Rest, Relaxation, and Rasta on a Beach in Jamaica
How to take a Caribbean Vacation without Worry
Recently the Sery Content Development shareholders held their annual meeting on the north shores of Jamaica.
Of course when I say “shareholders” I mean me; because I’m the only shareholder in the company. So every year I like to hold the shareholders meeting in a great location, and bring the family along to enjoy the trip too.
Naturally, I report back here so that if you’re traveling to the same destination, it’s a quick reference guide on what to expect.
So, if you’re heading to Jamaica soon, here are my experiences, and what you can expect on your trip to this tropical Caribbean island.
Staying at the Royalton White Sands All Inclusive Resort
When we were planning the trip, we headed over to Costco Travel to get everything taken care of in one place. Often the price is a little better than if you book everything separately, and plane tickets are for better times of the day. So instead of leaving at 6am and getting in at midnight, it’s a little more reasonable. I’ll get into the airline fiasco at the end.
For now, I want to talk about the all inclusive resort. No worries about having to figure out meals, no worries about drinks, no worries about anything… right? Well, for the most part that’s the truth. I think the easiest way to divvy this travel story up is to break it into sections: a pros and cons for each adventure an aspect of the trip.
Pros of the All Inclusive: Now, I haven’t stayed in an all inclusive resort before, so I can’t compare how this one is to another. But I can compare how it is to other resorts and hotels. The room was about what you would expect from a seaside resort. Nothing terribly fancy, a couple beds, a mini-fridge, but we weren’t there for the room. Upon arrival we received a bracelet with a little circular card on it. That acted as our key card to the room, and showed that we were paying guests so we could access the restaurants and bars.
From there we didn’t really have to carry anything if we didn’t want to. We could walk up to any bar (or swim up to a couple of them), get just about any drink we could imagine. We could walk into the restaurants and order anything on the menu. Unlimited drinks, refills on food if we so desired, and only a couple of the restaurants had reservations required.
Lounging on the beach, servers would occasionally bring you your drinks. If you tip them, they come back more often. Of course we were more interested in exploring and hardly sat in one place for that long. Especially when you’re a pale skin ginger like me, you tend to shirk the sun.
Cons of the All Inclusive: The biggest pitfall was the lack of variety available. Not the food, there was something like 11 different restaurants at the resort, and each one was themed with a different type of food. The lack of variety had more to do with the drinks.
There was Red Stripe Beer on tap, a bunch of well liquors to make mixed drinks (most were made pretty weak), and two types of wine. Not a real big deal, but if you wanted a known brand of liquor you had to pay extra for it.
Restaurant hours were a little odd. There were only a couple of restaurants open for breakfast, one was a west indies buffet that was just downstairs from our room. That place was rarely crowded and had unique and delightful food. But then they closed at noon. And only the gourmet buffet and the jerk hut were open for lunch. Everything else was closed until dinner. While the buffet had a lot of options, it also had a lot of people. The jerk hut only had a couple options, and was a good place to get a little snack if you didn’t want to eat lunch right away.
Finally, the other con was the beach bums that roamed around. I’ll get into that at the bottom in the “Things I wish I had known” section.
Excursions on the Island to Experience the Area
When you’re in a foreign land, you can certainly hang out at the resort the entire time and get a nice relaxing vacation in. But why not head out to the island and see what there is to offer?
During this time of Covid, most of the island is closed to tourism. You have to stick with what they call the “Tourism Corridors” that consist of most of the coastal areas. You’re not supposed to go inland, and the capital Kingston is off limits (I’m sure there are special exemptions, like if you have family there).
But most of the activities take place in those corridors anyway. You can sign up through most hotels, or plan out your own (check down below in “Taking a Trip to Falmouth” for how to do that).
Cliff Jumping, Ziplining, Tubing
Our first trip was through Chukka; an adventure company. They have a ton of different options that include horseback riding, four wheeling, and more. We opted for the cliff jumping, ziplining, and tubing down the river. Unfortunately, we didn’t have a waterproof camera case, so I have minimal pictures of this section of the trip 🙁
Cliff Jumping into White River at Blue Hole
Our first stop was at Blue Hole. It’s a popular place beneath some gorgeous waterfalls. Our guide explained that the large pipeline that ran alongside the road was under maintenance, so the water levels in the river were much higher than usual. And that meant we couldn’t go into the upper pools.
No worries, he took us to a small platform (I call it cliff jumping, but really it was a man made concrete cliff), that was around 10 feet off the water. We jumped in, did some flips, and floated just a little ways down to the rocks. From there he led us to the next platform.
On this one, there was a rope swing that we used to launch into the lower pool.
Ziplining the White River Valley
We took our plunge into Blue Hole, which despite being in the tropics was actually a bit on the cool side. It turns out that 9am in the jungle is rather shaded. Then we headed up the valley a little bit to another small shop where we got geared up for the zipline canopy tour. We donned harnesses, helmets, and gloves, and followed the guides into the jungle where 5 sets of ziplines were set up.
We took turns cruising through the tops of the trees and over the White River. It’s a whole new experience to get up into the trees instead of being on the ground. Regardless of where you are, a zipline is a fantastic experience to see the world from a different perspective.
Tubing the White River
Once our zipline was done, we removed the gear and piled into a van to take us up the valley even farther, so we could get into inner tubes and float the white river back to where we were ziplining.
Most of the float was pretty leisurely, but there were times where if you went left instead of right, you’d get caught up in some bramble. At these places cords were strung across the river, and we were instructed to grab on and pull ourselves to the proper side so we didn’t pop the tubes.
A few areas had some “rapids” and the guide had us go through one at a time to ensure that if we did flip our tubes, we were able to get back in, or at least float alongside them until it was safe to get back in.
Pros of Swimming at Blue Hole – This somewhat hidden gem would be hard to find without booking the excursion. The guide was awesome, and he even jumped with Holden when Holden was too scared to hop off the platform on his own.
Pros of the Zipline Tour – The guides were awesome, and explained not just about the zipline tour, but also about the Jungle, different plants that we were seeing, and some of the history of the area and how the plants were being used in the past.
Pros of the Inner Tubing Experience – It was a nice and relaxing trip down the river. Coming from Montana where we have some good whitewater, none of it was actually scary. There were a couple of spots where locals set up a “bar” and sold you drinks as you floated past.
Cons of Blue Hole – I’m not 100% certain, but Blue Hole looks like you could access it on your own without paying for the experience. It certainly looked like locals would come party on the opposite bank at least.
Cons of Zipline – Like most ziplines it wasn’t really long. I’m sure we spent more time getting set up than on the actual zips.
Cons of Tubing – Those drinks on the river were nice, but they said “oh just pay when you get done.” But there wasn’t a word on how much. It turns out the beers were $6 each… pretty pricey for anywhere, especially in Jamaica where most prices were a bit less than what you’d find in the States.
All in all the excursing was something like $150 per person. But it helps you get out and experience the area without having to worry about planning, setting things up, equipment, getting lost, or injuring yourself. The guides were awesome, but there’s a few things to know about these trips before you head on one (see “Things I wish I had Known” down below for the deets).
Swimming with the Dolphins
Dolphins are pretty amazing animals. And if you’ve spent much time on the coast, you’ve probably seen one or two. Bottlenose dolphins are found just about everywhere in the world where the waters are warm enough. And while you can certainly swim near them in most areas, it’s a special treat to swim with them.
We didn’t really know about swimming with the dolphins until we got down to Jamaica. But there were ads about it, so we signed up for a swim.
At Dolphin Cove, they have a bunch of dolphins that are kept as pets. They have large “pools” that are attached to the ocean, so they have plenty of room to swim and be free. You can choose the Encounter, the Swim Adventure, or the Royal Swim, each one offering a bit more and costing a bit more. We opted for the middle package.
We were paired up with another family, and followed our trainer. He had two dolphins that he worked with. He gave us the lowdown on what to expect. We would grab on and have them pull us back to the dock, or get pushed as we were on a boogie board, or dance with us as we bobbed in the water.
All of those were great, and a lot of fun. It was amazing to be able to touch, and feel these animals. If you have ever thought that a dolphin was soft and squishy, they only look like that. A couple of times I bonked my shins against them, and that really hurt.
The cove supplies a photographer, and after she left, our trainer looked at us and said “Who wants to do more?” Naturally we all said huzzah, and he let us get pulled back in another time. And then gave us more from the Royal swim adventure; like where the dolphins came up beneath you, put their noses under your feet, and launched you into the air.
The entire experience was amazing. Including the non-dolphin parts. There’s a jungley adventure area to tour while waiting for your dolphin swim. Macaws, iguanas, and more to keep you entertained.
Pros of Swimming with the Dolphins – In the wild you wouldn’t be able to touch these creatures. But when you buy a package like this, you’re right there hanging onto them. If you’re nice to your guide, they give you little bonuses… sometimes. The group right next to us didn’t get any perks.
Cons of Swimming with the Dolphins – Before heading to Dolphin Cove we bought a waterproof case for my phone. We paid way more than it was worth at the gift shop at the resort ($40 I think). Then saw the exact same case at Dolphin Cove for $25. But that’s not the worst part. We couldn’t even take it out on the dock while we swam with the fishes. They said it was because the dolphins might steal our phone and hide it and play with it later… or eat it. But I’m 99% sure it was actually because they wanted you to buy the pictures they took. They were good pictures, but for a family of three it would have added $190 to our adventure.
All in all swimming with the dolphins is likely a once in a lifetime experience. So it’s worth the $500+ that it cost. You get up close and personal with them, you get to experience how amazing they are, and that hands-on teaches you more than staring at them in the ocean could ever teach. Keep reading to the Things I wish I had Known section to find out what else you should be prepared for on your dolphin adventure.
Taking a Trip to Falmouth and Jamaican Culture
When we booked our excursions, the tour company lined up our drivers for us. We didn’t have to worry about any of that. Our guide that took us to Blue hole, ziplining, and tubing, was with us through the entire day. She stayed with her van while we did our adventures, and then drove us to the next spot. When we met her she was very excited to tell us that she was TerryAnn with TerryAnn Tours, but a lot of people just call her TT for short.
It was over an hour in the van as we traveled to Blue hole, and TT was awesome at explaining the area, the history, how the roads were built, and everything you could ever want to know about Jamaica. She was loud, excited, and fun to be around.
She gave us a business card, and said that she was trying to start her own business as a driver and guide around Jamaica. Her goal was to break away from working for someone else, to working just for herself. Sounds like something I train people how to do with my No to Grow program. So we asked if she could take us into Falmouth, the nearby town, in a couple of days. She agreed, and we called her through WhatsApp the night before to confirm.
Our goal was to experience Jamaica outside of the tourist bits. To see what life is really like, and also to get some souvenirs that aren’t your typical knickknacks. Our first stop was at the grocery store so we could pick up some coffee and rum for less than what the hotel was selling it for.
Jamaican Blue Mountain coffee is some of the finest around. It’s smooth and lacks the bitterness found in many other blends. But it’s pricey. You can get it on Amazon for about $70 per pound, in the hotel gift shop for about $50 per pound, or at the local grocery store for $32 per pound. Still expensive, but much less than at the touristy places.
Once we were loaded up on goodies, we headed over to the open air market down by the docks… where the cruise ships come in. This market was more of the same tourist junk you find everywhere. Most was probably made in China, and shipped over to be sold as “authentic” Jamaican goods. Some of it was handmade, some artists were crafting right by their shops, but most was just trinkets.
I bought a hat, Holden bought a wooden lizard and a wooden turtle, Jessica got a couple bracelets.
Near the grocery store there is a small shop called Juici Patties. This place sold Jamaican beef patties, and a couple kinds of drinks. That’s it, no outrageous menu. These beef patties were awesome. It’s spiced up ground beef in kind of a little hot pocket type deal. They’re quick, easy, probably loaded with calories, and delicious. Best of all: they were really cheap too. We ordered 4 of them, and our total was under $5 American (I think it was about $750 Jamaican). If you go, definitely stop at Juici Patties.
Then we hit up the Falmouth Marketplace. This place was wild, and the true Jamaican cultural experience.
The market is a permanent flea market and farmer’s market. I’m guessing the tents out front get taken down through hurricane season, but there are large structures that house the produce area that are always there. TT guided us through, and explained all about the different fruits and veggies we were seeing.
She explained that the massive piles of ginger root were because there’s a special tea that is brewed up for Christmas every year that involves a lot of ginger. I pointed at different fruits and she explained what they were, how they were typically eaten, and more. We bought a pineapple and a papaya to take back to the hotel, and ate a couple of oranges while we walked.
The rest of the market was clothes, and home goods, and more. TT told us that the market would soon get really busy because that’s where all the locals would be coming to do their Christmas shopping.
If you head to Jamaica, and you fly into Montego Bay, you need to hire TT as your driver. She will pick you up at the airport, take you to your hotel, drive you around, explain the history, and show you the places where most tourists don’t go. You can find her on her Instagram page @terryanntours
Things I wish I had Known Before I Went
We went into this trip fairly blind. We had never been to Jamaica before, there was relatively limited information online about what to expect, and so we just headed on down with the expectation that we would have some fun on the beach. Which we did, but there’s a little more to be prepared for.
Bums on the Beach – The beaches are all basically public property, even if they’re at the resort. The thing is, only the guests can go up by the chairs, the locals have to stay down near the water. And there are a lot of locals that bum around the beach and try to sell you stuff. Everything from ganja, to shirts, to coconuts, to guiding you to find nice shells. They are mostly harmless. Aggressive salespeople, but friendly (and probably stoned most of the time) and just living the tropical life. Ignore them, or say no thanks and they leave you alone.
But, I did befriend a couple of them. They gave me information on the area, told me what to look out for, and all of that. If I did need something, I bargained with them by saying I’d get them a beer from the bar instead of paying a dollar or two. Most of them, if you asked the cost, they would say “Oh I don’t know, five dollar, ten dollar, whatever you want.”
If you buy anything from them, just know that you can bargain, bargain, bargain. They’ll start really high ($25 for a t-shirt) and you can get them much lower.
Tipping – Going into it we were told that tipping wasn’t expected at the resort, but if you gave a couple bucks here and there, you would get better service. So I took about $200 in one dollar bills. That worked out okay, but ended up being not as great later.
First, we didn’t lounge about on chairs and get served much. Most of our drinks we just went up to the bar. The dollars came in handy when we needed special service, like having our pineapple and papaya sliced for us we gave the chef a few dollars. I gave my beach bum friend, Igrade (I have no idea how to actually spell it), $5 and a beer when he brought me a conch shell.
But when you’re on your excursions, things are a little different. Every guide was absolutely awesome, and deserved a tip… but I ran out of cash for some of them. Then there was the tip for our drivers, who deserved more than just a couple of dollars… especially TT who spent her entire day with us.
So, when you’re going to Jamaica, bring plenty of one dollar bills so you can tip your servers at the restaurants. But then bring other denominations as well, and make sure that you have plenty with you. Remember, each guide deserves at least $5 (we tipped our dolphin trainer $20 because he gave us so many bonuses).
Along those lines, if you buy a beer on the river, make sure you have enough cash. I wasn’t expecting $6 beers, and only had $10 with me. So I had to tell him that’s what he had to accept. And that also meant I couldn’t tip our tubing guide.
Bring the right Gear – You’re in the ocean, oceans are wet. Before you head down, bring waterproof cases for your phones and cameras. You can get good ones for about $10 on Amazon.
Bring a snorkel and mask. Our resort lent them to guests at no charge, but when the water was clear, they were booked out all day long. Bring your own and don’t worry about borrowing.
Water shoes are great. Get a good pair. The ocean has pokey things in it. And sting rays. I stepped on two of them.
Buying Pictures – When you go to something like a dolphin swim adventure, they have photographers that take your picture as you go along (the tubing place did too). And they’re outrageously expensive. For a single image they want $35, or all the pictures for $190 (for a family of 3, it varies depending on how many people in your group). We didn’t realize at the time, and I don’t know if it would work, but try bargaining with them. The pictures are already taken, they can’t get the time back, so $50 is more than they will get if you walk out.
Independent drivers/guides – Hire TT. She’s a great guide.
Planning Your Trip to Jamaica
From my experience, this country is pretty relaxed, and there are plenty of places where you can stay to have a great time. You can book an all-inclusive, if you don’t want to worry about food and drink, or you can get an Air BnB to get a little more of the authentic feel. Once you’re in the country, it’s easy to get around, it’s not incredibly expensive (except some of the tourist stuff), and TT is just a phone call away.
When we booked, we booked it all through Costco Travel. We have not had much luck with using their services!
13 days before we were to depart, I had an email from Costco saying there were changes to my plane schedule. I called, and it turns out that American Airlines had canceled our flight from Billings to Texas. This meant that the entire getting to Jamaica and getting home schedule was all thrown off.
Their solution was to travel down on a different day, extend the vacation by a day, maybe take a different airline, but they weren’t really excited to work with me on it. Plus, to change the dates at the resort would result in hundreds of dollars of fees, plane tickets would be immensely more expensive, and overall it was… well a fiasco.
I spent about 3 hours that evening trying to figure out how to manage the trip.
Finally, I was able to come up with the idea to fly down on American Airlines, on an all-night flight, and back on Delta with a stop in Atlanta for the night. The good part: Costco was able to refund just the airfare portion of the trip, and the new flights, although longer, were actually cheaper. The bad part: flying all night really sucks.
Thanks for reading my immensely long trip report. If you plan to take a little trip down to the island of Jamaica, I hope you have found value. Feel free to reach out at email@example.com if you have any questions or need more details on exploring Bob Marley’s homeland.