Where Are We Going? The UP Team’s Winter 2025 Travel Plans

Winter — love it or hate it, it’s here. For some, the arrival of the snow is exciting. For others, it means “time to book a trip to a warm place.”

Our team will be busy this winter, heading to every continent but Antarctica. Within the U.S., you’ll find our team in Arizona, Florida, Hawaii, Illinois, and Massachusetts over the next few months.

Ryan Smith, News Managing Editor

I have a busy winter coming up, which means there’s a lot of travel in store.

For context, I moved to Barcelona at the end of August, and I finished visiting every country in the world in 2023. Now, my travel plans include visiting friends and seeing other parts of countries I want to return to.

In late October, my sister will be in Europe for work and we’re meeting in Riga, Latvia, for 48 hours. After that, I’ll stick around the Baltics to see parts of Latvia, Lithuania, and Estonia I haven’t visited before.

In November, I’ll be at the Chicago Seminars, a major points and miles conference (and I’m flying there in the new Iberia A321XLR business class, which is exciting), and I’m attending the Most Traveled People summit in Addis Ababa. I also want to visit the remaining states in Germany and the Netherlands I haven’t visited, so that will probably happen in November also.

In December, I’m planning to check out the Azores and Madeira for a few days, and then my parents are coming to visit for Christmas. That will be exciting, since they’ve never been to Spain before, and we’ll spend a few days each in Barcelona and Madrid.

I have a few ideas kicking around for January and February, but nothing solid yet.

Lori Zaino, Senior Content Contributor

This winter, my family is hoping to experience a white Christmas in Chicago, flying from our home in Madrid (MAD) to ORD on the nonstop Iberia flight for the holidays. We booked one-way tickets on Iberia in economy using 20,000 Avios per person.

Then, we’ll fly to Cancun on New Year’s Day to deice. I paid cash for the flights on American Airlines — relatively cheap at about $230 per person — because no one wants to take a 9 a.m. flight on New Year’s Day.

We booked an all-inclusive Iberostar property for around $350 per night, which will help me accumulate those IHG One Rewards points for a trip to Thailand next summer. That said, I’m staying alert to any Black Friday hotel deals I might come across that might be a better deal.

I snagged what I consider a solid deal for our flight home: $1,100 per person for American Airlines business class on the Boeing 787-8. We fly from Cancun (CUN) to New York (JFK) and then to Madrid (MAD). My husband isn’t too thrilled about sitting in a rear-facing seat, but it’s the easiest way to keep an eye on our 4-year-old during the flight.

Christine Krzyszton, Senior Finance Contributor

Kicking off winter travel, I’ll be flying the Delta Air Lines inaugural flight from Atlanta (ATL) to Marrakesh, Morocco (RAK) with a group of like-minded Delta loyalist friends. I redeemed Chase Ultimate Rewards points for the flight and upgraded to Delta One with a systemwide upgrade.

December brings a trip to Madrid to use up the twice-yearly Chase $250 hotel credit for The Edit, which comes with my Sapphire Reserve for Business℠ and my Chase Sapphire Reserve^®. Madrid has several affordable properties in The Edit collection. I also plan to use my twice-yearly $300 prepaid credit from my Platinum Card^® from American Express at a Fine Hotels + Resorts property there.

Christmas is always in Tucson, Arizona, with my son. I always book one-way flights, usually on American Airlines. However, this year, I’ll compare using Points Boost with my Chase Sapphire Reserve card to redeem Ultimate Rewards points in the travel portal or transfer them to United Airlines MileagePlus for a redemption, whichever is a better deal.

Winter travel continues with a highly discounted business-class fare from Oslo, Norway (OSL) to Bangkok, Thailand (BKK) with a friend. Redeeming Membership Rewards points earned on The Business Platinum Card^® from American Express and receiving the 35% points rebate was a great deal (valid on select flight redemptions, available up to 1 million points per year). The flights are on Finnair and will help me earn over 35,000 American Airlines AAdvantage miles and Loyalty Points. We took the same trip last year, positioning to OSL with a $687 premium economy SAS fare.

Stella Shon, Senior Features Editor

What better way to kick off the new year than by heading to my favorite place on earth? My partner and I are spending a week on the Big Island and Maui in Hawaii with 5 of our friends. Since we’re traveling over the holidays, everything was on the pricier side.

Luckily, Delta Air Lines offers seasonal nonstop flights from our home base, Salt Lake City International Airport (SLC), to Kona International Airport (KOA). (I feel for our East Coast friends who have a much longer travel day ahead!) Our one-way tickets cost $419, but I decided to put the purchase on my Amex Platinum card to earn 5x Membership Rewards points on flights booked directly with airlines or through AmexTravel.com (on up to $500,000 per year).

On top of that, as a Platinum Medallion member, I’ll earn 9x SkyMiles for every dollar spent. This flight alone will push me past the threshold for Gold Medallion status — though I’ve already accepted that Platinum status for 2026 is, sadly, not in the cards. That’s fine by me, as I’ve been intentionally trying to scale back my travel lately.

I also charged our $110 interisland hop on Southwest Airlines to my Amex Platinum card, but we lucked out with a great deal for the flight home. For the nonstop from Maui (OGG) back to Salt Lake City, I redeemed just 18,000 SkyMiles per ticket, thanks to the 15% award discount available to eligible Delta cardholders.

Since we’re traveling with a large group, we booked 2 spacious Airbnbs. We made the reservations through Delta’s Airbnb portal to earn 1 SkyMile per $1 spent (every mile counts!) and paid with my Chase Sapphire Preferred^® Card to earn 2x Chase Ultimate Rewards points on travel. With the total cost coming to $6,000, that means 6,000 extra SkyMiles and 12,000 Ultimate Rewards points toward future adventures.

Juan Ruiz, Senior Editor & Content Contributor

During the holidays, we usually stay put in South Florida and enjoy time with family and friends. But come January, I’ve got a big bucket-list trip lined up — one that will finally let me experience Emirates Game-Changer First Class.

I managed to snag a seat in Emirates’ floor-to-ceiling private suite on the Boeing 777 from Chicago (ORD) to Dubai (DXB) — the only U.S. route offering this incredible product — redeeming Skywards miles just before Emirates restricted First Class awards to elite members.

I’m beyond excited for this flight. On the way home, I’ll be flying Qatar Airways Qsuites — widely considered the world’s best business class — for the fourth time. Every time I fly it, I’m reminded how lucky I am to experience products like these.

I’m also tacking on a visit to Kuwait, where I redeemed 3 Free Night Certificates from my Marriott Bonvoy Boundless^® Credit Card‘s welcome bonus for a stay at the St. Regis Kuwait City.

Beyond that, I’ve got a few shorter trips planned — New York City and Atlanta domestically, plus Mexico and Costa Rica internationally — to check out the new Waldorf Astoria Riviera Maya and Waldorf Astoria Costa Rica, Punta Cacique.

Hot Tip:

You can sometimes snag Emirates First Class even without elite status. The trick is to book a business class award with miles, and then upgrade to first class using more miles. Unlike many airlines, Emirates doesn’t seem to restrict these upgrades, giving savvy travelers a chance to experience the luxury suite for a lower price.

Jarrod West, Senior Content Contributor

In about a week’s time, my wife and I are heading out on a trip that has been at the top of our “must-visit list” for years — a safari at Masai Mara National Reserve in Kenya.

For travelers like us who try to use points and miles as often as they can to lower our out-of-pocket costs on travel, an African safari can be a tough nut to crack, given how few hotel options there are for redeeming points and miles (at a reasonable rate) and how expensive the cash prices can be otherwise.

Fortunately, we managed to secure 5 nights at the JW Marriott Masai Mara, allowing us to take advantage of the fifth-night free benefit on Marriott award bookings. The downside is that the 4 nights we paid for using points still cost an eye-watering 656,000 Marriott points.

We earned these Marriott points through a combination of sign-up bonuses from Marriott credit cards and transferring some Chase Ultimate Rewards points to Marriott during its 70% transfer bonus last year.

While this is undoubtedly a large number of points for one booking, it is not uncommon for the cash price at the JW Marriott Masai Mara to be $4,000 or more per night, meaning our 5-night stay would have cost $20,000 or more. Plus, the property is all-inclusive, so all of our food and beverages for the 5-night stay will be covered as well, further increasing the overall value we receive from our award booking.

Overall, this gives us a valuation of 3 cents per point for this redemption, which is over 3x our usual valuation of Marriott points and even 50% higher than our valuation of Chase Ultimate Rewards points.

Additionally, while we paid 164,000 points per night for our booking, factoring in the fifth night free, a few weeks after we booked, Marriott increased the number of points required to book the property to over 200,000 points per night. This is yet another reminder for you to use your points when you earn them, rather than hoarding them, as devaluations across all programs are inevitable.

To get to Kenya, we will be flying Turkish Airlines business class from Newark (EWR) to Nairobi (NBO) with a connection in Istanbul (IST), booked for 88,000 United miles per person and about $100 in taxes and fees. We booked this by transferring Chase Ultimate Rewards points to our United MileagePlus accounts.

On our way home, we’ll fly Ethiopian Airlines business class to Geneva (GVA) and then United Polaris business class back to New York City, for a total of 90,000 Air Canada Aeroplan points per person, which we transferred over from our Amex Membership Rewards accounts.

Michael Y. Park, Senior Editor and Content Contributor

You know how you sometimes have this thing that just tells you urgently that it’s time to go somewhere, as if you were a migratory bird reading the winds? For some people, when they start to see the first daffodils emerge, they know it’s time to immediately book a flight to Japan for late March for the cherry blossoms? Or how the first chilly autumn breeze fills your grandparents the overwhelming urge to flee to sun-baked earth and golf-cart-clogged streets of the gated senior communities of Florida or Arizona?

Well, for me, the big call to migrate isn’t south or east but north — to Montreal when our household has run out of its supply of Montreal-style bagels. (And, yes, I live in New York and can get bagels here, but comparing New York bagels to Montreal bagels is like comparing New York pizza to Chicago pizza. They’re just different animals.)

I also like unique and historic properties, rather than chains, so when American Express announced its refreshed benefits for the Amex Platinum card but also revealed that it’d honor the $200 prepaid hotel credit for The Hotel Collection and Fine Hotels + Resorts from the old benefits for existing cardholders, I booked 2 nights at the historic Hotel William Gray in Vieux Montreal through AmexTravel.com.

The hotel bill, which I had to prepay, came to $812.89 with taxes and fees, but I’ll get the $200 as a statement credit, along with $100 for qualifying hotel activities, late check-in and early checkout, if available, and a possible room upgrade. I get 5x points on my card for using AmexTravel.com, so I expect 3,665 Membership Rewards points from this purchase.

Of course, St-Viateur Bagel and Fairmount Bagel are both in Mile End, so I also booked a night at the Vogue Hotel Montreal Downtown, Curio Collection by Hilton, which happens to be an FHR hotel, allowing me to cash in on the new Amex Platinum hotel credit of $300 semiannually through AmexTravel.com.

The Vogue came to $379.51 including taxes and fees but before the statement credit, also comes with breakfast for 2, a $100 property credit, early check-in and checkout, if available, and a possible room upgrade. Since I prepaid through AmexTravel.com, earning me 5x points, I expect to earn 1,590 Membership Rewards points.

And, of course, I’ll get plenty of tout garni bagels to bring back.

Chris Hassan, Social Media and Brand Manager

This holiday season is going to be one for the books for me and my family. Since we are based in Brazil, this is actually my kid’s summer vacation, which means more time to travel!

We will start by spending Christmas and New Year’s with my family in New England before jetting off to Japan for a few weeks of exploring. My wife and I visited Tokyo for 48 hours last year. As you can imagine, that is not nearly enough time.

Ever since, we have been searching for 4 business class seats so that we can return as a family. Well, thanks to some award alerts from Upgraded Points, we actually have multiple business class flights booked to Japan. Now, we just need to decide which one to keep!

We will either fly ANA’s A380 from Honolulu (HNL) to Tokyo or Japan Airlines’ 787 from Los Angeles (LAX) to Osaka. Either way, it will be a memorable flight. But who knows, maybe award seats will open up on the new JAL A350-1000 and we will change our plans altogether — another benefit of booking with points and miles!

Our rough plans include a week at the Conrad Osaka, paid for with points from my Hilton Honors American Express Aspire Card, followed by a week in Kyoto, and then a week in Tokyo. I haven’t decided where we will stay in Tokyo yet, but the newly renovated Park Hyatt may be worth the splurge.

Regardless of where we lay our heads at night, I am so excited to explore Japan with my family.

Katie Corrigan Seemann, Travel Partnerships Manager

My winter travel is kicking off with a trip to Europe to visit the Christmas Markets. I’ll be flying into Frankfurt on Lufthansa business class, which I booked with Air Canada Aeroplan points. We’ll spend 2 days there visiting markets in both Frankfurt and Cologne. Then we’re stopping in Stuttgart, Germany, for 3 days to visit the markets there, plus we’ll do day trips to Esslingen and Ludwigsburg in Germany, and Strasbourg, France. Finally, we’re going to Zurich for a day before flying home in Swiss Air business class, a flight I also booked using Aeroplan points.

My post-New Year travel is still a bit up in the air. I currently have a booking at the Alila Ventana Big Sur in February, but I don’t have flights yet, so I really need to get going on that. I also have trips to Mexico, Hawaii, and Cape Cod in the works, but nothing is set in stone yet.

James Larounis, Senior Content Contributor

I’m headed down under (again) to Australia for New Year’s Eve. What used to be a “once in a lifetime” opportunity for me has now turned into a repeat adventure to see one of the coolest fireworks shows on the planet! I’ll also combine this trip with a visit to the Australian open.

I snagged an award in Qantas business class for 80,000 AAdvantage miles one-way and then paid 110,000 AAdvantage miles one-way in Qantas First coming back — 2 rare redemptions!

In February, I’ll be headed down to Honolulu to escape the cold on the east coast. This has been an annual trip with friends just to thaw out in some sunshine for a few days. I managed to get lie-flat seats going there for 55,000 AA miles, and I redeemed 40,000 miles for Hawaiian Airlines lie-flat business class coming home.

Layne Fable, Social Media Associate

I’m wildly excited to be escaping somewhere tropical for the winter months!

I signed up for the new Atmos™ Rewards Ascent Visa Signature^® card and earned 80,000 bonus points from the welcome offer, so I will be using those points to fly business class to Hawaii. Now, I just have to convince a friend to come travel with me to take advantage of the $99 (plus taxes and fees) Companion Fare offered by the card.

After Hawaii, I plan to hop over to Guam to explore a bit. There is no better feeling than being in a brand new place for the first time.

Lastly — I will be heading from San Diego (SAN) to Newark (EWR) for Christmas, and I’m checking my inbox religiously for an Upgraded Points award alert to book my way home for the holidays in comfort.

Keri Stooksbury, Editor-in-Chief

When you get a text from a friend that says, “Hey, want to meet me in Paris?” the right answer is almost always a resounding “Yes!” As such, I’m now booked for a week in Paris in November, my first time back in over 15 years.

Thanks to a tip from Escape Houston, I realized that the flights I was eyeing on Delta and Air France had dropped dramatically in price over the course of a few days. Air France’s nonstop flights from Houston (IAH) to Paris (CDG) were the same cash price as Delta’s 1-stop flights, and using my SkyMiles on either airline would have delivered less than a cent per mile, so I paid just under $560 for the round-trip Air France flight in economy.

To sweeten the deal, I was able to apply a $50 Chase Travel credit that my Ink Business Preferred^® Credit Card had been targeted for, bringing my total out of pocket to $508.33.

For the multiple school holidays this winter, my family and I will be using our new Six Flags/Cedar Fair season passes across amusement parks in San Antonio, Dallas, Atlanta, Charlotte, and possibly Ohio. We last held this pass in 2019, and it was a gateway to discovering that we indeed could travel and thrive as a family of 5, so long as roller coasters and chicken tenders were involved. Fast forward to 2025, and my kids are tall enough to ride everything, and they are all thrill-seekers, so we’re all looking forward to exploring more parks.

Hyatt Place and Comfort Suites across these destinations tend to best suit our family, with most rooms offering 2 queens and a sofa bed. To make these stays more affordable, I plan to use Ultimate Rewards points transferred to World of Hyatt and buy Choice Privileges points.

Looking further ahead to 2026, I have a January trip to New York City to plan. This will be my first time there in what seems like 20 years, and I’m excited to start arranging flights and a hotel!

Final Thoughts

We’re crisscrossing the globe this winter, heading to places warm and cold, familiar and new.

The best part about earning lots of points and miles is redeeming them. Some of us are visiting family, others are meeting family in a new spot, and other team members are heading to bucket-list destinations for the trip of a lifetime.