Where Are We Going? The UP Team’s Winter 2026 Travel Plans

Our team is taking 2 very different approaches to travel this winter: more of it and less of it. Some of us are packing in as much as we can, while others feel like they need to take a breather and concentrate on just 1 or 2 important trips.

At any rate, you’ll find us high and low, far and wide this winter. Let’s take a closer look.

Ryan Smith, Director of News

I’ve spent most of the last few months in Mexico and Central America. When I leave Mexico in the first week of November, I’ll have been to every state in the country — something I’ve also done in the U.S. So where next?

I’m spending a few days at the Chicago Seminars, the largest and oldest points-and-miles conference, before heading to the Faroe Islands for my first visit. From there, I’m bopping around Europe for a few weeks to attend a music festival with friends, visit Northern Ireland for the first time, and even visit some of the Channel Islands (in between France and the U.K.) for the first time.

I’ll spend Christmas and the New Year in Hawaii with family, then in January I’ll head to western Canada for snow — something I haven’t seen in nearly 2 years. February brings a trip to the Middle East, with a stay at the Miraval Red Sea, hopefully.

After that, I have a lot of “maybe” items on my March calendar. It could change 73 times between now and then, so we’ll see what happens.

Alberto Riva, Director of Features

Winter means skiing for me. That’s why I’ve already renewed my Ikon Pass for the 2026-27 season, taking advantage of early-bird pricing since I knew I’d be skiing more than enough days to justify its $1,349 price. With lift tickets at many U.S. mountains costing at least $200, you don’t even need to be a hardcore skier to come out ahead with a season pass. Ski just a week a year, and you’re already paying less than you would by purchasing tickets every day.

The Ikon Pass includes more than 70 destinations worldwide, so I’m pretty sure I’ll be able to find places with plenty of snow and reasonable crowds, even as climate change upends long-held assumptions and high visitor numbers stress some resorts.

I already know that I’ll be spending time in the Alps. The list of Ikon Pass destinations includes Valle d’Aosta and the Dolomites in Italy, where pass holders can ski without limits for 7 days in each area. Both of them are within comfortable driving distance of Milan’s Malpensa airport (MXP), where nonstop flights from my base in New York City land every day and can be booked for reasonable amounts of points, even in business class.

And what if this winter turns out to be as dry as the last in the Alps? Then I might set my sights on Utah or the Canadian Rockies, where my wife and I have a soft spot for Banff. Courtesy of its big Japanese diaspora, the town also happens to have some of the best ramen restaurants we’ve been to — and few things can beat a steaming bowl after a day on the slopes.

Lori Zaino, Senior Content Contributor

My winter travel plans aren’t as exciting as in other years. But sometimes, the least thrilling travel plans are when I really value having a stash of points and miles. Family matters will have me flying between Madrid (MAD) and Chicago (ORD) every couple of weeks for most of the winter.

Thanks to Iberia‘s off-peak awards, I was able to score some one-way tickets to Chicago in economy for 16,000 Iberia Avios, and the return trips to Madrid in business for just 40,5000 Iberia Avios. Being able to get back and forth affordably and comfortably (at least on the overnight flight) makes tough family situations slightly less stressful. A few of the trips are paid tickets on American Airlines, which will hopefully get me closer to AAdvantage Platinum status.

I will have a little fun over the Christmas holidays, though. My family and I are flying to Fuerteventura, my favorite of the 7 Canary Islands, for a winter sun getaway. We paid 8,000 Iberia Avios per person, each way, for our flights between Fuerteventura (FUE) and Madrid. Hotels weren’t cheap around the holidays (and sadly, my favorite hotel there, the Sheraton Fuerteventura, is undergoing a renovation on my travel dates).

However, I hold the highest tier of Barceló elite status (My Barceló Unique), and one of the status perks is 10% off the final room rate, which we’re using at the Barceló Castillo. I can’t wait to relax and soak in the sunshine.

Christine Krzyszton, Senior Content Contributor

A friend and I are off to Shanghai in November. We found a great deal on Delta Air Lines via Hong Kong (HKG). I used The Business Platinum Card^® from American Express to book, taking advantage of its 35% points rebate (airline preselection required, allows up to 1 million points rebated per year), and upgraded to Delta One using my Global Upgrade Certificates (GUC). I also used the Amex Business Platinum card’s up-to-$300 prepaid hotel statement credit (available semi-annually) to book and cover a night at The St. Regis Shanghai Jingan.

And since we both need Marriott hotel nights to polish off Titanium Elite status for the year, we booked the Courtyard by Marriott Shanghai Xujiahui for several nights at a rate of just 17,000 Marriott Bonvoy points each.

Other winter plans include my annual pilgrimage to Puerto Vallarta, where I booked a downtown beachfront hotel through American Airlines AAdvantage Hotels to earn mega Loyalty Points toward Executive Platinum elite status. Plus, I’ll also receive thousands of redeemable miles for the booking. I was lucky to find a one-way flight on American Airlines for just 10,000 AAdvantage miles.

In February, I’ll be off to Uzbekistan on Qatar Airways in Qsuites, a flight I grabbed during an incredible sale. I also have a couple of weekends planned in one of my favorite cities — Oslo, Norway — where I always use my Choice Privileges points for hotels.

Juan Ruiz, Deputy News Editor

Last winter was all about bucket-list travel, from flying Emirates “Game-Changer” first class suite and Qatar Airways Qsuite to staying at luxury resorts in Mexico and Costa Rica like the Waldorf Astoria Riviera Maya and Waldorf Astoria Costa Rica Punta Cacique. This winter, I’m intentionally dialing things back.

Between home renovations, the kids’ school schedules, and everything else going on, I’ve decided to keep most of my travels closer to home.

The one trip I’m especially looking forward to is spending Thanksgiving in New York City with my family. We’re planning to catch the Macy’s Thanksgiving Day Parade, and I booked the Hyatt Centric Times Square, a Category 6 property, for 29,000 World of Hyatt points per night. It’s just a few blocks from the parade route along Sixth Avenue, making it a convenient base for the trip. I transferred Chase Ultimate Rewards points to Hyatt at a 1:1 ratio before the recent changes and applied a Suite Upgrade Award so the 5 of us can spread out a bit.

Beyond that, I’ll probably play it by ear, squeezing in a few getaways using Atmos Rewards points to fly American Airlines to the Caribbean from our home in South Florida.

I’ll likely return to chasing aspirational premium-cabin awards next year. But for now, I’m looking forward to slowing down, staying closer to home, and enjoying a more relaxed winter.

Daniel Ross, Senior Content Contributor

After almost 2 years of constant travel, I’ve closed the chapter on digital nomad life and started putting down roots in Rio de Janeiro. For the first time in a long time, I’m not craving being constantly on the go. Instead, I’m using the extra time from my slower pace of life to jump through the various bureaucratic hoops that will hopefully lead to becoming a legal resident in Brazil.

That doesn’t mean travel is completely off the table. I have a couple of domestic trips booked in Brazil — the first to São Paulo at the end of October. It might only be a short hop from Rio, but I’m looking forward to being back in the air after more than 6 weeks since my previous flight.

It’s the second trip I’m most excited about. LATAM has just received its first Embraer E195, which will fly its first passengers on December 1, 2026. While I would have loved to be on the inaugural journey, ticket prices were steep. Instead, I’ll be taking the airline’s first flight to Cabo Frio, in the state of Rio de Janeiro. The airport is the gateway to some of the most beautiful beaches in Brazil, and until LATAM’s arrival, it had no commercial flights. Cabo Frio will be the first of many destinations that LATAM’s Embraer will unlock for Brazilians and foreign tourists alike.

At the end of the year, I have a final trip with Air France to qualify for Flying Blue Platinum status, but I’m keeping the details close to the chest for now.

Keri Stooksbury, Director of Travel and Credit Card Editorial

After repatriating from Qatar to Houston in 2025, we had a big family decision to make: get a dog or get Six Flags season passes. Well, 4/5 of the family voted for Six Flags, and here we are, finishing the last few months of our pass validity before my kids remind us they’re owed a dog.

Over the last year, we’ve scanned in at 11 parks across California, Canada, Georgia, Mexico, New York, North Carolina, Ohio, and Texas. The Texas parks stay open through winter (will it be 90 degrees or 30 degrees … who knows with Texas weather?), so we’ll be visiting Six Flags Fiesta Texas in San Antonio and Six Flags Over Texas in Arlington in November and December. I prebooked a bunch of Hyatt properties in the area ahead of the May devaluation, so these trips are pretty turnkey.

I’m also excited to give Upgraded Points readers a peek inside The Westin Riverwalk, San Antonio, Caribe Hilton in San Juan, Puerto Rico, and Embassy Suites by Hilton Aruba Resort.

Katie Corrigan Seemann, Director of Hotel & Travel Partnerships

After a busy summer and fall, my winter travel is looking fairly tame. My husband and I are kicking things off by spending a week in Mexico. We’ll stay 3 nights at Secrets Playa Mujeres Golf & Spa Resort and 4 nights at the Fairmont Mayakoba.

After that, we’re heading to Raleigh, North Carolina, to visit my brother. Since that trip will include my daughter’s birthday, we’re spending a couple of nights at the Renaissance Raleigh North Hills Hotel, which is in the heart of the neighborhood’s vibrant shopping and dining area.

I have a handful of other plans in the works, but nothing is set in stone. I’ll hopefully schedule trips to visit family in Minnesota (where I will be getting my first tattoo), and I’ll head back to Mexico to review 2 hotels for Upgraded Points — Almare, a Luxury Collection Resort, Isla Mujeres Cancun, Adult All-Inclusive, and Impressions Isla Mujeres. Keep an eye out for those reviews later this winter.

Jessica Merritt, Senior Editor and Content Contributor

I’m staying close to home in Texas for most of my winter adventures, but have a couple of holiday theme park trips planned.

In November, I’m staycationing at 2 boutique Bunkhouse hotels in Houston and getting another step closer to a Hyatt Brand Explorer award.

Then I’m heading back to Walt Disney World for the holidays with my family. It’s the most magical season at the parks, with holiday overlays on some of my family’s favorite rides, festive decor, and treats. At the EPCOT International Festival of the Holidays, we’ll explore holiday traditions and food from around the world.

We’re staying at a Thousand Trails cabin for most of our time in Orlando, but I booked the avid hotel Orlando International Airport by IHG for our last night to make getting to our morning flight a little easier. I used part of my Capital One Travel credit from my Capital One Venture X Rewards Credit Card to cover it.

After Disney World, we’re heading to Six Flags Over Texas for my first time back at the original Six Flags in about 20 years. I’m excited to experience Holiday in the Park and squeeze in a few more thrills to close out the year with a personal record of 60 days spent at theme parks.

Final Thoughts

From Macy’s Thanksgiving Day Parade and domestic skiing trips to focusing on family or going to lesser-visited islands, our team has a lot on the horizon. You’ll find us in some exciting places this winter.