Fabulous Trips, Super Cheap (Part 1)

The promise of AmazingWorldAdventures is that you can take incredible trips without breaking the bank. Today I’m going to share a little of my process with you.

My 20 year old daughter, who has been my default travel buddy for several years now, recently started planning her own trips independently of me. She texted me one day and asked, “So I discovered I’m awful at planning trips. How do you do this?”

That became my inspiration for this article.

Fair warning: parts of my process can be rather labor intensive and time consuming.

First you must realize that I almost never start out with a specific destination in mind. Rather, I think about a specific type of destination and a short list of places that fit the bill.

In the beginning, I keep as much flexible as I possibly can. The more “must-haves” on your list, the more you should be prepared to pay.

Right now I have three trips planned and paid for in the next six months. In an effort to illuminate some of my travel planning process, I’m going to share some details of these and how I came to the decisions that I did.

Bogota, Colombia – November 2015

  • People traveling: 2
  • Length of Trip: 6 days
  • Destinations: 2
  • Total combined cost: $791

Later this month I’m going to Bogota, Colombia. The destination was one of the last things I settled on. This trip was inspired by the fact that my daughter will be away for college over the Thanksgiving holiday. Living alone, I have no particular reason to be home.

I also knew that this is a big holiday weekend in the US. At my day job, we have four consecutive days off. Ideally, I could find a reasonably short trip that would enable me to get away without using up any vacation time at work. (In reality, I tacked on two extra days and booked a six day trip.)

One of my favorite sites right now for researching flight information is Orbitz. Not because I have any brand loyalty to them but because they are one of the very few sites which lets you search +/-3 days for both departure and return.

The results come back as a sort of pivot table of date combinations with the cheapest price shown for each combination. The lowest prices on the entire table are even highlighted for you. Though sometimes the lowest price is for a 9 or 10 day trip and paying only a few dollars more will get you a 5-6 day trip.

Don’t forget that each day you’re away you’ll have to pay for food and lodging! So paying an extra $20 or even $50 per plane ticket for a shorter trip may be worth it.

Like anyone else, I would love to take much longer trips all the time. However, when you travel multiple times per year a shorter getaway may be all you need. Or life’s constraints such as work, school or family obligations may necessitate a shorter trip.

Speaking of cheap, economizing for me does not mean staying in hostels or couch surfing. I have nothing against either of those things in principle and might even do it some day for the experience but I can usually find good deals in other ways.

Back to settling on a destination. Very often, what I will do is open up a map or pull up a mapping website to look at the region of the world where most of my potential destinations lie.

I love to be warm so my destinations of choice are frequently in the tropics. Being limited to only 4-6 days, I want somewhere I can get to in 8 hours or less (if I flew nonstop).

Map in hand (or on screen), I will simply spend hours plugging in flights for my chosen date range from airports near my home to one destination after another. I make notes about the most appealing balance of departure/return/cost information for each locale until I have a list of 15-20 possible trips.

A word on departures. I live in northern Delaware. The nearest major airport to me is Philadelphia but Washington, DC and New York City are both within a reasonable driving distance and often cheaper to fly out of. I will absolutely drive 90 minutes to DC in order to save $400 on flights for two people. (My cutoff varies but in general it’s around $50 per ticket to DC or $100 each to NYC. If I can’t save at least that much, I’ll just fly out of Philly.)

A Sneaky Trick to Get a Free Vacation

Want a free extra mini vacation tacked onto your “real” vacation? Of course there is only one answer to that question.

A strategy I use, and which I have yet to find a good travel website to help me plan, is to take my layover into consideration when booking flights.

There are plenty of websites which will let you reduce or eliminate your layover(s). What I want is the exact opposite. I want to find the longest layover practical and it must be in a place that I have never been before or otherwise find interesting.

Driver waiting for us at the airport in Panama City

Driver waiting for us at the airport in Panama City

When I took my daughter to Peru in 2014, I engineered an 11 hour layover in Panama City. That was enough time to hire a driver to meet us at the airport and take us on a tour of the Panama Canal and Panama City before dropping us back at the airport for our connecting flight. Total cost of that extra little vacation destination: $130, all inclusive.

In Lima, Peru we had a 4.5 hour layover during which we went to the beach (cost $45). In Denver, CO we had a 5 hour layover during which we went into town for dinner (cost $60). Both of those felt a little rushed, which gave rise to my rule: the minimum layover you should aim for is 6 hours.

On this flight to Bogota, I managed a 19 hour layover back in Panama City. A friend who is going with me has never been there so we’re staying overnight and will go see the Canal as well as go swimming in the warm, tropical waters of the Pacific Ocean (cost $47).

Incidentally, I finally settled on Bogota for a few reasons:

  • Round trip flights were insanely cheap at only $232 per person
  • I was able to get that 19 hour layover in Panama for an added extra destination essentially for free
  • Friends of mine live in Bogota and have offered to show us around
  • I’ve never been to Colombia, so this will be an adventure

Although I have friends there, I rented a place to stay rather than imposing and asking to stay with them. Especially as I was bringing along another friend they haven’t met before.

My favorite first stop for lodging is AirBNB. I have used them approximately two dozen times and never once had a truly bad experience. The worst experience I ever had was staying in a sort of broken down basement but the woman offering it for rent was very up-front about what it was like and I knew before booking what I was getting into so I have no complaints about it.

Usually I would prefer to book a room and stay with someone local. If there are four or more of us traveling together, then I will usually opt to find an entire place all to ourselves. Either way, the places I find are always cheaper than a hotel and almost always much nicer.

One more little luxury that I’ve discovered during my travels is that in many countries you can hire a chauffeur for the same price as renting a car for yourself. For our Bogota trip, one of my friends hooked me up with a friend of hers whose husband has been out of work. For the exact same price as I’d pay to rent the cheapest economy car possible, this new friend has agreed to be our private chauffeur and tour guide while in town. She’ll make good money for her family and we get a much richer experience from our vacation!

After round trip flights ($465), lodging in Bogota ($129), hiring a driver in Bogota ($150), overnight lodging in Panama City ($39), renting a car in Panama City ($8) our total cost before food and souvenirs is only $791. That’s all inclusive for two people for six days!

In future installments, I’ll share decisions that went into planning other trips. Eventually, I hope that a picture will emerge that will help others emulate my process.

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