Okay, I think I’ve shared enough of the basics to talk some simple trip strategies. These strategies may or may not result in a (mostly) free trip but a highly subsidized one. But if you plan ahead (and get the right card — by which I mean I hope you got a Chase Sapphire Reserve VISA Infinite (review) when the bonus was 100,000 UR points), you can still do very well.
Two travelers, two cards. Now, this strategy can be many combinations, but the current “easy” option would be for each traveler to get a Barclay Arrival Plus World Elite MasterCard (review). Each annual fee is $89, but it’s waived in the first year, and the initial bonus is currently 50,000 “miles” after spend of $3,000 in the first 3 months. You also earn these miles at a rate of 2% on all purchases. All points can be redeemed starting at 10,000 miles for $100 toward all or a portion of your travel purchase of $100 or more made within the past 120 days. When redeeming points for travel, you also receive 5% of those points back, making this, in effect, a 2.1% cash back card (optimally). So, very simply, use one card to book your transportation and the other to book your lodging. The beauty of this system is that you don’t have to make plans far in advance or even make your spending bonus before booking your trip; just go on your trip and keep spending until you make your $3,000 spend, then redeem your miles (at a minimum, 56,000, or $560, because of spend) for that portion of travel. If you can book your travel in segments, pay off one segment in full and then utilize the 5% miles back plus any additional earning over the next 120 days in order to pay off the other segments. With two travelers with one card each, you’ll save at least $1,120 on your trip.
Two travelers, four cards. Again, this strategy has many combinations, but I’m going to stick with the Arrival Plus for lodging and go with another “easy” solution for transportation with the Barclay (American Airlines) AAdvantage Aviator Red World Elite MasterCard (review). Easy because there’s no minimum spend, just pay your $95 annual fee, make one purchase, and you earn 40,000 AAdvantage miles. Some words of warning regarding airline miles: PLAN AHEAD. Especially in this age of devaluing miles, you’ll definitely be challenged to find flights that can be redeemed using the minimum amount of points. For instance, I had to cherry pick to find flights between Honolulu (HNL) and Los Angeles (LAX), 9/13/17, and the return, 9/17/17, that would only cost the 40,000 miles round trip (for Economy MileSAAver fare). Seats are often released for award fare around 330-360 days out, and this is when you might find the most availability and the cheapest award fares. Might. Because this depends on a whole lot of variables. But I’m trying to simplify here. If you PLAN AHEAD, however, you will often get your airfare reserved for the minimum amount of miles, at the same time, having enough time and flexibility to find your lodging. So, in this example I created above, with round trip economy airfare fully covered with 40,000 (x2) AA miles, and 3 nights to party in L.A., you’d have $1,120 to cover lodging costs (plus seat upgrade? plus rental car?). So, there you go: a trip totally paid for with points and miles minus $95 (x2) in annual fees.
Like Maui said, “You’re welcome.”
Real life examples of the scenarios above are coming soon.