Bleisure Travel At Its Best – Our Latest Trip To Costa Rica

We recently took a five-day trip, Thursday to Monday, to Tamarindo, which seemed a perfect example of bleisure (business + leisure) travel. We timed the trip around the annual homeowners’ association meeting at our condo complex, so it was first and foremost a business trip.

Once we had the dates for the trip, we lined up other business meetings and errands since many things are best handled live – in fact, some things can only be handled live. Of course, since Costa Rica is a place that we love, we squeezed in our favorite leisure activities in-between.

A trip to the cable company is rewarded by a picture-perfect sunset

With several recent big tax and business law changes, one errand we had was to re-title our cable/internet accounts to ensure we were getting the proper tax credits for our business expenses.

This errand was earmarked for the day we arrive because traveling to Tamarindo is so easy, and we would arrive by early afternoon. The direct flight from JFK to Liberia takes four and a half hours, and then a shuttle van (Tamarindo Transfers and Tours is our preferred company, air-conditioned and with WiFi!) takes us directly to our condo complex in under an hour and a half.

The cable office was still closed for lunch when we arrived, with no indication of what time they would reopen, and with a line forming outside the door, so we went to The Falafel Bar (one of our favorite restaurants) for our own lunch. Once we returned, the office was open with just one person ahead of us. Luckily the office is in a commercial center with some fun shops, so I got to browse at a boutique two doors down, and Scott handled the account re-titling in minutes.

We had enough time left to get settled at our condo, change into our beach wear, stop at a restaurant on the beach for a drink, and catch a gorgeous sunset at 5:45p.

Three business meetings are coupled with our favorite burger and shake place

The next morning was the HOA meeting, which took three hours! It was very worthwhile, however, to get maintenance updates on the property, hear from other owners (who are onsite much more than us) and go line-by-line through the financials and future budget. It was nice to hear that the condo complex came in under budget, and we even found additional efficiencies for the coming year that enabled us to afford all of the recommended projects.

That afternoon we also met with each of our two property managers. We are looking at some design updates for one of our condos, including a possible kitchen renovation. We met with our condo managers to discuss options for cosmetic updates, like a new dining set and artwork, and also options for the kitchen from a gut remodel to a more modest cabinet refacing. We’re still getting quotes.

With our house property manager, we did a walk-through of recent updates, including a complete replacement of the outer decks and several new furnishings. We also talked about future projects – with a property that sleeps 10, there is always something to do!

Even after all of these meetings, it was just mid-afternoon. With sunset still a few hours away, it was too early to go to the beach as Scott tends to get sunburned. Instead, we ducked into Surf Shack, our favorite of many excellent comfort food places in Tamarindo, (Surf Shack chocolate peanut butter is our go-to milkshake) for an early dinner, and then went to the beach to watch another gorgeous sunset.

Reconnecting with key business contacts is also reconnecting with friends

We were only two days into our trip, and the preplanned business errands were done. Still, we managed to check off two additional quasi-business items from our list.

First of all, we have a running list of Tamarindo restaurants we want to try, which is business because we want to know our local market, including the restaurants. In September, when we were here for a full month, we pulled the Top 30 list on TripAdvisor, as well as local recommendations, and have tried to eat at each one. We are almost done dining at each of the Top 30, but there was one top restaurant on the list, Antichi Sapori, that was closed at that time since it was the low season.

In addition to finally trying Antichi Sapori for dinner, (delicious, great service and a cozy, private outdoor location), we were joined by another couple, who are expats to Costa Rica. While this wasn’t a business meeting, these friends are also business contacts. We had dinner with them on our first trip almost three years ago, and their local knowledge of Tamarindo helped us build the real estate team we use today – they connected us to our real estate attorney, who connected us to both of our property managers, one of which was also our realtor and who connected us to our local accountant.

Reconnecting with friends ends with potential business leads

With one full day to go before heading back to New York City, and a Sunday at that, we expected a 100% leisure day. We went for a morning walk on the beach, followed by breakfast at outdoor Breakfast Grinds.

We cooled down in the pool and even took a nap. Then, I got pinged by a professional colleague I had met years ago who had just arrived in Tamarindo with her husband. Are we available to meet for drinks?

After another sunset walk on the beach, Scott and I headed to Casa Luna in Langosta to reconnect with someone I had not seen in years. We had spoken on a career panel together and stayed friendly since we are both in the executive coaching space, and she’s a fun person. Turns out, she is now working at a top university and offered to refer me to possible coaching opportunities there!

We, of course, offered to share our local knowledge of Tamarindo since they are interested in buying in an international, warm weather place. It was a serendipitous and fun way of capping off a truly bleisure trip.

The easy trip back allows work and play to continue

On the last day, our shuttle van was picking us up at 10am, so we first had time for a walk and a lovely breakfast on the beach at Waffle Monkey.

We got to the airport with plenty of time to enjoy the airport lounge access that comes with our Sapphire credit card (we figure we have already used hundreds of dollars with that perk alone). With our laptops, we have been able to work while flying. I wrote this post in the air, and I also put together my slides for a workshop I am leading later this week.

Choosing to work on the flight back means only two movie reviews to share

I opted to work, rather than watch movies on the way back. But I did see two movies on the initial flight, The Hummingbird Project and Saint Judy.

I love movies with money themes (I profiled six of this genre from 2019), and The Hummingbird Project fits right in there. Starring Jesse Eisenberg and an unrecognizable Peter Skarsgard sporting a bald cap, The Hummingbird Project is about two trading firm employees who try to construct a cable tunnel connecting electronic exchanges in Kansas to New Jersey in order to process trade orders 1 millisecond faster. It sounds like an esoteric bore, but it was quite fascinating to watch this crazy project unfold, as well as see Salma Hayek hamming it up as their former boss who doesn’t like the fact that two key employees bolted on her (and doesn’t take it without a fight). If you like Wall Street-based films, like Boiler Room or Arbitrage or of course Wall Street, you’ll like The Hummingbird Project.

Saint Judy is a legal drama, based on the true story of Judy Woods who successfully argued for asylum for a female Afghan refugee in Los Angeles and changed asylum law affecting women going forward. Not as suspenseful as The Lincoln Lawyer or as melodramatic as Philadelphia, but still enjoyable, especially if you like courtroom movies.

In less than two weeks, I have 17+ more hours of flying time (each way) for our Philippines trip, so stay tuned for more movies!

Our next international bleisure trip is now TBD

We had another international bleisure trip lined up – Singapore in March – but this has been postponed till summer in light of the coronavirus outbreak, since the event was a pan-Asian conference.

On the domestic front, however, now that Florida is our primary residence, all our New York City stays are travel stays and most will be a blend of business and leisure. The first such trip is this week – we return to New York City so I can speak at a women’s professional event, teach at a graduate business school and tape a podcast. At the same time, we can reconnect with family and friends and return to our favorite restaurants.

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Do you have any bleisure (or just business or leisure) travel coming up?