Improve Your Travel Experience


One discretionary expense where we probably overspend is travel.  Both my wife and I work full time jobs so getting away from it all is a priority. While on vacation we tend to splurge more on things like restaurants and entertainment, which we do much less when we are at home.  Within Travel there are two budget-busting categories: Airline Tickets and Hotels.  While there is not much you can do about plane ticket prices besides the usual buy early/use miles/use price comparison sites, there is a growing list of options to combat steep prices that hotels charge for the privilege of parking yourself in their room overnight.

While Travel would be one of the last categories to cut for me, I have always tried to minimize what was spent on accommodations.  I know that for some people where they stay defines the trip, but I’d rather spend my time and money outside of the hotel room.  This meant that during my college years I stayed primarily in hostels while travelling through Europe. To this day it’s probably one of the best ways to see the world while meeting people from all over and spending very little compared to hotels. Of course today we have an even cheaper alternative of staying somewhere for free using sites like

Ever since getting a “real” job and getting married I’ve become less inclined to stay in hostels or sleeping on someone’s couch for free.  It’s something better suited for younger single people than married couples or anyone travelling with kids.  Luckily, there is a “why didn’t I think of that” business that provides the sensory bouquet of a hostel suitable for any age category and family makeup.  I’m talking about airbnb, of course.

Like all great ideas, the concept behind airbnb is brilliantly simple – bring crowdsourcing to the short-term rental market dominated by hotels.  Anyone with a place to rent out can join for free and post an ad describing their rental and availability.  If someone likes your place, they will submit a reservation request which you can approve or deny.  If you approve, airbnb will handle all the dirty work of handling money, insurance and cancellations taking a nice cut for their troubles.  The end result is that there is more competition in the rental market leading to more choices and cheaper prices for travelers.  At the same time, renting out unused space can provide a nice side income to anyone who does not mind becoming a part-time landlord.

One of the coolest features of airbnb, though, is that it allows you to stay in unique places that would otherwise be inaccessible.  Take a look at this list and I bet you’ll start saying “Wow, I want to stay there” over and over again. When was the last time you got this excited about a hotel?

When we traveled to Italy a couple of years ago one of our most memorable stays happened in Rome where we booked a room walking distance from the train station in someone’s apartment converted into 3 separate bedrooms with 2 shared showers.  I must admit, it took a little convincing to get my wife to agree to stay there for the 3 nights that we were spending in the city.  However, by the time we checked out we agreed that it was one of the highlights of the trip.  The lady that ran the business lived in the apartment next door and was great in getting us feeling like the locals shortly after we arrived.  Not only did we pay less than 50% of what the nearest hotel wanted to charge us, but we also got to interact with Italians in a way that goes much further than the usual order at the restaurant or a sightseeing ticket purchase.

We have not traveled in a while because we were too busy with our baby, but when we had to go to Milwaukee for a wedding last month we turned to airbnb to find a place to stay.  I did look at the “reduced rates” offered to the wedding guests but they were dismissed rather quickly at around $150 per night.  A search on did not yield better prices in walking distance to the wedding.  Listed on airbnb there were a couple of properties that fit the criteria but one in particular caught our attention.  It was advertised as an “East Side Arts & Crafts Tudor” and was listed at $70 per night.  Besides being on a direct bus line from the airport the owner promised to include 2 bicycles which sealed the deal for us.  We wanted to explore the city in the 3 days we were staying there and I can think of nothing better than doing it by bike.

The reservation process was simple and straightforward.  After getting a confirmation from Maggie (the owner) we used a $25 gift card* to reduce the rental charges even further and booked the room.  Before arriving we contacted Maggie and she answered a couple of questions that we had about our stay (Best way to get to the house from the airport? Do the bikes come with a lock?  Stuff like that…)

When we arrived we found the keys in the place specified by Maggie and checked ourselves in.  It was a slightly surreal experience since there was absolutely no one in the house but us and the 2 dogs that slept peacefully on the owner’s bed.  Maggie was at work and the 2 other bedrooms that she rents out were empty.  We were told that we’d be staying in the room on the third floor so we got unpacked, showered in the second floor bathroom, found the bikes and headed downtown which was a pleasant 15 minute ride away.

The wedding was the same night so we actually did not meet the owner until the morning after.  Maggie was a very pleasant lady who works in photography, travels a lot, lives in the house by herself with her two dogs and rents out the rooms on airbnb.  She’s been doing it for a couple of years now and had only good things to say about the people that she met through airbnb.  It sounds like a lot of renters come via University of Wisconsin at Milwaukee since her house is just a couple of blocks away.

We rode our bikes everywhere while in Milwaukee and were very impressed with the biking culture and the infrastructure. Plenty of dedicated bike lanes and green-ways made cycling the best way to explore the city. It’s really popular here, so much that you can see small billboard type advertisements on bike lanes inviting you sties like, it’s kinda funny to see for the first time. It was fun to pull up to the Harley-Davidson museum on our bicycles navigating the sea of Harleys parked around the building.

Staying at the hotel would not only be double the price but also much less entertaining as well.  We would not have met Maggie who provided an interesting perspective on the local life.  We would not have bikes at our disposal to take in the city at our own pace.  We would not have stayed at a cool house that was nicely decorated by someone with an eye for arts and crafts.  In the ocean of cookie cutter Holiday Inn’s, Marriott’s and Sheraton’s, it’s refreshing to stay in a place that has unique personality.

If you feel like trying out something a bit more adventurous than the same old hotel room, I highly recommend considering airbnb for your next trip. There is no better way to take something as pre-packaged and generic as a hotel stay and turn it into a truly unique experience that you will remember for many years to come.  Upon return, you might even find yourself entertaining the idea of listing your spare space on airbnb as well, just like us!

A couple of cellphone pictures from our recent stay in Milwaukee via airbnb:

Tudor House


3rd Floor Room


Bed Nook


First Harley-Davidson


Readers, have you vacationed with airbnb before? How was your experience? Would you consider renting out your space with airbnb?


* If you would like to save $25 on your first booking you can click the link on my “Recommended” page.


7 thoughts on “Improve Your Travel Experience

  1. We airbnb’d once in a pinch and it wasn’t the best experience. I think in the future if we airbnb it’ll be in spaces that are empty except for us rather than a bedroom in a share. What is fun is traveling for a couple months at a time and just renting a small studio apartment – sublets are awesome!

    • That’s the “adventurous” part I mentioned 🙂 Travelling with airbnb can definitely be a hit or a miss but to me it’s worth it. I think finding a sublet and staying in a small apartment would be great if you had longer than the usual 1-2 weeks vacation.

  2. We haven’t tried airbnb yet. I like staying in hostel and similar places though. We’ll probably travel more next year when our kid is a bit older and I’ll definitely check out airbnb.

    • With the kids airbnb should work much better than a hostel. When we’ll travel with our little one we’ll book through airbnb and probably try to get the whole place to ourselves so we don’t disturb anyone else. That’s what I like about airbnb – flexibility.

  3. We also tried airbnb and we really had a great experience as we got a very comfortable accommodation and warm welcome from the condo owners. I guess its really hit or miss whether its in airbnb or couchsurfing. We can only do so much. We can read, research, ask for feedback from others but it might not guarantee a comfortable stay once you’re there.

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