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TRY A FAMILY SAILING VACATION

What’s it really like to be a family who sails?

Ever Thought of Going on a Family Sailing Vacation?

Maybe – maybe not. But follow us along as we explain how this might be just the ticket you’ve been looking for. Consider this your fair warning that if you try a family sailing vacation, you might never consider any other holiday.

The broad strokes of a family sailing vacation

Simply explained, a sailing vacation is getting on a sailboat for about a week or more and sailing around different islands and villages, experiencing the culture of the land, local foods, wine and drinks, the ocean, sailing (of course), and for those who love to snorkel – the colorful coral and fish life under the surface. Read What is a Sailing Vacation for more info.

WHO CAPTAINS THE BOAT?

Assuming you are not (yet) experienced enough to operate the boat, a professional captain is hired to sail the boat to its different destinations. The captain is usually a local who knows all the good stops, bays, beaches, snorkeling spots, restaurants, and secret hideaway caves or other special spots. Upon request, you can hire an extra crew member to cook up delicious food delights and serve drinks throughout the week.

If you’re hoping to bareboat, you’ll need to have the proper qualifications, a sailing resumé and/or license, and enough parental supervision onboard if your kids are young. Let’s just say that you don’t want your skipper also responsible for watching kids while under sail. Read Why hire a Skipper for your Sailing Vacation for more info.

LET’S TALK ABOUT THE BOAT ITSELF

For families, we generally recommend a catamaran, unless cost is an issue.  They are bigger, more ‘homey’, and tend to be more comfortable for children. It sails through the water without leaning over, so it’s easy to walk around and you’re far less prone to seasickness. Overall, we typically consider catamarans to be more kid-friendly.

A 40-foot catamaran has 4 cabins and 2 heads, while a 45-foot catamaran has 4 cabins and 4 heads. A 50-foot can have up to 6 cabins and 5 heads! Each cabin typically has a queen size bed, but some cabins can have 2 bunk beds.  In other words, each boat is different, so tell your agent exactly what you’re hoping for in terms of cabins and heads and we’ll do our best to find the perfect boat for your trip.

Boats come fully provisioned for utensils, plates, pots & pans, a coffee maker, sheets, pillows, and towels. In other words, a bareboat isn’t bare, but you do have to provision for groceries — unless you have requested a hostess, who will chat with you ahead of time and do your shopping for you.

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A Lagoon 42ft Catamaran

WHERE TO GO ON A FAMILY SAILING VACATION

Whenever someone is considering a family sailing vacation (including us), we always like to start with the ages of the kids and their interests. The goal is, of course, for your kids to have the time of their lives, so if your kids love to swim, make darn sure that you’re going somewhere with warm water and lots of beaches. We usually suggest planning an itinerary with shorter sails and lots of varied activities. Even the most sail-happy kids need to get off the boat and see some sights.

In terms of locations, this depends entirely on the interests and vacation style of the family. We love the history, culture, and cuisine of the Mediterranean and find that kids love it too. Kids also tend to like the gorgeous white sand beaches and crystal clear warm waters of the Caribbean, or even something more exotic like Thailand or the Seychelles. Since NauticEd had been to almost every sailing destination ourselves (and we’ve sailed lots with kids), we can advise which location is best depending on the ages and interests of your kids.

Your options include chartering a boat yourself or with friends, a captained charter, and also consider a family-friendly sailing flotilla in locations like the BVI’s, Greece, Croatia, and more. A flotilla includes other families as well as activities for everyone. Read Benefits of Flotilla Sailing for more info.

Our team can help you decide where to go – we have taken many sailing vacations with our own families! Contact us if looking for charter or flotilla ideas.

HOW TO ENTERTAIN KIDS ON A BOAT

While reading a book on the deck sounds like the perfect way to spend an afternoon, your 8-year-old might find it, dare we say, boring. Thankfully, there really is no shortage of activities to do with kids on a family sailing vacation.

  • Water activities like snorkeling, swimming, kayaking
  • Sailing (obviously), but including new skills like tying knots, navigating, setting sail
  • Relaxing activities like card games or reading (but just a little)
  • Nature watching and documenting, looking for fish or dolphins, and maybe even drawing them
  • Star gazing and storytelling
  • On-shore activities and sightseeing
Kids bouncing on the catamaran trampoline on a family sailing vacation

Bouncing on the “Trampoline”

YOUR NUMBER ONE CONCERN, SAFETY

Parents always ask whether it’s safe to bring their kids on a family sailing vacation and we understand the concern. Any activity in and around water needs to be treated with proper care and concern to ensure safety for your family — sailing is no different.

We always recommend a safety briefing from the skipper right at the start to set some safety rules. The added authority of the skipper tends to lead to better compliance, in our experience. Generally speaking though, when sailing with kids:

Daughter takes the helm in a Tutu on a family sailing vacation
  • Always wear life vests when not in the inside cabin.
  • Listen to the skipper.
  • Never leave the boat without permission.
  • Never go to the front of the boat without an adult.
  • No running or horsing around, ever.
  • Always swim in twos and never in a marina
  • Don’t play with the VHF
  • Don’t touch or play with a line or anything attached to it without an adult helping
  • Never put any part of your body between a boat and another object (like a dock, another boat etc.)
  • Decide which adult is on “duty” and is in charge of the kids at any given time (make a schedule, if you need to) and verbally acknowledge if you’re switching — no assumptions.

For younger kids, there is an option to add a safety net around the perimeter of the boat for an added layer of safety. We also suggest a personal locator beacon (PLB) to be on board if you’re nervous. This device is thrown into the water in the unlikely circumstance that anyone falls overboard to ensure you can track the exact GPS location of the person in the water.

THE NUTS AND BOLTS OF A FAMILY SAILING VACATION

Start planning: 9-12 months in advance

Make the reservation: 4-9 months in advance, depending on the location and time you’d like to go

Pack: Lightly (there are no roll-aboards for monohulls)

Prepare: Take an online course so you know exactly what to expect before you even step foot on your charter boat. We’re biased, but our Yacht Charter Crew course is the best teaching on how to make the most of your family sailing vacation. It teaches the ins and outs of charter sailing, including setting great expectations for yourself, your charter company, and the boat itself.

AN AMAZING FAMILY EXPERIENCE

CoVID times or post-CoVID, a sailing vacation is the perfect getaway where you can have time to yourselves outside in the wind and experience the freedom of a horizon. Life can be a little too hectic sometimes and it’s easy to let days or months go by without feeling like you’re able to connect with your family. This is where a family sailing vacation really shines. Quality time to share memorable adventures, learn new skills, and build relationships.

Yes, we realize that this sounds like a lot for one vacation to do, but we’ve heard over and over again (and we’ve experienced this ourselves) just how incredible time on the water can be with your family. You bond over adventure, learning new skills, first-time experiences, stretching your imagination, and breaking boundaries of fear.

Smiling child enjoying a sunny day on a boat, with water and mountains in the background.

Oh, and there are experts involved

Any time you’re bringing your kids along for a new experience, there are bound to be extra questions and concerns. This is why we always recommend booking with an experienced sailing vacation agent and we often also suggest trying out a flotilla. This gives you the added security of having experts along the way, answering questions and helping you and your family learn during this incredible experience.

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Author

  • Trisha Evelyn

    I find myself drawn to any project that allows me to learn and use my creativity to solve problems - and sailing tops my list!

    View all posts
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Home » Sailing Vacations Planning » Try a Family Sailing Vacation
Last updated on June 29th, 2025
USVI Yacht Charter and Sailing VacationsWoman swinging on a tire under a palm tree in U.S. Virgin Islands' crystal clear waters, labeled American Paradise.Aerial view of a serene tropical beach with turquoise waters, lush greenery, and a lone palm tree. Ideal vacation spot.Best USVI Beaches