Where Are We Going? The UP Team’s Winter 2024 Travel Plans

It’s that time of year again when the staff of Upgraded Points talk about what insane travel plans we’ve made up, either because we’re trying to earn elite status or we’re enjoying the fruits of earning far too many points and miles.

And this year’s a good one! Let’s take a look at where everyone is planning on going.

Alberto Riva, Editor and Content Contributor

AvGeek Flights

This January, I booked a crazy trip from New York (JFK) to Detroit (DTW) to Tokyo (HND) to Guangzhou, China (CAN), to Kathmandu, Nepal (KTM), to Singapore (SIN) to New York (JFK) by myself for over a week —- just for pure aviation-geek reasons.

The reason? There is only 1 airline flying the Airbus A319neo in the world: China Southern.

It’s used for Chinese domestic flights and makes for a far more interesting hop from the airline’s Guangzhou hub to Kathmandu, where the plane’s performance is perfect for the high-altitude airport.

So, I’m off to KTM to fly this rarity. Nepal in January is not great for mountaineering or trekking, but I’m not going to go all the way there and not see Everest!

To get there, I’m flying Delta Air Lines to try the last business class seat I haven’t flown on Delta: the Delta One Suites on the A350. (I’m not counting the A350s Delta bought from LATAM in a 2-2-2 configuration in business class, since those will be converted to proper Delta One.)

I’ve booked premium economy for roughly $1,000 and applied a Global Upgrade Certificate to try out these seats. Traveling via Tokyo from Detroit offers a more convenient connection for me than Seoul, which would also be a possibility.

And, with a departure in Kathmandu connecting to Singapore, the longest nonstop flight in the world — from Singapore to New York — is relatively cheap. So I booked Kathmandu (KTM) to Singapore (SIN) to New York (JFK) on Singapore Airlines for $1,800 — in business class, not economy! It was so attractive that I didn’t even look at the points options. 

How am I paying for these? 

• Delta Flights: Delta SkyMiles^® Reserve American Express Card to earn 3x SkyMiles on Delta Air Lines; the card also earns 1 Delta Medallion Qualifying Dollar (MQDs) per $10 spent, helping me earn Delta elite status.
• All Other Flights and Hotels: Chase Sapphire Reserve^®, earning 3x Ultimate Rewards points on all travel purchases.

Skiing in Utah

I love skiing out west and will spend as much time as possible on the slopes in both March and April 2025.

I will use the up to $200 Delta Stays credit from the Delta Reserve card and the up to $150 Delta Stays credit from the Delta SkyMiles^® Platinum American Express Card on 2 separate occasions to book hotels in Salt Lake City and save $350 in total.

From the city, it’s a quick drive to world-class skiing at Alta, Brighton, Solitude, Snowbird, Deer Valley, and Snowbasin.

It’s cheaper to stay in Salt Lake City than at a resort, and there is so much more to do in the city after skiing. To get there, I will use SkyMiles, which may be a terrible currency for booking long-haul business class award seats but often shines on domestic redemptions in economy.

My move is to book economy and then get upgraded because of my Delta Diamond Medallion status. That’s exactly how I did 2 ski weeks last winter.

For cars, I have begun booking Sixt more often lately, as it’s often cheaper than Hertz, Avis, or National. If Sixt has a 4WD with a ski pass-through in Salt Lake City when I need it, that’s my move.

Brett Holzhauer, Content Contributor

Birthday in Spain

This winter, my girlfriend and I are heading to Ibiza and Madrid in Spain for my birthday. To get there, I booked round-trip premium economy flights from Chicago (ORD) to Madrid (MAD) using 51,000 American Airlines AAdvantage miles.

Once there, we’ll stay 1 night at the Hyatt Regency Hesperia Madrid, which I booked using the free night certificate I got from a Brand Explorer award. In Ibiza, we’re planning on staying in an Airbnb.

British Virgin Islands

After that, we’re headed out to the British Virgin Islands for Yacht Week over New Year’s Eve! 

We are doing some in-between travel to get where we need to go, including booking 1 night in Tortola, British Virgin Islands, at a Wyndham. I transferred the necessary points over from Capital One Miles at a 1:1 ratio to Wyndham Rewards.

Carissa Rawson, Senior Content Contributor

I was all ready to start my contribution by letting you guys know that I’m traveling far less than usual. Then, I looked at my calendar, Googled the actual winter dates, and … well, it turns out I have quite a few things going on.

Am I sorry? No. Do I have 2 working feet with which to accomplish this? Also no. But hopefully, by the time I get halfway through, I’ll be off my crutches and sprinting through the airport again.

Adele in Las Vegas

We’re off to a strong start in late November, and I’m going to watch Adele on her second-to-last weekend of performing her Las Vegas residency before her indefinite retirement.

Now that my sister works at a Marriott, I’m never allowing her to quit. Even though I’ll be staying over a weekend, I’m paying just $128 per night for Mandalay Bay, including resort fees, thanks to her family discount.

I haven’t booked my flights for this yet, but since I live in San Diego and matched over to Frontier elite status, it’ll cost me about $40 round-trip for flights.

Maldives

I know what you’re all thinking. “Really, Carissa, Maldives again?”

Yes. This time, I booked a 5-night stay at the Mercure Maldives via Luxury Escapes. I’ve become a raging proponent of purchasing vouchers for the Maldives for years, and I’m always one to put my money where my mouth is.

To pay for this, I used my Chase Sapphire Reserve card to earn 3x Ultimate Rewards on travel, which I’ll put to good use later.

For $2,500, my boyfriend and I will stay 5 nights in an overwater villa with all-inclusive food and drinks, plus transfers are included. I’ve stayed at the Mercure once before and found it has the best snorkeling I’ve ever seen, so I’m happy to return.

My flights are a little more complicated, mostly because we’re heading straight out of the Maldives to Scotland for Christmas and New Year’s, but they look a little something like this:

• San Diego (SAN) to Boston (BOS): $236 in economy with Alaska Airlines
• Boston (BOS) to Doha (DOH): Qatar Airways Qsuite using 70,000 JetBlue TrueBlue points
• Doha (DOH) to Malé (MLE): Qatar Airways economy using 17,500 American Airlines AAdvantage miles
• Malé (MLE) to Dubai (DXB): Etihad business using 20,000 Air Canada Aeroplan points
• Dubai (DXB) to Edinburgh (EDI): British Airways business using 42,500 AAdvantage miles

Scotland

It’s been nearly a year since I was last in Scotland, which is entirely too long for my taste. Since my boyfriend is Scottish, we’ll be spending the bulk of our time with his family in Shetland. I count this a win since he has an entire house there and charges me zero points per night to stay.

However, we’re also spending New Year’s Eve (or Hogmanay) down in Edinburgh. If anyone has traveled to Edinburgh during New Year’s before, they’ll know it’s the most eye-wateringly expensive time of the year to visit.

Worry not, though, because I have cobbled together 7 full nights for very little out of pocket:

• 3 Nights at The Caledonian Edinburgh, Curio Collection by Hilton (Formerly the Waldorf Astoria): 190,000 Hilton Honors points plus $431, of which up to $200 is covered by the American Express Fine Hotels + Resorts credit offered by The Platinum Card^® from American Express
• 4 Nights at the W Edinburgh: $586, thanks to my sister’s incredible Marriott discount

For anyone wondering, I have decided to upgrade to the Marriott Bonvoy Brilliant^® American Express^® Card to take advantage of free breakfast and Platinum Elite status for all my upcoming Marriott stays.

I’ve also booked a flight home from London (LHR) to San Diego (SAN) using 62,000 AAdvantage miles and $343.

Birthday in Las Vegas

I normally spend my birthday in the Maldives but canceled international trips in favor of staying nearby.

To that end, my friends and I are taking a weekend trip to Las Vegas, where we’ll be staying at the Las Vegas Marriott for just $92 per night, again thanks to my sister’s discount (Marriott really didn’t know what it was getting into when it hired her).

California Cruise

In mid-February, I’m taking advantage of 1 of my many free cruise offers to sail Royal Caribbean down to Mexico.

Several members of our Level Up Facebook group took advantage of these cruises earlier this year and had a great time, so I decided to go again.

Bora Bora

Shortly after returning from my cruise, I’ll be heading back to Bora Bora and my favorite Hilton hotel, the Conrad Bora Bora. What started as a solo vacation 4 years ago has morphed into a family tradition, and now 6 of us will be sipping overpriced cocktails poolside in February.

To pay for this, I used 480,000 Hilton Honors points, most of which were bought on sale. I also used the free night award from my Hilton Honors American Express Aspire Card*. In total, I’ll be staying 6 nights.

The card also gives me complimentary Diamond status, which means I’ll be getting free breakfast during my stay.

* The information regarding the Hilton Honors American Express Aspire Card was independently collected by Upgraded Points and not provided nor reviewed by the issuer.

Antarctica

They say that the third time’s the charm, and it certainly is for me, as I booked yet another trip to Antarctica in mid-March. This time, my boyfriend and I will be heading down past the Antarctic Circle on a 12-night journey with Atlas Ocean Voyages.

I sailed with this cruise line earlier this year and loved it so much that we booked again while still on board. Total cost? $6,849 for an all-inclusive journey, including tips, Wi-Fi, and a room with a veranda.

Earlier this year, American Airlines also had a mistake fare from Denver (DEN) to Buenos Aires (EZE) for just $860 round-trip in business class. You better believe I snapped those tickets right up.

Christine Krzyszton, Senior Finance Contributor

Luxumbourg

In late October, I visited my 100th country. I’m very excited to have chosen Luxembourg.

I purchased an American Airlines economy fare for $592 and upgraded to business class with my systemwide upgrades. Systemwide upgrades are earned by reaching Loyalty Point milestones with AA.

I stayed at the Doubletree by Hilton Luxembourg using Hilton Honors points. The nightly rate was just 40,000 points, while the cash rate hovers around $150.

I also booked a guide via Viator for around $100 for the day to see the city and countryside. I earned American Express Membership Rewards on my Viator purchase via Rakuten, Chase Ultimate Rewards points by paying with my Chase Sapphire Reserve card, and 5% back in Viator Rewards. Now, that’s what I call stacking!

Air France Island Hopper

I’ll next travel to the Caribbean in early November with friends to complete the Air France Island Hopper. We’ll visit Fort-de-France in Martinique, French Guiana, and Guadeloupe.

There were no great redemptions here; it was just a bucket list trip. I did use the $150 Delta Stays credit included with my Delta Platinum card.

Delta Inaugural From Boston to Honolulu

Also in November, my Delta friends and I will be flying on the inaugural flight with nonstop service from Boston (BOS) to Honolulu (HNL). That should be a fun trip!

December in New Zealand

I’ve booked New Zealand on Delta Air Lines in December. I purchased Premium Select seats with Ultimate Rewards points and upgraded with a global upgrade certificate earned by reaching Diamond Medallion status. 

January in Puerto Vallarta

January brings relaxation as I head to Puerto Vallarta, Mexico, for 10 days.

I’ll use 140,000 Marriott Bonvoy points to stay at the Sheraton Buganvilias Resort for 5 nights and extend my stay with free night certificates earned on my Marriott Bonvoy credit cards.

James Larounis, Senior Content Contributor

Holidays With Mickey

At the end of this year, I have a week or so planned at Disney. Since I am a proud Disney Vacation Club (DVC) owner, I’ll be staying at Disney’s Grand Floridian Resort & Spa and Disney’s Old Key West Resort, all by using my DVC points.

Conference in Istanbul

In February, I’m taking a trip to Türkiye to participate in a Rotary conference. I used 2 American systemwide upgrades to upgrade my entire trip from Washington, D.C. (IAD) to Istanbul (IST).

For hotels, I’ll be staying at a Hilton in Istanbul, where the conference is under the conference rate, so nothing too exciting.

Winter Fun in Hawaii

I’m also staying 1 week at the Hyatt Regency Waikiki using a Suite Upgrade Award.

Since I’ll be in Los Angeles for a conference, I’ll be flying Hawaiian Airlines on the new 787 from Los Angeles (LAX) to Honolulu (HNL). This cost just $200 in cash and 25K miles to upgrade. 

Juan Ruiz, Senior Editor and Content Contributor

Thanksgiving in Colombia

As I do every year, I will be traveling during Thanksgiving week. I am excited to visit the coffee region of Colombia with my family.

I used the Avianca LifeMiles+ subscription, a monthly plan that allows for the purchase of discounted LifeMiles along with some appealing benefits, including complimentary flight cancellations or ticket changes and a 10% discount on Star Alliance flights, which includes flights with Avianca.

As I frequently book 5 tickets for me, my wife, and kids, the 10% discount on awards significantly reduces the miles I need to use.

Starting the Year in NYC

In January, I’ll be in New York City for a conference, and I used the $300 annual Capital One Travel credit from my Capital One Venture X Business Card*×Information collected independently. Not reviewed by Capital One. to prepay for my hotel.

Rescheduled Disney Cruise Line Trip

In addition, I will be cruising with Disney in January since my initial October 2024 sailing was canceled due to Hurricane Milton.

Wedding in Prague

My winter vacation plans will conclude with a business class flight to Prague for a good friend’s wedding. Because there are no direct flights from the U.S. to Prague, I transferred my American Express Membership Rewards points to the Air France-KLM Flying Blue program and booked an Air France business class ticket to Prague with a quick layover in Paris for only 50,000 miles.

Given that the cash cost for this ticket is more than $4,000, I’d say I did reasonably well with a 7-cent-per-point redemption, given that we value Flying Blue miles at 1.3 cents apiece.

Katie Seemann, Senior Content Contributor and News Editor

Mother-Daughter Trip to Europe

My mom turned 70 this year, and I wanted to do something really special for her, so I planned a mother-daughter trip to Europe. We’re flying United Polaris business class to London, which I booked for 60,000 Aeroplan points plus $56 each.

We’ll spend 3 nights at Andaz London in a suite (I was able to use a Suite Upgrade Award).

Then, we’ll take the Eurostar to Paris where we’ll spend 4 nights at the Hôtel du Louvre. Since both hotels are part of World of Hyatt, we’ll be able to take advantage of my Globalist status for free breakfast each morning. Then, we’ll fly home in Air France business class, which I booked for 50,000 Flying Blue miles plus $382 each.

Post-Holiday Trip to NYC

After the holidays, I’m going to New York City, where I booked a suite at the Park Hyatt New York.

Family Time in St. Kitts

I’ll then enjoy a family vacation in St. Kitts at the Park Hyatt St. Kitts, also in a suite, thanks to Hyatt Suite Upgrade Awards.

Keri Stooksbury, Editor-in-Chief

As American expatriates living in Qatar, my family of 5 doesn’t often make it back to the U.S., but we will be visiting family for the first time in 2 years over the winter holidays.

Road-Tripping Around the Southern U.S.

Unfortunately, Qatar Airways was a bit restrictive with its award space, so we’ve chosen to fly Turkish Airlines to Atlanta (ATL) and drive to Tennessee and North Carolina.

Booking Flights

I was able to secure 3 round-trip award tickets in Turkish Airlines economy class from Doha (DOH) to Istanbul (IST) to Atlanta (ATL) for 88,000 United MileagePlus miles and $77 in taxes and fees each. I needed 2 more award tickets and stalked the award calendar for months to no avail.

I finally purchased my own ticket for $1,420 and a ticket for my oldest son for $1,295 using Turkish’s student flight ticket discount, saving about 9%. Yes, we’re on 3 separate record locators, and this almost certainly will split our group up across our 4 flights, but I’m crossing my fingers that I’ll at least be able to arrange to sit with my older son.

Using my ticket price as a gauge, I received about 1.5 cents per mile in value on my award redemption, a touch higher than our valuation of United miles at 1.2 cents each. While not an incredible redemption, it’s a lot better than the huge out-of-pocket cost we would have faced.

The bulk of my holiday travel purchases have been made using my Capital One Venture X Rewards Credit Card*×Information collected independently. Not reviewed by Capital One.. I purchased my flight via Capital One Travel to earn 5x miles on flights, and I earned 2x miles for my son’s ticket, which was purchased directly with the airline. The Capital One Venture X card’s travel insurance benefits are excellent for coverage should we have issues with our flights or baggage along the way.

Rental Car and Hotels

My Atlanta rental car is also booked through Capital One Travel, earning 10x miles for car rentals. The card offers fantastic auto rental collision damage waiver coverage.

While we’ll stay with family for part of our trip, I have 2 opportunities to book hotel stays in Tennessee. As part of Bilt Rent Day in October, I enrolled in Hilton Honors Gold elite status through the end of 2024. So long as I stay 8 nights at Hilton before December 31, 2024, I can keep Hilton Honors Gold status through March 31, 2026.

Hot Tip:

If you missed the Bilt Rent Day promotion, Hilton is offering an identical status match challenge, which you can apply for here.

It just so happens that a Home2 Suites is near one of our stops and is one of the cheapest options in the area, so I’m going all-in on this status challenge. Even better? I saved about 16% by rebooking my hotel to take advantage of Hilton’s Season to Stay sale. I started my booking at Capital One Offers to earn an additional 11% cash-back.

The only stay I have left to book will likely take advantage of my Chase Sapphire Preferred^® Card‘s $50 hotel credit stacked with a targeted promo to earn 10,000 bonus points with a Chase Travel booking of over $400.

Ryan Smith, News Managing Editor

My wife and I seem to be on a monthly travel subscription. At one point earlier this year, I actually managed to be home for 33 days straight, surprising many of our friends and family.

As 2024 ends and 2025 starts, we already have trips booked through March — yes, every month between now and then, if you were wondering. Here’s what we’re up to for winter.

Dia de los Muertos in Mexico

At the end of October, we continued our annual tradition of attending Dia de los Muertos (Day of the Dead) in a different part of Mexico. This year, we spent a few days in Merida before passing the holiday itself in Oaxaca.

We stayed at the City Centro by Marriott Oaxaca, a brand we were unfamiliar with, so that was a learning experience. It was really cheap, and we were happy to try it out.

Business Class to Brazil

From Mexico, we found a crazy cheap business class ticket ($397 each!) with Avianca down to Brazil to take care of some family stuff.

We’re there for 10 days in early November before flying home in Copa Airlines’ new business class. I’m pretty excited to check that out, as I’ve never flown a lie-flat seat on a Boeing 737 before.

Soccer in Buenos Aires

The soccer team we follow in Brazil qualified for the final of the Copa Libertadores — the top tournament in all of South America. The final this year is in Buenos Aires, so we’ll be home for 10 days before heading back to the southern hemisphere. We booked premium economy flights with United Airlines for $548 each to get to São Paulo (GRU) and then paid around $100 each for Aerolineas Argentinas flights to Buenos Aires (EZE).

Since hotel bookings were crazy for that weekend, we got a night at the DoubleTree by Hilton Buenos Aires for 50,000 Hilton Honors points, then we’re staying at the Duhau Palace-Park Hyatt Buenos Aires. It was charging $1,800 per night or 25,000 points, which is a crazy redemption value. Unfortunately, it was booked the first night, which is why we wound up at the DoubleTree.

We have 24 additional hours to kill before the award flight we found coming home. We’ll spend a day at the Park Hyatt Mendoza using a Hyatt Category 1-4 free night and then fly home in LATAM business class, which we booked for 50,000 Alaska Mileage Plan miles each.

December in Florida and Hawaii

In December, we’re visiting my parents in Florida for a few days to close out our 2024 trips.

In January 2025, we’re heading to Maui, Hawaii, for a week. A timeshare offer included flights out to Hawaii plus a few nights in a hotel, though we’re staying longer.

The rest of the time, we’ll be spending 2 nights at the AC Hotel by Marriott Maui Wailea using Marriott Bonvoy points, 2 nights at the Hyatt Regency Maui using World of Hyatt points, and 1 night at the Hana-Maui Resort using a Category 1-7 certificate.

Snowboarding in Lake Tahoe

In February, we’re heading to Lake Tahoe for a few days of snowboarding and will fly JSX for the first time. We’re very curious about that experience.

While we couldn’t use miles for the flight, we will earn miles with United.

And we found nights at the Category 8 Everline Resort and Spa for just $350, so we snagged those quickly.

Final Thoughts

Phew! Our team is busy this winter, with travel plans ranging across all 7 continents. Using a variety of points, cash, and credit card statement credits, we’re maximizing our travel and enjoying the ride. We can’t wait for next season!

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