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

Wondering what the Upgraded Points team is up to this fall? Just like you, we’re busy earning and redeeming points and miles, and we have exciting trips in the works.

Here’s a look at where we’re going over the next few months.

Ryan Smith, News Managing Editor

After moving to Barcelona last week, I’m getting my new life organized. That means I need to stay put for a bit to regularize my visa situation, get a cell phone plan, and take care of other life necessities.

That won’t last long, though.

In early October, I’ll be in Lisbon, Portugal, for a few days for a conference.

I’m anxious to visit Spain’s 3 exclaves: Ceuta, Melilla, and Peñón de Vélez de la Gomera — all of which are attached to Morocco on one side with the Mediterranean Sea on the other side. Getting to know more of my new home country includes these locations, which I’m very curious about.

In November, my sister is heading to Europe for a work trip and wants to visit a country she’s never been to before, so we’re meeting in Riga, Latvia, for 48 hours. From there, I’ll explore some parts of the Baltics I’ve never seen before, like areas outside these countries’ capitals.

I also have plans to be at the Chicago Seminars in early November. Later that month, I’ll head to Ethiopia for the Most Traveled People (MTP) Summit, including a meetup with other people who’ve been to every country in the world — many of whom I only know online. Meeting them in person will be great.

Juan Ruiz, Senior Editor and Content Contributor

With the kids back in school, my fall travel will include quick weekend trips from South Florida to places like Naples, Atlanta, New York City, and the Dominican Republic. But the highlight is a family trip to Peru booked entirely with points and miles.

I used my stash of Alaska points from the Alaska–Hawaiian merger to book 5 round-trip LATAM tickets from Miami to Lima for just 35,000 miles each (17,500 each way). Those miles even covered our domestic flights within Peru, leaving me to pay only a few hundred dollars in taxes and fees.

For hotels, I turned to the Marriott Bonvoy Boundless^® Credit Card, which I opened when it was offering 5 free night certificates for new applicants. I redeemed 3 nights at Tambo del Inka, a Luxury Collection property in the Sacred Valley with its own train station to Machu Picchu, and 2 nights at the JW Marriott El Convento Cusco. Together, these redemptions saved us at least $2,000 on hotels.

This trip blends Lima’s world-class food scene with one of the New 7 Wonders of the World. Thanks to points and miles, I get to share it with my whole family without the hefty price tag.

Katie Corrigan Seemann, Travel Partnerships Manager

I’m kicking off my fall travel with a trip to Walt Disney World with some of my Upgraded Points co-workers to attend a media event. The cool part is that I am bringing my daughter so she can see me in action while we have some theme park fun.

Next, I was invited to Puerto Vallarta to check out the Dreams Bahia Mita Surf & Spa Resort. Since this is a family-friendly all-inclusive, I’ll bring my husband and daughter so we can enjoy a fun long weekend together. I was really impressed by my stay at Dreams Estrella del Mar Mazatlán Golf & Spa Resort last year, so I am looking forward to trying out another Dreams location.

I have a couple of other trips that are still being planned, but I am hoping to make them work. First, I just found out that my husband earned a trip to Thailand from work, so if all goes well, we’ll head to Phuket in November. I’m also working on planning a trip to Europe to visit the Christmas markets with a friend in early December. My Seats.aero alerts are set, so hopefully some good deals will pop up soon.

James Larounis, Senior Content Contributor

I love Disney cruises, and I’m taking a 3-night sailing from Fort Lauderdale to the Bahamas soon.

In October, I’m heading to London. I found out that some friends are going to Marrakech, Morocco, around the same time, so I’ll hop down there from London to meet up with them for a few days before heading back to London for a bit before returning home.

Chris Hassan, Social Media and Brand Manager

This fall is proving to be busy for me, at least to start.

I’ll be kicking things off in Orlando, first for Universal’s Halloween Horror Nights, and then I’ll hop over to Walt Disney World in support of our “Magic in the Air” sweepstakes. Be sure to enter for your chance to win a vacation package to The Most Magical Place On Earth!

After that relaxing trip, my family and I will head to São Paulo. My wife is taking our daughter to see the Backstreet Boys, and I can’t turn down the opportunity to eat my way around town while they are at the show. Plus, we will stay at the brand new W São Paulo again, which is always a treat.

To finish off the month, I will fly up to Martha’s Vineyard for my annual guys’ weekend with my childhood friends. It’s not the most convenient location, but it’s beautiful, and the price was actually pretty reasonable.

I booked American Airlines economy seats from Rio de Janeiro (GIG) to Boston Logan International Airport (BOS) for 20,000 points each way, transferred from my Citi Strata Premier℠ Card. I’ll hop over to Martha’s Vineyard on JetBlue for 9,700 points transferred from American Express.

The rest of the fall is still up in the air, but I’m sure I will book something else with all of the award alerts we have been sending out lately!

Jessica Merritt, Senior Editor and Content Contributor

I’m heading to Denver for a family vacation in October! This is a familiar spot for us, and October is my favorite time to visit Colorado. It offers perfect sunny-yet-cool fall weather with bright yellow leaves on the aspens and a chance of snow at higher elevations.

We’re flying Frontier Airlines on an unbeatable round-trip fare of $190 total for all 5 of us using the Discount Den’s Kids Fly Free feature. I booked a vacation rental on Capital One Travel using my Capital One Venture X Rewards Credit Card’s $300 travel credit and some of the miles I earned with my welcome bonus offer. Airport rental car prices were insane (and I’m not a fan of the rental car shuttle), so we’re picking up a more reasonably priced car downtown and riding the RTD-Denver A Line train from Denver International Airport (DEN) to downtown Denver’s Union Station.

Stella Shon, Senior Features Editor

My travel schedule is lighter than usual this fall, though my partner and I will be attending 2 weddings in North Carolina soon. Since we’re already well into the second half of the year, I’m making an effort to hold on to my Delta elite status, though it looks like I’ll likely drop from Platinum Medallion to Gold for 2027. Even so, I still find status worthwhile because I live near a Delta Air Lines hub, and perks like Comfort+ upgrades 3 days before departure and complimentary preferred seats make a big difference for my domestic trips.

For these weddings, I booked both round-trip flights using my Delta SkyMiles^® Platinum American Express Card, which earns 3x miles on Delta purchases. I’ll also rack up 1 MQD per $20 in eligible card spend, in addition to the 1 MQD per dollar on airfare. After these 2 flights, I’ll be only about 1,000 MQDs shy of securing Gold status for next year.

For one of the weddings, we’re spending 2 nights at The Carolina Inn in Chapel Hill, North Carolina, a Category 4 property in the World of Hyatt portfolio. Because it falls on a peak football weekend, the rate was 18,000 points per night. Still, with cash prices running close to $500 a night, we’re getting nearly 3 cents per point in value.

To book, we transferred Bilt Rewards Points and Chase Ultimate Rewards points to our World of Hyatt account at a 1:1 ratio, and a friend generously shared a Guest of Honor award. That gives us Globalist perks during our stay, including free valet parking, complimentary breakfast for 2, late checkout at 4 p.m., and more.

Lori Zaino, Senior Content Contributor

My fall travel schedule feels calm after a summer full of flying, driving, and riding the rails. However, I will be taking Renfe’s AVE train from my home in Madrid to Malaga to see friends for a weekend in October. I’m staying at my favorite hotel there, the H10 Chroma. It has a super chic rooftop bar and pool. Although H10’s loyalty program isn’t quite as lucrative as Hyatt or IHG One Rewards, I love that all members automatically get a 5% discount on all bookings.

Beyond that, my travel plans aren’t as whimsical as prior years. Due to a family member’s cancer diagnosis and impending treatment plan, I’ll likely be flying between Madrid (MAD) and Chicago (ORD) a few times this fall.

Although this certainly isn’t “fun” travel, family emergencies are a time when I value frequent flyer miles and points more than ever. Thanks to a big stash of Amex Membership Rewards and Chase Ultimate Rewards, I know I’ll be able to transfer these points to Club Iberia Plus and use them to fly starting at just 16,000 Avios per way, off-peak in basic economy (a total steal!) at the last minute between the 2 cities nonstop, ensuring I can offer in-person support when my family needs it the most.

Christine Krzyszton, Senior Finance Contributor

I took advantage of the SAS Premium Economy sale and booked a trip to Alesund, Norway, in September. I paid for it with 50,000 Ultimate Rewards points and booked 4 nights at 15,000 points per night through Choice Privileges.

Earlier in September, I’ll be joining friends at the annual SpotLAX (sponsored by NYC Aviation) and Cranky Dorkfest in Los Angeles for a weekend of plane spotting and catching up with a bunch of aviation enthusiasts. There weren’t really any deals on hotels, so I transferred Ultimate Rewards points to World of Hyatt to stay at the Hyatt Regency LAX.

Final Thoughts

From Spain to Brazil and across the U.S., the Upgraded Points team is traveling a lot this fall. Some of us are booking cheap travel and earning significant rewards by using the right credit card, while others are taking advantage of their points and miles to book trips, sending our team to theme parks, cruises, and other fun trips this fall.