Sailing sounds like it’s only for couples, newlyweds or families with older or grown children. We didn’t like that stereotype. Why couldn’t we take our 18 month old on a sailing charter? We didn’t see why not. Life is all about the experience so we set off on a 8 day bareboat charter to the British Virgin Islands. With our crazy, fireball 18 month old.

Are we crazy? Slightly. Was it a trip of a lifetime? Hell yes. Did we plan this trip willy-nilly? No, we planned and prepared and packed everything to a T. Chris sailed with Landfall Sailing for over a year to prepare for this bareboat sailing trip. We carefully thought of everything that could go wrong and WAY over bought things on Amazon. Safety was our number one concern. That’s why we chose the British Virgin Islands. Everything is within sight, sail days are a few hours long and the sea is quite calm, even during storm season.

We had some issues, learned some lessons and like I said above, had the best vacation we’ve ever been on. The views are incredible, beaches are pristine and the people are the friendliest locals we have EVER encountered on our vacations. They are so happy to live in paradise and I would pick up and move there today just to be that happy and carefree.


Our lessons learned caused me to write a few tips for those attempting a sailing vacation like this.

I read a ton of blogs and talked to other sailing families and you don’t quite get it until you are in the moment.

  1. Plan ahead. (On everything.) Timing of the trip, where to sleep, where to eat, etc. Timing of the sailing trip is key. We went during storm season like beginners (or idiots) and not one, but two tropical depressions passed over us. Not fun. Luckily we stayed in the North Sound, Virgin Gorda for those two nights and felt pretty safe. Also, timing of the trip is important for what places are open. We had very limited restaurants open and I didn’t plan for dinner meals in our provisioning. Provisioning is KEY when sailing with a toddler. You do not want to take a cab to the store with a toddler in a foreign country. Plan your sleep arrangements before you book your boat. We put Crosson in his own room and he slept so much better than he would have in our room. It was only for sleeping. No playing, no movies, just sleeping. I’d suggest this to any family but it’s what was best for us. Plus it gave us time to relax after he went to bed!
  2. Bring friends or family. If it’s your first long sailboat trip bring an extra hand or two. One person has to always have eyes on the baby so it’s nice to have an extra hand with the sailing. (Or holding all the bags…) We got a Lagoon 400 S2 catamaran and knew to invite a friend. We are so thankful we did. The boat was big enough for the 3 and a half of us. Baby had his own room, friend had his own room and we had the master suite. We turned half the master into the playroom which was perfect!
  3. Bring entertainment. Book a boat with wifi or bring an iPad with a bunch of movies and shows downloaded. Buy toys and pack them before the tot can see them. He was so excited to play with brand new toys onboard. Paper and crayons are perfect and fit easily in carryons.
  4. Pack the essentials. Sailing in the Caribbean is easy because you’ll probably wear your swimsuit the entire time. Crosson wore a diaper 3/4 of the time because it was so hot. Don’t over pack clothes, instead overpack diapers, everyday snacks, toilet paper, and wipes. I think i’d pack sheets for us next time. I overpacked granola bars and they were the perfect snack on the boat.
  5. Prepare for an accident. Figure out with the first aid kit is on the first day. Why is this on my list? Oh, maybe because Crosson jumped off a couch and sliced his head open on a step. We patched him right up and carted him to the nicest private doctor in town. We were prepared for something but not this. At least we knew where the first aid kit was. All is well and the doctor in Virgin Gorda was fantastic. Bring your own life jackets and invest in a harness. Safety is key.
  6. Treat yourself and family to a nice hotel on the last day of vacation. Disembarkment syndrome is a real thing. I was swaying for hours after we landed. Thank God we booked a suite at the San Juan Courtyard. Crosson had his own room, a kiddie pool, life-size Connect Four games and a lot of rum drinks for me.
  7. Have fun and take a ton of photos. It’s a grand adventure sailing with a toddler, you better get proof you did it. Whether there were bumps in the road or smooth-sailing,  it will be a vacation you will always remember. Capture the smiles in the babies as they run into the ocean, the smiles as dada holds the toddler as he steers the vessel. Capture all the places your toddler will fall asleep and the moments you’ll have together. The British Virgin Islands were the perfect spots for our first big charter and we highly recommend it for any family wanting to sail with the little ones.
Scrub Island Resort of Marina Cay | Hi Lovely | British Virgin Islands

Scrub Island Resort off Marina Cay

The Baths of Virgin Gorda | Hi Lovely | British Virgin Islands

The Baths of Virgin Gorda

Top of the Baths of Virgin Gorda | Hi Lovely | British Virgin Islands

The best view in the BVI. Top of The Baths Restaurant

The Baths of Virgin Gorda | Hi Lovely | British Virgin Islands

Sailing with a Toddler | Hi Lovely | British Virgin Islands

The Baths of Virgin Gorda | Hi Lovely | British Virgin Islands

Sailing with a Baby | Hi Lovely | British Virgin Islands

Benefits of Entertainment and Sailing Vibes

Sailing with a Toddler | Hi Lovely | British Virgin Islands

Naps during Dinner… Whatever it takes.

Sailing with a Toddler | Hi Lovely | British Virgin Islands

One happy sailor.

Have any other tips on sailing with kids?? Leave them below!