The 50 Most Beautiful Cities – Did Your Favorite Make The List?

The Flight Network, a deal-focused travel provider, polled over 1,000 travel writers and agencies (including Costa Rica FIRE!) to come up with its 2019 list for the 50 most beautiful cities. And the top 10 winners are:

1. Paris
2. New York
3. London
4. Venice
5. Vancouver
6. Barcelona
7. Cape Town
8. San Francisco
9. Sydney
10. Rome

In addition to our hometown New York City, I voted for Tamarindo, though it’s really a town, not a city. The five South and Central American cities that did make the list included Rio de Janeiro in Brazil (15), Buenos Aires in Argentina (20), Quito in Ecuador (32), Cusco in Peru (34), and Cartagena in Colombia (44).

It was fun checking off cities we had already seen, seeing what was already on our dream list of travel destinations and discovering new ones to add to our list. Did your favorite city make the list?

Travel plans resemble a logistics puzzle

We are excited to reach the empty nest stage because it gives us freedom to travel outside the rigid (and expensive) school calendar. The obligations on the college calendar are definitely an improvement over the K-12 constraints. Since airfare to and from the home city is often the biggest expense, it would be nice to stay in one continent for months at a time and knock off multiple cities in one long trip.

However, there are still school events, like family weekend and the major holidays, which make extended travel difficult. In addition, Scott has his marathon schedule (he’s trying to run a marathon in all 50 states), and I have consulting commitments. While we did have an uninterrupted month of travel to Costa Rica in September, the rest of the year is planned around consulting (New York, California, Connecticut) and running (the Tucson Marathon in Arizona in December).

We also have our real estate business to factor in. We want to trim our Florida rental portfolio, and we currently have one of the condos on the market. However, the tax hit on that condo would be over $20,000, so we are reconsidering whether to sell right now or move into the place first, establish residency and sell once we have the capital gains exemption (if the home you sell is your primary residence and you have lived there two of the last five years, a married couple can exclude up to $500,000 in gains from tax!).

Moving into the condo would take time and some renovation. Already, we’re considering shortening or even postponing our previously planned Asia trip in first quarter 2020. That would keep us from knocking several of the beautiful Asian cities off the list!

Decide where to travel based on where the travel deals are

One good thing about having a flexible FIRE schedule is that you can jump on travel deals as they arise. Since most of these top 50 cities are major travel destinations, they are serviced by multiple carriers, and there should be some destination on sale somewhere.

When we decided to spend two weeks in the south of France, this was in large part due to seeing a cheap flight using the Skyscanner Everywhere search. I have also heard of people finding great deals using Momondo and Google Flights.

I have also signed up for alerts on Airfare Watchdog and Scott’s Cheap Flights (another Scott, not my husband). I am using the alerts just to get myself familiar with prices so that I will better know a deal when I see one. We haven’t so far used any of the alerts to actually book a trip. I actually find the frequency and amount of information to be more overwhelming than directly useful right now, but since we want to travel a lot, I think of the overwhelm as a research investment.

Scott is the go-to person in our household for discovering new places using AirBNB. Most recently, during our monthlong stay in Costa Rica, we took a side trip to the Caribbean side and stayed in an AirBNB in a small town, Cahuita, close but still away from the most touristy locations. It was a treat to sample mom-and-pop restaurants and see the neighborhood kids coming to and from school.

Build travel around work – and work around travel

We are already planning travel around work. In the fall, I typically spend a few days coaching at Yale in New Haven, CT, and while that’s commutable on a daily basis from our New York City place, we’re staying in the New Haven area instead. This will allow us to sample the local restaurants and attractions on my off-hours.

During the marathon trip to Tucson, AZ, we are staying there a week longer than we need to, and adding some real estate business in Phoenix, as well as a bucket list trip to Sedona. If we need to be somewhere for work, might as well get some travel out of it!

On the flip side, I also look at where we like to travel and figure out how to generate work out there. Sometimes it’s just continuing my existing work virtually – I have been coaching, writing and even did a media guest spot while in Costa Rica. Sometimes, it’s pitching clients who have offices in geographies where we want to be – we built a two and a half week trip all over India out of one assignment and saw beautiful city #48 (Jaipur, India) in 2017.

A geography where we like to travel is one criteria for how we pick our real estate geographies. It led us to pivot to vacation rentals in Tamarindo and to sell our rental portfolio in Indianapolis.

We are prioritizing our next international trips around destinations we are also considering for real estate. There are so many places to go – might as well get double-duty with one trip!

NOTE: Photo at the top of the page is Buckingham Fountain in Chicago (#25)