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Well, we’ve already written about our worst travel moments of 2018, and while they’re fun to read and look back at, it’s definitely more enjoyable writing and reminiscing about our best travel moments of 2018.

Traveling to Cuba

We’ll just go ahead and start with our trip to Cuba right off the bat because it was definitely the number 1 best travel moment of 2018 for us!

Cuba One Week Itinerary

Cuba is an incredible country that surprised us beyond our wildest beliefs. We think this was because we were always subconsciously told that Cuba was a bad, dangerous place due to our upbringing in the United States. While this was never outright said to us, it was always implied simply by the fact that Cuba was never really discussed outside of there being an embargo and having a Communist leader.

There were a few extra hoops to jump through to travel to Cuba, but they were totally worth it. The country is like no other place we visited, and it was incredibly enlightening to learn so much about the history, people, and culture from the locals we met there.

Go to Cuba American 4

If you want to go to Cuba as an American, you can! And we highly recommend it! Here’s our Guide for How to Go to Cuba as an American.

Check out our One Week Itinerary for Cuba and 10 Do’s and Don’ts of Traveling to Cuba too.

West Cost Trip

In our effort to travel to all the places we want to see (i.e. everywhere), we took a west coast trip at the beginning of summer that included Seattle, Portland, San Francisco, and Los Angeles.


We had never been to the Pacific Northwest before, and we’d both been wanting to visit before we even met. Seattle and Portland certainly did not disappoint either. We loved both of the cities, although they are different.

Departure Rooftop Bar Portland

During our trip, we were also able to meet up with quite a few friends which made the entire trip that much more special.

Taking Advantage of our Southwest Companion Pass

The Southwest Airlines Companion Pass is what drove most of our travels in 2018. The Southwest Companion Pass means Buy One, Get one Free flights, so obviously once we had it in hand, we had to take advantage of it.

Southwest Companion Pass

We wanted to travel as much as our schedules and budgets could allow, and we believe we did a good job of that by going to many of the destinations that Southwest flies too. Unfortunately, we’re not going to earn the Companion Pass for 2019, but we have tons of points racked up from using the Southwest credit card which have already paid for a few different flights in 2019.

Getting Back to Denver

We first went to Denver in 2017 and absolutely fell in love with the Mile High City. In 2018, with our Southwest Companion Pass in hand we made use of a long weekend and traveled back to Denver. We really wanted to see if we still loved the city or if our love for Denver was just because it was a new city for us back in 2017.

Denver Confluence Park Fall

Well, we found out that we still loved Denver and had a great time exploring it a second time. Denver has outstanding breweries, some of the best outdoor activities, and superb restaurants, including one of our favorites, City O’City.

City O City Food Denver
BBQ Tofu Mac n’ Cheese Bowl from City O’City

Barbecue in Austin

Last February, we traveled to Austin, Texas for a long weekend and loved the city! Our hopes weren’t too high for Austin even though so many people told us how cool it was.

La Barbecue Austin Texas

Honestly, Austin blew us away. They had tons of food trucks with delicious food, but our top highlight was the barbecue in Austin. We decided to eat at La Barbecue, and although we had to wait for about 2 hours to get our food, it was worth every minute. Austin is well-known for their barbecue, and it definitely didn’t disappoint.

Ziplining in Costa Rica

We spent one week in Costa Rica last summer, and while we had some of our bad moments, we also had a bunch of awesome ones. Our best travel moment in Costa Rica in 2018 was ziplining. It was great flying over the jungle and seeing it from above. They even had 2 ziplines where we were flying like Superman, face down over the rainforest.

Zip-lining Monteverde Costa Rica

Traveling in Milwaukee

For now, Milwaukee is where we live. While we don’t have specific plans to leave this hidden gem of a city, it’s always a possibility as we like to live in and explore other cities around the world.

Milwaukee, Wisconsin

This year, we’ve really made an effort to get out and explore Milwaukee. All too often people, including us, forget to get out there and travel in their own city. There’s plenty of things we talk about checking out in Milwaukee but never seem to get to because “we can do them any time.”

However, in 2018 we’ve made a push to try new restaurants (like all these awesome pizzas places in Milwaukee), go to new places, and do new things. While there’s still a lot more we have to do on our “Milwaukee Bucket List,” we’ve done a fair number of them this year.

What are some of your best travel moments of 2018?

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