5 Month Self Tour of The Caribbean

SuewhereWhyWhat on the beach, Antigua, Caribbean

Updated on February 20th, 2020

“The key lesson I learnt? Don’t over plan so you can make the most of all the opportunities that come your way!”


Dominican Republic, Costa Rica, US Virgin Islands, British Virgin Islands, Cuba, Antigua, St.Martin, Cayman Islands, Jamaica, Turks & Caicos.
11 countries Dominican Republic (DR), Costa Rica, US Virgin Islands (USVI), British Virgin Islands (BVI), Panama, Cuba, Antigua, St Martin, Cayman Islands, Jamaica and Turks & Caicos (TCI). Follow the links above to read more or see my Video Diaries here.


While 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, namely 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!)) but often you have to work hard not to always travel via the US, which came up regularly on Skyscanner. This takes a lot longer than is needed & costs more.

Although I was originally planning on flying one way to the region, this proved to be a very expensive way of doing it so after a visit to Trailfinders, I booked a return flight (6 months later) to Punta Cana in DR
SueWhereWhyWhat Horse Riding & Sailing in the Caribbeanwhich 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, DR & 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 but still had to get off at each destination, go through some kind of security check & then queue to get back on, with the same crew!

Longest flight – 33 hours from Havana to USVI via 12 hours in Panama & 6 hours in Fort Lauderdale, USA
Longest non-plane journey – 27 hours beating against the waves, current, rain, wind & squalls sailing back from St Martin to Antigua.

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

We were doing 2 hours watch on, 4 hours off but 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, but again this became quite varied through my time on the islands. Beds included 3 weeks staying on a yacht in USVI & BVI, sailing on a catamaran for 7 days from Antigua to St Martin & back and 2 fitness & yoga retreats, in DR (eXtreme Hotel) & Cuba (Mhai Yoga with Retreat Insider).

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“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, but I was determined that if I was stopping in Jamaica I should at least sample it for a few days.

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

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!


SueWhereWhyWhat & Ivy the Cat at her home while Housesitting in Grand Cayman

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, but meant my sister arrived home in Sydney to 45 degrees F 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


Planning a trip like this I realised the importance of having time alone & time with others, depending on what I’m doing & how I’m 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! To find out more see my blog post, or video diary of the experience.


SueWhereWhyWhat & her crew in team kit, after taking part in the St.Thomas's Regatta, St.Thomas's, BVIDuring 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 and I really felt part of something as the event (St Thomas International Regatta – STIR) gathered speed & crew arrived from all over the world. See my blog post if you want to learn more about the experience.

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 &  companions for the remainder of my time in the Caribbean (sailing to St Martin), housesitting in Grand Cayman (Trusted Housesitters) & my stay at Hacienda Los Guayacanes in DR). Pineapple was also the venue for the best meal of the trip, a communal dining experience where everyone brought or did something to contribute & 20 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 – getting up every morning to sit on the beach meditating while watching the sunrise 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 RicaCahuita & Tortuguero, Caribbean Coast, Costa Rica

“I will never tire of being woken to the sound of the monkeys. It was either the weird sound of the aptly named Growler Monkeys or the noise as the Capuchin Monkeys made their way across the trees, roofs, furniture or whatever was in their way. Magical!”

Hacienda Los Guayacanes, DR – 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 calm of the water, while I lay on my back looking at the swallows as they soared around the end of the dock, 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. USVI – the week before the regatta, I was at the yacht club needing the bathroom, which 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, DR – on a hike with my “Pineapple family” the day before I headed home, I made 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.

“I realised 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, 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 placeThe 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 is 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, CubaMhai 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 appeared to lose control through feeling the vulnerability that I fight against for most of the rest of my life. 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, CubaGetting 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. I will share the full experience here in a few weeks so watch this space!

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.

What do you think?

Where have you been in the Caribbean & where would you recommend for my next visit?
What have been your best & worst experiences while travelling?
What is on your Life List that you have achieved this year?

To see more of my photos from my trip please visit my Gallery page!

My Gallery


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