Sailing St.Thomas to Trinidad

Prelude: The night that started it all

It started on a balcony. Austin, one of our best friends (and the current Captain of Flying Ginny, a 55ft Lagoon Catamaran) came to St. Thomas to hang out with Stephen and I for the night before he flew home for a couple weeks in June. (Side note: Tortola, the island where the boat is docked, doesn’t have direct flights to the states, so he needed to get to St Thomas first). Sitting there that beautiful evening we were just talking about our plans for the summer. One thing led to another, when he eventually came to mention how he might have to deliver Flying Ginny to Trinidad for maintenance and security from the potential caribbean storms. HAVE TO?! Sounded awesome to me. However, he mentioned the current crew wasn’t able to help with it so it might not be happening. We sat there for a minute and thought, why couldn’t we help? I conveniently just got my STCW in South Africa a few months ago allowing me to work on boats…and Stephen also just got his Captain’s license. One thing led to another on that balcony, and within 15 minutes we were so hyped the famous last words of “were doing this?!” Came out of our mouths. BOOM. Just to help you understand the weight of those words, If we say were going to do something, we ALWAYS do it. And that brought us to today, August 2nd….

8.2.16 : Day One: Departing the US Virgin Islands 

The day has come. It’s been our excitement for the past two months since we had this idea/plan that night on that balcony and to feel it finally coming together is surreal. If someone told me a year ago I would be sailing 600+ miles through the caribbean sea stopping at over 13+ islands with 4 of my closest friends, I would have just laughed. Overnight sails with nothing around but the stars, hiking to isolated waterfalls, wake-boarding new waters, diving different underwater terrain. This trip should be nothing short of “once in a lifetime.” We want to share this experience with others, but also give us something to look back on to remember all of the finer moments with the greatest people on this beautiful caribbean adventure. Getting picked up on the dinghy on the easternmost point of St. Thomas this afternoon was when the reality set in. We ARE doing this. With the sun setting at our backs, we head west for Nanny Cay, Tortola. Ginny….were coming for ya.

8.3.16 : Day Two : Setting for St. Barths (distance: 100 miles)

TODAY’S THE DAY! The first sailing stretch will start this evening around 4pm and we will be arriving at St. Barths tomorrow morning/afternoon. The thought of an overnight sail is pretty damn exciting. We will be taking 3 hour each watch shifts overnight, all overlapping by an hour for the sake of company and safety. This will be one of the two longest stretches out at sea we will be doing on this trip.

Phillipa, the current head chef and first mate on Flying Ginny is also coming on this trip. Lucky us 🙂  Her and I got up nice and early to get provisions done for the trip for food and supplies for the drop off of the boat in Trinidad, while the boys (Austin and Steveo), stay on board to do routine and thorough checks on the boat. After provisions and checks were done, we leave the “home” dock Ginny has been at this past season and stop to fill up with fuel. Shortly after,  we head to Road town to check-out of Tortola and pick up one last person, Eryn, who just ferried over here to meet us from her flight to St. Thomas earlier this morning.

Finally, were having some lunch with the whole crew all on board, and then WE ARE OFF. 100 miles here we go! Cant wait to write about how the night goes…Next stop: St. Barths.


8.4.16 : Day Three : Night sail and Arriving at St. Barths

We made it! 100 miles directly into the wind. Lets just say none of us really got to sleep last night. The wind gusts were getting up to 25-30 knots and the waves were in short increments of 5-6ft each. It was not a “luxurious cruise night to St. Barth’s” Most of us only got about 2-3 hours of napping sleep last night. Our watch shifts were done in 3 hour segments all overlapping by one hour. I was on watch first from 9pm-12 midnight. As my shift came to an end, Stephen and I were doing a safety check on the engines for Oil and coolant when we realized our starboard engine was leaking the flushing salt water into the hull by a small hole in a hose (normally it empties out into the ocean). When we woke up Austin to tell him about it, Phillipa heard a sloshing noise in the floorboards. We did indeed have a bit of water in the hull. The bilge pump that usually pumps out any water that fills up in the hull, wasn’t working. So with the combined leak and the malfunctioning pump, we had to figure out how to get the water to stop filling up. We were at this point exactly halfway between Tortola and St. Barts. Talk about adrenaline rush. We sure weren’t tired anymore. Austin luckily had an extra bilge pump on board. With the quick replacement of that, the water was quickly pumped out and we were able to continue to St. Barths, where we fixed the saltwater leak once at anchor.

Celebrations were had once we dropped that anchor. Sleep deprived and exhausted, we suddenly felt a second wind with our desire to get to land and explore the new island. A quick dinghy ride over and we were in French territory. A victory cocktail was certainly in order after booking our quad bikes for the full day of exploring tomorrow! After a bit more walking around town on the beautiful charming cobblestone streets, we head back to Ginny for some tapas and some home made Pad Thai for dinner! The sunset certainly didn’t disappoint either.

8.5.16 : Day Four : Exploring St. Barths

The sleep we all had last night was certainly needed. We ended  with a movie and all passed out around 9:30pm. Probably the best thing we could have done considering the day we had today. Chicken Curry (Eryn) and I woke up around 8 and had a nice workout on the bow while Austin and Stephen finished up fixing that leak from our starboard engine. By 9:30am we were ready to explore, coolers packed.

Once we got our bikes, we headed off to the first beach which was absolutely breathtaking. The hotel to our right was probably close to 2K a night with sea bob rentals (those underwater jet ski things that pull you). Tempting…haha. But we continued on because of how much we wanted to see in just one day. We hit different lookout spots, beaches, shops, and eventually came down to Baie De St Jean where Nikki Beach is located. We figured “When in St. Barth’s….” and went there for lunch. Holy hell was the food incredible!! Not just amazing presentation but it also tasted better than it looked. They don’t lie when they say the french know how to cook, thats for sure. 

After lunch we head out to search for the natural crystal pools. No lie we probably circumnavigated the island about 4 times that day. The streets are clean, well kept, and they’re all paved in concrete which is considered luxury. The island had a feel of Cape Town, South Africa when we hit the western side. Huge mountains right up to cliffs and ocean with lots of wind. Brought back a lot of memories and it was really cool to explain to my friends who I had wished had been in Cape Town with me a little of what it felt like there.
We headed back to the boat around sunset because of some passing rain storms to have beer chicken cooked on the grill and coconut milk kale for dinner. We are certainly eating well on this trip so far. After a few cocktails and a decision to continue the exploration of the island at night, we get back on our bikes and head west. We stumble across this bar in the middle of nowhere. Now, keep in mind we are in total chill/active gear because we are, well, four wheeling. This bar/restaurant was about 100 dollars for every round of 5 drinks. Crazy. Beautiful people everywhere, dressed to impress for sure. Dancers every 15 minutes came out for a show on a stage in the most epic costumes (they even had people on stilts balling out in full American flag gear haha), killer DJs (europeans know how to do that kind of thing apparently). By 1am we were fully committed in “i don’t really give a fuck” mode and took over the dance floor. Im hoping the looks were because of how sick our dance moves were and not the fact we weren’t in $3000 dresses and suits HAHA! What a night. Dropped off the keys to the bikes and we head back to the boat to depart for St. Kitts in the morning! St. Barth’s, it certainly was a pleasure.

8.6.16 Day Five : Sail To St. Kitts

Well, today we say goodbye to St. Barths. 5am is our departure time. Sails up, engines off, and we cruise for about 10 hours. Within the first 30 minutes at 5:30am the first edible fish was caught, a delicious black fin tuna. Within ten minutes it was bagged and put in the fridge ready for dinner! Our second fish was exactly what we were looking for. About five hours later, we caught a 35lb Wahoo passing over a sea mount. Austin and Eryn cleaned this guy ending up with 25 wahoo steaks! Pulling into Port Zente off the South Western side of the island, we drop anchor and prepare to head on land to see what we can do with the time we have left (and to check into customs). Its already 3pm, and we plan to be underway to Guadaloupe by 5am the next morning. Getting our things together we hop into the dinghy and head for shore. The boys go to check into customs while we hang around the local shops and grab a drink at the first bar we see. After meeting up (customs took a while), we head to the largest mariott in the world for some sun downers. What was going to be a chill evening ended up with us at a casino before heading back to the boat for dinner. Lets just say it went pretty well 🙂 We had the most amazing dinner with our fresh tuna tartar, blackened wahoo on the grill and a salad. Food comas happened soon after that and we head to bed to start our early morning off to Guadeloupe.

8.7.16 : Day Six : Arriving at Guadeloupe


The day started, 5am yet again, with both coffee and rods out. Sailing off the point of Nevis (An island just south of St. Kitts) we head for open water. About a 45 mile sail south. Fifteen miles into open water, we hear our starboard rod zip out. First Mahi!!!! This fish fought us for about 80 yards of line and we had it to the boat in 15 minutes. As we touched the leader, the fish breaks free during his last intense fight. What an incredibly beautiful colored fish! We were hyped because that means they’re around and hungry. About an hour later, SECOND MAHI! We had to get this guy this time, but as we get him close to the boat the line completely snaps! Talk about a moment of struggle haha. We continue to Guadeloupe and arrive just around sunset. We choose to pick up a mooring at this small group of islands called Les Saintes, on the central-western side *The western side of most of the islands we hit will be more calm than the eastern side because the island blocks the wind and rough swell*. As were motoring up still in 300ft of water. Im showering off the starboard side while Curry is showering off the Port side. We had still left our lines out, so as I’m rinsing out my shampoo the fishing line zips out!! FISH ON! What better thing to do between your shampoo and conditioner than reel in a perfect black fin tuna for dinner!! Finally, we had caught a fish today. And I gotta say mid shower at sunset was a pretty epic time.(back of the boat showers in our bathing suits are our preferred shower location haha). We proceed to have some more delicious fresh tuna for an appetizer, and some of the leftover blackened wahoo, chopped up mixed into a “wahoo salad” that we put inside of pan fried pita bread. My God. We certainly have been eating well. Thats sustainable living.

8.8.16 : Day Seven : Explore Guadeloupe

Waking up in the morning was glorious. The spot we stayed at just felt like we were on a different planet. Water so clear and still you can see 50ft down, you literally feel like you’re flying. Sunrise coming up behind Guadeloupe, coffee in hand. Stephen and I reach for our gear and head off for a 8am dive. So many Yellowtail Snapper everywhere! It was certainly a spearfisher’s heaven as well. We swim back and have to get off of our mooring because apparently they were there for the scuba and snorkel tours the island gives. Perfect timing as we head for the main marina: Basse-terre. Here, we get to land where the guys check us into customs. Curry, Phillipa and I find a spot to relax where we finally find wifi after two days, and wait for them to meet us. As we chat to our Waiter who happened to know some English rather than French, we ask him to see if we can get a taxi to take us around the island. He regrets to inform us that there are no taxis as it was already 3pm (French Island), but that he had called his WIFE coming to take us around and show us the island since she speaks since great english. What?! This plan just went from 0 to 100 real fast. Her and her daughter arrive 15 minutes later, and we pack into her car and her nephew who also decided to join us in the island activities! Three locals, two cars, and a brand new island!! Our first stop was hands down one of the most mind blowing places on earth I’ve ever been. You start a hike through thousands of banana trees down into the tropical forest where you walk with no shoes because of how soft and muddy the ground is. It actually felt really good. We hike down about 20 minutes, the sound of raging water gets louder when finally you come to a beautiful valley with a freshwater river up to a pool where this giant waterfall flows into! We were all in heaven at this point. 


Next, she then takes us to the red river where we rope swing at the base of another waterfall and jump into its pools! You’re thinking probably the same thing we were, how did we get so lucky meeting this family… But she didnt stop, she then takes us at sunset to the side of Guadeloupe’s volcanoes to relax in the hot pools. What. A. Day. The evening was finished off with a fresh shower on the boat, nice clothes, and a dinner near the marina where they all joined us. Our view of Guadeloupe by sitting in one restaurant talking to one person changed everything in seconds. This is proof that good things happen to good people. In return we offered to have her and her family sail with us to the neighboring island the following day…

8.9.16 : Day Eight : Explore Terre De Haute
Auntie Sophie (What Austin ended up calling her by the end of the evening lol) and her family met us at the dinghy dock at 10am to bring them on board. They of course bring fresh croissants and pastries. The french sure can bake! We enjoyed a day sail with perfect weather over to the neighboring island where we grabbed a mooring ball. Once in the harbor, Phillipa and I cooked a really nice lunch for everyone. Fresh sliced Tuna with sesame and soy, grilled pita and hummus, tomato mozzarella and balsamic, a fresh salad and some chorizo sautéed in honey, garlic, with a red wine reduction. Safe to say….it was a hit.
We head to land shortly after where shopping, ice cream, crepes and wandering around takes place 🙂 It was so quaint it almost felt like being in a section of Disney World. After leaving them at the ferry dock to head back to their home island Guadeloupe, we head back to the boat to grab the wakeboard. Sunset is hands down the best time to wakeboard around the islands, you’ll never experience anything like it.


Smiles all around, we head back to the boat. Sun drained and exhausted, we finish off with a light dinner of shrimp and mashed potatoes cooked by Curry! Were excited for the next morning, where our usual 5am sail begins to the next island. Dominica

8.10.16 : Day Nine : Coming to Dominica

The sun rising this morning was one for the books. Sun peaking up between the islands to our left as we continue south. Today is a relatively short sail, 6 hours and we will be there with good winds. Eyes on the horizon and feet up on the sun beds, we cruise at a good 6.5 knots to our next destination.

As we approach with Dominica on our left, the waves go from 3-4ft to 0. It was like we were on a lake. Gotta love protection from the island itself. We head for Roseau, to hopefully find a mooring ball or place to anchor. As we approach, a quick little wooden boat zooms up to us and welcomes us to the island! How awesome. He tells us to follow him to the fuel dock and there he sets us up with a safe mooring ball. “If you guys need absolutely anything I will be right over there on shore keeping a safe watch on your vessel.” Great hospitality already! We decide to take it easy this afternoon. As the guys check us into customs, Curry and I do a nice workout on the bow, take the paddle boards out, and we even get in some wake boarding. It was flat as a lake after all. We decide to treat ourselves for dinner with Scallops tonight in a brown butter sauce with rosemary, and cabbage sauteed in butter with some balsamic. We sure were eating good tonight.

8.11.16 : Day Ten : Exploring the Island of Dominica

We wake up with somewhat of a plan today (kinda). One of Stephens coworkers has cousins here, so with a bit of his help we head to land to meet up with Shan who is a local that said he would take us around. He picks us up in a lime green van that looked like the mystery machine (we got a good laugh in) perfect size for the 5 of us. And Shan and his driver David head for the mountains. We do a good bit of driving, straight up the winding roads until we are so high we get into the clouds! The temperature difference was amazing. Phillipa was actually cold. We get to the top of the mountain where we enter a park, and come to this massive freshwater lake! It was actually pretty eerie. Clouds moving by us, a slight chill in the air and a lake. It was really cool to start at the top to see where all the waterfalls end up flowing from.

As we pack back into the van, we head down a ways which takes us to our second stop. The trench to the waterfall. It was amazing, ill try my best to explain this. You walk down into a pool and begin swimming through a trench that was about 15ft walls up out of the water and 15 ft deep below us. The opening was no more than 4 ft wide for a ways until it opened up like a cave on each side near where the waterfall was! This was one of the coolest things we’ve seen so far. 


Packing up we head for the next stop, Traflagar Falls.

What an incredible sight. Two waterfalls, one dropping 75ft and the other dropping 60ft both joining at the base by rocks and pools of raging water. You can climb and swim in these pools too which was pretty awesome. We spent about 45 minutes here before pressing on to our next location, the hot pools.


These hot pools were so quaint and quiet it felt like you were in a spa. With different pools at different temperatures you could hop around from pools ranging from hot tub hot to swimming pool warm. After swimming in all the cold fresh water we were happy to spend some time here.


Finishing up our afternoon we head to get lunch at a local caribbean spot. We take our food back to the boat where we crash out for a nice afternoon siesta 🙂 food coma anyone? After napping for a bit we take the dinghy out to hunt for lobster off this reef and also get in some more wakeboarding. What better way to end the night than laying out on the nets of the catamaran listening to some music staring up at the stars with all your favorite people. Dominica, you were a beautiful, lush, wet, amazing place and we hope to see you again soon. Tomorrow, off to Martinique

8.12.16: Day Eleven : Sailing to Martinique

Today it is Stephen and I’s turn to sail. Anchor up, sails up and we head for Martinique. Fort de France is the port we head for. No luck was had catching anything on the way over but it still was perfect weather for us which we were grateful for. Seven hours at sea and we finally pull in. What a charming, well built city. Stephen and Austin head for customs to check in while Phillipa, Curry and I head for some french espresso (much needed) and the shops. We meet back at Hasta La Pizza around 5:30pm where temptation kicks in, and we get, well, a pizza. While the guys were checking in they met some locals who recommended we check out a restaurant/bar called Sunset. We realize the walk was a bit far so halfway into it we ask how to get a taxi. These two local guys tell us they will take us and we are on our way! Arriving, it appeared to be just opening. We have a couple delicious Mojitos at sunset and discuss plans for the evening. Looking around this charming, elegant, yet beachy feeling bar they seemed to be getting ready for something big. Speakers were being tested, DJ setting up, they were even adding lavender scented water to the sand covered floor. Fancy. To our convinience, we see a small unused dock slightly out to the left of the bar, after asking the bartenders if we would be permitted to use it, we grab a taxi back to the boat to change, have some tapas and plan to head back here via dinghy a bit later.
Lets just say it was an awesome local vibe, great music, dancing happy people, we even treat ourselves to a bottle of champagne in celebration of making it half way!

Waking up we get final things done needed for the boat, grab some veggies to pair with our meals, grab some McDonalds because they actually had one, and get back on the boat around noon to head for St. Lucia!

8.13.16: Day Twelve: Departing for St. Lucia

St Lucia was nothing short of a good time. During our sail, we reel in a solid 40lb Wahoo which we proceed to grill to make two massive bowls of (our new favorite) fresh wahoo salad. We still have two freezer bags full of raw fish to put away for later.

Pulling in around sunset, we see a massive stage on the palm tree filled beach lighting up the sky with music pumping from the sound system they clearly had. We tried to look up what was going on but couldn’t find much about it except that it was an all weekend festival. We are all exhausted, and after some thinking, we do the smart thing and save the visit to shore for the morning. After checking into the island tomorrow, we will grab our tickets by dinghy and head for the music.

8.14.16 : Day Thirteen : Expect the Unexpected

Nearly a hundred catamarans were anchored here, some tied up together to make mini islands. This festival was also set next to the Sandals resort where Curry and I decided to take a lovely afternoon stroll/lounge in the swinging beds while the guys enjoy a few coctails in the ocean. After a couple hours, we head to the boat for some lunch, and to pick up Phillipa who has been on board cleaning and making adjustments before her departure from St. Vincent in two days. We enjoy some more delicious Wahoo salad and head for the evening concert. All we knew about it, was that he was the number one performer in the caribbean from Trinidad. Here is the most insane part of all… drum roll please. It is Benji. We didn’t find out until his opening song…the song we had all been jamming out to “Differentology” throughout the whole trip. WHAT!!? You should have seen us, we lost it. Nearly the only white people in the crowd we were raging harder than anyone else. We were watching the song we loved, live, on a beach in St. Lucia. Life. Is. Good.


8.15.16 : Day Fourteen : Our Long Sail to St. Vincent

Up at 8am, we hit the high seas for St. Vincent.
65 miles away we are basically in for a full day at sea, sunrise to sunset. Sail days consist mostly of music, lots of sun, the occasional meal, naps, and watching islands approach/pass by. By the end of them though, we are all exhausted from the constant rocking and draining sun. Arriving at sundown, we anchor in a beautiful quaint marina where we take showers off the back of the boat, and prepare delicious Steak and potatoes we treated ourselves to for Phillipa’s last night on board. One thing is for sure, they can cook one HELL of a steak. With Grill master Austin and Phil’s special garlic sauce drizzle, it might have to be close to best ive ever had… and thats saying a lot.

8.16.16 : Day Fifteen : A visit to the Garden of Eden

Phillipa is making her last cleaning/ arragning efforts on the boat this morning before her flight out of here at 2:30pm. The rest of us arrange a local named Desmond to take us up to what they like to call “The Garden of Eden”. Once we began our walk through, we understood why. Beautiful gardens all constantly watered by the natural fresh water rivers and rainfall from the mountain. This rain forest made for the most lush, green, colorful gardens we have ever seen. Walkways were not perfectly trimmed, so it gave the feel of legitimately walking through a forest. There was constant shade from the tall healthy trees. The coolest breeze from the altitude we were at. It was an amazing experience for all of us.


Heading back to the boat around 1pm, we sadly say our goodbyes to Phillipa who heads off to Portugal to see family. Anchors up, and we head for The Grenadines!

8.17.16 : Day Sixteen : Reaching the Grenadines : Bequia

What felt like the shortest sail so far, we arrive only an hour and 15 minutes later at Bequia. Anchoring off of a beautiful beach around 3pm, we hop in the dinghy and drive around the corner of the island to see the ruins and dive the legendary reef here. I dive often, and I have to say i’ve never seen as many fish as I had on this one reef. The coolest part was swimming around the corner, it drops like a shelf into abyss of ocean where I swear I could hear dolphins clicking and singing away. Sunset approaches beautifully, yet another perfect weather day. The dinghy ride back with tunes and good laughs ends us at the boat where we take the paddle boards to shore to watch the sunset and throw around a football. Im overwhelmed with happiness, we are in a beautiful place, with crystal clear water, watching the sun set and the full moon rise. I swear that paddle back was just as lit up from the moon as it was from the sunset. We had shadows on the sand bottom below us.


On board we have some dinner and our dessert that consisted of frozen raspberries,butter cookies, and white chocolate (oh my god was it good). Food comas take place, air conditioning turned on, and we head for bed to conquer tomorrow in the Tobago Cay’s.

8.18.16: Day Seventeen : Fantasy Land

 

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