500 Days on the Road: Top Highlights and Lowlights from Our Last 100 Days
After completing our five-week, 5,000-mile (8,000 km) road trip last week, we reflected during those long drives on our past 100 days. These included sunny days in Lisbon, travels through Ontario and Quebec in Canada, and an epic road trip along the U.S. East Coast and South.
Here are our top highlights and lowlights from the last 100 days:
Top Travel Moments
Beach Days in Cascais, Near Lisbon
One of Lisbon's greatest assets is the miles of beaches surrounding the city, easily accessible by a 40-minute train ride to Cascais (opt for the left side for stunning coastal views). We loved strolling the promenade, relaxing on the sunny Atlantic shores, and exploring the town's charming tiled houses and narrow alleys. Knowing it might be our last beach time for months, we made multiple trips, discovering excellent restaurants across budgets and cuisines.
Read more: 33 Things We Love About Lisbon
Cycling Through Ottawa
We enjoy bike rentals in most cities, but Ottawa stands out with over 200 miles of pristine cycle paths connecting the city center to lakes and farmland in under 30 minutes. We spent seven hours exploring on rental bikes, thoroughly enjoying Canada's capital.
NYC to NOLA Road Trip Highlight: Labor Day in Savannah
Our New York to New Orleans road trip peaked during Labor Day weekend in Savannah. It was perfectly relaxing yet active. We savored the Craft Brew Fest at the Westin Savannah, sampling domestic and international brews, an exceptional Sunday brunch, and one of the comfiest hotel beds since our Ottawa house-sit.
NYC to NOLA Road Trip Highlight: New Orleans
New Orleans exceeded expectations with its layers of charm—from the Garden District and Magazine Street to Treme, City Park's sculpture garden, and the enchanting French Quarter. It's far more than Bourbon Street.
Arriving in Chicago for My Birthday
On our 500th travel day, we reached Chicago just in time for my birthday—my first home celebration since 2003. A dear friend from the landline era hosted a gathering with closest pals, warming our hearts after months on the road.
Favorite Places from the Last 100 Days
Lisbon
We chose Lisbon spontaneously in May, and it quickly became a top European city. Sunny vibes, cultural diversity, rich history, tiled architecture, and its exotic language captivated us.
Montreal
Montreal blends Europe's best with North America's appeal: bike-friendly, delicious food, and laid-back coffeehouse culture in Canada's largest French-speaking city.
Charleston, SC & Savannah, GA
These Southern gems fueled a classic rivalry, but we adored both. Savannah's quirky mysticism complements Charleston's timeless charm—no compromises needed.
New York City
NYC never disappoints. We revisited icons like the Statue of Liberty, Ellis Island, Top of the Rock, Central Park, Greenwich Village, Times Square, and 5th Avenue. New explorations included Brooklyn, Coney Island, and Brighton Beach's Little Odessa.
Most Disappointing Places
Atlanta, Georgia
Atlanta didn't live up to hype. Despite hip-hop fame, we found little promotion. Buckhead, Vinings, CNN tour, and World of Coca-Cola were highlights, but its car-dependent sprawl lacked serendipity and charm.
Interstate Highways
Over 8,000 miles driven included monotonous interstates: repetitive fast-food chains and budget motels. Scenic stretches like DC to Asheville were exceptions.
Memphis
Memphis's blues, soul, and Elvis legacy felt faded. Beale Street is overly commercialized; downtown shows decay with rusty signs and empty buildings.
Toronto
Toronto offers great food and street art, but lacked the charm of Montreal or Ottawa's ease. Expectations led to mild disappointment, though we still enjoyed it.
Best Food Moments
Indian Food in Lisbon
Portugal's Goa history brought excellent Indian spots to Lisbon, ideal for vegetarians amid seafood dominance. Affordable and delicious options abounded.
La Grande-Mère Poule Breakfast Café, Montreal
This charming spot serves hearty, healthy breakfasts: pancakes, French toast, and diverse egg dishes.
Eggplant Parmesan Pizza in New York
Our new NYC must-eat: thin, breaded eggplant Parmesan slices atop classic NY pizza near Wall Street. Elevates the traditional sandwich.
Mary Mac's Tea Room, Atlanta
Authentic Southern fare: Chicken and Dumplings, Crawfish, fried green tomatoes, mac 'n' cheese, broccoli soufflé, okra. Pair with Mint Julep or Peach Iced Tea; end with banana pudding or peach cobbler.
Travel Recommendations
Couchsurfing
No accommodation costs in Canada thanks to a five-week Ottawa house-sit and Couchsurfing in Toronto, Montreal, and Quebec. Locals provided insider tips and authentic experiences, saving money and revealing hidden gems.
Hotwire.com
Hotwire's mystery deals offered up to 60% off by selecting area and star rating pre-booking. Ideal for our U.S. road trip budget, landing us in upscale hotels without disappointment.
Worst Travel Moments
Movie Tour in Savannah
Expecting insights into Midnight in the Garden of Good and Evil and Forrest Gump locations, we were let down by shallow narration, lackluster guide, and tourist traps. Skip it.
Laptop Burn-Out
Our Asus Netbooks served 500 days until one crashed (data backed up) and the other nears failure. Transition to a new MacBook Air was challenging; Asia awaits a replacement.
Travel Mishaps
No Map, No Hotel in Boston
A hot drive from Quebec City led to a late-night Boston arrival without reservations or maps, prioritizing a meetup. After a full hostel, we roamed until 2:30 a.m., then slept in the car near Harvard. Lesson learned.
More Tops and Flops:
Our Tops and Flops of 400 days: Panama, Germany, Italy, Spain
Our Tops and Flops of 300 days: Guatemala, Honduras, Nicaragua, Costa Rica
Our Tops and Flops of 200 days: Mexico, Belize, Guatemala, El Salvador
Our Tops and Flops of 100 days: Las Vegas, California, Arizona, Mexico
