How We Scored an All-Inclusive Anniversary Trip for Nearly Free
Jamaica on Points.
Think an all-inclusive hotel in the Caribbean is out of reach because it’s too expensive?
Think again!
My husband and I took our 15 year anniversary trip to Montego Bay, Jamaica back in October. We had been to the Bahamas together on a cruise years ago, and I had already been to Mexico with my mom back in 2018, so we were looking for somewhere we hadn’t been before. We love the Caribbean, so Jamaica was the place we chose for this anniversary trip. The travel was smooth, the weather perfect, and this was our first time ever going into an airport lounge! (Who ARE we?!?)
Here’s how we did it:
Starting with the airfare - we flew Southwest, of course ;) We used points from when we had opened a personal and business card in order to get the Companion Pass, so we still had points leftover after all 6 of us going to PCB back in May. We’re big fans of the Southwest Companion Pass (SWCP) because of our big family, so you’ll see it mentioned in almost every trip we take! With this perk, you’re able to change your companion up to 3 times per year, so for this trip, I changed my companion to Samuel.
We purchased our airfare through Southwest and spent a little over 28k points + $149/round-trip each. If this was a domestic flight, we would have spent $11.20 round-trip each, but international destinations will always be more expensive. If we paid cash, this airfare would have been over $2,000!
We had a very short layover in Orlando (MCO). When I say short, I mean we literally got off of our first plane, used the restroom, then got in line to board our next flight to Jamaica! It was great to move on to our next flight.
Now to the Resort:
We spent three nights at the Secrets St. James in Montego Bay. This is an all-inclusive adults-only property that we booked through Hyatt after transferring Ultimate Rewards points. We booked it for 30k points/ngt for a total of 90k points. Cash rate would have been over $1,400. If you’re not sure how to transfer UR points to travel partners, I have a step-by-step post here.
This resort was in a beautiful location on the island. The view from our balcony was amazing, and it was nice to be able to sit outside and take in the sights. I will say, this property is not the quietest atmosphere, so if you’re looking for a more peaceful place to spend your anniversary, I would suggest a different location. It was fine for us for the most part, but we were directly above the pool, and they started playing music around 10 in the morning. We were out most of the day anyway, which is why it didn’t bother us too much.
This property has multiple restaurants, and you'll see this multi-cultural food theme across most of this line of all-inclusive properties. These properties (but not limited to) Secrets, Dreams, Zoëtry, Breathless, and Sunscape. There’s usually always a French restaurant, Italian, Mexican, American buffet style, and local cuisine included within these all-inclusive properties. I enjoy the multitude of choices, and the food at this particular location was very good. There are also other food throughout the resort, such as a jerk chicken and pizza station where you can just walk up and grab a slice as you head to the beach or pool, and also a sit-down lunch spot. This is where I scarfed down a yummy salad and fish tacos that were 🤌🏼
The view from our balcony. This was a standard room for 30k points/ngt.
My husband and I love doing things together when we’re on a trip. Lounging around the beach or pool is great, and we love that as well, but we enjoy experiencing new adventurous activities. So, when planning this trip, we knew we wanted to do some type of activity on the water. When looking through the Chase portal, I saw a parasailing activity available to book with points. This is something you don’t see often, because most people want to save their Chase points for airfare or hotel, and rightfully so, but for now we like to use our points to get as much of the trip for less as possible. We booked our parasailing experience through the portal for 16,410 points/ea instead of paying $410.25 for the entire excursion. This included transportation to and from the activity. It was a blast! I highly recommend parasailing if you haven’t tried it or are interested. Our guides were super fun and we were up in the air a good while. It was an experience we will always treasure doing together! We also snorkeled, but we paid cash for that through the resort itself. That was better than booking through another company because there were only 4 of us, so we had a lot of time out on the water. We even got to hold a sea urchin!
Our confirmation after booking our excursion through the bank portal.
One day when we were heading to the beach to swim, one of the employees of the resort asked us if we wanted to go out into the water. We immediately said yes as he gave us a great price, and Sam loves to sail so it was a no-brainer. As we glided along the Caribbean sea, he gave us some tips about the island and talked to us about what the locals did for fun. Those natural, spontaneous moments are one of the things we love most about travelling!
The beach right on the resort and the boat we went on to go snorkel
We were sad to leave this resort as it was situated in a beautiful location, and we really had all we needed at the resort.
When researching this trip, I saw some reviews about the wait time on arrival at the Montego Bay airport being up to 2-3 hours. Being that this was our anniversary trip, I did NOT want to wait that long before getting to our final destination! It was recommended to purchase the Mobay VIP Airport Fast Track Pass. With a quick check inside the bank’s portal, I saw it was available to purchase with points also — so that’s what I did. Although the arrival wait wasn’t too bad, I was glad I bought it. We were escorted through the airport when we arrived into Montego Bay, which was nice in itself, but the lounge access upon leaving to go back to the States is what really sold us and is where the pass and its benefits shine!
We arrived at the airport early, checked in, then went straight to the lounge, and let me tell you…the pass is ENTIRELY WORTH IT just for the lounge. It had an entire salad bar with snacks, a drink bar where you could get any drink you wanted, including coffee. And this airport is set right next to the Caribbean, so you could sit in your comfy lounge chair sipping your drink while watching planes take off against the sea!
I highly recommend getting this pass if you go to Jamaica. You can learn more about it here.
We also paid for the private transfer to and from the hotel with points instead of cash, bookable through the portal as well. It was 6,400 UR round-trip total for both of us.
Sipping on a mocktail while waiting to board while looking out onto the runway with the Caribbean in the background
In Summary:
Airfare: Southwest & used a Companion Pass: 56,274 points total + $300 for taxes/fees
Hotel: 90k points total for 3 nights + $0
Excursions, Airport Transfer & Lounge: 53,455 UR points total +$0
Original Price we would have paid for this trip: $4,200
What we paid after using points: $300
