Travel 2019 – Kicking Off A Big Year

2019 will be a major transition year for us. After 23 years of raising two kids, our younger child goes off to college in August.

Caroline and I have had the year 2019 circled on our proverbial calendar for a loooong time. We’ve always been interested in travel but never really had the luxury of doing it, partially because my full time corporate career didn’t leave a lot of room for taking vacations, and partially because we’ve spent the last 15 years building our real estate portfolio, prioritizing the use of our money to fund real estate investments.

Structuring our lives to enable travel

Over the last few years, we have re-organized our lives in such a way that will support us being able to travel. You might say it is the culmination of our three year experiment!

First we significantly expanded our real estate portfolio, then I quit my job to focus on building ecommerce skills, and lastly, we are now in the process of trying to create additional online streams of income in our areas of expertise.

Also, in the last few years we purchased rental properties in Jacksonville and Costa Rica that we can stay in ourselves, so that during some of our “travels” we will still be able to stay in a place we call ours, and in a location very familiar to us.

We want to create a lifestyle in which we can work virtually from anywhere. In our perfect world, we will travel to places when the weather in that place is at least 60 degrees during our time there!

Testing out and loving travel

We dipped our feet into the deep end of the travel pond in 2017, right after I left my corporate job, travelling to the Philippines, India, England and Greece during that year, the first 2 trips with our older daughter and the last 2 with our younger daughter.

We also took a road trip that summer with our younger daughter to the middle of the United States to watch the solar eclipse, and we made numerous trips, just the 2 of us, to Jacksonville and Indianapolis where we own properties, to places like San Francisco, New Orleans and Seattle where Caroline had business, and multiple times to Costa Rica as we looked at real estate and ultimately purchased three vacation rentals.

It was a lot of travel that year, and we loved it! Most importantly, we validated for ourselves that we indeed do like to travel and see new places, and get a sense for how we like to travel and the kind of accommodations we will need. We will be able to transition into the traveling phase of our lives feeling very prepared.

Over the past year we hardly traveled – just one trip to Costa Rica and one trip to the Philippines. Instead we have been focusing more on supporting our younger daughter through all of her school and after school activities, as our traveling has been disruptive to her.

Kicked off the year with a trip to Costa Rica

At the moment, we are in Costa Rica for our first travel of the year. While this trip is mostly centered around business, dealing with our 3 vacation rentals here, it is fine because that is how we plan to travel in the future, traveling but also working as digital nomads either in building our own business or working with clients remotely.

On this trip, as with most others we plan to take in the future, we probably spend about half of our day working, whether it be physically dealing with our properties or working on our websites or content, and about half of the time enjoying ourselves, whether it be the daily walks we take first thing in the morning, the daily walks we do at sunset, or sampling the local shops and restaurants.

This trip is too short at only 6 days, including the travel days, so we are very much looking forward to when we can kick off our longer term travel in August.

Where will we travel in 2019

Back to the main point, once our younger daughter is off to college in less than 7 months, Caroline and I will officially be empty nesters, and nothing will hold us back from travelling.

The big question though, is where to go. We already have a list of our 100 dreams of travel destinations, and we also have several locations we’ve been very interested in seeing. We also have to figure out at what times of the year we want to travel and what times of the year we need to be around for our daughter, particularly around her school breaks. More than likely, in the next few years we will construct travel blocks of time that directly correlate to the college school year.

Therefore, at the moment, we are trying to decide where we will go from late August through December. It will depend on several factors, including where she goes to college, what her schedule is, how much we have to pay, and what trip, if any, we take with our daughter in the summer before she goes to school.

At the top of our list is visiting France, Spain and Portugal, and tentatively we are thinking to travel there from late August through late October. We’ve always been interested in this region as a place to perhaps invest in real estate and we’d love to scout it out. Our older daughter spent 2 summers in Spain and we’d love to visit some of the spots she has been to (Alicante, Basque Country), and perhaps she can get some time off from work to join us.

Caroline has a friend in Galicia, Spain, and another friend who has invested in real estate in Porto, Portugal, and another friend with a rental investment in the south of France – a good start for boots on the ground research. We also love the beach, and all those countries have great beach options to explore.

Then we are thinking we might spend November in Costa Rica. The rainy season typically wraps up in October, but the high tourist season doesn’t usually start until Thanksgiving week, so we can probably stay for a few weeks where (a) the weather should be great, and (b) our condo will likely not be rented.

Then we will probably spend December and January on two activities: seeing family in New York and spending time at our condo in Jacksonville.

And after that, who knows!