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Stories and Tips from an Airbnb Veteran

I’ve used Airbnb since 2014 and have stayed at over a dozen homes now. I’ve had the full range of experiences from amazing to uneventful to full on nightmare. Fortunately, I’ve only had one really bad experience on Airbnb. It’s an amazing service and has changed my life in a lot of positive ways. It’s been a great way to get out of my shell and be put into situations I would usually avoid like interacting with other human beings!

Here’s some anecdotes and tips from my most memorable Airbnb experiences.

It Starts: My First Airbnb Story

My first Airbnb was at The Treehouse Room near Laconia, NH. I had already visited Laconia a few times with friends where we stayed at the Margate restort. This was my first solo trip and I wanted to try out Airbnb, which I had been hearing more about. The room was only $45/night which was a lot more affordable than any of the hotels, resorts, or other B&Bs in the area, even though I was visiting off season.

The host was a nice lady who lived in a giant house built in the 1700s. She had two cats, which was great since I love cats, and a few acres of land to explore. The room itself was small but met my needs.

It was a bit awkward staying with an older lady alone at first, but she was easy to talk to and very generous. She would make me breakfast and one day even made me a grass fed steak dinner! It gave me a great first impression of the service and I was eager to try it again. The only major downside was there was no Wi-Fi so I ended up working out of a library for most of the trip.

TIP: When picking your first airbnb, it can make it easier if you pick an area you’re already familiar with. Since I already knew the Lake Winnipesaukee I wasn’t worried if the reservation went south. Also make sure they have Wi-Fi! Many of the locations out in the boonies don’t have good phone service, so you at least want Wi-Fi to make calls, texts, or emails.

Jamacian Me Crazy: My Last Minute Airbnb Story

One day I had the spirit of travel overwhelm me. I had to get out of my apartment and hit the road. I drove all the way to Brattleboro, Vermont and began exploring. I didn’t have an Airbnb booked yet, because I assumed I could find one last minute. I booked one that was available, waiting for the response.

I then drove to Manchester, VT where my “Airbnb” was. It was starting to get late and the host hadn’t confirmed the appointment. One thing about Vermont is it’s a sleepy state. There is no night life in VT, so everything closes by 7 o clock on a weekday. Not to mention spotty phone service. I ended up stranded in a Dunkin Donuts, the only place still open, desperately trying to find an Airbnb.

I was ready to just check-in to a motel when finally I heard back from a place in Jamaica, VT. She said she could rent me a room for the night if I got there before it got too late. It already was dark so I hit the road again. The Airbnb ended up being in the middle of nowhere, which is saying something when you’re in Vermont. After driving down a few dirt roads in the dark forest, I finally found it.

It was a relief to have a place for the night but I was rattled. I made sure from then on to book my Airbnbs in advance. Even if the Airbnb has the Instant Book option, which means you don’t need the host to confirm it, it doesn’t guarantee you’ll have a place the same night. It ended up the host of the place I had booked was out of state and had forgot to close out the dates!

TIP: Common sense advice but always make sure to book several days in advance! Most Airbnbs will give you a full refund even if you cancel 5 days beforehand. Make sure to check their cancellation policy as each place is different.

Oats n Goats: Staying on a Farm

I booked an Airbnb near Shelburne, VT on one trip. It was run by a couple who rented out rooms to travelers on their self sustaining farm. They had goats, chickens, bees, and a huge garden. They also had a lovely Collie dog they let me play with, or distract while they milked the goats.

I really enjoyed staying on the farm and seeing all the animals. One day while the couple was milking the goats, one of the goats escaped from the pen. The female partner yelled “Runaway goat!” as it barreled towards me. Instinctively, I grabbed the goat by the collar and used its momentum to spin it around so it ended up running right back into the pen. Warren and Melanie were impressed with my quick reaction. I’m not sure where that came from since I never worked a farm in my life. Maybe I missed my calling?

TIP: There are a lot of different kind of places to stay on Airbnb. Many of them also offer experiences you might not normally have access to. It’s a great opportunity to learn about other ways to live. You might also get to do fun activities, like wrangle in a runaway goat!

Hablo Ingles? Staying in Miami FL

While I was snowbirding in Florida in 2017, I booked a place in Miami. I had never been to Miami and while I had heard mixed things I wanted to experience it for myself.

I ended up staying in West Miami in a Cuban Neighborhood. I was the only gringo there. A few of the local restaurants only spoke Spanish which led to some awkward interactions. The most shameful was when I was at a breakfast place and the waitress only spoke Spanish. I couldn’t remember how to say do you speak English (Hablo Ingles?) so I just blurted out “ENGLISH?!” I felt like a tool.

The family was very nice. It was run by an older Cuban lady and her mom. She got very excited whenever I spoke any Spanish. Most of the younger generations spoke English in the area, so it wasn’t much of a problem.

Even though many people in Florida had only bad things to say about Miami, I had a great time taking tours of the city, including Little Havana, Wynwood Walls, and the more posh districts like Coral Gables. Food was amazing too as expected.

What was not so great was the traffic. It was like LA traffic except most people drove like they didn’t have a license. I learned to drive into downtown in the late morning, park my car in a garage, and then walk or use the free monorail. I would then uber to the beach and drive home at night after the traffic thinned out.

TIP: Staying with a family from a different ethnicity can give you a whole new perspective on a city. It’s important to put aside prejudgements of a place based on second hand information when traveling. If you’re in a traffic dense city with a flexible schedule, try to plan around it.


This blog post ended up being longer than I expected so I’ll be breaking it into two. My next post will get into my stay at a trailer park in St Augustine, unexpected guests in Savanah, Georgia, and my Airbnb from hell in St Pete.

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