Best places to stay in Jamaica – Along with an incredible story of my first visit

This is a short compilation of some of the best places to stay in Jamaica, along with an incredible story about my first visit to the Caribbean island.

Jamaica is a Caribbean island with lush landscape and a laid back vibe. This tropical island has beautiful mountains, rain-forests and sandy reef-lined beaches. Most of the lodging options are all-inclusive resorts clustered within Montego Bay and Negril, which is known for its diving and snorkeling sites. Jamaica is probably most well-known for being the birthplace of famed reggae musician Bob Marley, who is the venerated idol of the island.

Beautiful wild and exotic Caribbean beach

Best Places to Stay in Jamaica

Jamaica Inn – Located in Ocho Rios, the Jamaican Inn has bee serving guests since 1950, providing a home-away-from-home experience. Lodging options include suites, cottages, bungalows and villas – with cerulean walls, wooden furnishings and white and yellow or blue decor that pay homage to the beach, sea and sky, each with private balconies or verandas. Beautiful manicured grounds, open-air restaurant, ocean spa and a host of beach amenities, this is one of the best places to stay in Jamaica.
Iberostar – Located in beautiful Montego Bay, this 5-star- hotel is situated directly on the beach. The property has elegant colonial design and provides a host of water sports to enjoy.  Three are three specialty restaurants on-site. In addition to luxurious accommodations guests will find exquisite gastronomy, as well as a a full range of entertainment. Iberostar is one of the best all-inclusive hotels in Jamaica. This resort has three different levels to choose from, including Iberostar Selection Rose Hall Suites, their highest end portion of the property.
Jamaica Sunset
Round Hill Hotel and Villas – This hotel has been around since the early 50s and has hosted classic celebrities such as Grace Kelly, Cole Porter and Jackie Kennedy. This boutique property has a timeless elegance  with just 36 guest rooms. The decor was designed by Ralph Lauren and really embodies a Caribbean feel. There are also 27 villa suites that boast open-air living rooms and verandas available. Some of the villas have private pools with lush foliage surrounding them. If you’re looking for the ultimate exclusivity in Montego Bay, this is the resort for you.
Rockhouse Hotel – This is another lovely boutique hotel, this one is located in Nigril and stretches across the cliffs of Pristine Cove. This property is nestled among eight acres of tropical lush gardens, where thatched roofed villas are perched right on the water’s edge. There is a dramatic 60′ negative-edge pool for guests to cool off in, or, they can take the rock carved stairs down to the cove for snorkeling on the reef. Rockhouse Hotel is has to two award winning restaurants with a holistic approach to well-being.

Jamaica resorts

Now that you know where some of the best places to stay in Jamaica are, let me tell you about my first experience to this tropical paradise.

I visited Jamaica for the first time in the year 2000. I was supposed to go with a buddy of mine, but he back out at the last moment, so I said to myself, “screw it, I’ll go by myself.” I had reservations at an all-inclusive resort called “Hedonisum II” in Nigril. [Some of you may have heard of this legendary place]. After collecting my luggage, I went outside to look for my hotel transportation.
While walking around aimlessly, a guy came up to me and said, “Ya Mon, welcome to Jamaica Mon.
Best places to stay in Jamaica .Best places to stay in Jamaica 3
He extended his hand to shake mine, while at the same time he placed a bag of pot in my palm. I quickly said “What’s this!?” and tried to give it back to him. He raised his hands up and said, “Be cool Mon, just $50.” I laughed and said “No way!” Knowing it was highway robbery.
Jamaica airport
He then said, “How much you pay Mon?” I said, “$20.” He replied, “No Mon, that’s not enough Mon.” We settled on $25 while we walked toward my awaiting resort van.

After about an hour and a half drive to the hotel in Nigril, I headed toward the lobby to check in. Just as I was doing so, I could hear a loud sound near the beach. Everyone’s attention was diverted as a helicopter landed. Out came a guy in a flight suit walking toward the lobby. A moment later the helicopter took off. As I was heading toward my room, I passed the guy in the flight suit and said, “That was quite an entrance!” He laughed and said, “I’m a Canadian military pilot stationed in Haiti and my buddies dropped me off for some R&R.” I said something like, “Welcome, maybe I’ll see you around.

Rejection, or was it?

As I made my way through the resort grounds toward my room I was giddy. I was so excited to be in Jamaica and couldn’t wait to get my vacation started. When I reached my room I was a bit disappointed, it was not luxurious at all and didn’t match the luxuriousness of the grounds. I told myself not to worry about it as I would not be spending much time inside.

It was early evening, after getting freshened up I headed to the beach where I saw tables set up for dinner. (Many people don’t know, or won’t believe this, but I am actually pretty shy, so coming to Jamaica by myself, to a resort like this, was really out of my comfort zone). After walking around the beach for a bit, I scanned the area and saw this very attractive woman eating by herself. The gentleman that I am, I went up and asked if I could join her. To my delight, she enthusiastically said yes. After about a 15 minute conversation, her boyfriend showed up. I was very deflated. A labored conversation ensued, and soon I excused myself.

I ended up going to bed very early that night in order to get up for a sunrise snorkeling cruise. The cool thing about Hedonisum II (at least when I went nearly 20 years ago) is that everything is included. When they say all-inclusive, they really meant it.  On the snorkeling cruise I met the dude (I’ll came him Dave since I can’t recall his name) who landed on the beach in the helicopter. We really hit it off and ended up spending most of the day together. As a matter of fact, we ended up befriending a group of people about 15 strong (guys and gals). It was so cool because throughout the week I was there, I always had someone to do something with. The group was mainly professionals, there were a couple of doctors, dentists, lawyers and a couple of accountants in our group.
One of the expectations of staying at Hedonism II is that you let your guard down and just have fun. All kinds of fun. To this day, that week was one of the most memorable of my life, hence me being able to tell this story all these years later.
One of my favorite activities of all time is water skiing, which is just one of the many amazing activities the resort had to offer. I skied almost every day. They also had Hobie Cats (small sailboats), kayaks, workout facility, basketball court, indoor squash courts, volleyball courts on the beach, the list went on and on. They even had a trapeze!
I should also mention that Hedonism II is broken up into two parts, the nude and prude sides. We all were staying on the prude side and never even ventured to the nude side, not until the very last day. That story in a bit…trust me, it’s worth reading, especially if you’ve gone this far.
Couple having cocktails in hot tub in Jamaica

One evening after dinner I was walking to one of the bars—while passing one of the many hot tubs I saw that couple I met at dinner the first night, they were both getting it on with another couple in the tub. I just had to laugh, because it all started to make sense to me…they were looking for some inclusionary action. It’s very possible that if I wanted to, I could have been one of their participants.

The Big Birthday Concert in Jamaica

Bob Marley is highly revered in Jamaica, and during my visit, I discovered I would be there for his birthday—which is like a national celebration. Come to find out, one of his son’s, Ziggy Marley, would be performing just down the street from our resort. It was not difficult to convince most from our group to join in on the festivities and attend the concert. I think our hotel provided transportation to the concert, which was at a bizarre, but cool venue. There was so much traffic that the resort van could not drop us off right at the venue, so we walked just a bit to the concert site. We felt like we were lost because there was no amphitheater or similar venue anywhere in sight, so we just followed the crowd.
Along the streets there were all kinds of vendors selling traditional Jamaican arts & crafts, as well as plenty of paraphernalia. When we reached the venue, it was nothing more than a person’s back yard. I was convinced that we were in the wrong place, but after asking several people, they all confirmed it was correct. It reminded me of a high school party that kids throw when their parents go out of town, where they charged an admission and provide beer and a band. It was just like that, very informal, but cool at the same time.
Regaee music
After a couple of warm up bands, Ziggy Marley and the Melody Makers took the stage, playing many of his dad’s songs in tribute to his lasting memory. It was such an incredible evening. We all looked at each other in amazement that we were in Jamaica on Bob Marley’s birthday and got to see his son Ziggy perform. It was one of those memories for the books.

Well into the wee hours of the morning, we stumbled back to the hotel, which might have been a mile or two away. I don’t know if this is true now, but apparently back then it was not very safe to be white and be walking around aimlessly. I think this is why the all-inclusive hotels got so popular, guests never needed to leave the property, which was much safer.

Close Call with Sharks

About mid-morning the next day, Dave and I boarded a boat we thought was a cruise of sorts. Come to find out, it just took us about a quarter mile away to a small island. Once we got off the boat we quickly discovered it was an afternoon of drinking games. We both looked at each other and decided, this was not for us, especially after the previous Ziggy concert. We decided we would get back on the boat as it was heading back to our hotel. We quickly realized there was a problem, it had just left the dock!
Facing the prospect of staying on this tiny island while everyone got drunk was not appealing. We gazed out at our resort across the water and decided…we would swim back! As we approached the shore, just before diving in, we decided to make it a race. The “race” element quickly descended into survival. There were boats zipping back and forth, and, it was a long way away. Both of us were in pretty decent shape, but with all the waves and other impediments, it quickly took its toll. I don’t know how long it took us, but as we neared shore, we basically let a wave wash us onto the beach where we lied there for several minutes. We were both exhausted!
View to the Long bay in Jamaica
The resort had about 5-6 Hobie sailboats, all but one just had a main sail, the other also had a jib. If you’re not into sailing, a jib is an additional sail in front of the boat, which makes the ride much faster and more exciting. Dave and I had gone sailing nearly every day. Each day we had our fingers crossed we could get the boat with the jib, but it was always taken.  On this day, we got lucky and as it was available. Dave was a good sailor, I on the other hand was a novice. I had been sailing many times before, but really didn’t know too much.
The winds were perfect and once we got away from shore we attached our trapeze (a harness that lets you extend your body off of the sailboat) and launched the jib. As soon as the jib caught air we took off. It was incredible how fast these small boats can move when you’re able to catch so much air. With just the bottoms of our feet on the boat running on a single hull some 5 feet in the air, we were zipping along the water at maybe 25 knots. We were having fun touching the water with one hand and splashing each other. It was an adrenaline rush!
Sailing on a cat with a trapeze
In a split second a gust of wind began to lift us up higher and higher. We were almost a full 90 degrees in the air, maybe 15 feet high. The boat was essentially on its side. Fortunately, Dave was an experienced sailor. Just before we tipped over and capsized the boat, he let out both lines (main and jib sails) and the boat came crashing down on its second pontoon. We were both shaken from the experience. It was such a close call.

Enough fun for one day, we took the boat slowly back to shore. When we arrived, the attendant said, “Ya Mon, looks like you two almost tipped it.” One of us replied, “Yeah, that was indeed a close call.” The attended then said, “Good thing you didn’t” One of us asked why, as if there was another concern other than the obvious. “Lots of sharks out there Mon.” We both looked at each other with level of gratitude.

Bob Marley Would be Proud

On our last day we all gather in one of our new friends’ room to decide how we would close out this extraordinary week. (Many of us checked-in on the same day, or the day after). We were chatting about what the heck we were going to do with all of our pot (each had his/her our own stash), as we clearly could not take it with us back home. I had a brilliant idea and yelled out “Everyone, give me your rolling papers and pot.” I went into the next room, attached all the papers together and rolled the largest joint anyone had ever seen.
After finishing the extraordinary task, I got everyone’s attention and said, “This is what we’re going to do…we’re going go to the nude side (our first time even talking about it).” Before I could finish, I was getting some dissenting audible sounds from several in attendance.” I got their attention again and finished….”We’re going to the hot tub and we’re going to smoke this!” From around my back I whipped out the giant joint I had just rolled. Everyone was in amazement and someone chimed in and said “Let’s do this!” Off we went.
Map of Jamaica
We walked outside toward the imaginary line that separated the nude and prude sides of the resort. With some trepidation, we crossed over. We discovered a massive hot tub, maybe large enough for 30+ people. If I recall correctly, there were seven guys and five women in our group. We all quickly got out of our clothes and into the hot tub. There were only about 5 other people in this massive tub. I soon took an entire book of matches and lit them all up. With a huge flame in hand, I lit the massive joint. The blaze from my hand and the huge puff of smoke garnered a bit of attention. As I passed the joint around, someone said, “My god, even Bob Marley would be proud of this!” We all bust out laughing and soon the tub was near capacity.
I had been getting close with one of the women in our group, and since it was our last night together, we parted from our friends and took a romantic moonlit stroll along the beach. We discovered some hammocks hanging between two palm trees and could not resist laying in one, with the full moon nearly overhead. We laid there for what seemed like a couple of hours of talking, cuddling and kissing. We ended up spending the entire night together and had breakfast the next morning. As we were parting ways at the airport we both thought, why the heck did we not spend more time together?
Best places to stay in Jamaica
It was not only an incredible vacation, but a wonderful time in Jamaica. I hope you enjoyed this post on some of the best places to stay in Jamaica, as well as my story about my first time visiting the tropical island. If you have any questions, please feel free to leave a comment below.

Mike Shubic

Mike Shubic is a seasoned road trip travel video blogger, traversing the byways of the world looking for those hidden gems of the road. From unique destinations, unexpected discoveries, creative cuisine, intriguing inns to exciting attractions…the road is his page. The experiences are his ink. And every 300 miles, a new chapter begins. Whether you live vicariously or by example, Mike will do the exploring so you can have an adventure.