After 7 years permanently on the road for OLX, I longed to decrease business travel. Sadly, the insanity of the US immigration process, meant that the tech team for my new projects had to be in Ukraine, Romania and Argentina rather than New York. While those destinations and closer than most of the OLX destinations, business travel still decreases my quality of life and takes time away from things I would rather be doing like playing video games 🙂

Besides it’s probably not wise to be spending my winters in Ukraine in the middle of war with Russia. I longed to find a destination that could serve both as a gathering point for all my friends, a fun haven of respite from the urban jungle of New York and a great location to move as many of my programmers as possible.

As a good nerd, I wrote a model with the following variables:

• Frequency of flights from New York
• Duration of the flight
• Whether the flight was nonstop or not
• Distance from the airport to the city
• Water temperature in the coldest month
• Number of days of wind above 15 knots (higher being obviously better for kiting 🙂
• Cost of labor
• Cost of living
• Cost of land
• Cost of constructionv
• Murder rate
• Kidnapping rate
• Availability and reliability of high speed Internet
• Ease of immigration

I then went to visit the top destinations in the model: Miami, the Bahamas, Anguilla, the BVI, Costa Rica, Cancun, Tulum, Belize, Bonaire, Playa Grande, Punta Cana and Cabarete.

On a weighted average basis Cabarete ranked by far the highest, but each location had its advantages.

• Bonaire had the strongest wind, the highest water temperature and direct 4 hour flights from the US, but it’s a tiny island of 15,000 people making it impractical and expensive.
• The Bahamas are closer to the US and more developed, but the water is relatively cold in the winter, everything is expensive because the country’s tax system is based on 100%+ import tariffs. The labor market is tight and immigration difficult.
• Belize had by far the lowest cost of land, but is hard to reach, does not have much wind and poor rule of law.
• Tulum was gorgeous, but too far to be practical.
• Playa Grande had a 90 minute drive from the airport and little wind.

Cabarete had the highest weighted average:

• Local people are really nice
• It has 2 daily three and a half hour flights from NY
• Puerto Plata airport is 20 minutes from Cabarete
• There are countless other daily flights to Santiago, 80 minutes away
• Outside of Cabarete land is inexpensive
• Labor costs around $200 / month
• Super high end construction costs only $150 / square foot
• Immigration laws are lax
• The water temperature is 77 degrees in the winter
• There is wind almost every day from January to September (with a wind probability over 90% in the summer and around 70% the rest of the time)
• The rainy season is limited to October 15 – December 15 and even then you still have a 50% wind probability
• The murder rate and kidnapping rates are low
• While the Internet and electricity are not particularly reliable, you can compensate for them with a good generator and by bonding multiple connections together (cable + ADSL + wifi)
• It’s a large beautiful country with dramatic landscapes and the tallest mountains in the Caribbean. Excluding Cuba it’s bigger than all the other countries combined
• It’s a “proper” country with 10 million people with a good labor force and a large enough tax base that tariffs are reasonable

It’s not to say it does not have disadvantages.

• The water is murky and not beautifully turquoise as in much of the Caribbean
• It’s one of the worst countries in terms of reported traffic accidents and road deaths per capita
• There are lots of petty thefts meaning you need guards on your property
• There are way too many guns and drinking and driving
• The permitting process for construction is complex and opaque
• Import tariffs on cars and TVs are high
• There is still some corruption

Even though it ranked highest in the model, Cabarete was a choice both of the heart and of the mind. When I first went there I fell in love with the place and the people. It’s beautiful, raw and authentic. It’s still untouched by “modern civilization.” It stands in stark contrast to Punta Cana in the southern part of the country. Punta Cana also ranked very high in the model and has prettier beaches, but I did not like the resort type atmosphere and overall feel of the place.

Cabarete here I come!