I took a one-week trip through Jamaica, attending a wedding at the Sandals Resort in Montego Bay and exploring many of the island’s cities, towns, and natural wonders, getting a “real Jamaica” experience.

Photo: Sandals Inn

Ya Mon!

I landed in Montego Bay at 3pm on a Friday. My friend who was supposed to have arrived a couple hours earlier was nowhere to be found even though the arrivals board said his flight had landed 😲 I figured he had forgotten he needed to bring a passport or was kicked off the plane for being drunk and disorderly but he showed up after about an hour – apparently his flight was indeed delayed.

We took a 5-minute van ride to the Sandals Inn (aka Sandals Carlyle), our home for the weekend. Montego Bay has three Sandals resorts – if you stay at one, you have access to all three. They’re a little ways apart from each other, but there’s a free hourly shuttle. I liked this because we (and almost all of the wedding guests) were able to stay at the cheaper Sandals Inn yet spend most of our time at the upscale Sandals Royal Caribbean.

Sandals Royal Caribbean

While checking in, we were delighted to be offered rum punches and warm towels, and I quickly noticed that all of the resort employees used the phrase “ya mon!” (aka “yeah man”) constantly. It’s a fun Jamaican thing! We got to our room, which was fairly simple but quite nice and looked out onto the Sandals Inn’s very fancy pool and hot tub.

Eager to take advantage of the all-inclusive experience, I went to the resort’s outdoor bar while my friend showered and was delighted to see a big menu of colorful blended drinks – most of which I’d never heard of before. I ordered a drink and began chatting with a friendly middle-aged couple sitting next to me, who I was delighted to discover were also from Colorado. Then I quickly realized that they were part of the wedding party and I had actually had lunch with them in Denver when the groom came into town for his bachelor party a couple months before.

Night 1 Fun

Having missed the hourly shuttle to the other Sandals resort, my friend and I took a taxi and met up with the rest of the wedding guests. Unfortunately a thunderstorm forced our planned catamaran cruise to be postponed but we had a nice dinner at Sandals Royal Caribbean instead. Everyone at our table ordered several cocktails and we quickly became the “fun table” 😜

After dinner, a bunch of us gathered in the Cricketer’s Pub, where I ordered a quesadilla (my 2nd dinner) and we all enjoyed our first Hanky Panky shots, which were sweet and delicious. The bartender had fun cheers he led the entire room in and we had lots of laughs and fun. We took the 11pm shuttle back to Sandals Inn and went to their late night food spot where I ordered a caesar salad (my 3rd dinner) before calling it a night.

Enjoying Cricketer’s Pub with fellow wedding guests

On A Boat

We woke up and enjoyed a breakfast buffet at Sandals Inn. Our catamaran cruise was rescheduled to 10am so we took a shuttle to Sandals Montego Bay and hopped on the boat. Unfortunately, the resort’s bar didn’t open til 10 so we weren’t able to grab a drink on land but luckily our boat ride turned out to be a boat party! We had a DJ, bartender, and yummy snacks – it was such a fun time sunbathing, dancing, and admiring the view of the Jamaican coast.

The unforgettable boat party

We requested snorkeling on the boat ride and about halfway through, we were set loose into a breathtaking bay. There were colorful fish, stunning coral, and lots of delightful underwater sights. I was especially drawn to a bright blue fish that had several different shades of the hue and seemed to literally sparkle. After 20 minutes or so of snorkeling, we got back on the boat and the party continued as we got down to excellent 00s hip hop.

Swim-Up Bar, Swim-To Gazebo

After the boat ride, it was time for our next planned activity: a pool party at Sandals Island, a resort-owned isle just a 3-minute dragon boat ride from Sandals Royal Caribbean. My friends and I first swam to a really cool gazebo situated a few hundred feet into the ocean and hung out on “lily pad” type floating rubber pads the resort placed in the ocean. We then jumped into the pool and swam over to my first-ever swim-up bar that had barstools in the water. Service was slow, but it was a very cool experience – we all enjoyed a round of colorful Bob Marley drinks.

I explored the island and discovered the resort’s only Jamaican eatery – an outdoor jerk restaurant. I had a yummy lunch and then heard rumors of there being a nude beach on the other side of the island so I took the rest of my food there πŸ˜‡ Sadly, most people weren’t nude and none of my friends wanted to participate. After some more drinks and pool time, we got back in the dragon boat to head to the mainland to get ready for the wedding’s rehearsal and dinner.

Sunset at Sandals Royal Caribbean

A Night of Shame

We did a quick wedding rehearsal and then headed to the Royal Caribbean’s main restaurant for a lovely wedding party dinner. I declined wine and ordered some fruity cocktails instead as we enjoyed a gourmet meal and dessert. After dinner, I took a dip in a lovely, quiet pool surrounded by palm trees and tropical plants. Then I noticed some of my fellow wedding guests playing croquet and I excitedly joined in. My first round wasn’t very impressive, but I won the second time πŸ˜›

We returned to Cricketer’s Pub for a #NightofShame aka perfectly excessive drinking. We did tons of Hanky Panky shots, stronger shots, cocktails, and more. After quite a few drinks, I created a new dance move I called the Drunk Octopus. We laughed, we danced, we took tons of photos – it was a great time. We caught the last shuttle back to our Sandals Inn hotel and it was a serious party bus as we did karaoke and caused quite a fun ruckus. We jokingly referred to the fact that we were staying at the cheapest of the resort’s hotels (“Motel 4” πŸ˜‚) because we were too wild for the nicer ones. After some more late night food, it was time for bed.

A Day In The Water

We caught the 10am shuttle to Sandals Royal Caribbean and enjoyed their breakfast buffet. My friend and I then headed to the dock and took a free mini catamaran boat ride through the bay – it was very peaceful and our boat driver was quite friendly. Then we enjoyed drinks while dipping in the pool until it was lunchtime. Since it was the day of the wedding, the groomsmen and I all had lunch together – they opted for a buffet lunch while I did that and additionally ordered a caesar salad and pizza from outdoor eateries at the resort. It was a good choice because there weren’t too many spectacular options at the buffet. I was quite full by the end though and definitely ate less than half of the pizza!

With a few hours to spare before we needed to get ready for the wedding, my friend and I headed to the quiet, palm tree-enclosed pool and relaxed on floaties for a few hours. A server came by and offered us drinks – yay! Unfortunately, I accidentally knocked over my friend’s drink with my floatie so I offered him mine πŸ˜‚

Then I waited with the other groomsmen in the hotel room for a while before a photographer came and did a fun indoor and outdoor photo shoot. Then, we had another wait before we got a call that it was our time to go outside and begin our walk into the wedding.

I Choose You

Within seconds of being called outside, we began to walk in turn into the wedding, which was under a gazebo on the water. I was thrilled that one of my favorite songs – Sara Bareilles’ very relevant I Choose You was one of the walk-in songs. There were about 30 guests so it was a very intimate, lovely setting. The bride’s brother MCed and there were some sweet prayers and kind words during the short and sweet ceremony. After it was done, the bride and groom signed a marriage contract on the beach and plenty of photos were taken.

The bride and groom!

For the reception, we hopped on the dragon boat for a quick ride back to Sandals Island. There were tons and tons of delicious finger foods, sweet cocktails, and cute decorations. There was even a karaoke booth which I was so excited about – after gorging for a while, one of the bridesmaids asked me to lead off the karaoke with her and we sang Whitney’s I Wanna Dance With Somebody. As we belted, the bride and groom walked in and then they did their first song as husband and wife.

A Wild Reception

After some great karaoke and several walks over to the bar for cocktails, we sat at our tables for dinner. The DJ was on point – playing all the classic pop and hip hop tunes we love. I kept walking over to the bar to get shots for my table and cocktails for myself 😍 There was a crossword puzzle about the bride and groom which my table got hilariously competitive about but sadly my team lost 😭 The post-dinner activity was human bingo in which we had to form words with other people using the first letter of our names. I won that one – yay!

The bartender poured these all simultaneously from one shaker!

Then it was time to dance and wow – what a dance! The non-dancers in the crew gathered at a table to play banana grams πŸ˜„ while the rest of us boogied on the dancefloor, taking advantage of our strong buzzes. My friend had the wonderful idea of moving a picnic table onto the dancefloor and standing upon it to pour champagne into the wedding guests’ mouths – it was a big hit! The reception came to a close with a few others and myself dancing on the picnic table.

Back on the mainland, we dipped in the pool due to the heat and gathered at Cricketer’s Pub for a cute afterparty with more fun dancing. Then we had a wild final bus ride back to Sandals Inn and plopped into bed.

One Last Morning

It was time to leave the resort the next day and we were devastated 😫 We took the shuttle to Sandals Royal Caribbean, enjoyed the breakfast buffet with a view of the sea, and I got in several drinks and some quality pool time before it was time to depart on a journey to see real Jamaica (read: outside the resort, away from the tourists). We took a taxi to the Montego Bay bus station and began our journey to Ocho Rios, Kingston, the Blue Mountains, and Port Antonio.


Click here to continue reading my Jamaica blog as I climb a mile-long waterfall and am sketchily taken to a wonderful vegan restaurant.

Click here to read the final piece of my Jamaica blog as we dip in and take a bamboo raft around the incredible Blue Lagoon in Port Antonio and have the wildest Couchsurfing experience ever back in Montego Bay.