An Ocean Adventure – Sailing From The Caribbean To Chesapeake Bay

For as long as I can remember I have dreamt about taking a sailboat on a long ocean passage. I was finally going to achieve that dream by sailing from the Caribbean to the United States. The two week voyage would be the longest I’d ever been to sea.

My sailing adventures began in university when a friend and I signed up for a sailing vacation in the Mazury Lakes District in Poland. We spent 2 weeks sailing every day on the two biggest lakes in Poland. Our sailboats were small dinghies which could accommodate 3 people; a helmsman and 2 crew. At night we slept in tents on the lakes’ shores. It was a wonderful adventure exploring parts of the lakes not accessible by regular means of transportation. This trip instilled in me a love for sailing.

Since then, I have sailed in different parts of the world on larger sailboats. These trips though were always within few hours of land. My dream of experiencing a long offshore passage eluded me until June of this year. Dan, the brother of a good friend of mine was planning to sail from Saint Martin in the Caribbean to Annapolis in the USA. He invited me and another friend, Dave, to join him for the two week, 2,000 nautical miles, blue water sailing trip. With no hesitation, I took up Dan’s offer.

The first part of the journey for Dave and I was getting from Calgary, Alberta to Saint Martin. A stopover in Miami ended up being more of an adventure than we had planned. As luck would have it a tropical storm was hitting Miami hard when we arrived. Rain was pounding. Streets were flooded. And apparently, roofs were leaking. Arriving at our hotel after midnight we were greeted by a toothless night receptionist. Our room was pre-paid, but before we could speak, the receptionist uttered ‘we don’t have any double rooms left’. He added, ‘there’s one room available, it has two beds, but the ceiling is leaking, and one bed is soaked, but you can sleep in one bed if you want…’ After a quick discussion Dave and I concluded that even though we like each other, we won’t sleep in the same bed, so we left. Outside, standing in the pouring rain, we started calling other hotels. A lady of the night, in a sleazy dress approached us and asked if we have a light. We realized then what kind of hotel it was.

As our plane was approaching Sint Maarten airport the next morning it felt as if we would crash into the beach. The landing strip is right beside Maho Beach. As we flew over our plane was only a few feet above the beachgoers below. What an incredible landing!

Unfortunately, we didn’t have time to explore the island since we still had to prepare the boat for our voyage. The airport is in Sint Maarten, the Dutch side of the island and our boat, “Three C’s” was on the French side in L’Anse Marcel Bay.

Three C’s is a brand-new Bali 5.4. The French made catamaran is 54 ft. and worth USD $1.7 million. It is more of a party boat than an ocean crossing vessel though. With 6 staterooms, each equipped an ensuite including hot showers, and a gourmet kitchen with a full-size fridge, it is a floating penthouse. It was unlike any boat I had ever sailed.

Our captain, Dan, was already on board when Dave and I arrived. The afternoon was spent getting provisions. We needed a lot of food and propane for our 2-week journey. We had planned to leave early the next morning, but it took us much longer than expected to figure out how to operate all of the electronics and controls.

Finally, by 4 pm the following day Captain Dan declared that we were ready to cast off. After filling up the boat’s fuel tanks with 1,200 liters of diesel we were on the way. Soon after leaving the bay, we tried to hoist the main sail when we discovered that two of the main sail slides were damaged. The boat had been delivered from France to Saint Martin a few days earlier. Since it was a brand new boat, we think the French sailors must have encountered heavy winds and damaged the slides on the journey. It would have been nice if they told us this before we left the marina.

It took the three of us a while to figure the best way to repair the broken part. Using a combination of cordage and parts of the broken sliders we were able to jury-rig a solution and hoist the main sail. We were on our way.

The crew consisted of; Dan, my friend Dave and myself. Dan is a US Coast Guard Captain with a long history of sailing in different parts of the world. Recently retired after selling his successful software business, he now spends his free time on the ocean moving sailboats between different locations. My friend Dave grew up in Sault Ste Marie, Ontario. With easy access to the Great Lakes, sailing became second nature to him. In the 1990s two of his friends were circumnavigating the Earth on a 32 ft. sailboat. He joined them in South Africa and helped bring the sailboat to the Caribbean.

An ocean passage of this length requires the boat to be sailing 24 hours a day. There must always be someone on the bridge, especially at night. We had the day and night divided into 4 hour shifts. The person on the bridge had to watch for passing ships, trim the sails, correct the course and watch for unforeseen dangers.

Dave had the first evening watch from 8 pm to 12 am; then Dan from 12 to 4 am; and then me from 4 to 8 am. Every 3 days we would shift by 4 hours so my next three shifts would start at 8 pm and end up at 12 am. We all agreed, the worst was the night watch between 12 and 4 am. Even with the waxing moon providing light, the darkness envelops you. After couple of hours staring into the heart of darkness, your mind plays tricks on you. Deprived of regular sensory feedback, you begin to see and hear stuff that is not out there. Or maybe it’s out there, but your senses interpret it in a way that pleases your brain.

At the end of one of his night watch shifts Dan insisted he saw a talking seagull. When I arrived to relieve him at 4 am I saw the seagull on the bow. I tried to talk to it but the bird didn’t reply. Dan, still convinced it could talk, said ‘It probably doesn’t understand your Polish accent’.

Dave on the other hand, after a night watch shift, swore he saw Greco-Roman gods flying off the bow. Led by Venus, the gods flew toward the sky in an easterly direction. Later, he even poked his head through the skylight to see if they had returned.

What Dave probably saw was the rare alignment of 5 planets. With no light pollution, we were able to see this incredible event at night. This alignment won’t happen again until 2040. It was impossible to take a good quality image of it at night on a rocking boat. Here is a shot by Tallahassee meteorologist Wright Dobbs.

Alignment of Planets – Image credit: Wright Dobbs

During one of my dreaded night watch shifts I had a bizarre adventure. We were just about to exit the Bermuda Triangle when suddenly, out of nowhere I saw a humongous octopus emerging from the sea. Each of its eight arms were the size of tree trunks. Massive suction cups clung to each arm. I knew right away, this beast was a Kraken!

The skylights in both Dan and Dave’s cabins were open. Seeming to know this the Kraken dipped two of his arms down the hatches and lifted both of them onto the deck. I panicked at first, but after a few seconds realized what I had to do. I grabbed bolt cutters and started to lob off the Kraken’s arms. Dan started yelling; ‘kill the Kraken, kill the Kraken….’. At the same time Dave was yelling; ‘release the Kraken, release the Kraken……’ Dave’s yelling confused me. I wasn’t sure if he wanted me to release him from the Kraken or to let the Kraken go.

After a brief hesitation, I finished cutting off the two Kraken arms and set the captain and Dave free. Oh my, they are safe I thought as I looked up at Dave’s grinning face. Suddenly, I felt a gentle tap on my shoulder. I opened my eyes to see a grinning Dave in front of me.

‘Sleeping on your shift again?’ Dave said.

‘Come on Dave’, I said ‘no appreciation for saving your life?’

Maybe these events occurred, or maybe we were simply providing entertainment to each other. Only the three of us will know for sure.

Out on the open ocean we had only moderate winds (12 knots) and our boat speed was 6 knots on average instead of the anticipated 7 knots. In order to reach Annapolis in two weeks, we determined we would have to use the boat’s engines when the winds were lower than 12 knots. We were glad then to have 1,200 liters of diesel on board.

Dan’s initial plan was to stop overnight in both Turks and Caicos and The Bahamas. With the slower than expected boat speed, we decided to only stop in Providenciales, Turks and Caicos. After 4 days of sailing, we dropped anchor in Providenciales’ Turtle Bay.

Customs and Immigration procedures take a while when you arrive by boat. Either you have to go to the customs building or wait on the pier until border officials arrive and clear the boat for entry. Luckily we were allowed to wait in the Turtle Bay Marina’s reception until they arrived.

Providenciales is a lovely city. My daughter Eliza lived there for eight years and still has some friends in town. She arranged for us to have a delicious meal of fresh red snapper from Mango Reef restaurant and free beers in the Shark’s Bite pub.  

After spending the day enjoying the island, we cast off at dusk and took a direct course toward Chesapeake Bay.

For the next 6 days life on the boat returned to normal. We had the monotonous tasks of: sleeping, tending to the boat, cooking dinner, socializing, and reading. The monotony was interrupted though with two days of strong winds up to 28 knots. Because of the strong winds we had to reduce the sail area down to the second reef. Even with a smaller sail we were still able to gain speeds of 11 knots. The Gulf Stream added an additional 2 knots to our speed. We were flying across the waves!

You would expect that being on a boat in the middle of an ocean the landscape never changes. You couldn’t be more wrong though. The slightest change of wind causes the waves to form different shapes. Spectacular sunrises and sunsets are different every day and various cloud formations make them even more spectacular. On cloudless nights the moon, especially a full moon, creates a river of light stretching from your boat to the furthest point on the horizon.

There were a few seagulls, but mostly we didn’t see any birds or animals. After days of being alone we were surprised to be joined by a pod of dolphins.

When we reached the Tropic of Cancer we were able to observe another astronomical phenomenon. During the northern summer solstice, the sun is directly above the Tropic of Cancer. While crossing it at noon on the solstice, the sun was at its highest point and was right above our main mast. I checked my watch to be sure, and the sun was right on time.

After 11 days of sailing we could just make out a funny looking structure in the distance. Diamond Shoal Light is just off North Carolina’s coast at the entrance to Chesapeake Bay and marked the final stage of our voyage. This area has notoriously rough waters and sailing into Chesapeake Bay wasn’t a pleasant experience. We were nearing our two week deadline so had to use the engines, but the wind was gusting up to 20 knots straight at our nose. The boat was rocking wildly and the sound of waves slamming into the bow was deafening. After few hours of rough sailing the winds finally died down and it was much more pleasant.

Chesapeake Bay is the largest bay in the USA. The numerous ports around it, service hundreds of container and tanker ships a day. We even saw US warships and aircraft carriers. It is very busy in the water and requires constant watch to prevent a collision. Fortunately, our catamaran had an electronic system called AIS that exchanges information with ships equipped with the same system. The information includes the boat’s name, size, position and speed. The screen displays each ship as an icon and indicates the possibility of collision. At any given time in Chesapeake Bay, we had up to 10 large ships around us. It was hectic and makes you realize why all of the right of way rules exist.

An interesting feature in the Bay is the Chesapeake Bay Bridge-Tunnel. The car bridge becomes a tunnel, submerging below the water in Chesapeake Bay. It was built so that large ships could pass through the bay and cars didn’t have to wait for ferries to cross.  

After a day of navigating between the giant ships in Chesapeake Bay we dropped anchor in Fishing Bay for overnight stay. It is a beautiful area surrounded by estate houses with manicured lawns and private docks.

Our trip was coming to an end, but a last minute change meant that instead of sailing to Annapolis, we were to leave the boat in Severn River. To celebrate our successful journey we celebrated with a nice dinner in the local pub and copious beer. The next morning we said goodbye to Three C’s and had to get to our hotel in Annapolis by car.

What an experience!!! Despite the monotony of a long passage, the sailing itself was an adventure that draws you in like a drug addiction and I’m pretty sure I’ll be doing more of it. 

Coming Next – What To Do In Calgary This Summer

For extra pictures from Canada click here. For pictures from other blogs go to Gallery at

To read about more of our adventures go to Destinations.

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