Getting a chance to go boating in Bermuda was the most exciting thing on my mind when we began planning our trip to the island. Sunny skies, calm waters and the wind whipping through my hair as I glided across the surface of the ocean towards untamed beaches with dolphins jumping near the bow. My children laughing hysterically in my lap as they practice driving and my wife standing at the bow while the wind whips through her shawl. This is how I dreamed of our big day in Bermuda where we would rent a boat and travel the spectacular azure waters of this North Atlantic country.

That was the dream. The reality, however, has a way of slapping you in the face like a giant salty wave of irony.

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Boating in Bermuda

My family had woken up early on our first morning of our Easter long weekend in Bermuda and excitement filled the air. We were only in this tiny north Atlantic nation for four days and we were anxious to make the best out of our short visit. In my excitement, I was determined that we would go boating in Bermuda and explore the exquisite coastline of this beautiful country.

That I hadn’t driven a boat in about 20 years, and I’d never driven one on the ocean, were trifling details that I was not prepared to let get in my way. It was low season in Bermuda, but we hadn’t considered that with this being the long-weekend, boats might be in short supply. Fantasea Bermuda was the only company with a rental still available, and at $350 for a 4-hour rental, the price was comparable to the others we had been looking at.

Getting to the Dockyards

We packed up for the day, making sure we had enough food to keep us going on the water and grabbed a taxi from outside our hotel, the Fairmont Southhampton, to take us to the Royal Navy Dockyards on the North-West tip of the island.  The drive along the South rd. was nice, giving us a chance to see the pretty towns and locals preparing for the upcoming Easter Kite Festival.

Tip: Bermuda does not allow car rentals to foreigners. You can rent scooters or hire a taxi to get around the island.

We weren’t exactly sure where we were supposed to pick up the boat at the dockyards, but our excellent taxi driver made it his mission to ask every person he saw. A nice gent waiting for the bus let us know that it was probably over at Pier 41. Sure enough, a member of the Fantasea staff was waiting next to the Pier 41 building. We profusely thanked our cabbie, whose name I, unfortunately, didn’t catch and jumped out to meet the Fantasea Bermuda agent.

The agent introduced himself as Simon, a friendly, knowledgeable fellow who got to task showing us the boat and giving me a refresher on how not to die while out on the ocean. “Lifejackets are here, maps are here, here is how you steer, raise/lower the engine, etc.” 5 minutes later I was a seaworthy captain, ready to take the helm for a day on the high seas! Our boat would be a 30′ pontoon boat with a 30 hp engine. We loved that it had a bathroom on board, the ability to put a sun shade up, and plenty of storage space to keep things dry. The $350 price included enough gas to see us through the day and a cooler full of ice for our food and drinks.

Tip: Much of Bermuda is shut down during Christian holidays. Taxis are still available, although they too are in shorter supply.

Out to Sea

The boys excitedly climbed on board our luxury yacht and took turns sitting in the captain’s chair while I untied the moorings and got us ready to head off. I started the engine and, with a smile, pushed us off the dock, heading through the marina towards the open waters. The ride was pretty smooth as we exited the marina into Great Sound and began southward looking to follow Simons direction of following the coast to the third bridge, called the Waxford bridge, and crossing over from Great Sound to the Western shore where we were told we could find some beautiful small islands and quiet beaches. This is around where things started going awry on our journey.

Who Needs a Map?

The first issue we had was completely not seeing the first bridge that lay hidden behind a pier and is barely visible from the waters. Shortly after missing the bridge, a gust of wind ripped the map from my hands and into the water. No big deal right? I’ll just turn around and we’ll go back and get it.

Turns out getting a floating piece of laminated paper out of the wavy ocean while maneuvering a floating brick in a wavy ocean isn’t as easy as it sounds. On my fifth pass, I finally ran over the map, and it was never to be seen again. Somewhere, on the bottom of the ocean, a fish knows exactly where I should have been going. C looked at me and said sheepishly “Can we go back and see Simon?” This is when I should have picked up the clues that this day was not going to be as easy as I’d hoped.

Apparently losing a map is a common occurrence when boating in Bermuda, as we found another map on the boat. So, we soldiered on, enjoying the gorgeous weather and marvelling at the spectacular Bermudian coastline. Since we had missed the first of the intended three bridges, my bridge miscount led us not to the Waxford bridge, but rather to Somerset bridge. Touted as the world’s smallest functional drawbridge, it definitely didn’t fit the description that Simon had given us, but three is three, so we waved to the tourists taking in the quirky little bridge as we putted through the narrow passageway into Scaur towards Ely’s Harbour.

Things Go South, Too Far South

Ely’s harbour is a pretty area with beautiful small islands lining the edge of the bay. It has a mishmash of boats from luxury to decrepit heaps. The harbourmakes  for a nice glimpse into the colourful personalities that inhabit the island. On our right as we entered Ely’s harbour we could see a very cool rock formation called Cathedral Rock that consisted of dozens of stone pillars holding up a ceiling of stone above. At the time, however, we thought we were actually entering Great Sound.

Trying to get to the HMS Vixen

We decided that we would try to visit the famous wreck of the H.M.S. Vixen, a Royal Navy gunboat, that had been purposely sunk near Daniel’s head. We exited the harbour and began making our way south. We had already travelled too far south. However, this meant we were already well past the Vixen and were now making our way towards the windward side. The waves began to pick up and soon our little S.S. Minnow was being tossed up and down. The water was spraying up over the bow, soaking our poor, unexpecting family. As we rounded further around the south of the island, Christina and I kept our eyes open for a patch of beach.

Wrong Turn

We needed a break from the pounding waves and the spray pouring over our bow. Bermuda allows private beaches. Each one that we saw that seemed like it would offer respite was posted with “No Trespassing – Private Beach” signs.  It turns out that finding a piece of hidden paradise while boating in Bermuda isn’t as easy as I would have thought. The kids at this point were wet and miserable. D was trying desperately to crawl inside Christina. He wanted to escape the onslaught of ocean water that was slapping him in the face.

C, and I will forever be proud of him for this, sat stoically with the “I hate this, but Dad looks Super Stressed, so I’m not going to say anything” look on his face. We reached the next point, where we thought the H.M.S. Vixen should be. We were greeted with nothing but more waves. Christina and I made the call to turn back rather than risk further trauma to the kids. Anchors Aweigh? Anchors Away

Entering Ely’s Harbour

We turned back towards Ely’s harbour, enjoying the respite of having the wind at our backs rather than in our face. As we entered the harbour I noticed a small nature reserve on one of the outermost islands that had an empty beach. It looked like a fantastic place for the kids to play. I slowed the boat down and tossed the anchor,getting ready to go to shore. The area was beautiful. The rock formations were gorgeous and the sandy shores made for a magical paradise. The rocks along the coast were sharp, but the sand looked to be as soft as pillows. “Kev” called Christina from the back of the boat. “Are we supposed to still be moving towards the rocks?”

I looked up. Those sharp rocks certainly looked closer. I looked down at our anchor, which was uselessly dragging through the soft, sandy bottom, refusing to catch on anything. I looked up at the very sharp, very pointy rocks that were now just inches away from our bow. I hopped up to stop us from crashing the boat into them. The pointy ground dug into my feet, but I managed to slow the boat enough to keep us from causing any damage.


I pulled up the anchor looked up again in time to see the rear of the boat swinging towards another set of rocks. Christina jumped to the front to hold the bow steady and I ran through the front door of the boat towards the stern. What I hadn’t thought of though was that the front door of the boat wasn’t open. Gracefully, I smashed my shins into it, flipped through the air and landed with a thud on the floor of the boat.

D looked on horrified and the supportive words of my eldest son “Daddy! You landed on your face!” I meekly lifted myself up and climbed onto the back of the boat pushing hard off the rocks. I dropped the engine and roared the boat backwards. I needed to escape this trap, obviously set by pirates to ruin our perfect beach picnic. I sat down on the captain’s chair to catch my breath. Christina pointed out my now multi-hued, purple, black and bloody shin. “Swell” I said.

Finding Our Private Beach

Defeated, we made our way back through Somerset bridge. The boys pleaded desperately for us to “Just go back and see Simon”, and at this point, I wasn’t arguing. We entered Great Sound and were surprised to see a large hydrofoil sailboat tearing along the waters. We were lucky enough to catch the Artemis Racing Team practicing for the upcoming 35th America’s Cup that would be held in Bermuda. Watching the boat convinced us that our roaring 30 HP motor could definitely keep up with this wind-powered light-weight.

Tip: A pontoon boat with a 30 hp motor definitely cannot keep up with an America’s Cup level sailboat.

Declaring victory, we continued on, catching a glimpse of a green sea turtle before it ducked beneath the waves. After a rough beginning, things were looking up. Low and behold, there, nestled into a small bay was a quiet beach. With no signage telling us to keep out. There was an old stone dock next to a ruined boathouse. We climbed out and settled down on the beach, breaking out our well-deserved sandwiches and bananas. The kids spent the next while enjoying dry land. They splashed in the quiet bay and build ferocious sand-dinosaurs.

All’s Well That Ends Well

It had been a rough go for a while, but we all stuck together and weathered the storm. Christina and I smiled at our giggling children and counted our blessings. We had survived the day and would have some great stories to tell. We were looking forward to heading back to Horseshoe Bay and flying C’s homemade kite in the annual Kite Festival.

I asked the kids if they wanted to go boating in Bermuda again the next day. They looked at me and they both screamed “NO!”

Boating in Bermuda - Pinterest
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Kevin Wagar

Kevin Wagar is a creative designer and technology expert living in the Greater Toronto Area. His beautiful wife Christina impressed on him her love of travel and they have made exploring the world an integral part of their life.
With the birth of their two boys, Kevin and Christina have made it their mission to show others that travelling with children isn't as scary as it sounds and that kids can benefit from experiencing the world outside of their front door and beyond.
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