We’re going to Italy in September on the Viking Cruise Italian Sojourn, an 8-day cruise around the Italian peninsula. You can’t pay for the cruise with points, so we paid with cash, which was a very quick way for us to earn the welcome bonus on the Southwest card that gave us the Companion Pass.

Outbound Flight - Air France Business Class (lie-flat seats!) from Boston to Rome. The deals on the flights to Italy were much better from Boston than from New Orleans, so it made sense for us to use our Companion Pass to fly to Boston first, and then book the business class flight from there. This is called a “positioning flight.” The cash price of the two tickets was $9,889.80, or we could transfer 212,000 Chase Ultimate Rewards points to Air France and only pay $487.20 in taxes and fees. This comes out to a value of 4.44 CPP and a cash savings of $9,402.60! Just for reference, a reasonable economy flight would’ve cost about $1,700, so we’re still coming out ahead compared to the cash price of economy.

Return Flight - British Airways Business Class (lie-flat seats!) from Venice to New Orleans. The cash price of this flight was $14,484.35 for the two tickets, or we could transfer 220,000 Chase Ultimate Rewards points to British Airways and pay $1,000 in taxes and fees. This comes to a value of 6.13 CPP and a cash savings of $13,484.35! Again, for reference, the cheapest reasonable economy flight would also cost about $1,700.

Flights - Cash prices were reasonable, so we saved our points and paid cash for the flights. Greg’s flight was $203.60, with Jen’s only costing $11.20 with the Companion Pass. Total out-of-pocket cost was $214.80 round trip. If we didn’t have the Companion Pass, the price for 2 tickets on the same flight would’ve been $567.20, for a total savings of $352.40.

Hotel - Intercontinental New York Barclay - Paid for using the remaining 2 of the 5 free nights in the IHG credit card welcome offer, as well as points to cover the 3rd night. We already had some IHG points from the spending on the card to earn the welcome offer, and recently, Chase had a 70% transfer bonus to IHG. We didn’t have this trip planned at the time, but we knew we’d be using those other 2 free nights at some point. We transferred 15,000 Chase points, and with the 70% bonus, got 25,500 IHG points. The total cash out-of-pocket for this stay was $134.00. Had we not used points or free nights, the cash price of the same room for the same nights is $1183.85, for a total savings of $1,049.92 and a points value of 2.01 CPP.

Flights - This was after we got the companion pass with the welcome offer on the Southwest credit card. We also used 27,592 Rapid Rewards points from the welcome offer to cover Greg’s flight and Jen was added for free as the companion. The only cash out-of-pocket was $22.40 to cover the taxes and fees. The cash price for 2 tickets on the same flight is $941.92 for a total savings of $919.52 and a points value of 3.25 CPP.

Hotel - Home2 Suites by Hilton Pompano Beach Pier - The stay was paid for using 181,000 Hilton Honors points, most of which were received from the welcome offer and topped off with points we earned from spending on the card to earn the welcome offer. We had to pay $114.37 out-of-pocket since we didn’t have enough points to cover the full cost, but with the $50 credit that comes with the Hilton card we have, that fee was knocked down to $64.37. The cash price of the same room for the same nights is $1593.05, which comes to a redemption of 0.84 CPP. With Hilton Honors points typically being valued at 0.6 CPP, this was a successful redemption. Factoring in the cost of the $150 annual fee, we’re saving $1,378.68 for this stay.

Flights - Cash prices were reasonable, so we saved our points and paid cash for the flights.

Hotel - Kimpton Gray - Paid for using 3 of the 5 free nights in the IHG credit card welcome offer. This was before we created this website, and we didn’t keep track of the cash price of the room, but trust us, it was way more than the $99 annual fee we paid for the card especially considering that the Kimpton brand is part of IHG’s luxury hotels!