How to travel with friends using travel rewards

When it comes to booking travel, couples who share a rewards card have an advantage. When you book with rewards on a shared account, you 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 golden.

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

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

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 value for everybody. Be prepared to part ways on at least one leg of the journey.

On a recent trip to Greece with two friends, for example, 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 17 transfer partners to choose from.

Friend No. 2 booked her flight with bonus miles earned from an American Express® Gold Card, giving her access to similar partner airlines (minus United, plus Delta) 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 ours is a hub city for American Airlines, it’s the default airline where we all live, including many overseas flights — and they were having a flash sale. Our flight was retailing for $916 the day we booked.

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

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

For the record, booking with airline miles 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.

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 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 points. 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 or parking. We decided it wasn’t worth the hassle.

Remember: Saved time is saved money (and rewards points), 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.

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.

Hotel rewards (or point transfers) are perfect for that. If I book with my Sapphire Preferred or Ink Business Preferred® Credit Card, hotel purchases earn 5X points – 10X if you have the Chase Sapphire Reserve® – and help me qualify for the $50 annual Ultimate Rewards hotel credit.

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.

If you don’t have points and a friend is using theirs to cover your hotel for more than one night, offer to pay them back the dollar value for your half, just as though he or she had paid cash. If they say no, grab the check at dinner.

Consider booking homestays

Homestays like Airbnbs don’t let you use hotel points and point 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 space, and a kitchen can save money on meals out. I’ve found a rented home can comfortably accommodate all ages at once, from kids to seniors, more conveniently (and economically) than a hotel.

Plus, many travel credit cards consider homestays a travel expense and reward Airbnb and VRBO bookings. On a recent trip to Washington, D.C., with a friend, I booked an Airbnb on my Sapphire Preferred and was able to get a 25 percent back using Chase’s Pay Yourself Back program.

Two of us booked Airbnb’s in Greece using Sapphire Preferred and earned 5X points. In many of the villages and islands we were visiting, hotel chains were not an option. Besides, we liked the hominess of shared kitchens and seating areas and being within walking distance from the action, instead of isolated in a resort.

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.

Use your travel perks to benefit the group

If you’re booking group travel on different rewards cards, check the card benefits first. It will help you get the most value from your collective card travel insurance. Your card may have trip cancellation and trip delay insurance, for example, but others may not. Travel insurance 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.

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.

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 Preferred card to book the car we shared. Rental car insurance provided by the Chase Sapphire Preferred and Ink Preferred covers not only the primary cardholder but any additional driver listed on 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 a collision damage waiver (saving us up to $30 per day, which is what rental companies charge for that), primary insurance up to $75,000 and roadside assistance for up to $50 per event (for up to four events per year). Friend No. 2’s Amex Gold benefits would have provided only secondary rental insurance up to $75,000 and no 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 $2,500 for emergency medical expenses (with $50 deductible) via our Sapphire Preferred cards, but one would have been out of luck with her Amex Gold, which offers no emergency medical coverage. Fortunately, we didn’t have to put that to the test.

Help your friends score bonus points

Part of the reason friend No. 1 could cover her flight to Greece with points was because I convinced her to sign up for the Sapphire Preferred card last summer, when Chase was offering a 100,000-mile signup bonus. (Current offer is 60,000 points, after you charge $4,000 in the first three months.)

When I was on AA.com booking my own flight, I noticed the Citi® / AAdvantage® Platinum Select® World Elite Mastercard® was offering a 75,000-mile signup bonus (now 50,000), after $3,500 in purchases 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.

Her new card and its bonus points didn’t arrive in time to cover the flight to Greece, but the 75,000 miles she pocketed means we now have enough AA 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.

Artur Starke
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