Planning takes a long time. I’m a little obsessive about my planning. I plan way in advance, but only because I search for days. Sometimes I leave it for a week and continue searching.

I’m currently planning a long trip coming up in the next two weeks. I have a layover in Costa Rica for the night. I used to live in Costa Rica, so I remember what it’s like to get around.

I’ll be landing at SJO (San Jose International Airport), the capital of Costa Rica. From there I have to get to my hotel and/or hostel. At this point, I’m going to pick whatever is most convenient (but usually I pick whatever is cheapest.)

While I was living in Costa Rica, I remember public transportation being extremely slow. So, I looked at hotels in the city center, the downtown area. Only about 25 to 30 Kilometers from the airport. Most of these hotels do not offer shuttle services. But offer private cars to pick you up and drop you off at around $40 each way (Aloft Hotel)… But that’s not exactly in the city center. It’s midway. Getting to the city center will cost about $60 to $70 in a taxi if I choose that route. That’s too much for my cheap travel budget ways.

Therefore I looked up how long it would take for me to get to the city center from the airport if I take a commuter train and bus… google maps says it will take me 2.5 hours… Ha! I don’t think so… but that’s about par… getting anywhere in Costa Rica takes hours.

Hotels that are next door to the airport offer shuttles, and some are as cheap as $50 USD a night. All I need is one night, but then I have to sacrifice the fact that I will not be able to walk to anything. But this might be my best option.

Hostels vs Hotels

I LOVE LOVE LOVE Hostels. It’s not for everyone, but as a highly introverted person, it puts me in a position where with many other people for as low as $10 USD a night. When I was living in CR about 11 years ago, it was $2 USD a night… it’s gone up way too much, but the prices are still good. I make lots of new friends when I’m in Hostels and some hostels have shuttles that pick you up from the airport.

I found Hostel Pangea in the center of the city, which offers a paid shuttle “for cheaper than a taxi ride to this part of town.” At $9 USD a night, the ride is $60 round trip. It’s not bad, but at this rate, I rather get a hotel room and just chill. Or make my way myself for two hours on a train or $2 on a bus.

So what will I pick? I’m still searching. If you’re interested in booking a hostel, use my affiliate link here: Hostelworld.com. This just means I’ll get a commission if you book using my link at no additional cost to you.

Choosing a flight

Flights are often tricky, but I’ve learned not to panic. I often play around with flight times, airports, cities, airlines, red-eye vs day time flights. All of these parameters will come up with different price options for you. I choose one-way tickets versus round-trip tickets… sometimes two one-way tickets are cheaper than one round trip ticket.

I check several times a day, several days during the week. If my trip is far enough in advance I check during the following weeks.

I often use google.com/fights… Sometimes ill check Orbitz, Expedia, Kayak… If I do check other websites, I go with STATravel.com or CheapOair.com. They have worked for me in the past. Let’s not panic. If you see a good price, chances are the price will change the next day. It will go up at times, and down and times. Sometimes the price will go up and down. Just be patient and play around with the settings.

It’s kind of like marriage. When you see the one, you’ll know. Then you gotta pounce, get it and don’t let go! But, really… You’ll see a price that’s lower than what you’ve been seeing. That’s how you know there is no better deal. That’s how I choose my airfare.

I have my airfare picked out after Costa Rica to make my way back to LA for a layover where I will go home, repack and get back on the plane.

How do you pick a hotel or airfare? Got any tips to share? Leave a comment with your knowledge.

—Mucho Love

James Quintanilla