It had been five years and nearly 35,000 nautical miles of hard sailing—including three years in Antarctica and Chile—when we finally turned north for the Caribbean. We were ready for a change and the chance to swim in warm, crystal clear, blue waters again, and it was time to get Zephyros, our 47-foot Boréal, in for a tune-up at a proper yard.
Trinidad’s reputation for boat work made it an obvious choice, so we reserved a spot in the Peake Yacht Services yard for the 2022 hurricane season (July-November), fully expecting our visit to be mostly work and little play—which is also part of Trinidad’s reputation. But what we found was much more, and our experience there was only enhanced by the three weeks we spent meandering Trinidad’s largely unsung neighbor, Tobago, after our work at the yard was finished.
We left for Chaguaramas, Trinidad, from Mount Hartman Bay, one of Grenada’s popular southern bays, on August 31. We’d stopped in Grenada to get our paperwork in order and the permits for our cats to clear customs with us, which took an unexpected six weeks. The Peake yard worked with our changing and sliding arrival dates, remaining accommodating throughout the process.
Some people are nervous about this 95-nautical-mile passage because there have been pirate incidents along the route in the past. The Trinidad Coast Guard requests that boats file a float plan before transiting, and they monitor VHF 16 with a high-powered antenna and repeaters. We know of a couple of incidents when the Coast Guard has come as far as the offshore oil platforms—30 nautical miles off Trinidad’s northern coast—to tow and assist boaters having problems like malfunctioning engines or flooding. They understand that cruisers have concerns and are taking maritime safety and security seriously.
We departed before sunset to work our way through the shallows and reefs of Grenada’s southern coast. The overnight sail began with a bit more breeze than forecast giving us a nice reach for the first three hours; but then the winds faded and we motorsailed. Just after midnight, a 30-knot storm cell provided a bit of excitement before we found ourselves in light air approximately 10 miles north of the brightly illuminated Poinsettia and Hibiscus oil platforms. With some 30 miles to go, the engine was back on and the rest of our passage was uneventful. After the sun rose, we saw red clouds of scarlet ibises making their morning commute en masse from Trinidad to Venezuela, which sits just 15 miles to the west. It was a stunning welcome to a deeply green and rugged coast.
Boat Work and Street Food
We didn’t know quite what to expect from Trinidad, but we had been warned that the only real cruising to be done was in Tobago. In Trinidad you did boat work. We discovered that there was a little more to it if you dug beneath the surface. There are a couple of lovely anchorages and island areas to explore just outside of Chaguaramas. A calm, secluded bay is certainly a possible escape from boat work, or a safe respite on your way out of Chaguaramas or while waiting for the current to ease on your arrival.
Birdwatchers have long booked special trips to Trinidad, where unique species are found at any time of year. More than a dozen species of hummingbird are there, as well as the beautiful scarlet ibises we saw that first morning. Leatherback turtles nest and hatchlings emerge on the beaches. There is some hiking just outside Chaguaramas, and the more adventurous can find tar pits and waterfalls to explore farther afield.
Oil revenue may dominate the economy, but Trinidad’s true riches are found in its biodiversity and multicultural people. The cultural mixing pot has resulted in a street food connoisseur’s dream, and during our time at the boatyard we took full advantage.
A short walk outside the yard we discovered our first local dishes—freshly squeezed fruit juices, spicy doubles (chickpea mash, spices, and fried dough), amazing rotis, perfect coconut bakes, rich flat breads, and mouth-watering stewed or roasted chicken, beef, and plantains. The proud, loving people who prepared the foods and welcomed us to enjoy them only made everything taste even better. Indian, African, and Caribbean flavors mixed with tropical fruits in delicious ways. If ever you thought your taste buds could take a little more, rich hot sauces were standing by to add an extra kick.
These food stands provided value-priced, masterfully prepared meals that we didn’t have to make when our galley was inaccessible, or our water-cooled refrigerator was shut down while on the hard. We enjoyed these, as well as rich curries and fresh grilled fish, for weeks before we ventured further afield on a Taste of Trinidad tour, which should be on every visitor’s to-do list.
Our host was Jesse James, vice president of the Yachting Services Association of Trinidad and Tobago (YSATT) who originated the Taste of Trinidad tour. With a mix of cruisers we knew and new friends we got to know over the day, we set off in Jesse’s 15-passenger tour van for breakfast at about 9:30 a.m. The tasting began immediately with items like coconut bake, doubles, cheese and meat pies, curries, pilau (an Indian-style curry rice dish), provision (a mixture of native starchy fruit and root vegetables like plantains, cassava, yams, and taro), and more. As the day continued and we made our way around the island, we refreshed ourselves sampling juices like sorrel (tastes like cranberry and the holidays when seasoned with cinnamon and spices) as well as some peanut punch (a peanut-flavored milk drink).
There were stops at fruit stands for chiquitoes and silk figs (two types of small, sweet bananas), portugals (clementines), and to see giant squashes and the large Brazil nut. The day also featured local delicacies from salted fish and chicken liver to cow heel soup and barbecued pig tail. While some of these were harder to love (the consistency was our personal hurdle), we made sure we tasted everything and could certainly appreciate the complex and intriguing flavors. It was an unforgettable experience as we explored the island and its foods and Jesse taught us about Trinidad.
By 9:00 p.m., we had sampled 55 different local dishes and several beverages carefully selected from street food purveyors over half the island. We rolled out of the van that night, and nobody ate again until sometime around dinner the next day when our normally ravenous teenage boys were finally ready for a snack. As for our favorite dishes, we can still taste the saheena (deep-fried callalloo—a bit like spinach) melting in our mouths and dream of the hot pholorie (fried dough with a delicious mango sauce).
We took a few more trips to explore Trinidad, but we were really there to work on the boat, and it dominated most of our time. Other friends enjoyed trips to see the scarlet ibises and hummingbirds and take in some nearby hikes. We took time out to enjoy the Diwali (Indian festival of lights) celebration, and while Carnival wasn’t happening while we were there, it is, of course, said to be incredible.
One thing we didn’t encounter while in Trinidad was a sense of danger or violence—something we knew the island has a reputation for, and which, in fact, was noted in a March 2023 Sunday Express story as being one of the issues affecting the local yachting industry (the other was a rather laborious customs and immigration process). To us, it just never was an issue. The Chaguaramas area is isolated and safe. Port of Spain is like any big city—there are areas where you shouldn’t go or places you shouldn’t be after dark—but for cruisers taking basic precautions, that’s not really an issue.
Like most long-time cruisers, we don’t really like being stuck on the hard and sweating through maintenance projects, so we were motivated to get the boat back together and sailing again. The official end of hurricane season passed but the rains continued, with our hired painters working around almost daily deluges and a few other projects still underway. Eventually, we’d completed as much work as we could stand, and as soon as we reasonably could, we were off to Tobago.
Cruising Around the Corner
Tobago is 60 nautical miles northeast of Chaguaramas and about 20 nautical miles from most of northeast Trinidad. The post-hurricane-season passage is almost always a motorsail (or straight motor) to windward as you first travel east closely following the Trinidad coast to avoid the strongest currents, then turn north to cross to Tobago. We had the wind within 15 degrees of our nose the entire passage despite the dogleg course; but no matter, we were finally underway again. On November 20, 12 hours after leaving Chaguaramas, the anchor was down in Store Bay, Crown Point, at the southeast end of Tobago. For the first time in almost three months, it was time for a sunset swim in the cool, inviting water.
Tobago is a beautiful contrast to the industrialized Chaguaramas. The people are as friendly and welcoming as their country-mates in Trinidad, the bays are uncrowded, the water is clear, and the island is easily explored. Most boats explore only the northwest (Caribbean) coast, but when the swell shifts to come from the north, the southeast (Atlantic) coast can suddenly become the protected side of the island, and its less popular anchorages come into their own.
When we first arrived in Trinidad, the boatyard helped us prepare the mountain of paperwork for customs and immigration, making check-in relatively easy. When we sailed for Tobago, the customs and immigration offices in Chaguaramas prepared transfer packages for us to take to their offices in Scarborough.
From our anchorage in Store Bay, it was easy to catch a ride into Scarborough to check in. The large buses are cheap, though they seem to run about once an hour at best. Unlike Trinidad’s maxi-taxi system—15-passenger vans, white with colored stripes for the sector of the country you are traveling in, which stop with the wave of a hand and pile in as many people in as possible—Tobago’s maxi-taxis seem to only operate for large, pre-arranged groups. Walking along the road looking for a maxi-taxi that wouldn’t come, we asked a local how the system works in Tobago. We learned that if you stand on the side of the road, someone will soon offer to give you a ride for a small fee negotiated on the spot. In Tobago, almost everyone behind the wheel is an opportunistic taxi driver.
Once checked in at Scarborough, we were able to get a “Permit to Bay Hop” that let us cruise the southwestern portion of the island and proceed to Charlotteville in the north, where we had to obtain another “Permit to Bay Hop” for the northeastern half of the island.
This creates a slightly odd situation where you can slowly explore the first half of the island, but then you must jump to the end before backtracking to continue exploring the rest of the coast in between. Given the island is only about 22 nautical miles long, the extra miles required to follow the rules are not terribly onerous, and customs does regularly drive the coastal road noting which vessels are moored in each anchorage. Tobago seems to be of two minds—the robust bureaucracy with numerous forms done in triplicate (or more) making carbon paper a sought-after commodity, and the relaxed Caribbean island time attitude that dominates all else. If one chose to flout the rules a little and got caught, it’s hard to know how things might turn out.
We spent several days enjoying the plentiful food and beverage options around Crown Point and generally relaxing after the yard period. This is an area where Trinidadians come to escape, and it was easy to understand why. We took in the opening World Cup matches there and provisioned the boat a bit more with the island’s largest grocery store within walking distance. Provisioning in Tobago was easy, and we prepared a full U.S.-style Thanksgiving dinner with a turkey and all our favorite sides and desserts.
As the days passed, we moved up the coast, around Pigeon Point and Bucco Reef to the Mount Irvine anchorage, where we found a nice beach bar, a few more pleasant restaurants, and a good fruit and vegetable stand within walking distance. We also enjoyed a walk over to Bucco, famous for its all-night party on Sundays—called Sunday School—and its goat races in the lead-up to Easter.
Mount Irvine put us in the front row to watch one of the best surf breaks in the Caribbean, invited us to snorkel a little, and allowed us to easily rent a car to explore a bit more of the island’s lush green interior, including the oldest protected tropical rainforest in the western hemisphere. Our two days with the car found us intimately watching and feeding hummingbirds more than once. You can feel and hear their wings flapping like little fans as they buzz by you. They feel like an ethereal presence when they weightlessly land on your fingers to eat from small, handheld feeders.
Birdwatching, waterfall hikes that wound through cool forests, scenic views, and more delicious dining were the menu as we explored the island by car. As we’ve learned to do while cruising, we drove everywhere we could, stopped anywhere that looked interesting, and didn’t worry too much if any attempted side adventure went a little awry (we never did find one particular waterfall, though we had a nice hike for several hours along the stream).
We were never in a hurry in Tobago. When we told customs that we wanted three weeks to go from the southern end of the island to the northern end, they laughed at us before signing the permit. We moved slowly from anchorage to anchorage up the coast, found some lovely bays and visited small towns and cafes where beautiful arrays of colorful hummingbirds swarmed the feeders.
In Castara, we found a waterfall and swimming hole a short walk from the beach, and more places to watch the World Cup matches with local residents. We discovered traditional community brick ovens on the beach where we enjoyed the local fresh-baked breads and other treats. We try to sample quality ice creams wherever we go, and we found some refreshing rum-raisin, guava, and ginger blends that were worth the effort to track down despite teenage gripes about the occasional uphill walks to get there.
Whether we were traveling the island by car or on Zephyros, we encountered more birdwatchers than sailors. The busiest anchorages had fewer than a half-dozen boats and never felt crowded. It wasn’t hard to find a good anchorage where we could spend the night alone, as we did in Englishman’s Bay.
When shifting winds and swell rotated to come from the north, we found that Pirate’s Bay and Englishman’s Bay both started to become a bit rolly. No problem, we sailed (motored) around to Batteaux Bay in Speyside, where we were all alone until joined by a friend we cajoled to sail up the Atlantic coast from Scarborough to share the anchorage. Another boat eventually joined us as well, but there was more than enough room for us all to be well spread out.
In Speyside, we found more delicious dining, more World Cup, great snorkeling from the boat, and enchanting views. It was here that we took the opportunity to enjoy some world class scuba diving along beautiful, healthy coral reefs and to see one of the world’s two largest known brain corals.
Small islands also offered enticing opportunities to explore by dinghy. One day we ventured out to the ruins of an old estate house on Goat Island that is said to have once been a residence of Ian Fleming. As the sun set each evening and the stars came out, we looked out off our stern towards the Atlantic with the Fleming house and its island magically silhouetted against the sky and ocean. It was easy to imagine 007 emerging from the surf or Chitty Chitty Bang Bang soaring overhead.
We spent almost three weeks relaxing and exploring Tobago before we slipped back into Charlotteville for a few brief hours to clear out for Grenada. We were surprised to find 10 boats in the anchorage, where they had all apparently gathered to rock together in the northerly swell, missing an opportunity to see and enjoy the other coast.
We quickly headed out as the trade winds reestablished and the swell shifted to be more from the east. With our bodies once again mostly adjusted to the pleasant Caribbean temperatures and daily swims, Zephyros’ cruising readiness refreshed and restored, and our memories filled with the rich experiences of unexpected adventures and the warm hospitality of the people of Trinidad and Tobago, we set off on an overnight sail back to Grenada and kicked off our Caribbean sailing season.
Jon, Megan, Ronan (16) and Daxton (14) Schwartz have been cruising full time aboard their Boréal 47 since 2017. They were awarded the Barton Cup—the Ocean Cruising Club’s most prestigious award—for their most recent project of completing a largely offshore circumnavigation of South America, during which they transited the Panama Canal, sailed to the Galápagos and Easter islands, extensively explored Patagonia and Tierra del Fuego, made two extended sails to the Antarctic peninsula, visited the Falkland Islands, St. Helena and Ascension, then returned to the Caribbean. They are currently sailing in northern Europe. They post passage updates to their blog www.svzephyros.com and to Facebook: sailingzephyros and Instagram: sailing.zephyros.