About a year ago, amid a pandemic, we bet on the future and booked a week on a private sailboat in the Caribbean. Brian and I did this 20 years ago in the British Virgin Islands – this time though it was going to be different. First of all – last time it was 6 adults, and 4 of us never stepped on a sailboat, no kids, Brian and Darren (kiwi) were captaining us, we provisioned and cooked ourselves close to every meal. This time, it was 2 adults (1 still rather clueless on all the sailing jargon) and 3 kids. The best part though was that we had a captain and a chef to go with us!

A few tricks we learned very quickly.

• The boat moves all the time. Not sailing – you actually only sail for like 2 hours max a day from one area to another where you hang out. I think we all brought a series of bumps and bruises hitting something or doing some elegant entry/exits to paddleboard or dinghy. I was particularly great at entertaining everyone with my not so graceful landings – where I literally couldn’t step on the paddleboard from the boat and ended up hanging in between until I dropped. Well, made for lots of laughs.
• The bathrooms/toilets – agh – they are kind of like the airplane ones but no toilet paper in it – I was mortified the first days that this trip will end with us replacing the plumbing b/c one of the kids flushed it. You also become very conscious of the fresh water supply – noone pushed but still showers were incredibly efficient (and since I don’t know how much an average shower takes, it was in/out). Later I learned there is a desalination apparatus on the boat for bathrooms but still.
• When we sail, everything needs to be connected or pinned down or adios hats, towels, anything – sounds logical.
• Boaters are fun people – you get to see the same boats in the bays as they are all doing similar trips – typically families, large adult retiree groups or multi-family trips.
• No bugs! At least no visible bugs which is alright with me – but invisible, yes – I had bites everyday but never knew where it came from – mystery to date.

The crew

Awesome people – both in mid-20s, Kelsey, American, was the captain, and Simon, the chef is from Sweden. It sounds like an idyllic job for most people but it is a ton of work – 14 hours a day while the charter is in. They were doing anything/everything to make our trip once in a lifetime experience so we don’t have to do a thing and just enjoy ourselves. Simon – always ready with an appetizer, drink, dessert, or some special for the kids; Kelsey making sure we were tubing, paddleboarding, snorkeling – always keeping us informed what the itinerary is and where to see what fish/turtle. And never far away with killer jalapeno margaritas or local painkillers + working the engines, anchors, and the dinghy. Trivia gurus too which we enjoyed quite a bit. They bravely endured constant questioning from Mia and Lucas’s late sleep-ins.

Activities

What didn’t we do? While my primary objective was to get through 3 books (only got through 2), sit on the deck with hat on and do nothing else – we pretty much snorkeled everyday and I did try paddleboarding and liked it. Kids fished, tubed, ran on the water mat, captained the boat, hung from the boat, and other things that I just watched – they were on all the time (and noone got seasick). I was trying to be off all the time.

All in all – this was probably the best and most relaxing vacation we took – even though being stuck on a small boat and even smaller rooms together after 2 years of pandemic sounded like a totally insane idea of relaxation. Clearly space is not crucial, the surroundings and the company are. I know this is not an average family vacation – and for us neither – but I can see more of this in our future. Maybe with friends, who is in?

If you’d like to book and give it a shot – I highly recommend Doug at Canvas Yacht Charters who walked us through it and was very transparent.