduras, Nicaragua and Costa Rica
Our Tops and Flops of 200 days of travel: Mexico, Belize, Guatemala and El Salvador
Our Tops and Flops of 100 days of travel: Las Vegas, California, Arizona, Mexico

Cordie Plaster

Wednesday 12th of October 2011

Hello, I think your website might be having browser compatibility issues. When I look at your website in Chrome, it looks fine but when opening in Internet Explorer, it has some overlapping. I just wanted to give you a quick heads up! Other then that, fantastic blog!


Wednesday 12th of October 2011

Hi Cordie, thanks for stopping by and commenting! We've heard from several people now that there seem to be some issues with the site and we're trying to fix them.. Hope everything will be back to normal asap!!


Tuesday 27th of September 2011

Congrats for 500 days on the road! I'm sorry you found Atlanta disappointing but if you go there again, definitely hit me up for some awesome food recs. You're right - it is one of those cities that are very destination based --- you need to know where to go --- but there are some cool spots to find (and, yes, a car is definitely essential there). So glad that you loved Savannah and Charleston, though. Now you just need to make a trip to my favorite city in the Southeast and in the United States - Asheville, NC!


Tuesday 27th of September 2011

Akila - thanks for commenting! We absolutely loved the South, and obviously should have looked to you for recommendations! How silly of us. But, we did manage to make it to Asheville, too and we loved it!!! We only had 24 hours there after we were re-routed on our coastal road trip thanks to Hurricane Irene, but even just one day was great. It is just so good to know that towns/cities like Asheville exist in the United States - the mindset, the action, the deliberate attempt at something SUCH good food! Yes, we'll have to make a trip back to Asheville someday soon!


Monday 26th of September 2011

What a fun road trip! Where are you heading next?

We've been debating Lisbon back and forth, and just recently a lot of people seem to be recommending it. I'm thinking it will need to get added to our November itinerary... :)


Tuesday 27th of September 2011

Thanks guys! The road trip was incredible, and now we are in Chicago resting up for our big trip to South East Asia! We fly to Bangkok in October and can not wait for this next exciting part of our lives! Now, about Lisbon - go!!! I suppose it depends on your personal travel style and taste, but it's just so great! I don't know about November weather - the beaches won't be as warm, it won't be as sunny, but we just loved the style, the flair, the food, the culture...but I digress...:-)


Friday 23rd of September 2011

Congrats on 500 days! You need to bring that US road trip to the west coast!!


Sunday 25th of September 2011

Thanks Kim! We did the west coast last year, just at the start of our trip. But Vegas and California are definitely calling again soon!

crazy sexy fun traveler

Friday 23rd of September 2011

Glad you had so many great moments ... but we like to remember those not as good, too, right?


Sunday 25th of September 2011

Sure, we remember all the mishaps and the hard times, too. But honestly, we didn't have thaaaat many tough moments in the last 100 days. I think our first foray into Asian travel this year will bring many more!