Hey, y’all. Winter is here, the sky is grey, and (as expected), the vibes are low. To combat that, I think it’s important to have dreams and goals and hopes and things to look forward to. Enter: my 2026 travel bucket list.
This list might exist only in my imagination (and now also in this digital space), but what are Januaries for, if not a little manifestation?
Here are all the places on my travel list for this year.
Maui, Hawaii
This destination, I’m happy to say, is coming true. In February, Chad and I will head to Maui, ready to relax and explore and enjoy every drop of paradise. This will by my second time, and Chad’s first; I can’t wait to return and share such a special spot together.
This vacation will count as our annual warm weather winter trip—a must for getting through the dreary Midwest winter.
Madison, Wisconsin
Honestly, I’ve never been! As I’m nearing the 4-year mark of living in Wisconsin, it feels like it’s probably about time to visit the state’s capitol city.
I’ve heard great things about Madison, especially the vibe, waterfront, coffee shops, and summer farmers market.
Colorado
Listen, visiting my home state is nothing new. However, I have a few different ideas this year to make our trips count.
- A fall road trip with some Wisconsin friends, showing them all of the places we talk about constantly, including our hometown and favorite western slope spots
- An extended weekend trip either to Denver or a mountain town, to spend some quality time with our besties
- Grand Junction, of course, to spend time with my parents
Fox Cities, Wisconsin
In fall 2025, we took a shopping trip to the Fox Cities area (Neenah and Appleton), and really enjoyed it! I’d love to return again this year.
Chicago, Illinois
Seeing as we live so close to Chicago (it’s around an hour and a half drive), I’m on a mission to go both more often and more casually. I’d love to continue exploring different neighborhoods, and I hope this year brings me to a Cub’s game.
Northern Michigan
Michigan is calling my name. After last year’s visit to Grand Rapids, I’d love to explore more—especially the Northern part of the state. Traverse City or Mackinac Island are calling my name.
Toronto
This year, one of Chad’s 2026 side quests is to go out of the country. While this might be tricky with my passport set to expire (oops), I’d love to join for a quick trip.
Why not visit our neighbors to the North? Toronto is on our list, especially since it’s a quick 1.5 hour flight from Chicago.
Where to?
Where will the wind take you this year? Let me know what’s on your travel bucket list.
Established in 2018, Sunshine with Savannah is a catch-all blog with an emphasis on weekend travel, millennial-style marriage and fun, reflection-based musings, outdoor adventure, home design, and all things lifestyle.
Though the content is diverse and varied, the heart of this space stays true to a single, guiding principle: a simple pursuit to find sunshine, wherever I go.
My wife and I lived in Chicago for 5 years…so much fun! Yes, see a Cubs game, and go below Michigan Avenue for a “Cheezborger! cheezborger!” from Billy Goat’s Tavern…you have a great list planned, so much fun to focus on getaways…we are eyeing San Sebastián Spain, and head to London for a quick fun trip in March!
All of these are bucket list worthy and I’m looking forward to reading of your sojourns!
We just visited Chicago for the first time back in August and I can’t wait to go back. It’s easily one of my top 3 cities in the world!
This year we are spring breaking in Saint Lucia and heading back to England to visit my husband’s family, though this time we will be adding Wales and Italy to our itinerary. ☺️