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

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

Carissa Rawson

Senior Content Contributor

268 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: Stella Shon
Stella Shon's image

Stella Shon

News Managing Editor

94 Published Articles 672 Edited Articles

Countries Visited: 25U.S. States Visited: 22

With a degree in media and journalism, Stella has been in the points and miles game for more than 6 years. She most recently worked as a Corporate Communications Analyst for JetBlue. Find her work in ...

Table of Contents

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Winter is finally behind us, and spring is in full swing, which means we’re all already looking ahead to summer and all the travel that comes with our favorite season.

So, where is our team jetting off to this summer? We surveyed the team, and you can read on it to find out what some of us have cooked up. And spoiler alert — there are some pretty cool places on this list!

Carissa Rawson, Senior Content Contributor

I’ve spent the last 4 months traveling almost nonstop, with first class flights around the world, trips to the Maldives, Bora Bora, Qatar, the UAE, the U.K., all over the U.S., and even a cruise down to Antarctica. Suffice it to say I am tired.

Conrad Bora Bora Rawson
My real flex is booking 3 rooms at the Conrad Bora Bora on points. Image Credit: Carissa Rawson

So it is with great pleasure that my summer plans this year are very limited. While I have a number of stays at the Rio Hotel and Casino Las Vegas coming up (to earn World of Hyatt Globalist status), that’s about it until July, when we have our next Level Up meetup. Even then, it’s going to be in my hometown of San Diego.

After the meetup, I have nothing until August, when my family and I are traveling to South Africa for a safari. I’ll be gone for a total of 13 days, and I’m pretty pleased with how the booking has turned out:

  • $187 for a flight from San Diego (SAN) to Dallas Fort-Worth (DFW)
  • 75,000 American Airlines miles and $384 in taxes and fees for a flight from Dallas (DFW) to Johannesburg (JNB) via London (LHR)
  • $222 for intra-South Africa flights, including Johannesburg (JNB) to Capetown (CPT)
  • 6 nights at the Hyatt Regency Cape Town for 22,500 points: Used a suite upgrade award (SUA) for a Regency Suite
  • 5 nights on safari at a private game lodge: $1,299 for 2, with meals and game drives included via a Travelzoo vacation package
  • 75,000 American Airlines miles + $346 in taxes and fees for a flight from Johannesburg (JNB) to San Diego (SAN) via London (LHR) and Miami (MIA)

Safari aside, I’m most excited about getting to fly British Airways’ A380 to South Africa. Although its business class is outdated, I have Oneworld Emerald status and already picked one of the few window seats with direct aisle access for free. Plus, who doesn’t love sitting on the upper deck?

I earned most of these points through spending on my Chase Sapphire Reserve®, Simply Miles purchases, and American Airlines hotels, though, of course, I’m using more cash than usual for this trip.

Hot Tip:

Need to feel inspired? Have a look at our top European destinations for summer 2024.

Chris Hassan, Social Media and Brand Manager

Summer is approaching quickly, but since I live in Brazil, that means it’s winter! Unfortunately, winter break for my kids is only 2 weeks long, so we need to be efficient with our travel time.

We like to travel to New England in July to see my family, as the weather is nice and a lot of our friends are also on vacation.

We will likely stay with family for that part of the trip, but getting there this year will be via LATAM in economy for 37,500 Virgin Atlantic points. Nothing glamorous, but the price is right for a family of 4 from Rio de Janeiro (GIG) to Boston (BOS).

On the way back to Brazil, my kids are trying to convince me to stop in Florida to check out Tiana’s Bayou Adventure at Walt Disney World and DreamWorks Land at Universal Orlando if they are open.

Since Breeze Airways just launched nonstop flights from Burlington, Vermont, to Orlando, it’s not the worst idea. But I may need to sneak off to San Diego to hang out with our awesome Level UP Travel Group!

Breeze Airways Ascent Class A220
Breeze’s fresh new Ascent class. Image Credit: Stella Shon

Although that is all pretty much booked, there is still 1 summer trip on our wishlist…seeing Taylor Swift in London! We’ve got the tickets lined up for August, I just need to figure out how we are going to get there… 

Christine Krzyszton, Senior Finance Contributor

Summers in northern Michigan are some of the best anywhere. For this reason, I tend to keep my otherwise busy travel calendar to a minimum during the peak of the season.

I will start the season with a trip to New Zealand in May. I booked the trip for around $1,100 with Delta Airlines using the Pay With Miles benefit from my Delta SkyMiles® Platinum Business American Express Card.

Delta One Cabin
Upgrade to Delta One with a global upgrade certificate. Image Credit: Stella Shon

I upgraded the round-trip flights to first/business class with my Delta global upgrade certificates, which I received by earning Diamond Medallion status.

Hotels in Christchurch, Wellington, and Auckland are covered with Hilton Honors points earned on my Hilton Honors American Express Aspire Card* and IHG One Rewards points.

I then have a long weekend planned in Bogotá, Colombia, in June. I found round-trip first/business class flights from my small home airport for around 50,000 Chase Ultimate Rewards points with my Chase Sapphire Reserve card. I love the 1.5 cents per point redemption value when I find inexpensive flights.

In July I have the Upgraded Points meetup event in San Diego firmly set on my calendar for July 27th.

I’ll play tourist in my hometown in the month of August, then jet off to Iceland and Spain in September.

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

James Larounis, Senior Content Contributor

I’m headed to Singapore in late May into early June for another Rotary International Conference. I’m going to do a weekend trip after the conference to Kuala Lumpur since it’s relatively nearby and I’ve never been. I’ll be flying Singapore Airlines business class, which I booked for 80,000 Air Canada Aeroplan points.

Singapore Airlines Airbus A350 Business Class - Turndown Service
Singapore’s business class can’t be beat! Image Credit: Greg Stone

For hotels, I’m sticking with my favorite chain, World of Hyatt, and will be staying at the Andaz Singapore for 20,000 Hyatt points per night.

In late June, I’m headed to Kansas City for the Airliner’s International conference. The trip has been booked with cash, so it’s nothing special, but I’m definitely excited to go!

In early June, I have a tentative trip booked to Santa Barbara thanks to a cheap $600 one-way business class fare in a lie-flat seat on American.

Later in July, I’m headed to San Diego for the UP meetup! I found a $500 one-way Alaska Airlines first class nonstop fare from D.C., which I snagged as soon as I saw it. I’m staying just 1 night at the Courtyard Old Town, which I booked using a Marriott free night certificate from the Marriott Bonvoy Boundless® Credit Card.

From there, I’ll head to Boulder for a Boy Scout conference I’m helping with on their emergency management team. After that, I’ll spend a few days in Colorado Springs to see the area.

In August, I’ll be making a quick trip to Chicago with my Rotary district to visit the headquarters in Evanston. Later in the month, I plan on attending the U.S. Open tennis tournament before heading to the Toronto International Film Festival in early September.

Juan Ruiz, Senior Editor & Content Contributor

This summer is filled with exciting travel opportunities from my perspective. In June, I’m excited to visit the St. Regis Bermuda, a hotel that has caught my attention for a while now. I’m really excited about my upcoming trip to Bermuda, especially because I’ve heard so much about its beautiful pink sand beaches.

In a few weeks, my wife, 3 daughters, and I will be embarking on a trip to Naples, where we will have the pleasure of exploring the beautiful Amalfi coast for an entire week. I managed to secure economy seats with Air France using the airline’s Flying Blue miles for our trip to Italy.

Air France Business Class cabin 1
Flying Blue is one of our favorite programs. Image Credit: Daniel Ross

However, I was pleasantly surprised when I was able to secure 5 business class seats on Air France from Rome (FCO) to Paris (CDG) and then back home to Miami (MIA), all for under 50,000 miles per person for the one-way journey.

I absolutely love the Flying Blue program because of its incredible award availability, fantastic rates, and frequent transfer bonuses.

Lastly, we have plans to fly to London in August to see Taylor Swift. Fortunately, we managed to secure tickets for The Eras Tour at face value for her London show. It turns out that traveling to see her is a much more cost-effective option compared to watching her perform in my hometown, where resell ticket prices are exorbitant.

We will be flying round-trip from Miami to London on Virgin Atlantic, and I redeemed 25,000 points per person for these flights.

I intend to redeem World of Hyatt points to cover our hotel stay. That way we’re not spending a lot of money on airfare or hotel to see the pop icon in London Town.

Katie Seemann, Senior Content Contributor and News Editor

I’ve got a couple of fun trips coming up this summer that I am excited about. 

First, in May, my husband and I are going to Paris and Amsterdam to celebrate our 20th wedding anniversary. To get there, we’re flying in Air France business class.

I was able to take advantage of a 25% transfer bonus from American Express Membership Rewards to Flying Blue, so I only paid 44,000 Amex points (55,000 Flying Blue miles) plus $207 for each flight. 

I paid 165,000 World of Hyatt points for 4 nights at the Park Hyatt Paris-Vendôme. Yes, it’s a lot of points, but this is a points-bucket-list hotel that I’ve been eyeing for years, so it was a perfect opportunity to splurge.

Park Hyatt Paris Vendome
A bucket list hotel for many. Image Credit: Hyatt

Then we’re spending 3 nights at Andaz Amsterdam Prinsengracht, which cost me 87,000 Hyatt points

For our return flights, I transferred 48,000 Citi Points to Flying Blue (also with a 25% transfer bonus) to book 2 KLM premium economy tickets. I also paid $232 in taxes and fees for each ticket using my Chase Sapphire Reserve card.

We flew in American Airlines premium economy home from Europe last summer, and it was very comfortable, so I am excited to try out KLM’s premium economy product.

Later in the summer, I’m taking a family trip to Monterey, California. We’re staying at the Hyatt Regency Monterey Hotel and Spa on Del Monte Golf Course.

I booked 4 nights for 83,000 Hyatt points and applied a Suite Upgrade Award, so we’ll have a little extra space. Plus, I shared Guest of Honor awards with the rest of my family members so they could take advantage of my Globalist benefits, too (most importantly, free breakfast!)

For my flights to California, I used American Airlines miles. I was able to book 3 round-trip flights for just 18,500 miles each. The cash cost was ~$600 each, so I am getting over 3 cents per point in value for this redemption. 

Keri Stooksbury, Editor-in-Chief

As a remote worker based in Doha, Qatar, my office can have whatever view I’d like, so for the third year in a row, I’ll be traveling with my kids to Phuket, Thailand. Accommodation prices have increased since 2023, but the convenience of easy access to beautiful beaches, delicious noodles, and shopping can’t be beaten.

Pad See Ew Thailand
My kids can’t wait for smoothies and Pad See Ew at the beach. Image Credit: Keri Stooksbury

After a month in Thailand, we’ll spend 3 weeks in Hong Kong, Japan, South Korea, and Taiwan. This is not exactly the laid-back end to summer I was after, and I have a lot of planning still ahead!

While I’ve been lucky in years past to book the Doha (DOH) to Phuket (HKT) award flights on Qatar Airways through British Airways Executive Club or Qatar Airways Privilege Club, there was no availability for the dates I was after.

I found a reasonable one-way cash fare of ~$370 per person on China Southern through Capital One Travel, earning 5x Capital One miles on my purchase.

While this flight has a longer transit time with a connection in Guangzhou (CAN), I was able to utilize my $300 Capital One Travel credit on the Capital One Venture X Rewards Credit Card and a credit from price drop protection. I’m excited to try a new airline and check out the Priority Pass Select lounges in Guangzhou (there are 7!). 

Unlike Chase, Capital One miles are usable immediately after the purchase posts (not when the billing statement closes), so I quickly repurposed them to help pay for my return flight.

Again, I was unable to find a direct flight home from Osaka (KIX) on Qatar Airways, but by using, I was able to identify Etihad Airways flights connecting in Abu Dhabi (AUH) bookable via Flying Blue. I haven’t flown Etihad in over 10 years, and I’m interested to see how its economy product compares to Qatar Airways.

For 3 of the shorter flights throughout Asia, I’m tracking prices on Google Flights and am pretty close to booking. I’ve researched the low-cost carriers with the ideal flight times and fares. I’ve also added notes to my planning spreadsheet with their baggage policies to see what the size requirements are and what fees I may pay for any checked luggage.

We’ll be staying at an Airbnb in Phuket (earning 3x Avios via British Airways and Airbnb partnership and 2x Chase Ultimate Rewards points with my Chase Sapphire Preferred® Card).

I plan to book hotels for the rest of the trip, and having a planning spreadsheet to track ideal properties and rates has been helpful in keeping an eye on my overall costs. Because I have a larger family of 5, I typically struggle with finding a room (or 2) that can reasonably accommodate us. Ultimately, I have identified some contenders and hope to lock in our accommodations soon.

Hot Tip:

Many travel credit cards offer complimentary travel insurance, which can reimburse you for expenses incurred during travel delays, lost luggage, and more.

Lori Zaino, Senior Content Contributor

This summer, as a thank you to my in-laws for helping with our son throughout the year, we’re taking them on a summer vacation. My goal was to use points as well as maximize cash purchases to earn more points.

We’re starting by flying from our home in Madrid, Spain, to the Dominican Republic. I transferred Chase and Amex points to Iberia during their 30% bonus periods and spent 20,000 per ticket in economy to get us from Madrid to Santo Domingo, which cost 100,000 Avios in total for the 5 of us (my partner and son, my in-laws, and myself).

Iberia Airbus A330 at Miami
The flag carrier of Spain. Image Credit: Daniel Ross

We’ll start by spending 3 nights in the Renaissance Santo Domingo. We love the historic city in Santo Domingo, and I know my family will enjoy exploring it as we get over our jet lag.

I used Marriott points I earned as a welcome bonus offer from the Marriott Bonvoy Bevy™ American Express® Card. Partial ocean-view rooms were 20,000 per night, so 120,000 Marriott points in total for 2 rooms, 3 nights. Only time will tell if we’re upgraded due to my Marriott Gold elite status.

Then, we’ll head to Punta Cana—my toddler is very into swimming pools. Iberia eStore (the airline’s shopping portal) had a promotion running where I could earn 12 Avios/$1 spent on Barcelo purchases, so I opted to pay cash for a stay at the Barcelo Bavaro Palace. For 2 rooms for 6 nights, my total cost was over $4,000 for an all-inclusive stay.

This should yield me almost 50,000 Iberia Avios, which is more than enough for a round-trip, transatlantic ticket in economy on the airline (or more than enough for a one-way in business), which I’ll save for next summer’s travel plans.

I’ll also get 3x points per $1 spent by paying with my Chase Sapphire Reserve card, which means I’ll snag more than 12,000 Chase points.

Transferring these to Iberia during a 30% transfer promotion yields me almost 16,000 Avios. Overall, this means that for my stay, I’ll be getting nearly 66,000 Iberia Avois, which is almost enough for two roundtrip transatlantic economy tickets or one roundtrip in business.

Since I hold MyBarcelo status (MyBarcelo Intense, which is mid-tier), I got 10% off my booking and also get further benefits like late checkout and early check-in. After this stay, I should reach MyBarcelo Unique status, which is the highest status tier at Barcelo.

Hot Tip:

Remember, even if you pay for your summer travels in cash, try to double-dip to maximize those earnings.

After this, we’ll send my in-laws back to Spain (40,000 Avios for their Iberia tickets) and take three more days of beachy vacation at the Hyatt’s all-inclusive Dreams Onyx Resort and Spa (stay tuned for a review). I booked a Preferred Club Junior Suite with Pool View for 3 people (all-inclusive) for 32,500 Hyatt points per night, which I got from opening and earning the welcome offer on The World of Hyatt Credit Card.

The card also offers me Discoverist status, which means I’ll get late checkout. I dabbled with using fewer points and paying cash to add my son to the room, but in the end, I chose to just pay entirely with points.

From here, we’ll head to Chicago on paid tickets with American Airlines to see family before returning home to Madrid on Iberia (60,000 Avios for 3 tickets in economy).

Stella Shon, Editor and Content Contributor

Traveling to Europe in summer is notoriously expensive, but points and miles came to the rescue, thereby reducing the overall cost.

I’m looking forward to attending my second Eras Tour concert — this time in Edinburgh! While my friends and I were lucky enough to snag concert tickets, we had to find a way to get to Scotland with plenty of buffer time.

One of my friends is currently an American Airlines Executive Platinum elite status member, and he had 4 systemwide upgrades to burn.

We were able to find flights from my home airport of Raleigh-Durham (RDU) to London (LHR) via New York (JFK) for $900 per person. I paid with The Platinum Card® from American Express to earn 5x points on the taxes of the flights (up to $500,000 per year), so I earned 4,500 Amex points in total. Getting confirmed business class seats for $900 one-way in peak summer was worth it in my eyes.

We’ll stay at the Great Scotland Yard Hotel (booked for 20,000 Hyatt points per night), then take the scenic train to Edinburgh a couple of days before the concert.

On the return flight, we were hoping to book JetBlue’s new Edinburgh to New York nonstop route with Mint upgrade certificates, but it proved to be virtually impossible. JetBlue charges a dynamic rate for certificates on transatlantic flights, and it costs 4 certificates to upgrade one way of travel. Since I wanted to travel with my friend, we scrapped that idea entirely.

Virgin Atlantic Airbus A350 Upper Class Seat During the Morning
An Upper Class seat on a Virgin Atlantic Airbus A350. Image Credit: Greg Stone

Instead, we booked Virgin’s Upper Class flight from London after the concert for just 47,500 points. The taxes were nearly $900, but I also paid with my Amex Platinum card to earn an additional 4,500 points.

Final Thoughts

This summer looks to be a busy one for the Upgraded Points team, with journeys to the Caribbean, Europe, Asia, and even to see Taylor Swift. Of course, none of this would be possible without points and miles, which is why we spend all our time teaching you all how to do it as well!

The information regarding the Capital One Venture X Rewards Credit Card was independently collected by Upgraded Points and not provided nor reviewed by the issuer.
The information regarding the Hilton Honors American Express Aspire 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.
The information regarding The World of Hyatt Credit Card was independently collected by Upgraded Points and not provided nor reviewed by the issuer.

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

Carissa Rawson's image

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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