Trading Winter in NC for Puerto Rico: How I Actually Made It Work

January. 75 degrees out in the early evening. After a day of working on real estate on my laptop from my airy, second-story stucco BnB, I finally got to the beach at 6 p.m. I caught a beautiful sunset as I walked barefoot in the sand at the edge of the lapping waves.

People congregated in small groups to chat and soak in the ocean vibes. Some locals were playing dominoes—very popular in PR—and having a picnic dinner. I passed a fisherman with a bucket and rod, and I saw a couple of people out on the water on paddleboards.

The wide-open horizon on the west side of the island was a welcome sight, as was the feeling of warm air on my skin, wearing only shorts and a T-shirt. Just 24 hours before, I was bundled up in layers in North Carolina, where January temps were in the 20s and 30s.

I spent a month or two in Puerto Rico every winter in 2022, 2023, and 2024. It was a goal and a dream for a long time, and then one day I finally said, WTF, why don’t I just do it instead of thinking and talking about it? (This is the first year I haven’t gone, because I am in the process of building a house on my land in NC. I missed the break from winter though!)

It’s Not a Vacation (The Mindset Shift)

The foundational piece that makes this possible is that I work for myself, from home. I can work from anywhere with a Wi-Fi connection. I also set up my life years ago to have very low overhead so I could make art. That low overhead makes it much easier to take a month or two, pay for a BnB, and book airfare.

But the real secret to making this sustainable? I live in Puerto Rico on these trips. It’s not vacation mode.

Sitting on the beach under an umbrella and sipping drinks bores the crap out of me. Instead, I just do my normal life—exercise, work, play—but in a tropical environment. I work a few hours, take an ocean swim at lunch or later in the afternoon, walk on the beach, play pickleball, and explore. Even going to the grocery store is an adventure in a completely different place where most people are speaking Spanish. It’s incredibly rewarding to become immersed in another world for a month or two, rather than just visiting it.

The Operator’s Guide to Puerto Rico

If you want to pull this off without burning cash, you have to understand the mechanics of the island. This is a U.S. Territory, but outside of San Juan, it doesn’t have the same infrastructure as the mainland. Here is the playbook.

The Golden Rule: Avoid the “Gringo Price”

In PR, there is a “gringo price” (a large tax you pay for being a tourist during tourist season) and a local price. Your goal is to get the local price. You do this by making friends. Get involved in local activities—I did it through pickleball, but there is also beach tennis, volleyball, surfing, fishing, scuba, salsa dancing, dominoes- lots of activities! Once you connect with locals, you’ll get turned on to deals that will save you a ton on future trips.

Lodging Hacks

Book Early & Tweak Dates: Tons of people escape to PR for the winter. Start looking early. Tweak your app settings and dates to see if your desired place offers discounts for month-long stays.
Stay Off the Beaten Path: Being a few blocks off the beach or in the next town over from the tourist hotspots will save you money.
Network for the Inside Track: My first time down, I booked a 2-bedroom flat on Airbnb a few blocks from the beach for $1,400 a month. But after spending a couple of months there and making friends, I got the inside track on rentals not published online. I was offered a beautiful place in the hills with an ocean view, five minutes from the beach, for $600 a month. The gringo price for that same place would probably be $600 a week.

Transportation & Infrastructure

Getting There: Airfare to San Juan (SJU) is usually pretty cheap from most places. My last couple of trips were about $350 round-trip. From there, you can catch “pond hopper” planes to other destinations on the island for $50 to $75.
Rental Cars: Rental cars are expensive, and gringo prices peak from December to March. The best deal I got after networking with locals was $800 a month. Unless you are staying exclusively in San Juan, you will need a car to get around.
The Uber Illusion: Uber is widespread in San Juan (and possibly Ponce), but it is virtually non-existent in the more remote parts of the island. Do not count on it outside the city. Taxis are also subject to extreme tourist pricing and limited availability.
Bikes & Scooters: In San Juan, there are plenty of electric scooters and e-bike rentals via apps. In smaller beach towns, a great hack is to just buy a cheap bicycle when you arrive and re-sell it to a bike rental company when you leave, bypassing the jacked-up tourist rental rates.
Wi-Fi & Cell Service: While San Juan is a major, modern city, getting more remote means you may run into spotty Wi-Fi and dropped cell service. If your work requires high-speed, flawless internet, confirm the connection speeds with your host before booking.
Food: Grocery store prices are generally steeper than on the mainland. Local farmer’s markets are a great way to get quality food for less. I found a local fisherman by following a handwritten roadside sign and enjoyed amazing fresh caught local fish at low prices.

Bottom line

If you have a dream to spend time in Puerto Rico or somewhere else, maybe you can make it happen sooner rather than later. Especially if you have the ability to work from home. Be creative, minimize your monthly expenses to create flexibility.

I recommend Puerto Rico. It’s a tropical paradise and the people are friendly and interesting. Plus you’ll meet a mix of mainlanders and former mainlanders turned “gringo-rican”!

Get the Mark Cool Monthly Newsletter- Lifestyle design, Health hacking, and living a calm, grounded life in a noisy world…