Newsletter Thursday, November 14

This page was originally published in early 2023 and reflects the author’s financial decisions during that time. The card details have since been updated. 

Key takeaways

  • Traveling with friends can be a lot of fun, but only when everyone is on the same page about how to pay for it and where to go.
  • By pooling together credit card rewards and taking advantage of cardholder benefits, your travel group can save a lot of money overall.
  • Just keep in mind that you’ll have to be strategic with your points redemptions and decide what’s not only most cost-effective, but what’s most convenient, too.

When it comes to booking travel, couples who share a rewards credit card have an advantage. When you book with rewards on a shared account, you’ll automatically split the value of the rewards, both earned and redeemed. As long as one of you remembers to pay the bill on time, you’re practically golden.

It’s slightly more complicated to book travel with friends who each have their own travel rewards credit cards, but it’s worth the effort. As fun as it can be to travel alone or as a couple, there’s nothing like a shared adventure with friends.

Here are a few lessons I’ve learned for maximizing rewards and minimizing hassle when booking award travel with friends:

1. Start with the best flight for everyone

Begin by narrowing down dates and times that work for everyone in your group. Then, find the most convenient flights, and plug in each person’s rewards to determine the best points or miles value for everybody. Be prepared to part ways on at least one leg of the journey.

Choosing the flight

For example, on a trip to Greece with two of my friends, we all booked the same American Airlines flight using different rewards. Two of us had the Chase Sapphire Preferred® Card, so we had the same Chase transfer partners to choose from. Friend No. 2 booked her flight with bonus rewards earned with the American Express® Gold Card, giving her access to similar partner airlines via American Express Membership Rewards.

Ironically, the flight we chose was on an airline that wasn’t a transfer partner for any of our credit cards. Because we all live in a hub city for American Airlines, it’s the default airline where we all live, including for many overseas flights — and they were having a flash sale. Our flight was retailing for $916 the day we booked.

Paying for the flight

I used AAdvantage miles, friend No. 1 used Chase Ultimate Rewards points, and friend No. 2 used American Express Membership Rewards points. Two of us shared the first leg of the return flight as far as London, but then we had to transfer to separate flights on the final leg due to different award flight availability.

Given it was an American Airlines flight, I came out ahead using AAdvantage miles, but not by much. While I used fewer rewards (60,000 miles), the airline charged a $109 fee on top of that. The same flight cost my friend 77,000 Chase points (with no fee), booked through the Chase Travel℠ portal.

A word about airline service

For the record, booking with points or miles from a particular airline rewards program does not necessarily get you better service with that airline. A few weeks before departure, our direct flight to Athens was canceled by American Airlines and we were rebooked on a less desirable two-leg flight. My friends appealed to their card issuers — Chase and Amex — and were quickly transferred to another direct flight with aisle seats, no extra points required. I spent nearly two hours on the phone with the airline before I was able to get on their flight. And the airline charged me 10,000 extra miles to get my aisle seat back.

2. Keep it simple

Unless you’re planning a massive adventure or everyone is broke, traveling with friends is probably not the time to cobble together promotional one-way fares or shave off points/miles by booking flights that require long road trips to the airport.

On our flight to Athens, for example, we could have driven an extra hour to another airport and saved a couple hundred bucks worth of rewards. But flight times were better from our own city’s airport, and getting to and from the other airport would have cost us in gas, train fare or parking fees. We decided it wasn’t worth the hassle.

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Money tip:

Saved time is saved money (and rewards), especially if everyone is taking time off from their jobs. Besides, who wants to deal with an extra journey on top of a long flight? Rewards should produce a reward, not a hassle.

3. Pool your hotel points, or take turns

On an overnight in the city with a friend, I’m usually fine with two beds in one room in a well-located hotel, preferably with a good restaurant or free breakfast. If we’re staying a few nights, a kitchen and seating area comes in handy, too. But sometimes, you need separate rooms.

Pooling points for hotels

Hotel points (or rewards transfers) are perfect for that. For instance, if I book travel through Chase Ultimate Rewards with my Sapphire Preferred, my hotel purchases will earn 5X points. If you have the Chase Sapphire Reserve®, you’ll earn 10X points on hotel stays and car rentals booked through Ultimate Rewards. Plus, the Sapphire Preferred comes with up to $50 in statement credits each account anniversary year for hotel stays purchased through Chase Ultimate Rewards.

If you’re staying multiple nights in hotels, see if each of you can cover different nights with your points. Better yet, pool your points. Hyatt, Marriott and Hilton all let you pool points on a booking, with various limitations.

Taking turns to cover the costs

If you don’t have points and a friend is using their points to cover your hotel for more than one night, offer to pay them back the dollar value for your half, just as if they had paid cash. If they say no, grab the check at dinner or cover the hotel with your points the next time. Just make sure you’re not using a card with foreign transaction fees if you’re traveling abroad, otherwise you’ll be canceling out any rewards you earn on those purchases.

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Keep in mind:

Before the trip, you should talk about how you’ll pay for each part and who will owe whom if someone is covering someone else. It’s best to be upfront and to keep receipts as you go along so you can avoid arguments down the line. The last thing you want is your friendship to be soured because someone didn’t pay their fair share or someone else feels like they’ve been taken advantage of.

4. Consider booking homestays

Homestays like Airbnb don’t let you use hotel points and points transfers to book, but they’re better for group travel and off-the-beaten-path adventures. Renting a home or apartment with more than one bedroom allows everyone to have both private and shared spaces, and a kitchen can save money on meals out. I’ve also found that a rented home can comfortably accommodate all ages at once, from kids to seniors, more conveniently (and economically) than a hotel.

Plus, sometimes travel credit cards consider certain types of homestays as a travel expense and reward Airbnb and VRBO bookings. For instance, on a trip to Washington, D.C. with a friend, I once booked an Airbnb on my Sapphire Preferred and was able to get 25 percent back using Chase’s Pay Yourself Back program (which was an offer at the time).

On our Greece trip, two of us booked Airbnbs using our Sapphire Preferred cards and we earned 5X points. In many of the villages and islands we visited, hotel chains were not an option. Besides, we liked the hominess of shared kitchens and seating areas, and we liked being within walking distance from the action, instead of being isolated in a resort.

Deciding who will do the booking

It’s tempting to let one person in a group do all the travel booking, so everyone only has to pay one person back. If you have someone willing to do that, it can make things easier. But remember, only one person gets to pocket the travel rewards earned by the group spend.

5. Use your card’s travel perks to benefit the group

If you’re booking group travel on different rewards cards, check each card’s travel benefits first. Doing so will help you get the most value from your collective card-related travel insurance. For example, your card may have trip cancellation and interruption insurance and trip delay reimbursement, but other cards may not.

Travel insurance benefits can vary significantly between cards. Remember, your cards only cover you for what you purchased with them. Depending on the circumstances, you all may want to purchase separate travel insurance.

Being flexible with airport lounges

Airport lounge access would have been a nice card perk to have during our three-hour layover at London Heathrow. But if you’re traveling with a friend and only one of you has a card with lounge access, such as Priority Pass Select, it probably only gets the cardholder in. I say pull up to an airport bar instead.

6. If you’re renting a car, check your cards’ rental insurance

This is something you don’t have to think about if you’re traveling with a spouse who shares your credit card and car insurance policy. But with friends, you need to be sure you have good coverage and that it extends to everyone driving the rental car.

When I flew to Phoenix with a friend a couple of years ago, I used my Ink Business Preferred® Credit Card to book the car we shared. Both the Ink Preferred and the Chase Sapphire Preferred offer an auto rental collision damage waiver, which covers both the primary cardholder and any additional drivers permitted by the rental agreement.

Of all the cards we used in Greece, the Chase Sapphire Preferred offered the best rental car insurance. We rented cars in Greece with two different Sapphire Preferred cards, which meant we were covered by its auto rental collision damage waiver (saving us up to $30 per day, which is what rental companies typically charge for that). This insurance provides primary coverage up to the actual cash value of the car for theft and collision damage for most rental cars in the U.S. and abroad. Plus, the card provides roadside dispatch (fees may apply).

In comparison, friend No. 2’s Amex Gold benefits would have only provided secondary car rental insurance and the card doesn’t come with roadside assistance.

Grim reality

If my friends and I had rented motorbikes on the islands, none of our cards would have covered the damage to the bikes if we had wiped out. Two of us could have received travel and emergency assistance services from our Sapphire Preferred cards, but our other friend would have been out of luck with her Amex Gold card, which offers no emergency medical assistance. Fortunately, we didn’t have to put that to the test.

7. Help your friends score bonus rewards

Part of the reason friend No. 1 could cover her flight to Greece with credit card rewards was because I convinced her to sign up for the Sapphire Preferred card in 2021, when Chase was offering a 100,000-point sign-up bonus. Currently, the Sapphire Preferred is also offering a pretty lucrative welcome bonus of 60,000 points after you charge $4,000 to your card in the first three months of account opening, plus a $300 travel credit through Chase Travel.

When I was booking my own flight on American Airlines’ website, I noticed the Citi® / AAdvantage® Platinum Select® World Elite Mastercard®* was offering a higher welcome bonus than usual. (Currently, the card offers 50,000 miles after spending $2,500 within the first three months of account opening.) I didn’t qualify because I canceled an AAdvantage card less than four years ago, but I mentioned this deal to the friends I was traveling with. One applied the next day.

My friend’s new card and its welcome bonus didn’t arrive in time to cover the flight to Greece, but the bonus miles she pocketed means we now have enough AAdvantage miles for both of us to score another free, overseas round-trip fare, should the opportunity arise. I, for one, am always up for another international travel adventure with friends.

The bottom line

Traveling with friends can be a rewarding experience in more ways than one. You’ll create lasting memories together, and — by using credit card rewards — you can save money along the way. Plus, by using your credit card while abroad, you can continue to earn points on purchases (provided you’re not paying foreign transaction fees).

For best results, have an upfront discussion about costs and how to split things before the trip, as well as what credit card benefits and travel rewards you have available between the group. Don’t forget to also keep an eye out for lucrative welcome bonuses just in case someone is looking to open up a new card.

For more tips on planning your next vacation, saving on travel and maximizing travel rewards, check out Bankrate’s Travel Toolkit.

*The information about the Citi® / AAdvantage® Platinum Select® World Elite Mastercard® has been collected independently by Bankrate. The card details have not been reviewed or approved by the card issuer.

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