One thing we can all agree on; Summer’s warm weather comes and goes quicker than free pizza in the conference room. It feels like last month I was having an impromptu Sunday Funday on the first warm weekend in May… and next thing you know it’s Labor Day and I still haven’t been back to Iowa to see my Mom. To be fair, I go home for Thanksgiving AND Christmas AND Mother’s Day. Also, lets clarify as a gay dude in his late thirties, I have two season, indoors and outdoors.

So, what started out as a year off from the corporate grind has turned into a mission to turn my passion for traveling and new experiences into my career. You would be shocked at how many people I’ve met in the last 18 months of international travels who are doing the same. I met a South African in Phuket who cycles through two years of work and two years of travel. The most memorable was meeting a late 30 something New Yorker at a Cancun resort who had no problem telling everyone he was living off his inheritance till he retires to Ft Lauderdale. For the record, I’m doing ALL of this on my own dime.

So, along with my mission of inspiring others to hit reset and travel the world before they’re retired and stuck on a bus with forty other retirees, I want to share my travel plans and experiences with others. I would also love any advice you have.

Here’s 5 of the places I’m excited to check out this Winter (in chronological order)!

Mexico City, Mexico- I feel like such a hick having been to Mexico 10+ times but never having visited the capital city. This November I’m planning on staying at a cute airbnb in the Roma Norte neighborhood. Per my usual routine of taking a bike tour to get acclimated to the city, I then plan on doing lots of walking and eating and drinking. Outside of that, I plan on checking out the bustling San Angel Market and the ancient city of Teotihuacan (50 mintues outside Mexico City). One thing I love about Mexico is it’s very affordable (outside of Tulum, if you want to go to dinner and be surrounded by Americans and Europeans, Tulum is your jam!)
Puerto Vallarta, Mexico- It’s been a minute since I’ve been in PV but boy am I ready. I had a streak of five years in a row going every winter but took a few years off to check out Tulum and Holbox Island. I’m looking forward to a rotation of margarita’s and cerveza’s at the Blue Chairs and Mantamar Beach Club on Los Muertos Beach. I cannot wait for the insanely gorgeous nightly sunset over the Bay. It’s probably my favorite in the world.
London - I love visiting cities around Christmas to see how they get dressed up. I’ve been fortunate to see a lot of NYC and Chicago pre-Christmas but cannot wait to see how London gets down. While across the pond I‘m probably going to take a quick trip to Paris (they have 15 Christmas Markets)and the famous Cathedral Christmas Market in Cologne, Germany. Let me know if you have any suggestions!
Costa Rica- Two of my best friends just eloped here in September. I figured I should take the money I would have spent on their wedding and go check out the beach they got married on in Santa Teresa (and recreate their pictures). I also heard I should check out “Cloud Forest.” Apparently, its some of the purest air you can breathe in the world… and after spending a month in Ibiza this Summer, I’m very interested.
Peru- I must get to Machu Picchu ASAP. I’m obsessed with the 15th century Incan City on those plush green mountains. Plus, I’ve been obsessed with Peru since I was 7 and was given this amazing multicolored (foreshadowing?) winter hat from my Mom’s Peruvian friend. God, I wish I could get my hands on that hat.

If you have any suggestions, advice, or comments please share. The best places I’ve been to are typically tips from other travelers like you.