Everything You Need to Know About Cheap Caribbean's Deal of Fortune

By Maggie Reimherr

If you've been following along on Instagram and Facebook, you know that we got a killer deal on our Mexico vacation. The catch? We didn't know which resort we were heading to until a week before the trip. We chose to book through Cheap Caribbean and rolled the dice on their Deal of Fortune.

I wrote about the process of deciding to throw caution to the wind and book this mystery vacation over here a while back. (Side note: check there for my booking tips.) To recap: we decided to book a Deal of Fortune because I read every review on the Internet and thoroughly researched each resort option in the package we chose. We chose the 5-Sun Cancun deal specifically because we were cool with landing at any of the hotels listed.

Now we’re home from the trip. Did we like it? Was it an amazing find or a scam? Let's find out…

We got an email a week before revealing we'd be staying at Secrets The Vine Cancun, ranked #3 among every Cancun hotel on TripAdvisor. We knew we liked the Secrets brand because we stayed at Secrets Maroma Beach for our honeymoon last year. We also knew this was another resort that people rave about in this chain of properties. We were stoked. Side note: we’ll publish a separate post reviewing Secrets the Vine and comparing the 2 resorts in case you're booking a Secrets vacation soon and having trouble deciding.

So to give y'all a sense of just how good of a deal it was, let's talk numbers. We were at an all inclusive resort. That means unlimited food and drinks (yes, alcohol, too) were included in our package. Also included? A “run of house” room, fancy wording for “cheapest room we've got.” And finally… our price through Cheap Caribbean included airfare. I've priced it out below:

Full price 7 night trip for 2:
Run of house room booked directly through Secrets the Vine: $4500/week
Airfare (BOS to CUN to compare because we booked this out of Boston): $1200
Shared round trip transfer from airport to hotel: $60
Total: $5760

Our Cheap Caribbean Deal of Fortune 7 night trip for 2:
Total for run of house room, all inclusive food + drinks, airfare (BOS to CUN), shared round trip transfer: $2800

Yep, you read that right. We got a half price trip.

So should you book a Deal of Fortune even though you won't know where you're going until a week before? HELL yes. Spice up your life and save mucho dinero, folks!

Derek and I kept talking about how the trip felt like stealing because it was like, “Are they making any money off of us?” We honestly don't know how the finances work on their side. But we do know that as long as the Deal of Fortune exists, we will never, ever, ever book a full price resort vacation again.

The cool thing about getting such a stellar deal is that the pressure is off to get alllllll the bang for your buck. You want to lay at the pool all day, every day and participate in 0 activities? Go for it. Want to go to bed early and skip the evening show? Done. Wanna head up to your room at 3 o'clock and binge watch an entire series on Netflix? You're free to do that (and… guilty. We watched all of 13 Reasons Why on this trip).

On the flip side, you made it to a luxury resort in the Caribbean for half price. So live it up! Eat nachos by the pool, drink those unlimited margaritas and Coronas, go to the tequila tasting at 4 o'clock in the afternoon (#didthat), sing along to the cover bands at the evening shows, and order a 5-course meal just because you're on vacation.

I shared booking tips in my previous post about choosing the Deal of Fortune, so to figure out how to book, head over there. Now time for some DoF/all inclusive resort tips for when you're actually on vacation…


  • Bring cash to tip. You scored an awesome deal. Don't be stingy to the waitstaff.
  • If you're a honeymooner, be aware that the “run of house” room might be 2 queen beds. If your heart is set on enjoying your honeymoon on a luxurious king bed, set aside extra money in your budget and see if you can upgrade to a king suite once you get there. They offered us the upgrade to a king room in the "preferred club" section of the resort (which also would've allowed us access to an additional pool and breakfast/lunch restaurant) at $90 a night. We declined and took the 2 queens. And yes, because they knew this trip was for our anniversary, they left rose petals on one of our queen beds the first night. 
  • Also, honeymooners… I don't know if this is the standard across all resorts, but at both Secrets we've stayed at, the toilet was in a room that was basically just a frosted glass closet. So beware that not only are you adjusting to being married to a person, but you're also gonna have to get real comfortable with bathroom stuff real fast. Good luck.
  • If you're planning on a truly budget-friendly vacation without any extra activities, 7 nights may be a little long. The daytime activity schedule is fairly repetitive each day (but the entertainment staff is fantastic!), so you may feel a little bored of 7 straight days poolside. We booked an excursion, and I'm super glad we did to get away from the resort for a day. (Cancun specific tip: y'all have to go to Isla Mujeres. Book a catamaran excursion like we did - if you’re a Cheap Caribbean customer, you can book through your Amstar rep in the hotel lobby - or just hop on the ferry over to the island. Rent a golf cart. Barter for souvenirs with the locals. Eat an authentic Mexican meal, but take it from us - taste the sauce before you douse your burrito in habanero salsa and plz don't set your mouth on fire like we did.)
  • Bring a laptop for show/movie watching on lazy nights. We had a smart TV in our room but the smart part didn't actually work, so we ended up watching Netflix on Derek’s laptop a few nights.
  • Don't overpack. No, Maggie, you did not need that second pair of wedges.
  • Along those lines… if you don't regularly work out, you aren't going to start on vacation. Leave the 5 Fabletics outfits at home. Drink your pina coladas and pay for your sins when you get home.
  • If you need something, just ask… but know that it might be slow getting to you. All-inclusive resorts tend to run at their own pace. So when you order a water and a margarita from the pool waiter, you may not actually see those things for a half hour. Be patient. You're on beach time.
  • Eat your vegetables. It's so easy to let nutrition go by the wayside when you have an array of DELICIOUS foods at your fingertips 24/7. But trust me, if you don't eat your veggies, you won't be feeling good. Derek and I skipped karaoke night, which I would NEVER NORMALLY DO, because we were physically ill from eating too many carbs all week. Oops.
  • Stock up on sunscreen and other essentials back home. You don't want to pay resort gift shop prices for that SPF.
  • Take advantage of the onsite entertainment options! Last year, we went to a Beatles cover show at Secrets Maroma Beach that we’re still talking about. This year, we loved the Jersey Boys show at The Vine. 
  • For airport transfer… we booked shared transfer through Amstar and lucked out. We ended up having a van to ourselves on the way to the resort from the airport. On the way from the resort, we shared with one family. It cost us about $100 less than private transfer would, but I've heard it's a bit of a gamble... you could end up on a bus and stop at every resort along the strip before you get to yours.
  • Check ahead of time to see if the resort offers honeymoon/anniversary perks. Secrets brought a complimentary bottle of champagne to our room to kick off our stay as a little anniversary gift.

So all that being said... Cheers! Your vacation awaits! And now we want to hear from you… would you book the Deal of Fortune now that you've read about our experience?! And resort veterans - what are your all inclusive travel tips? Leave us a note in the comments or on social media!