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Where Are We Going? The UP Team’s Winter 2023 Travel Plans

Carissa Rawson's image
Carissa Rawson
Carissa Rawson's image

Carissa Rawson

Senior Content Contributor

271 Published Articles

Countries Visited: 51U.S. States Visited: 36

Carissa served in the U.S. Air Force where she developed her love for travel and new cultures. She started her own blog and eventually joined The Points Guy. Since then, she’s contributed to Business ...
Edited by: Jessica Merritt
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Jessica Merritt

Editor & Content Contributor

101 Published Articles 523 Edited Articles

Countries Visited: 4U.S. States Visited: 23

A long-time points and miles student, Jessica is the former Personal Finance Managing Editor at U.S. News and World Report and is passionate about helping consumers fund their travels for as little ca...
& Keri Stooksbury
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Keri Stooksbury


38 Published Articles 3324 Edited Articles

Countries Visited: 47U.S. States Visited: 28

With years of experience in corporate marketing and as the executive director of the American Chamber of Commerce in Qatar, Keri is now editor-in-chief at UP, overseeing daily content operations and r...

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Earlier this year, we broke down our team’s summer travel plans, with Caribbean cruises, Icelandic adventures, and even a stop Down Under. Now winter is rolling around, and we’re back with another edition — scarves and hats not necessary. Let’s take a look at the Upgraded Points team’s travel plans for winter 2023!

Carissa Rawson, Senior Content Contributor

Waldorf Astoria Maldives Ithaafushi
The Waldorf Astoria Maldives Ithaafushi has long been on my bucket list. Image Credit: Hilton

This was the year I vowed to stay home and hang out with my dogs. As you can probably guess, I failed miserably, though once I did manage to stay in the country for 4 months straight. I have plenty of plans for fall and winter, but I’m going to go just beyond 2023 to talk about my birthday plans for January 2024.


Because they’re really cool.

At the risk of sounding like a total snob, I usually like to go to the Maldives for my birthday. I had originally intended to make a change and head to the Seychelles, but when 5 nights of standard award availability dropped at the Waldorf Astoria Maldives Ithaafushi, I knew I had to act.

The Waldorf Maldives is the most expensive property in Hilton’s portfolio, which means it costs 150,000 points per night. Since Hilton Honors gives you a fifth night free with award bookings, I was able to book these 5 nights using just 600,000 Hilton Honors points. These were either earned, purchased (with a 100% bonus promotion), or transferred over from American Express Membership Rewards (at a 2:1 ratio).

However, this is just the tip of the iceberg. I also needed to arrange transportation. Since it was my birthday, I decided to jump on a newly-released first class flight from London (LHR) to Abu Dhabi (AUH). These are flown by Etihad’s A380 and include an inflight shower, which is something I’ve never experienced.

With a first class flight and first class accommodations arranged, clearly I needed to complete this high-end experience around the world. I then booked the remainder of my travel:

  • San Diego (SAN) to London (LHR): $755 + 40 PlusPoints for United Polaris business class
  • London (LHR) to Abu Dhabi (AUH): 62,500 American Airlines AAdvantage miles + $296 for Etihad first class
  • Cab from Abu Dhabi (AUH) to Dubai (DXB): ~$100
  • Dubai (DXB) to Malé (MLE): 19,500 Aeroplan points + $60 for Emirates economy
  • Malé (MLE) to Doha (DOH): 40,000 AAdvantage miles + $182 for Qatar first
  • Doha (DOH) to Tokyo (HND): 50,000 AAdvantage miles + $60 for Qatar first and JAL first
  • Tokyo (HND) to Dallas (DFW): 80,000 AAdvantage miles + 46.85 for JAL first
  • Dallas (DFW) to San Diego (SAN): $119 one-way in American economy

I earned United PlusPoints through a mix of clever flying and spending with United, while most of my American Airlines miles came from donations, earning me 50x miles per $1 spent.

Chris Hassan, Social Media Manager and Family Travel Contributor

Qatar QSuites, 777, Turndown Service with Lie-flat bed
Qatar Airways QSuites features double beds in business class, which is great for couples. Image Credit: Alex Miller

When my friend said he was getting married in Australia in February, I knew that was the perfect excuse to try and check off some bucket list flights. 

My first thought was Qatar Airways Qsuites. After a fair amount of searching, I found 2 seats for my wife and myself from Melbourne (MEL) to São Paulo (GRU) for 110,000 Avios each. I am based in Rio de Janeiro (GIG), and the wedding is in Sydney (SYD), but a couple of positioning flights are easily worth 30 hours in one of the best business class products in the sky.

I immediately transferred all of my points over from Livelo (a Brazilian flexible points and miles currency) and booked our return flights home, which was a very exciting moment. 

Then, I just needed to find a flight to Australia. There were plenty of options, but coming from Brazil meant a connection or 2, or in my case, 3 or 4.

When we sent out the deal alert for the Etihad Apartment, I knew this was the time to make a move. Normally we travel as a family of 4, and my wife and I have been dreaming about this flight. When 2 seats opened up from London (LHR) to Abu Dhabi (AUH), I snagged them. I even tagged on a flight to the Maldives for good measure at no extra cost. This is a bucket list trip, after all, right? All in, the cost was 62,500 AAdvantage miles + $300 each.

I’m not totally sure how we are getting to London or from the Maldives, but for now, this trip is shaping up to be epic! 

Christy Rodriquez, Travel and Finance Content Contributor

Air France A350 Business Class Back Angle
I can’t wait to give Air France’s business class a shot. Image Credit: Air France

My plans for this winter include a trip to Italy in just a few weeks! My husband, daughter, and I are going from Los Angeles (LAX) to Florence (FLR) on Air France business class. The return trip is from Rome (FCO) to Los Angeles (LAX), also in business with Air France. We booked all 3 of us for a total of $1,330 (those lap child fees get you!) and 370,000 Flying Blue miles (185,000 miles each).

We took advantage of a 25% transfer bonus from Amex to Air France-KLM Flying Blue to maximize our points. My husband got one of those 150k welcome offers from opening The Platinum Card From American Express, so that made a huge difference! We accumulated the rest through my Chase Sapphire Preferred® Card and spending on the Amex Platinum card.

It’s a 9-week trip, so that really rounds out my winter!

Katie Seemann, Senior Content Contributor

Le Meridien Maldives
The Le Méridien Maldives is a great use of points. Image Credit: Marriott

The only big trip I currently have on my calendar for this winter is one I am really excited about — the Maldives!

I’ve wanted to go to the Maldives for years but only recently convinced my husband that it’s worth the extra travel involved. We are going at the end of January (one of the best times to visit the Maldives) as an early anniversary trip.

As soon as we agreed on the Maldives as a destination, I knew I wanted to book the flights in Qsuites! This aspirational business class has been high on my travel bucket list, and I was excited to finally have the opportunity to book it.

One of the best ways to book Qsuites with miles and points is through American Airlines. I searched for award availability directly on and used ExpertFlyer to help determine which flights had Qsuites and which had regular Qatar Airways business class.

I paid 70,000 American Airlines miles plus $41.80 in taxes and fees for a flight from New York (JFK) to Doha (DOH) to Malé (MLE). I earned those miles mostly through credit card sign-up bonuses.

For my positioning flight from Columbus (CMH) to New York (JFK), I paid cash using my Chase Sapphire Reserve® to earn 3x points per $1 and have access to excellent travel coverage

Finding a return flight through American Airlines was a bit trickier because I didn’t have enough miles left. So, I booked my return Qsuites flight via British Airways for 85,000 Avios plus $334 in taxes each using miles I transferred from Capital One.

As for a hotel, I originally planned to book the Park Hyatt MaldivesPark Hyatt Maldives, but I ended up choosing Le Méridien Maldives for a few reasons. I had a stockpile of about 600,000 Marriott Bonvoy points that had been sitting in my account, gathering dust for years, and this was a great opportunity to get some value out of them.

I also had my heart set on staying in an overwater villa, and I couldn’t book one with points at the Park Hyatt Maldives. On top of that, I’ve had a few friends stay at Le Méridien and they had glowing reviews.

I booked 6 nights at Le Méridien Maldives for a total of 335,000 Marriott Bonvoy points. I also had to pay for the seaplane transfer to and from the hotel for $1,102 (a cost you’ll incur at nearly any resort in the Maldives). I am so excited that I was finally able to use those points that had just been sitting in my account for an incredible experience, such as an overwater villa in the Maldives.

Keri Stooksbury, Editor-in-Chief

My winter break 2023 was shaping up to be 2 weeks of touring through Sri Lanka — a somewhat quick 5-hour flight from my home base in Doha, Qatar. I’d bought the Lonely Planet book for inspiration and started asking friends for recommendations. I was even starting to get quotes from a few drivers and guides … all until my 3 kids dropped some truth bombs on me: They wanted a cold vacation. The snowier, the better. Now, Sri Lanka is known for a lot of things, but snow definitely does not top the list.

I’m still in the midst of figuring out our Plan B, and I’m only planning flights at the moment. I’ve started my research in 2 directions:

  1. Checking my credit card rewards and frequent flyer balances
  2. Having fun with Google Flights Explore feature

Where Can My Points and Miles Take Me? 

With a family of 5, I generally need pretty hefty balances to accommodate all of us on award tickets, and we always fly economy to maximize our miles. While I typically book Qatar Airways flights with British Airways Avios, I’ve seen some great economy award availability through American Airlines for the holidays, including 40,000 AAdvantage miles round-trip from Doha to Europe and 45,000 AAdvantage miles round-trip from Doha to Japan.

Thanks to welcome offers received recently on the AAdvantage® Aviator® Red World Elite Mastercard® (70,000 AAdvantage miles) and the Citi® / AAdvantage® Platinum Select® World Elite™ Mastercard® (75,000 AAdvantage miles), I’ve got a lot of AAdvantage miles to work with, but I’m about 18,000 miles short of having enough to fly the family to Europe round-trip.

If I were to donate to American’s Stand Up to Cancer promotion, I’d earn 25 miles per $1 donated (the 50 miles per $1 AA cardholder promotion that Carissa used has been exhausted), so 18,000 miles would cost $720. While the cause is great, paying 4 cents a mile to top up my account is not a tremendous value

Alternatively, I can explore paying for the outbound leg of the Europe trip with AAdvantage miles and the return trip with Avios (without having to buy any additional Avios). The BA award costs and fees are higher than with AA, but I would definitely consider transferring Chase Ultimate Rewards points to British Airways to take advantage of the current 30% transfer bonus

Is Cash a Better Option?

I love getting lost in where I can travel on the cheap with the Google Flights Explore and Kayak Explore maps. If we were to go to Europe, I would likely book a multi-stop itinerary into 1 city and out of another. As Kayak Explore only shows round-trip options between 2 cities, Google Flights is a much better tool for researching one-way travel.

I’ve seen a lot of incredibly affordable flights through Turkish low-cost carrier Pegasus Airlines to many of the great European Christmas market hotspots. 

Doha to Anywhere 12172023
Google Flights’ Explore feature is one of my favorites. Image Credit: Google Flights

I’ve gone so far as to pricing out 3-city, 4-leg itineraries for an astonishing $430 total per person. These flights are all on very budget European carriers, and we would likely need to travel very light (in winter, no less!) to avoid checked baggage fees, but for this crazy price, it might just be worth it. My P2 is also working towards a welcome bonus on the British Airways Visa Signature® Card, so cash flights would go a long way to helping knock out that bonus’ minimum spending requirement

So, Where Am I Going?

I think we’re pushing off Sri Lanka to Spring Break 2024, so it looks like my family is heading to Europe this winter break. While we have an idea of where we’d like to visit (Denmark, maybe Poland), we’re still weighing cheap cash red-eye flights on budget airlines vs. the comfort (but hefty award price) of Qatar Airways economy class. I hope to sort out flights soon, then I’ll be on to accommodations!

Lori Zaino, Content Contributor

Santa Cruz de Tenerife
A blissful beach in Tenerife seems just the ticket for winter. Image Credit: Hjrivas via Pixabay

This winter, my family and I will head to Tenerife in the Canary Islands from our home in Madrid, Spain. The Canaries are really the only warm spot in Europe in winter, so it’s where many Europeans head for a dose of winter sun. Some adventurous Americans head there on the relatively new nonstop United flight from Newark (EWR) to Tenerife (TFS).

My husband is a teacher, so we’re limited when it comes to dates. To save money and beat crowds, we almost always fly on Christmas Day.

This year, we booked our plane tickets on Iberia from Madrid (MAD) to Tenerife (TFS) using the Iberia Visa Signature® Card to get 3x Avios per $1 spent and a 10% discount. We prefer to save our Avios for long-haul flights between Spain and the U.S. or Latin America, where you can really maximize them.

Plane tickets were just over $210 per person round-trip, which is pretty reasonable given the peak travel dates. We saved nearly $170 per person by flying on December 25. We’re also chasing Oneworld status this year on Iberia instead of AA, which seems more feasible given our location in Spain.

We’re staying 1 night at the AC Hotel Tenerife, a Marriott hotel relatively close to the airport, as we get in rather late. Cash rates were low, so I booked a room for $160.

The next day, we’ll head to a family-friendly Barcelo resort in the sunnier southern part of the island for a week. Although I could have booked via, the rates are typically much cheaper on

Since I’ve reached the My Barcelo Intense tier of the My Barcelo Loyalty Program, I also get a 10% discount on bookings, among other perks. Rates were around $268 per night for half board, which is ideal when feeding my hangry toddler. I booked using my Chase Sapphire Reserve card to get 3x Ultimate Rewards points per $1 spent. Hopefully, after a week in the sun, we’ll be ready to tackle 2024!

James Larounis, Senior Content Contributor

American Airlines A321T Flagship Business tray table fully extended
I’m looking forward to flying American Airlines business class. Image Credit: Daniel Ross

In September, I’ll be traveling to London (LHR) for a work event. My routing will be Washington, D.C. (DCA) to New York (JFK) to London (LHR) with the same return, all on American. This booking was approximately $1,100 round-trip in economy/premium economy, and I upgraded to business class using American Airlines’ systemwide upgrades.

The flights I chose had confirmed upgrade space available, and even though the cash price was a little high, I’ll get back a chunk of this as a reimbursement. I’ll also have the ability to fly across the pond in business class. When you think of it, it’s only around $1,100 in business class round-trip, which isn’t a horrible deal!

In October, I’ll visit some friends in Sacramento. Then, we are flying up for a few days to Vancouver, a city I am very excited about seeing since I’ve only been there once and it was only for less than 24 hours! For this travel, I booked a nonstop flight from one of my home airports, Washington, D.C. (IAD), to Sacramento (SMF), for about 70,000 American Express Membership Rewards points towards the cost of a ~$700 one-way cash booking in first on United. I have The Business Platinum Card® from American Express, so I’ll receive 35% of those points back, which I thought was a somewhat decent deal considering I was not flexible on dates and far preferred the nonstop over connecting options that got in well past midnight.

I used the same method for the flight up to Vancouver (YVR) and redeemed about 30,000 Membership Rewards points one-way on Air Canada in business class. I valued the nonstop service, and with 35% back, I was satisfied with my purchase.

I mainly earn my American Express points from transit using the American Express® Green Card, or from dining and groceries using the American Express® Gold Card, though I’ve got plenty of airfare spend on my Amex Platinum card, too.

Back from Vancouver, I’m taking Alaska Airlines from Vancouver (YVR) to Seattle (SEA), overnighting in Seattle, and then flying back the next day to Baltimore (BWI). It was only around $600 in first class one-way, so it seemed like a reasonably good deal without having to deal with a red-eye flight.

Juan Ruiz, Compliance Editor and Content Contributor

I’m going to a few places this fall and winter, but I recently redeemed 16,000 Avios per person to fly from Miami (MIA) to Dublin (DUB) for a weeklong trip to Ireland with my wife and 3 daughters over Thanksgiving week.

I transferred Amex points to British Airways Executive Club and booked the return flight the same way for a cost of 32,000 Avios round-trip per family member. Cash prices for these flights were $900+ round-trip per person, so I almost tripled our valuation of Avios at 1.25 cents apiece with this redemption.

Ryan Smith, Content Contributor

Emerald Pool Dominica
Waterfall hikes are a top attraction in Dominica. Image Credit: haspil via Adobe Stock

I have been traveling a lot lately, hoping to complete my goal of visiting every country by the end of this year. I have 2 countries remaining, plus I am speaking at the Chicago Seminars (a points and miles event) in October, leaving me with 3 places to go for the rest of 2023.

In Chicago, I booked a Hyatt Place for 5,000 points per night for 2 nights. For flights, I used 19,000 United MileagePlus miles each way for the flight, but I was happy to do that to fly out of Santa Ana (SNA) instead of saving miles but needing an $80 ride each way to Los Angeles (LAX) — as well as the extra time involved.

For December, I booked an American Airlines cash fare from Santa Ana (SNA) to Dominica (DOM) via Miami for $400 and then used 20,000 Alaska Mileage Plan miles for my flight from Dominica (DOM) to Argyle, Saint Vincent (SVD), connecting through Miami. Flights were $950, so redeeming miles was definitely the way to go. I haven’t booked the flight home yet. Maybe I should do that soon.

Final Thoughts

As you can see, we have plenty of team members making plans for the winter already. Although the most popular travel destination is the Maldives, we’ve also got folks heading to Europe and even Australia. And while some of us are weighing cheap cash prices for flights, others are making the most by redeeming miles for spectacular options — including Etihad’s phenomenal First Class Apartment. We can’t wait for the reviews!

The information regarding the AAdvantage® Aviator® Red World Elite Mastercard® was independently collected by Upgraded Points and not provided nor reviewed by the issuer. 
The information regarding the Citi® / AAdvantage® Platinum Select® World Elite™ Mastercard® was independently collected by Upgraded Points and not provided nor reviewed by the issuer.
The information regarding the American Express® Green Card was independently collected by Upgraded Points and not provided nor reviewed by the issuer.
The information regarding the Marriott Bonvoy Boundless® Credit Card was independently collected by Upgraded Points and not provided nor reviewed by the issuer.

For rates and fees of The Platinum Card® from American Express, click here.
For rates and fees of The Business Platinum Card® from American Express, click here.
For rates and fees of the American Express® Gold Card, click here.
For rates and fees of the Marriott Bonvoy Business® American Express® Card, click here.

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About Carissa Rawson

Carissa served in the U.S. Air Force where she developed her love for travel and new cultures. She started her own blog and eventually joined The Points Guy. Since then, she’s contributed to Business Insider, Forbes, and more.

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