The memories and experiences I will write about in this blog were made possible by a very generous financial gift from our Aunty Stella back in Winnipeg. Our plan had been to see as much of Jamaica as we possibly could during our time there but her unexpected gift made it possible for us to venture out further, for longer and allowed us to enjoy comfortable accommodations worry free. Thank you again Aunty Stella, we will never forget our time in Jamaica because of you! 💗

Sailing into Port Antonio, we were immediately in awe seeing the mountains and lush vegetation. We had only sailed two days from Matthewtown, Bahamas but everything looked so incredibly different. We were happy to tuck Starship into her slip at Errol Flynn Marina. We were full of curiosity for this country that at the moment was so foreign to us.

As soon as we arrived, we were visited by officials from health, immigration and customs. We were loaded up with a pile of paperwork to complete but the officials were all very friendly and the process went quite smoothly. Once granted permission to step off the boat, we raised our Jamaican flag. I also happily noticed that there weren’t any noseeums to contend with. There were a few mosquitos but those I find easier to manage. It was so very hot though. Even the locals were saying it was hotter than usual.

Our first venture onto the streets of Port Antonio was overwhelming. There were people, cars and music everywhere. We quickly got the attention of many locals who offered us things like tours, coffee, taxi rides, jewelry, fruit, coconut water, weed, etc. The streets were full of various stands selling a wide variety of items. It took us some time to learn the currency conversion as well. Despite being Canadians, we manage all our money in USD. One USD is equal to about $150 in Jamaican currency. This means that we had to wrap our head around paying $850 for a pineapple when that really is only just under $6. I am not a fan of head math so I wrote up a conversion cheat sheet. Despite our intimidating first walk down some of the interesting streets of Port Antionio, we very soon became comfortable navigating ourselves around to get what we needed. We also became friendly with people like Patrick! Patrick is an entrepreneur who set us up with jewelry, spices and coffee…many of those items he gave as gifts to us. He is proud of his gorgeous country and made us feel very welcome.

Here is a picture of Patrick…if you ever find yourself in Port Antonio, go to the street corner where West Street, Fort George Street and Gideon Avenue all connect. You will likely find him there. Enjoy the items he can provide to you and tell him Amanda, Jason and Dylan say hello!

Once we had rested from our passage, we began making plans to do a self guided tour around the island. Collecting advice and ideas from the marina staff, we started to pull together a plan. The advice we received also included warnings about what it’s like to drive on the island. Many of the roads go through the mountains and it was advised that we never attempt driving at night. We were also told that drivers can be very aggressive and we certainly found that to be true. In our route planning we made sure that all our driving would happen during daylight hours. We rented a car and excitedly set off on a six-day trip taking us to Ocho Rios, Montego Bay, Negril and Kingston before landing us back onto Starship. Up to this point we had, again, been suffering with extreme heat on the boat. As we set off on our road trip, I was giddy with excitement knowing that we had many nights of air-conditioned sleeps ahead of us!

Our road trip started off strong with a super fun day at the Original Blue Hole just south of Ocho Rios! As we made our way down the windy roads we were welcomed by a tour guide named Lucas. At first, we didn’t fully know if we needed to pay a tour guide or if we could manage on our own. In the end we were thrilled to have Lucas spend the day with us. He worked so hard at making sure we really enjoyed our experience there and he led us to various pools and waterfalls that otherwise would’ve been off limits to us despite paying the admission fee. Lucas cost us $60 USD but we have no regrets. We spent the day laughing and enjoying the beautiful fresh water holes. Dylan kept asking Lucas for higher and higher cliffs to jump from and Lucas delivered! From dizzying heights, both Jason and Dylan leapt into the cool waters. I did a few more modest jumps – I am not as crazy as those two! The day led us through a variety of vendors and we enjoyed a bit of souvenir shopping, and a drink before continuing on to enjoy more beautiful waterfalls and fresh water pools.

Keeping a watch on the remaining daylight hours, we eventually found ourselves back in our car to grab a bite to eat and do our hour and a half drive to Montego Bay. That night we stayed at the Blue Orchid Bed and Breakfast. It was nice but we were not really there for long. The next morning, we enjoyed the breakfast and away we went to explore Montego Bay a bit.

Corny? Absolutely!…but how could we not play that song as we cruised around Montego Bay?! 😜

So at this point I need to write about the Jamaican cuisine! Oh-ma-gawd! I discovered I absolutely love Jamaican food! Those two weeks I enjoyed escovitch fish (deliciously prepared red snapper), curried shrimp, festivals (slightly sweet deep-fried bread), fried plantain, rice with peas, beef pattis and callaloo (a green, leafy superfood). Almost daily Jason would go into town in the mornings while I worked and he’d return with juicy, sweet pineapple. We soon found ourselves addicted to chewing on chilled sugar cane stalks. Not only did we love the taste of sugar cane but we found out it contained tons of nutrients including amino acids, minerals and vitamins such as calcium, potassium, magnesium, iron, copper, zinc, vitamin E and B,etc. That’s good news as we chewed a lot of it! 😆

We even stumbled across an Italian restaurant close to the marina that made insanely good pizza at a decent price! Yup, Jamaica fed us well! Oh and of course Dylan’s food likings are still pretty boring so he preferred to visit Port Antonio’s KFC! 🙄

After our yummy breakfast, we checked out of the Blue Orchid and spent the day driving around. Before we knew it, we needed to begin our drive to Negril to ensure a daylight arrival.

Arriving in Negril we stayed three days so we really got to settle in at Legends Beach Resort. Our boat life has us constantly on the go it seems so we really made a strong effort to slow down for those three days. We enjoyed the pool, a bit of fun souvenir shopping and some beach time.

Legends has a ‘sister’ resort called Samaras Cliff Resort. One day we drove over there for a change of scenery. Samaras is located on Negril’s majestic cliffs on the westerly tip of Jamaica.

The day we left Negril we had a very long drive planned. Wrapping around the southwestern side of the island we made our way to Kingston. Friends we had met had told us about a store in the city that Jason was super excited to check out – Durae’s Boat Sales & Marine Supplies. Located on a residential street, it is actually a big, two-story house that has been gutted and turned into a very well stocked marine store. Jason was in heaven! I eventually got bored and went to sit in the car to read my kindle while Jas and Dylan perused the many full shelves of marine goodies. Once he hit the two-hour mark, the owner poured him a rum to enjoy as he continued to look around!

With the light of day starting to fade we knew that we would not be able to make it all the way back to Port Antonio before dark. We were also advised by many that some areas of Kingston struggled with crime so we needed to choose our hotel stay carefully. We were not familiar with the city so we decided to really play it safe and booked ourselves for a one-night stay at the Hilton’s ROK Hotel.

Oh how I loved our one night at the Hilton! 💖

After we checked out of the beautiful Hilton, we went to several stores in Kingston looking desperately for cushions to use in our cockpit. The custom cushions for our cockpit died on us years ago and our cheap, replacement ones were pretty much done. With us needing to spend so much time in the cockpit on passages, we were very hopeful we’d find some patio-style cushions that would work for us. We gave up after looking in five different stores and were surprised they were such a challenge to find.

Settling into our two-hour drive to get us back to Starship, we found ourselves on windy, narrow, mountain roads with spectacular views.

We came across the most intersting cemetary I’ve ever seen. Life sized photos were put up to honour some of those who lay to rest there.

Back at Starship we knew we needed to change gears so to speak and start preparing for our crossing to Panama. We still craved one more fun day before we started to say goodbye to Jamaica. For the final day of our car rental, we packed up for a beach day and enjoyed Winnifred Beach. Winnifred is located within a secluded bay with white-sand beaches and clear water. For a good chunk of the afternoon we were in the water talking with a man from London named Cleveland. He was there on business but had family and property in Jamaica. Dylan enjoyed playing with his nephew and the other kids while we really enjoyed Cleveland’s company. We laughed when he said, with his lovely English accent, that we were ‘true gangsters’ for doing our sailing journey. He also said we were an inspiration to him. When we hear those types of comments, we really take them to heart. Like with many of our ‘fast friends’ we ended the afternoon by saying goodbye to one another as we hugged and wished each other well.

During our stay at Errol Flynn Marina, we also met a lovely family who had their catamaran anchored in the bay close by. We really loved getting to know Angie, Andy and their sons Riley and Daniel. Riley and Dylan really hit it off and baby Daniel was such a little cutie! It was sad to say goodbye to them when we left Jamaica but we still keep in touch by text. I have a strong feeling that we will see them again as we continue our travels and I really hope we do.

The morning we returned the car we also found a store finally that had outdoor cushions. They weren’t exactly what we were looking for but, in the end, they did add a bit of comfort to us on our passage.

The next two days were long for us. In the incredible heat, we did mast work, provisioning, fueled up and got the boat as ready as possible for what we knew was to be our longest passage yet.

Our passage to Panama included a very stressful experience with the Jamaican Coast Guard, fifteen-foot waves, motion sickness, strong lightning and minor injury. Those experiences were rewarded by a dolphin pod visit on day three, calmer seas on day four and the gift of arriving in Panama a day early due to strong, consistent winds. My next blog is all about the highs and lows of those days crossing the Caribbean Sea.

The blog below talks about why we have decided to add the above Coffee button. 😊

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