How to Shop the Black Friday Sale

Disclaimer: Some of the links in this post are affiliate links. This means I earn a small commission if you book/buy through them and I can keep providing free content like this!

It’s that time of year again, when we’re bombarded with Black Friday sales and have to decide what to spend our hard earned money on, or if we’re going to buy anything at all. In addition to Christmas presents, this can also be a very beneficial time to book 2024 travel!

There are lots of travel-related Black Friday sales out there, and I want to break down how I’m using them to get the most bang for my buck this year in hopes that it helps you, too!

Let’s talk about Black Friday Sale

I use Booking quite a bit to find hotel rooms and apartments to stay in when I travel. I use it so much that I have Genius status with them and usually get some sort of discount. If you don’t have this, I highly recommend checking the hotel website directly to see if it’s cheaper to book directly because a lot of accommodations will increase the price on Booking since they have to pay a commission fee to Booking if someone books through them.

That said, Booking is running a pretty good Black Friday sale right now – up to 50% off certain properties! And some of them are great deals! You just have to book before November 29th and stay before the end of 2024.

Pro Tip: Activate Rakuten’s 4% Cash Back

While searching Booking for accommodations for you next trip, keep in mind that Rakuten currently has 4% cash back for Booking. If you don’t have a Rakuten account yet, sign up here and get $40 for free! Yes, FREE!

As you shop around, you can enable the Rakuten Chrome extension to give you cash back on online purchases.

The real reason to use Rakuten has nothing to do with cash back, though. If you have an American Express credit card that has a partnership with Rakuten, you can earn points instead of cash back. Each 1% cash back is equivalent to 1 Amex point per dollar spent while Rakuten is enabled. So, if I spend $1000 on, I’ll get 4,000 Amex points transferred to my account ON TOP OF the regular amount of points I get from paying for the $1000 purchase.

Example Booking – Italian Villa in Tuscany

Say you wanted to take a family trip to Italy in 2024. I found a gorgeous estate in Tuscany that is part of the Black Friday sale. Villa Dianella is a wine resort just 30 minutes outside of Florence where you can do wine tastings, olive oil tastings, cooking classes, and just soak up the Tuscan country scenery.

In this scenario, let’s say you have a family of 6 and you want to stay here for 4 nights in August of next year. At this particular property, you’d need 3 separate rooms for 6 people which would usually cost $9,817 through Booking. During the Black Friday Sale, it comes down to $5,890 with 45% off!

Pricing on

Remember, though, properties usually hike up the cost a bit when they list on Booking, so I checked directly with their website and for the same dates, it would have been $7,500 for the same rooms. So, you’re still saving over $1,600 using Booking’s Black Friday Sale.

pricing from the Direct site

Of course, we have Rakuten enabled, so we’ll also get a whopping 23,560 Amex points transferred to our account once the payment goes through along with at least 5,890 points for the purchase, depending on which credit card you use to book. That’s nearly 30,000 points that can be transferred to an Amex partner to help with the cost of a flight to Italy!

The best part is, with this property (and many others), you can book now and pay later. In this example of going to Italy in August, you wouldn’t have to pay until July 2024.

Obviously, this is an extreme, relatively expensive example and there are much cheaper deals, but I wanted to use it to convey my message that by adding in Rakuten with an already great sale, you can see some serious savings for your 2024 travel.

Happy booking!

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