Boating in Bermuda: How to Traumatize Your Children for $350

Excited for our chance to go boating in Bermuda, we failed to check our sense of direction and ended up lost, wet, and nearly shipwrecked!

Boating in Bermuda to find the Best Bermuda beach

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 the 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.

Christina and the boys explore the historical Dockyards in Bermuda with kids

Pro-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 sunshade 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.

Toddler wearing swim gear walks along a boat pier - Boating in Bermuda

Pro-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 onboard 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.

a young boy sits on his Dads lap as they boat through a Bermudian harbour - Boating in Bermuda

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 marveling 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 put through the narrow passageway into Scaur towards Ely’s Harbour.

Natural stone columns hold of a roof of rock in a Bermudian harbour - Boating in Bermuda

Things Go South, Too Far South

Ely’s harbor 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 harbor makes  for a nice glimpse into the colourful personalities that inhabit the island.

On our right, as we entered Ely’s harbor 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 harbor and began making our way south. We had already traveled 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

Stunning grey rocks frame emerald blue waters in a Bermuda cove - Boating in Bermuda

Entering Ely’s Harbour

We turned back towards Ely’s harbor, enjoying the respite of having the wind at our backs rather than in our face. As we entered the harbor 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.

Stunning grey rocks frame emerald blue waters in a Bermuda cove - Boating in Bermuda


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 backward. 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 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.

The Artemis, an America's Cup racing sailboat skims across the waters in Bermuda - Boating in Bermuda

Pro-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.

A young boy in swim gear walks out of the waves of a small cove in Bermuda - Boating in Bermuda

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.

Two parents watch their children playing in the sand on the beach - Boating in Bermuda

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!”

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About the Author

Kevin Wagar is a professional traveler and family travel 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 traveling 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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  1. Even with all the misadventures, it sounded like you guys still had fun (you had, hadn’t you?). I would like to go on a boat trip as well with my (future) family, looking for our own private beach.

    That secret harbor looked like a nice swimming spot; too bad it isn’t safe. Anyway, you still found a nice beach to spend your day. 🙂

  2. That was one hell of an experience and it looks like the kids handled it well despite the mishaps. I can understand why they wouldn’t want to go back though for sure, when they grow older they would change their mind. It’s so amazing that you and your wife take your kids to your trips. I wish my parents did the same with us but they’re not really what you would call travelers.

  3. I feel so bad, but I am belly laughing over here at your misadventures! Only because in the end you are all safe and okay 🙂 but what a day!! Your kids are troopers. All of you will probably laugh about this till you are old and gray! Great story, I felt like I was right there with you.

  4. That sounds pretty rough (pun totally intended) but at least there’s a happy ending.

    You think you’ll be able to get your kids (or yourself, for that matter) on a boat again in the future?

  5. Oh this made me laugh! It was like the time that we tried to get an overnight train in India and it was nothing short of a disaster. This will make a great travel tale to tell though!

  6. LOL – thanks for suffering through that to give us all a good laugh. One day, you’ll look back at this and laugh too. It’s definitely more memorable because of all the things that went wrong. Glad you were able to catch a glimpse of the green turtle though. Good times.

  7. What an adventure and what an experience, kudos to the all of you for hanging on in spite of so many challenges. And I am sure you did get your moments of paradise in between.

  8. Haha quite an entertaining read! It looked worth the money with the beautiful photos you took and I’m sure the kids enjoyed it!

  9. Glad you finally found a patch of private beach! Your story reminds me of a time when I was about 7 or 8 and my dad and I rented a little sailboat… and promptly ran it into the reef. Hope your kids recover soon! 🙂

  10. What an adventure! Glad that it ended well at least. But still, that would definitely make for some story to tell well into the future 🙂

  11. Well the good thing is that you are all alive…. right? Things happen. At least this is something that you will remember forever.

  12. Beautiful photos- I love the azure tones of blue. I would probably be happier going to Bermuda than your kids, although I might take their advice and pass on the boating adventure.

  13. sorry, had to laugh a bit! I love how your children’s instrincts tells you to turn back and go see Simon. I’m glad everything worked out well. Lesson learned.

  14. I don’t have kids, but this sounds like am experience I would want to do on my own lol to avoid all the troubles. Beautiful pictures though! Memories are made in any instance through travel 🙂

  15. Hahha I was itching to find out what else could have went wrong as I was reading your post. Your style of writing made me giggle and needed to continue reading. I am glad you and your family got through all of that okay and now you guys have a great story to tell! Very proud of C for keeping a brave face for daddy and D for pointing out the fall hahah

  16. Cheers for triumphing through that day! It will be one for the books I’m sure! I find it ironic that you can rent a full-size boat but not a car?? Where is the sensibility in that? I saw the picture with the nasty gash on your shin… at least you have the battle wounds to prove the validity of your story 🙂

  17. Wow, you are so brave I would be panicking as I approached those sharp rocks with my anchor. Would you say sailing is like riding a bike? Like, you’ll always remember how to sail?

  18. Now that is what i call and adventure. Had me on the edge of my seat. Lucky you guys didn’t crash on to the rocks…that would have been BAAAAAAD. But in the end, looked like a piece of paradise that you stumbled on to.

    Lovely read guys!

  19. What a great adventure! I’m so glad you didn’t crash the boat. Sounds like a stressful time that ended up being rewarding when you found your beach 🙂 Bermuda is one of my fav places in the world!!!

  20. Ahh what a misadventure! Sounds like you survived and even had some fun in the process. This is exactly why we always have a skipper when boating – I don’t think we would have made it 😉

  21. It sounds like your boating plans work out about as well as mine have. It probably wasn’t funny while it was happening but it sure makes a good story now.

  22. I can completely picture all of this happening. On the upside, you definitely had a unique experience and a story for the ages! And you’ll never forget your trip to Bermuda. 🙂

    I’ve just started ocean sailing and the waves killed my impression of a leisurely jaunt along the California coast. Why do the movies always make it seem so easy and romantic?

  23. That is still a cool experiences to have. Laugh at it later 🙂 I will be there this summer.Cool pics

  24. In the moment, bad situations seem awful (and they are) but afterwards, isn’t it nice to have a good story and photos? 🙂

  25. The title made me laugh! Thank goodness you didn’t crash into the sharp rocks, hope your shins are healing well. Despite the unexpected adventures, I’m glad to see that it ended on a good note 🙂

  26. Hahah I adore the contrast between the gorgeous photos and your mildly traumatic story. Awesome storytelling as always, guys. I often feel that days gone wrong make for the best stories and this is solid proof. Looks like you had quite the experience though!

  27. Sounds like one hell of an adventure. I was in a tour boat in Phuket and we were stuck in a bad storm that day – Several people started crying and yelling at the guide – I am talking about grown ups from around the world. So, I think your kids did a pretty good job of braving the choppy waters. Plus, by the end of it, everyone was smiling – so it was great 🙂

  28. I shouldn’t be laughing but that’s some way to traumatise your children! I hope your shin is okay. Well you had a great story to tell 🙂

  29. Oh my! Family travel, worts and all. Sorry to hear your boat trip didn’t turn out quite as you’d hoped but I’m sure it’s one that you’ll be talking about for many years to come 🙂

  30. You got me with the title haha. Good or bad, I still consider it quite the adventure. After all, travel is not always gonna be smooth sailing – pun not intended – but I’m glad everything turned out okay.

  31. The title itself looks scary but despite all those ‘traumatizing’ incidents, it’s still one of the rare moments to cherish with the kids. Hope they change they mind someday and come back! Haha

  32. This must have surely been one hell of an experience, but in the end the paradise you got into would have been worth it. Love the way you have scripted the post. I will be off to Bermuda hopefully by the end of the year, can’t wait to try this.

  33. Omg you guys totally soldiered through that! I’m happy you finally ended the day on a good note, it certainly makes up for all the hijinx during the day! Having gone through family trip hijinx as a kid I can tell you that you guys will remember and laugh about this experience for years to come!

  34. Such a beautiful place. I have a friend who’s a native of Bermuda and he has nothing but high praises about the place. Quite the adventure with the kids too! It’s something they’ll look back on and laugh!

  35. As someone who has lived next to the water for over twenty years, I’ve noticed the ocean has a way of making sure you understand she’s boss. I’m glad the day turned out and no one was hurt. I agree this will become a legendary family trip story.

  36. Your children are very cute. I suggest you take them to a music festival for a few days where they can play around and create some artwork too! 🙂

  37. What an epic adventure, Love the cove even if you didn’t get to dock there.. what an amazing story.. love your writing! Heading to Bermuda in a couple of days and will be on the lookout for these amazing beaches and coves.

  38. Absolutely fantastic storytelling! I actually LOLed at a couple of points. Sounds like quite an adventure and I’m glad the day ended well.

  39. That sounds frustrating and exhausting, but hey, at least you’ve got a good story out of it. The kids will probably be talking about that day for years!

  40. Hi Kevin,


    Looks gorgeous down there but the dipping in da boat would have gotten to me. Count me in with your kids 😉

    Thanks for the fun story.

    Signing off from still sunny NJ.

    Blogging From Paradise

  41. *snort* I shouldn’t laugh, but even the title was a winner in my eyes. 🙂
    All the LOLs happening this end over your misadventures, “Can we go back and see Simon?” was indeed when you should have realised. 🙂 I am pleased that you are all okay and safe, and that you have kids that stuck it out, not sure I know any kids that brave. When I get around to having kids, I will encourage them to be as adventurous and trail blazers like yours. What a great story I am sure you’ll all be talking about at family reunions for ever more too.

  42. :S these are the kinds of stories which suck royally at the time, though are always hilarious to recount when you get back home!! Misadventures have a way of turning into your best memories once you’ve actually come through the day 😀 Crazy that it’s that hard to find a slice of beach in Bermuda which isn’t private! I had no idea!

  43. Sometimes the misadventures turn out to be the best stories. We recently had one on a trip to the Dominican Republic! At the time it wasn’t super fun, even though we kept smiling, but once it was over it was pretty funny.

    And I have to say your adventure led to some beautiful photos!!

  44. I’ve grown up around boats and big lakes, but have utmost respect for the ocean! My mother reminded me it’s better to know someone who has a boat than to be a boat owner.

  45. Very brave taking the boat out on the ocean. Perhaps after reading this they will reconsider renting boats to locals too. lol

    Seriously though while the scenery looks amazing I have to admit I am a big chicken and I was starting to feel a little traumatised too! Not sure I would be jumping back on the boat the next day either.

  46. Ain’t no bruise like a travel bruise! I’m not going to lie -I would have been miserable doing this! But your pics prove what a gorgeous country it is.

  47. Great story, really had to laugh out loud! 🙂
    I’m also glad to you’ve made it to the shore in one piece!

  48. Wow it seems like I hardly know anything about Bermuda besides all the mysticism surrounding the appearance of people out in the ocean. This post definitely gives me a nice preview of the place. A lot of other secluded islands nearby?
    It’s such a joy to see a family such as yours still making the time and effort to embark on adventures such as these!
    Any insights on how a trip to Bermuda will be like for a solo female traveller?

  49. Hi Kevin,

    It is interesting how Bermuda has so many private beaches, I was not aware of that! At least you found yours and you had fun with the kids. Amazing adventure, thank you for sharing the photos and video!


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