How to Escape Winter and Travel to Costa Rica

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If you know me well you know I live for lifestyle design. I dream of future vacations near and far and finally owning my dream home(s). I live for being the designer of my day, the architect of my life.

Last year we had had enough. We declared it would be our last Winter ever in New York City. We were sick of the gloomy days and heavy snow boots. We were sick of "second day snow" as we call it here in New York (or maybe that’s just me), when the dogs have all made their mark, when the beautiful sheet of first day snow soon turns into a dirt-marbled sludge. 

Being deficient in Vitamin D didn’t help either.

So we did what few people do when they’ve had enough of their shitty experiences: we made a plan. Somewhere warm. Morning dips in the ocean, afternoon hikes in the mountains. Daily yoga sessions, Tons of sunshine.

But how?

Her name was California. She’s always been beautiful. You see, I’ve wanted to live there since I was 15. My dad lived there with his first family in the 70s. They all had afros and wore flare pants. They even had a house with a SWIMMING POOL. In my eyes, they had it all.

But I wasn’t willing to settle just anywhere. I was looking for the right vibe. If a place doesn’t feel right then you just have to keep on searching. 

On my 28th birthday we road-tripped from Los Angeles to San Francisco. We AirbnB’d from Santa Barbara to Santa Cruz.

They were all charming in their own ways, some more or less than others. But none of them felt right. Santa Barbara encompassed our perfect lifestyle but was a bit of a sleepy town. San Luis Obispo had the perfect vibe but the homes were too far from the beach.

On the way home I couldn’t help but feel discouraged. I had put such a high hope in California. 

I even considered canning our idea all together, or better yet, possibly making the best of Winter by traveling to Upstate New York. The change of scenery may not make me want to claw my eyes out, I told myself. We could live in a cozy cabin cooking pasta and drinking red wine, cuddling by a warm fireplace. It’ll be like The Notebook. It wouldn't be ideal, but it would be good enough.

But if you know me, good enough might as well be failing. 

We decided to put a hiatus on our research and lo and behold, BAM. Within a couple of months Costa Rica came back into our radar. She came out of nowhere, like that person you saw every day at school who secretly had a crush on you but whom you ignored, vying for the attention of that popular one instead.

It was totally absurd - We just spent all this time in California and now we were willing to plan a whole 6 week trip in a foreign non-English speaking country we knew next to nothing about? Initially we were too busy trying to canoodle with California that we didn’t realize Costa Rica’s potential. We had thought she was too high-maintenance in the beginning. The daily rates were through the roof. But this time around, we realized Costa Rica was actually the more reasonable choice. The monthly Airbnb rates were up to 40% off. When we found our dream place on the beach we knew we had to go all in. 

We knew nothing about the Nicoya Peninsula, but our Airbnb host assured us we would wouldn’t starve and would have access to hospitals and vets if the need ever occurred.

6 months later we hope our experience can help you plan your ideal trip to Costa Rica. And at the very least, you can have a laugh at our expense from all the mistakes we made along the way. 

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We visited during the “dry” season (mid November-April, but with global warming ya never know). During the wet season it rains pretty frequently which can actually limit where you can stay as some of the many dirt roads are blocked with water. 


If you want to stay on or near the beach, you’ll have around a 3 hour commute from the airport to your residence. Shuttle services are usually provided if you’re staying at a resort or hotel (Which may include a ferry trip). 

Flights are cheap depending on the time of year. The two major airports in Costa Rica are San Jose and Liberia. For some reason flying into San Jose can be cheaper, but for instance it would’ve been a 5 hour drive to the Nicoya Peninsula vs a 3 hour drive from Liberia Airport.

Pro tip: If you plan on bringing checked luggage, especially items that are not of the ordinary, like a guitar amp, the airlines on the Costa Rican side have the discretion to NOT let you bring it back with you. 

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Our first night we stayed in a hostel. If you know me, try to picture me staying in a hostel.

We personally loved the convenience of booking through Airbnb. Our host was a wealth of information. As mentioned before, you could also stay at a hotel or resort. If booking Airbnb make sure the reviews were great. 

The only thing we wish we had known ahead of time is that our place had a caretaker who would be on the property at any given time of day (no biggie) solo or with his compadres. In Costa Rica, sometimes you just have to go with the flow.


A few things to note: not everything is mentioned in fine detail at the time of your booking. If you choose to use your credit card’s insurance, they will most likely want to charge a $2,500 USD security deposit (not including the cost of rental). We opted for their insurance in the end, which was $900 USD

Some car rental places offer WIFI and 24/7 roadside assistance at an additional cost. Looking back I wish we had booked both since Costa Rica SIM cards are pretty useless (at least where our house was).

Pro tip: you can try to barter with the car rental companies/compare rates at the airport to get somewhat of a discount if you are booking a monthly rental


At Liberia airport you can get a SIM card next to the area where you can exchange your cash. They're pretty affordable with different data options. Too bad the cellular range was pretty useless though, we had next to no connection inside our Airbnb place. It helped tremendously with driving, however.

As for GPS, the most accurate app to use is Waze (everyone will tell you Google Maps is horrible).


Costa Rica mostly has a mix of paved and dirt roads. The latter were not as crazy or bumpy as I initially thought. The main thing to look out for are river crossings. If you drive fast you’ll be fucked, but if you drive slow your car should be fine. 

Driving as a tourist in a rental car can make you a target. When you drive on main roads during certain times of the day the policia can pull you over for inspection. They tend to pull over car rental cars, not local ones. On one occasion they thought our empty sandwich bag was a marijuana container. 

Also carry a copy of your passport with you (choose to carry your actual passport at your discretion):

Policia (Spanish): Pull over
Us (Broken Spanish): Hello Officer, what seems to be the problem? 
Policia: Where is your passport?
Us: We have our drivers license but not our passport (who brings their passport driving?)
Policia: Give me $60,000 colones and I won't take your license plates 
*officer sees Anthony vlogging the whole thing* 
Policia (visibly angry now that he sees Anthony filming his attempted bribe): We’re taking your license plates.


We relied on a personal private driver during our stay (who also happened to be Gisele and Leo Dicaprio [respectively]’s driver), he was our hero after we killed our rental car in a river crossing. You can use personal drivers for long drives to and from the airport but be prepared to pay a pretty penny for each ride (around $200 one-way depending on the distance and how many people are in your party). 


Crime seems to be pretty low in Costa Rica. We always felt safe. The only thing that people apparently steal are flip flops and toothpaste. We often accidentally left cameras and laptops out in the open and they were always safe. Our toenail clippers on the other hand…


When we had a car (as you can see it went all downhill after that river crossing) we visited Sámara which was pretty touristy but had nice restaurants and beaches. Had we not involuntary manslaughtered our car we were also planning on doing hiking trips in the jungle and other fun photo-op worthy activities. Where you stay will determine the types of activities you may want to partake in, i.e. surfing, hiking, ziplining, etc…


If you’re planning a long trip like we did, stocking up on bulk food staples on your drive from the airport is your best bet. The more rural the area, the less options and quality of food. In Liberia they’re currently building a Walmart which would have been amazing for us but instead we went to another Supermarket that had pretty much everything we needed: bulk rice, bulk beans, a few cheap yoga mats, etc… the only downside was that their packaged food contains artificial dyes, ingredients etc… so if you're an anal-ingredient scanner like I am, you might want to turn a blind eye. The best food I had hands down was the fresh fruit. And everyone else would have added the fresh fish to that list.


OK so before going to CR everyone and their dog was like, “You’ll be fine, you don’t need to speak Spanish!” When in reality, we would have been absolutely screwed had it not been for my 4 years of High School Spanish class (muchas gracias Señora Reyes). Anthony, his brother Dave nor our dog Bowie knew any Spanish so it was my honored duty to communicate with Nacho, our caretaker, whenever the house’s gas tank would need a re-fill, or with the local guy who would drive into town every Saturday with fresh produce (our nearest "Bodega" was an hours walk away). Legitimately the only times we didn’t need to know Spanish were when we went out to dinner at our local restaurant since the owners speak fluent English, at some of the touristy areas, and when I called the local vet.

Pro tip: If you're going to wing it like we did, learn as much Spanish as you can and if not at least bring a language guide book with you. 

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The great thing about traveling to paradise is the weather is always the same, the only bad news is that there is no such thing as Amazon Prime, Instacart, or anything else that screams convenience. Bring extra of anything you know you’ll run out of (hair products, supplements, toiletries, etc…) bring tons of SPF and bug repellent (the mosquitos were surprisingly sparse). You don’t need many clothes or bathing suits (unless you’re Instafamous of course), and much to my skin’s relief you really don’t need to pack any makeup (unless you're trying to look snatched for those selfies).  


Yes, swimming tips. Good news, there’s nothing in the Pacific Costa-Rican ocean that will kill you. Bad news, there’s still some scary ass shit that will keep that head high while you’re swimming.

Later in the day when we would be catching waves we would see fish shoot out of the water like dolphins doing tricks at Seaworld. One of us saw jelly fish at one point, and at another point saw a dead water snake (apparently they won’t bite you, though).

Pro tip: do the sting ray shuffle when entering and exit the ocean. 



Surprisingly the easiest thing to navigate. I would generally stick to ordering Casado Vegetariano (rice, beans (no meat stock), vegetables, plantains), just make sure to say “sin lácteos” (dairy). There are plenty of fruit and water smoothie options as well. I had to get creative after a while substituting ingredients in dishes, but in the end the Casado always hit the spot. I cooked most meals at home, I even got ballsy toward the end and made homemade jam and whole wheat bread.

Hopefully these travel tips were of some use (or entertainment to you), as I continue to explore I'll always share my best tips with you! 

To Our Health,

Falcon xx

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