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Friday, February 3, 2022

Paradise Lost, Paradise Found (St Lucia & Tobago Guide)

Sunset in Castara - Never gets old
That’s it, another chapter and another four countries. Following the bicycle adventure and Canada/US road trip back to Denver, I left in October and made way to Guadalajara, which turned out to be a killer random trip exploring the cultural capital of Mexico. Met some great people, ate amazing food, drank too much tequila, etc. From there I flew down to POS airport in Trinidad. POS being a very appropriate call sign as Port of Spain airport is certainly not my favorite. 

I booked an apartment via AirBnB in Arima. Turns out this isn’t an area I’d recommend. Without transport you’re fairly limited, with transport you’re still fairly limited as there isn’t much to explore. If you know me, you know I’ve experienced some pretty sketchy situations in some of the many countries I’ve visited, but have to point out that Trinidad (Arima specifically) isn’t the safest place. In fact, I didn’t feel comfortable walking around after dark in certain areas. I know I know, sounds like a typical American unnecessarily worrying, and I hope you know that’s not my style, but there are dangerous pockets in Trinidad. Best to hire a guide, or be shown around with local friends. 

No Man's Land - Tobago
The only redeeming part of Arima was that my AirBnB host happened to be very nice and the auntie of Patrice Roberts, a famous Soca star. Soca is a style of upbeat music that dominates the West Indies. In fact, you’re hard pressed to hear anything else these days, especially leading up to Carnival, which is a party like no other starting with J’Ouvert in late February. You do occasionally hear older, lighter music from the likes of Calypso Rose and steel pan groups. 

Patrice, her aunt, their driver Richard, and I did a fair bit of exploring. We did a boat tour to see thousands of beautiful red herring in the Caroni Bird Sanctuary, which I’d highly recommend. We also ate a ton of food. I can’t count how many rotis I had, but doubles turned out to be my favorite. A little hard to explain, but basically a soft dumpling that serves as a ‘carrier’ for a spicy, slow roasted chickpea stew. Fun fact, fried chicken is very popular in Trinidad and the world’s busiest KFC is in Port of Spain. I’m fairly certain it’s the only business open 24/7 on the whole island. 

Argyle Falls - Tobago
From Trinidad I took the ferry over to Tobago for $6 US. The ride is around two hours, but not the Caribbean ‘out at sea’ experience I’d hoped for. The boat was packed with several hundred people, a lot of them moaning and getting sick in the bathrooms and off the back of the boat. However, once I arrived in Tobago I knew I was in an entirely different place. It’s like the super chill, stoned little brother of Trinidad. 

I’d been asked to build a website and do some general business consulting for a small hotel in Castara. One’s first drive in Tobago is a thrilling experience. The roads are narrow, full of blind corners, people drive too fast, and there are cliffs and landslides around every bend. You get used to it though, and soon enough I found myself behind the wheel ripping around the island like a local. The first drive from the port to Castara was a little intimidating however. 

Giving some sailing instruction in St Lucia
Castara itself is a sleepy little fishing village with approximately 600 residents. It’s about 3/4 of the way up the island on the leeward Caribbean (left/west) side. Most typical tourists (i.e. mandals, fanny packs, birdwatching hats, boozed up, all-inclusive loving, etc) choose to stay in the southern half of the island, Crown Point specifically. This is great because the north has been left relatively untouched and unspoiled. The culture, vibe, and cuisine all remains. 

Honestly I didn’t explore very much the first time in Tobago, but would be back soon to the Emerald Isle of the West Indies to explore and fall in love with its beauty and charm. I’m gonna go in chronological order, so will touch on that a bit later. For now let me hop over to the next country, St Lucia. In early November I chose to fly from Tobago to Trinidad to forego another experience on the vomit comet (aka the ferry). From POS, I hopped a Caribbean Airlines flight to St Lucia where Jen, the girl I was seeing had accepted a contract with the ministry of education. Little did I know it would turn out to be equal parts heaven and hell. 

View of the Pitons - St Lucia
St Lucia does have amazing things to see. The Pitons are beautiful and surreal, and the volcanic mud baths nearby are quite nice. Some of the smaller villages like Gros Islet and Soufrierre have amazing old houses and architecture. Speaking of Gros Islet, do NOT miss the weekly fish fry/lime there (lime = party/jump-up). The history, old military structures, and views from Pigeon Island are also a must see. 

For me the beaches of St Lucia are a major highlight. My favorites are Cotton/Plantation Beach, where Amy Winehouse hung out to pickle her liver in isolation. Donkey Beach is a strenuous hike past Cotton Bay, but totally untouched. Marigot Bay is beautiful and definitely worth a visit, but a little overrun with tourism. Anse Chastanet and Sugar Beach are both stunning, but both connected to very expensive all-inclusive resorts. The good news is because of the 'Queen’s Ring’ nobody can own the actual beach, so they’re all accessible. The resorts make it clear that you are second class, but can’t legally stop you from crashing the beach. However, the best part of St Lucia for me was the sailing.

I met a couple named Ben and Vicky who run a sailing training business (First4Sail), so decided to work with them to finally learn and become properly certified to sail. We ended up becoming good friends, so I was invited to several other events and races on Papagayo, the 40ft ‘one tonner’ race yacht that became my second home in St Lucia. We won our class in the Mango Bowl regatta, participated in the celebratory ARC flotilla conclusion, and I was even able to skipper an overnight to/from Martinique to give my passport a much needed stamp. In the end I now hold IYT (Int’l Yacht Training) Competent Crew, Flotilla Skipper, and Bareboat Captain certifications, can charter my own yacht, and have given sailing lessons of my own in Ben’s absence. If in St Lucia and you want to learn to sail or simply take a day trip, I would highly recommend First4Sail.

View from the top - Pigeon Island, St Lucia
So that’s the good, let’s get to the bad and ugly. In my opinion St Lucia is a country that has completely sold its soul. The disparity between rich and poor is blatant and disgusting. Every morning I would leave Ciceron, the neighborhood I was living. I would pass my neighbor Dermot who lives in a clapboard/tin shack. I’d hop a bus and be in Rodney Bay around 45mins later staring at $20mil mega yachts. There are countless all-inclusive resorts on the island (think $500+/night), three of them being the always-predictable and disgusting Sandals. Businesses are shuttered all over the island because tourists don’t leave their fenced retreats. They’d rather get drunk and cook their skin than get out to see the inner workings and culture of the country. From my experience it seems that a very small percentage profit from the larger resorts that dominate the island. The locals are left the scraps of a country that was once theirs. 

Marigot Bay - St Lucia
Although a new government led by Allen Chastanet has been recently put in place, crime is at an all-time high and the capital city (Castries) is a complete dump. The education system is set up in a way that benefits kids who live in better districts, and set up for failure in poorer districts. Private taxis are always filled with white folk, while inexpensive minibuses are filled with locals. A trip that would cost ~$1.25 US in a minibus costs ~$40 US in a taxi (a price set by the government). This means most locals are forced to ride the buses, which I did every single day for two months. I can report back that they are stuffed with people, hot, sweaty, and frequently unreliable. I was also concerned for Jen and glad I was there with her. In Ciceron and the city she was receiving comments and run-ups multiple times daily. I’ve never seen anything like it. Not in Africa, not in South America, not Stateside, nowhere. Furthermore, there aren’t many inexpensive local food options. There are more KFC, Church’s, and Domino’s Pizza choices unfortunately. There are rumblings of a Sandals being built in Tobago at present. I can only hope they don’t follow the poor example set by St Lucia. 

An example of the disparity in St Lucia
Charles Simonyi's $75mil US yacht pictured
When in St Lucia, I received a message from another hotel owner in Castara named Sharon that wanted a website built and some general IT and business assistance. She and I had become friends the last round, so she agreed to have me back as long as I wanted. The girl and I split in December (I’ll certainly take the blame for that - sorry J) and I was effectively done with St Lucia, so I decided to retreat back to the paradise of Tobago for five weeks to clear my head. I’m just wrapping up my time there (actually writing this from the flight out), and am feeling quite melancholy about leaving. I really grew to love Tobago, made a ton of amazing new friends, and felt like I have a second home. I also learned a ton about line fishing, pulling nets, spearfishing, and cleaning/cooking fresh seafood. In my free time I would sometimes help out at the beach bar and I became somewhat of a mainstay there. My smile returned in Castara chatting up folks, pouring drinks, laughing, and exploring. What I’m gonna miss most is waking up to the sound of the ocean, walking one minute from my balcony, and doing my daily yoga/meditation/work-out sessions on the beach followed by a swim with the lovely fish and rays. 

Taking in the mud baths - St Lucia
This round I was also able to fully explore the entire island. I became quite the tour guide and driver actually, and several tourists asked if I’d show them around. I think the moto racing background helped. I began to see the twisty roads as my own personal race circuit around the island. A sample day trip from Castara had us head north on the main road and stop briefly to enjoy Englishman’s Bay, which is a stunning untouched beach. From there on to Parletuvier and stop at Paradise Point, which is a bar owned by a nice older gentleman named Glasgow. The bar overlooks the bay with an amazing view. At the split in Parletuvier you can head up through the rainforest, which is a beautiful drive and will eventually take you to the windward/Atlantic (east/right) side of the island. Argyle Falls is just outside of Roxborough and is absolutely stunning. When there, be sure to hike up multiple levels to distance yourself from the tourists and enjoy the continuing falls.

After bathing under the falls at Argyle, you can continue to head north. Before leaving Roxborough I’ve found it best to fill up with gas at the station there. It’s always reliable, plus an added bonus, they sell peanut punch (my favorite drink on the island). You’ll wind your way through Speyside where you get a view of Goat Island and Little Tobago. Eventually you’ll make way to Charlottesville, which is another sleepy fishing village on the north tip of the island, and this is where it gets a little tricky. At the end of town there’s a sketchy dirt road (seriously, like Bolivian Death Road sketchy) that leads up to Pirate’s Bay, which is my favorite beach on the entire island. Seriously, a must see. There are no permanent structures, just a few sailboats and an old man that sells fresh lobster, coconuts, and beer. It’s what you would envision the perfect Caribbean day-on-a-beach experience would’ve looked like 25 years ago. 

Jay Star keeled over during the Mango Bowl - St Lucia
From Pirate’s Bay/Charlottesville you can head west and back down the other side of the island on a badly kept, but beautiful winding coastal road. This will eventually lead you past Bloody Bay and back to Parletuvier, where you can choose to see a second waterfall. It’s not quite as impressive as Argyle, but there’s never anyone there and a really nice second level pool for wading, swimming, and relaxing. From there it’s a short drive back to Castara where there is yes you guessed it, another waterfall. Warning, all of these things are very romantic and best shared with someone. I met a lovely Canadian girl named Dina and we experienced this on a day trip together. Dina, thanks for the lovely day. It was by far my favorite in Tobago. 

You can definitely spend another day exploring the much more trodden southern half of the island, but in my opinion the magic of Tobago is up north. Both Crown and Pigeon Points are worth seeing, but a bit too touristy for me. However, if locals aren’t your cup of tea, this is where you’ll find all the tourist eye candy. Also some good kite surfing spots and rentals. Mt Irvine beach is worth a visit as it’s the only surfing spot on the island. I only spent time in the capital Scarborough when I needed to do some shopping. Penny Savers is a chain and the best for this in my opinion. A boat trip is another mandatory way to spend a day in Tobago. It’s usually a day trip and typical stops are Buccoo Reef, No Man’s Land, and Nylon Pool. Note, BEWARE the rum punch! Although, it does seem to be a Tobago ‘right of passage’ to have too much rum punch on a boat tour only to spill out of the boat onto the beach at the end of the day. I won’t comment on whether or not this happened to me. 

Anyway, what an amazing, amazing experience I’ve had over the past five weeks. I can’t thank Sharon and Brenton enough for the hospitality. I’d highly recommend their guesthouse in Castara if you make way. The site I built for them, and info about their hotel can be found at Also thanks to all the new friends that helped make my experience so wonderful this round. Too many too list, but you know who you are. I’m really looking forward to visiting Castara again sometime again in the future with friends to show them around. My guess is not much will have changed. Doesn’t seem like it has for 50 years. 

From here I’m headed to Panama by way of New York. Interestingly, it was cheaper for me to fly to NY then down to Panama, than direct from Tobago. Doesn’t much matter as I’m really looking forward to connecting with friends in NY I haven’t seen since I left on the bicycle to begin this round of travels in early June. Also, a slice from Prince St and haircut from Freeman’s are both sorely needed. I’ll be in Panama yet again for eight days this round. First exploring a small hotel in Bocas, land and the beginnings of an eco lodge in a small village an hour south of Bocas, then a few days down in Playa Venao to catch up with old friends. 

DJ David & Look-up in Parlatuvier, Tobago
After Panama I’m headed to Cali, Colombia for a month to dig in and investigate a boutique hostel/BnB/work/live project that’s for sale. Also, my good friends Paul and Josh are visiting separately to give me a second opinion and to get in some trouble together. Can’t wait to see them. If none of the business opportunities come to fruition then well, who the hell knows?!?! I do have a flight back to Denver on March 9th, which I intend to take. Will be great to see friends and family there as well. Plus, my boy and I Conrad have been kicking around a Denver based business idea. 

I guess that’s enough for now. About to land and be cold for the first time in four months! Catch everyone on the flip, 


~ D

Little Bay - Castara, Tobago

View from Boathouse Beach Bar - Castara, Tobago

View from Mt. Dillon, Tobago

Caroni Bird Sanctuary - Trinidad

Caroni Bird Sanctuary - Trinidad

About to hop yet another delayed flight on Caribbean Airlines

View from Marie's Beach Bar - Rodney Bay, St Lucia

Pigeon Island, St Lucia

Looking towards Martinique - St Lucia

View of the Pitons - St Lucia

Trying to stay young at the mud baths - STL

Captain David making way to Martinique

Nice hotel pool overlooking Soufrierre, St Lucia

St Anne's Bay - Martinique

Headed into a squall in St Lucia

St Anne's - Martinique

A boy, a boat, and a beer

Jay Star sailing around Rodney Bay for the ARC Flotilla

Donkey Beach - St Lucia

Donkey Beach - St Lucia

One of the boats that got into a collision during the Mango Bowl

The minibuses weren't all that bad sometimes in STL

Looking down on Parletuvier Bay - Tobago

Typical sunset from Boathouse Beach Bar - Tobago

Untouched land just outside of Castara, Tobago

Yet another sunset from Castara, Tobago

And another...

And another...

Steps leading down to Pirate's Bay, Tobago

Argyle Falls - Tobago

Pigeon Point random view - Tobago

Road leading to Pirate's Bay from Charlottesville, Tobago

Freshly speared lunch courtesy of your bartender - Tobago

And another...

Pirate's Bay, Tobago

Sketchy road to Pirate's Bay, Tobago

Saturday, December 31, 2016

R.I.P. 2016 - Year in Review

Here's my attempt at 'understatement of the year'... 2016 was interesting. A number of astounding things unfolded. Some good, some bad, some horrid. All making my personal achievements for the past 365 seem insignificant, and absolutely trivial. 

In January, North Korea announced that it had successfully conducted a hydrogen bomb test. On February 1, World Health Org declared Zika a Public Health Emergency. Later in the month Bernie Sanders won the New Hampshire primary and gave hope to those of us who someday wish for climate change awareness, equal rights, accessible healthcare, quality education, and substantial change in the United States. 

In March, Obama became the first US president in 88 years to travel to Cuba, lifting the travel embargo. On March 22, attacks in Brussels killed more than 30. On Easter Sunday, a suicide blast in a park in Pakistan killed 69.  

On April 3, The Int'l Consortium of Investigative Journalists published the 'Panama Papers', which outlines how a Panamanian law firm established secret shell companies and offshore accounts for elite global power players. On April 16, a 7.8-magnitude earthquake struck off the coast of Ecuador, killing 663 people.  

In May, Eric Fanning became secretary of the Army, making him the first openly gay secretary in the US military. On June 23, the United Kingdom surprisingly voted to leave the European Union, effectively making England the butt of many a 'Brexit' joke. Unfortunately, later in November the world stage would have a new clown to mock.  

On July 19, sadly my birthday, Donald Trump officially became the Republican Party nominee for president. On July 26, Hillary Clinton became the Democratic Party nominee for president, and the first woman in the history of the United States to lead the presidential ticket of a major political party. On July 3, a suicide car bomb detonated in Baghdad, Iraq, killing at least 292. On July 14, a truck plowed into crowds on the Promenade in Nice, France, killing 85 and injuring 200.  

On September 9, North Korea claimed to have successfully detonated a nuclear warhead. In early October, Hurricane Matthew made landfall in Haiti, tearing through the Caribbean nation killing more than 500.  

On November 8 (after substantially losing the popular vote) Donald Trump was elected President of the United States. On November 22, the Dow Jones Industrial closed at over 19k for the first time ever, signaling that while humanity is lost, at least our economy continues to steadily grow. On November 28, a plane ran out of fuel and crashed near Medellin, Colombia killing more than 70 people, including the majority of the Brazilian soccer team Chapecoense.  

On December 10, 44 people are killed and 155 injured in bombings in Istanbul, Turkey. On the 11th, a bomb killed 25 during morning mass in Cairo, and another car bomb killed 20 in Mogadishu, Somalia. On the 19th, a truck ran into a Christmas market in Berlin, killing 12 and injuring 48.

Marking a very somber year, there were too many notable deaths to mention throughout. David Bowie, Harper Lee, Nancy Reagan, Prince, Muhammad Ali, Gene Wilder, Leonard Cohen, Fidel Castro, John Glenn, and many many more. Finally, there were far too many shootings in the United States to highlight. A sad fact about the state of our union in 2016.


From a personal perspective, again an understatement, 2016 was interesting. I was able to accomplish some lofty goals, and also travel to several far flung locations.

In early January I founded a group called the NYC Adventure Cycling Club. It now has a wonderful leadership team, over 1k members, and continues to provide unique group rides and 'overnighters' throughout the northeast. Most importantly, it allowed me to meet amazing, lifelong friends. Really, it was more of a social club on two wheels. Some have even said it's a "drinking group with a cycling problem". Regardless, big shout out to Colin and Chris. Keep up the amazing work running the show!  

A bit later in January, I was able to explore the amazing areas of Tulum and Akumal in Mexico. This was part of my family's annual 'Destination Christmas' idea, which has removed all gifts and replaced them with quality time together in an exotic environment.

In early February, my sister ordered and received a copy of 'Someday Never Maybe', a blog-to-book recounting my one-year, 24k mile motorcycle journey to/through Central and South America. This marked one of the first 'paid' copies to be shipped. Although it's family, and my sales will most likely remain in single digits, it feels nice to have a published physical book that I can look back on someday.  

In early March the NYC Adventure Cycling Club completed the first of many organized overnight rides. Although cold, we had a solid group of amazing individuals show. Thanks Chris, Anna, Bert, Colin, and George. We'll look back on that long weekend up to Harriman with fond memories of smiles, laughter, and good friendship.  

In April I traveled all over the United States for work on a whirlwind tour. Miami, LA, Seattle, Vegas, you name it. I was also invited on a fun trip to explore New Orleans with Jen. Later that month I joined my good friends Peter and Sam in Austin for a MotoGP boys weekend. Foggy memories of that one, but I'm certain we had an amazing time. Finally, I popped down to Nicaragua to revisit a few places I'd uncovered on my moto trip, and explore a couple of business opportunities.  

In May I continued to explore my incredible home, New York City. It takes awhile to feel 'at home' in NY, but I'd made friends, knew where my favorite bagel and pizza shops were, and was able to navigate the subway with eyes closed. I don't know if I'll ever be a New Yorker, but the city in Spring was beginning to unfold and present itself to me in a way that's hard to explain for those who haven't lived there.  

On June 11th, I quit yet another fantastic job, and my father and I set off from Brooklyn to ride bicycles for 100 days across the country. On September 18th, 4,519mi later, we dipped our wheels into the Pacific. Following the adventure, I was able to sample the #vanlife by renting a ridiculous minivan and road tripping through the PNW, into Canada, then back 'home' to Denver. It was a lovely way to end the bike journey, and nice to explore and spend more time with Jen.  

In October, I found myself in Mexico yet again. This round to explore the beautiful city of Guadalajara. I sampled wonderful tequila, met rad people, and ate fantastic street food. Later that month I made way down to the Caribbean. Jen accepted a one-year contract in St Lucia with the Ministry of Education, so I figured I'd spend time getting her settled in, and do a bit of 'exploring' myself. My first stop was the lovely fishing village of Castara, Tobago. 

Then from Nov 4th - Dec 28th I was 'living' in St Lucia alongside Jen. During my time there we explored the island together. I also checked another item off ye olde bucket list by spending a month learning and becoming officially certified to sail. I now hold Competent Crew, Flotilla Skipper, and Bareboat Captain IYT certifications, and can fully charter my own boat with confidence. I even captained an overnight trip to Martinique to explore St Anne's French bread and croissants. Happy to report, they're both amazing.

So now I find myself back in Castara, Tobago. I've been contracted to assist a small, boutique hotel to build their website and help with sales/marketing efforts. I'll be here for five weeks, then it's off to Panama to explore several land/business opportunities. Finally, at the end of Feb I'll make way to Cali, Colombia to spend some time dancing salsa, practicing Spanish, and looking at a business there. After that? Honestly I have no idea. An idea that's terrifying, but apparently just the way I want it. Some say life begins at the end of the comfort zone. Sure, we'll go with that, this year was slightly uncomfortable. 

What a fucking year...  Let's put 2016 to bed. See you soon 2017.