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5 Month Self Tour of The Caribbean

A blonde woman in a black dress and sunglasses standing leaning against a palm tree on a caribbean beach with an upturned boat in the foreground

Updated on May 14th, 2024

In 2018 I had the opportunity to travel solo around the Caribbean. Throughout the 5 months I spent in the region I learnt Spanish in the Dominican Republic, took a tour of Costa Rica, entered a sailing regatta in the US Virgin Islands, attended a yoga retreat in Cuba, partied in Antigua, sailed around St Martin & the British Virgin Islands & tried housesitting in the Cayman Islands. Here you can read all about my adventures!”


Dominican Republic, Costa Rica, US Virgin Islands (USVI), British Virgin Islands (BVI), Panama, Cuba, Antigua, St Martin, Cayman Islands, Jamaica and Turks & Caicos (TCI).


In 2018 my neighbours had their house renovated. I had the chance to loan mine to them while I left the country for 5 months. I decided to head to the Caribbean where I had plans to do some sailing, Spanish lessons, volunteering, travelling, achieve my goal of 60 countries by my 50th birthday & only need to pack clothes for 1 climate! At least that’s how it started but as you’ll see my plans developed as I went & the 5 months turned out to be a fun & varied adventure around this beautiful part of the world.

What did I do?

Different modes of transport used by SueWhereWhyWhat during her 5 Month Self Tour of The Caribbean. Yacht and Bike!

Throughout my time in the Caribbean I used yacht, ferry, catamaran, car, bus, horse, horse & cart, kayak, raft, sailing dinghy, motorized dinghy, zipline & bike but mainly between the islands got around by plane!”

This is not always as easy & straightforward as you think it should be. There are a couple of interisland airlines. InterCaribbean (used a lot & booked via their website) & LIAT (I didn’t use LIAT as they have a reputation for not running on time (‘Leave Island Any Time’ was the nickname I heard!)). However, often you have to work hard not to travel via the US, which came up regularly on Skyscanner. This makes your journey a lot longer than is needed & costs more.

SueWhereWhyWhat Horse Riding & Sailing in the Caribbean, 5-month-self-tour-of-the-caribbean

Although I was originally planning on flying one way to the region, this proved to be a very expensive way of doing it. As a result, after a visit to Trailfinders, I booked a return flight (6 months later) to Punta Cana in the Dominican Republic.
This made getting in & out much better value.

Most flights in 1 day – 4

From Antigua to the Cayman Islands we had to go via BVI, TCI, Dominican Republic & Jamaica, where we had an overnight stop before our final flight the next morning to Grand Cayman. This became even more ridiculous when we realised for the 4 flights we were on the same (tiny) plane. However, we still had to get off at each destination & go through some kind of security check. Then we queued to get back on, with the same crew!

Longest flight – 33 hours from Havana to US Virgin Islands via 12 hours in Panama & 6 hours in Fort Lauderdale, USA

SueWhereWhyWhat sailed overnight for 27 hours of beating against the waves, current, rain, wind & squalls back from St Martin to Antigua

Longest non-plane journey – 27 hours beating against the waves, currents, rain, wind & squalls sailing back from St Martin to Antigua.

We were doing 2 hours watch on, 4 hours off. Unfortunately, when I was on duty we always seemed to hit bad weather & I had to wake up the skipper. This was also unsurprisingly the roughest night’s sleep. Imagine sleeping in a bass drum during a heavy rock concert on a rollercoaster!

Total flights – 22 on a plane, 9 Ziplining, 1 Tarzan Swing & 1 Trapeze flight!

Again, I used a lot of different sources to get my accommodation sorted, mainly Airbnb & Expedia. Again, this became quite varied through my time on the islands. Beds included 3 weeks staying on a yacht in US Virgin Islands & BVI, sailing on a catamaran for 7 days from Antigua to St Martin & back and 2 fitness & yoga retreats, in the Dominican Republic & Cuba.

Most Extravagant Room Hyatt Ziva All-inclusive Hotel, Montego Bay, Jamaica

I had heard a lot of stories about how dangerous Jamaica was. If I’m honest I usually take this with a pinch of salt, often believing it to be a story to keep people spending money in the resorts.

SueWhereWhyWhat at the Hyatt Ziva All-inclusive Hotel, Montego Bay, Jamaica, 5-month-self-tour-of-the-caribbean

Usually I like to prove these things wrong. However, with Jamaica I heard it from too many people, with too much consistency to not take it seriously.”

I travelled through for 1 night with a friend & was disappointed that I didn’t feel safer & more confident walking in the Kingston suburb where we were staying. However, I was determined that if I was stopping in Jamaica I should sample it for a few days at least.

In the end, I bowed to peer pressure & found a deal on this beautiful hotel for 4 nights. It was my first experience with all-inclusive & I have to say I loved it! 4 nights was enough for me, I won’t rush to repeat the experience but being on my own, it definitely felt a much safer & more sanitized option.

Cheapest Room i.e. FREE! – In Grand Cayman
SueWhereWhyWhat & Ivy the Cat at her home while Housesitting in Grand Cayman

I was introduced to the fantastic world of housesitting with Trusted Housesitters. It had all been organised by my friend Caroline who I met in Antigua & for the responsibility of looking after our gorgeous cat, Ivy & watering plants for 10 days, we had full use of the house, car & a great location on Seven Mile Beach!

Total number of beds – 29
Most different beds in 1 country – 10 different locations in Costa Rica
Most different beds in 1 guest house – 4 in Pineapple House in Antigua. 

As I loved it so much I wanted to stay & so had to keep moving!


I left home unsure where & what I would be doing so loaded up on the common currencies just in case – US$, UK£, Euro, AUS$ & Canadian$.

When I left I was thinking I may go skiing in Canada & sent my skiing gear to Australia. It made sense at the time. However, it meant my sister arrived home in Sydney to 45 degrees with a case full of my thermals!”

SueWhereWhyWhat & fellow travellers, White water rafting & abseiling in Costa Rica with G AdventuresTotal number of currencies used
– 8 including 3 which had US$ (USVI, BVI & TCI)
SueWhereWhyWhat & her crew in team kit, after taking part in the St.Thomas's Regatta, St.Thomas's, BVI

Planning a trip like this I realised the importance of having time alone & time with others. It all depended on what I was doing & how I was feeling. In Costa Rica, I interspersed 2, week-long solo trips to both coasts with a G Adventures tour for 9 days to see the highlights of the country & experience the adrenaline activities on offer. This worked brilliantly & I met a fantastic group of people. Going white water rafting is a very different experience on your own, versus as part of a group!

During my time preparing for the regatta in USVI, I was living on a boat for 3 weeks at the St Thomas Yacht Club. It was here that I realised the importance & power of a community & how much I need & miss that, with my choice of lifestyle. The people here were so welcoming & helpful. I really felt part of something as the event (St Thomas International Regatta – STIR) gathered speed & crew arrived from all over the world.

Best community
Pineapple House, Antigua

On my first night in Antigua, I arrived at a party & feeling slightly unsure as my room had no windows or a lock for the door. The sign above the kitchen then said it all…

SueWhereWhyWhat and friends at Pineapple House, Antigua during her 5 months tour of the Caribbean in 2018.

Here’s to the nights that turned into mornings, with the friends that turned into family & I couldn’t agree more!”

SueWhereWhyWhat & friends, Pineapple House, Antigua during her 5 months tour of the Caribbean in 2018

I ended up staying for 3 weeks & made companions for the remainder of my time in the Caribbean. I went sailing to St Martin, housesitting in Grand Cayman & my stay at Hacienda Los Guayacanes in the Dominican Republic. Pineapple was also the venue for the best meal of the trip. It was a communal dining experience where everyone brought or did something to contribute. Twenty of us ended up sitting down for a delicious roast pork dinner one evening. None of it was planned, it just happened, that’s Pineapple House!

The key lesson I learnt?

Don’t over plan so you can make the most of all the opportunities that come your way!

Total Number of New Friends on Facebook – 51 (& lots more besides who “Don’t do Facebook!”)


SueWhereWhyWhat strikes a yoga pose at sunrise on the beach in Cuba.Best Sunrises

Mhai Yoga, Cuba – every morning we sat on the beach meditating while watching the sunrise. It will always be a memory I will cherish

Vinales, Cuba – a dark hike up the mountain to practice yoga as the sun rose over this beautiful landscape. I felt so blessed, lucky & grateful I couldn’t help crying.

Best Wake Up Call
Two cheeky Capuchins and one noisy Howler Monkey, in the trees of Costa Rica

Cahuita & Tortuguero, Caribbean Coast, Costa Rica

I will never tire of being woken to the sound of the monkeys. At times it was either the weird sound of the aptly named Growler Monkeys. Other mornings I awoke to the noise as the Capuchin Monkeys made their way across the trees. Or maybe the roofs, furniture or whatever was in their way. Magical!”

Hacienda Los Guayacanes, Dominican Republic

The final day of my trip. I decided to take in the early morning & have my last dip in the Caribbean Sea. So I didn’t have to carry wet stuff home with me, I also ticked off Number 64 of my Life List – Skinny Dip! The water was calm. I lay on my back looking at the swallows as they soared around the end of the dock. It is a moment I will always remember!

Best Sunset
Sunsets on the beaches of Costa Rica and Shirley Heights in Antigua.

Santa Theresa, Costa Rica – watching the sun disappear into the ocean while the surfers catch their last wave of the day.

Shirley Heights, Antigua – the sunset over English Harbour from the top of the hill, amongst historic buildings, strong rum & to the sound of an amazing steel band. I enjoyed it so much, I was there all three Sunday nights I spent in Antigua!

Worst Injuries

I’m a little clumsy so I wasn’t expecting to come away from this time without hurting myself a bit.

SueWhereWhyWhat - injuries, including a lumpy shin & bandaged toe during her 5 Month Self Tour of The Caribbean.

US Virgin Islands.

The week before the regatta, I was at the yacht club needing the bathroom. It was locked as everyone else had left for the night. I decided to go & use “natures toilet” on the beach. All was fine because it was dark, so nobody could see. That was until I was on my way back & stubbed my toe hard on a big brick on the sand. I ended up losing ½ a nail on my big toe & spent the next 3 weeks & regatta with a big bandage for protection. It hurt like hell but was an excellent talking point & way of making new friends!

Salta Waterfall, Dominican Republic.

I was on a hike with my “Pineapple family” the day before I headed home. It led me to I make a couple of bad judgement calls. The first was to believe the most important thing as we crossed backwards & forwards across the small river was to keep my shoes dry for the journey back to the UK. The second was that I could emulate the success that 16-year-old Forest achieved on our first crossing by stepping to have 1 foot on a rock & then leaping from there to the other bank. I forgot that Forest was a fit boy who is a good 2-3 inches taller than me.

As I fell hard on the rocks on one knee, soaked my feet in the water & ended up lying on the stones with a golf ball growing amid the grazes on my leg, I realised that maybe I had my priorities slightly wrong! I carried on with the walk, the waterfall was beautiful, but I made it home with wet shoes & a beautifully bruised leg!”

Most Emotional Moments
Scuppered ships at Nanny Quay, Bahamas, Caribbean and hotels waiting for restoration to take place

The Virgin Islands & St Martin

The aftermath of Hurricanes Irma & Maria showed how hard these islands, in particular, were hit by the devastation caused by mother nature last year. Seven months on, it was clear to see the wreckage still present around the coastline of all these islands. Look closer you see how many roofs are still missing on the properties & how many cars have at least one window taped up. And then you speak to the people & witness the tears well up in their eyes as they remember & you realise that the whole island is suffering from Post Traumatic Stress Disorder. Property recovery is one thing but the human & emotional impact of the devastation will take a lot longer to heal.

Sunrise Yoga and the hike to viewpoint in Los Acuáticos, Viñales, Cuba

Mhai Yoga with Retreat Insider, Havana, Cuba

I have done yoga before & although I always enjoy it, until I came here I didn’t really get the whole mind & body practice thing. I have so much to report on this experience over the next few weeks but between the music, the movement, the exercise, the relaxation & the people, it is the most I’ve cried in years. At the end of each session, I finished savasana in floods of tears. Amazing! I will be back & I will never doubt the power of yoga again!

 Most Surreal Experience
Mhai Yoga Shala, coloured ribbons blow in the breeze, at Mhai Yoga retreat, Viñales, Cuba

Getting my fortune told by a Santeria Priestess, Mhai Yoga, Cuba – ticking off Number 25 on my Life List. She said a lot (in a nutshell my life is flourishing but not without sacrifice, my romantic life is about to undergo a big change & I am a person who is always moving forward) & I’m yet to fully realise how much of it will become or is a reality.

Life List achieved – 7 ticked off for the first time, 5 revisited

25 – Visit a Fortune Teller
64 – Skinny Dip
77 – Visit Costa Rica
80 – Take Part in a Yacht Race
83 – Visit 60 Countries by my 60th Birthday
102 – Tour the Cayman Islands
104 – Visit Jamaica

Where next time?

There is so much of this beautiful area still to explore & next time I am interested in starting south in Grenada & working my way up through the islands with my sailing hat back on.

Interested to read more?

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5 Month Self Tour of The Caribbean

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  1. Absolutely beautiful trip and such good idea to travel and see all those beautiful places!
    What is shortest time possible to travel through all those island?

    1. Thank you Elena & that’s a hard question to answer. You can certainly get a flavour of each island in a week but personally, I prefer to take my time & delve a little deeper to see where, what & who the journey brings to. Although I recognise this is a luxury that many don’t have. I love the area though & can’t wait to return later this year.

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