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My 2020 travel goals


As I mentioned in my last post, in 2020, I’m not sure how much time I’ll have for travel. For that reason, I’m trying not to set as many travel goals as I normally do, but I couldn’t resist setting a handful!

Below are the places I’m hoping to see this year, both near and far.



My friends and I actually got as far as booking a hotel last December before we realized our dates wouldn’t work after all, so I’ve been eagerly anticipating this trip ever since! I’ll be going over MLK weekend in just a few weeks and staying at the newly renovated Caribe Hilton. I’m looking forward to exploring the charming streets of Old San Juan, trying some of the city’s restaurants and, of course, spending time at the hotel’s swim-up bar.


I’ve wanted to stay at Al Maha, a desert resort that’s part of Marriott’s Luxury Collection, for about a year now; it’s one of the best possible points redemptions in the Marriott portfolio, as award stays include all meals and two daily activities of your choosing. Rooms were not cheap in points, so I recruited my sister, a Marriott loyalist, to join me on the trip and spring for one night while I picked up the other. Somewhere in the planning process, we decided to go all-out and plan the fanciest trip either of us has probably ever been on, complete with stays at the Conrad Dubai and St. Regis Abu Dhabi, as well as first-class tickets home in the Etihad Apartments. To say I’m excited would be an understatement!

Gaylord Rockies Resort


Denver is a city I feel like I could keep going back to, always discovering new things to do and see. It’s been a few years since my last trip, and I have friends there I’d love to visit. Plus, now that I’m on the West Coast, I’m much closer than I was in D.C. As far as exact timing, I’m looking at April, when my favorite baseball team (the Chicago White Sox) will be playing a couple days at the Rockies’ stadium. I’m winding down the list of MLB stadiums to visit, and I’ve made a plan to visit a few each year over the next three seasons to finish it off. Colorado is one I haven’t been to, and I’m excited to get the chance to do it while watching my own team!


Ditto everything I just said about baseball for Denver, and sub in the Toronto Blue Jays. A trip to Toronto will help me check another stadium off my list while watching the White Sox, and better still—they’ll be playing over Canada Day! After spending last Canada Day in Vancouver, I vowed to be in the country for the holiday again this year, so the baseball schedule gods really couldn’t have done any better with this series. Plus, it seems like every major travel experience I’ve had over the last few years has brought me new friends from Toronto, and I’m excited to catch up with them all.


We’ll put this in the “not totally sure it’ll happen but really hope it does” category because Tallinn feels like it’s been on my list for a decade (and that might actually be true). I’m excited to see this European city, which from what I understand does a great job bridging the old and the new. I’ve long envisioned a road trip through Latvia, Lithuania and Estonia, but depending on what kind of time I have, I may just pop over to Estonia and save the bigger road trip for another time. Either way, you can bet I’ll be looking to either earn or redeem points at Hotel Telegraaf, a member of Marriott’s Autograph Collection, while I’m in town. 


Santa Fe was the first western city we hit on our moving road trip from D.C. to Portland, and I remember it so fondly, in part for that reason. I also instantly fell in love with the adobe architecture and the FOOD, which was some of the best I’ve ever had in my life. Just an hour or so after pulling into town, I was already googling flights from my future home and plotting out when I could return. While it didn’t happen in 2019, I’m not letting 2020 go the same way. I’d love to visit in the fall instead of the winter this time (although I did love seeing snow there!). I’ll definitely be staying again at La Posada de Santa Fe, a member of Marriott’s Tribute Portfolio.


Bend is about a 3-hour drive from Portland, and people absolutely rave about it for its wealth of outdoor activity options and solid food and drink scene. I’m hoping this one will be the easiest of my travel goals to cross off since it’s so close to home; it’ll just be a matter of finding a good time to do it!



Struggling to choose which Hawaiian island to visit after officially becoming West Coast residents, Jake and I had the idea of visiting a different one each year. We kicked things off with Maui last spring, and this time, I think we’ll try for Kauai. I’ve heard the natural beauty on the island is unrivaled, and there’s another Autograph Collection hotel there that I’d love to check out (Koloa Landing Resort at Poipu, to be specific). This one will probably happen next winter, possibly in lieu of our annual Mexico trip.

To see how I tracked against last year’s goals, check out this post! And to learn more about earning and using points and miles to travel for free, visit the 52 Cities free resource library or join me on a points and miles masterclass.

What about you? What are your travel goals for 2020? Tell me in the comments below! >>

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2020 travel goals
2020 travel goals
2020 travel goals





December 31, 2019



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