Sailing with Kids

Imagine this: You wake up and look out at the horizon, there is blue ocean as far as the eye can see. Behind you is a sleepy, little seaside town, with its charming beach houses, set against the white-sand shore and gentle waves. You hold your little ones close and can’t believe you get to share this unique experience with them every morning. I’m talking about sailing with kids. This is something that Nate and I have talked about doing for years, but have been too intimidated to try.

We’re back with Part 5 of our How to Make Travel Affordable Series and I’m so excited to introduce Laura from Releasing the Bowlines! Laura’s family sold everything they owned, except what fit on their boat, to pursue their own dream of exploring the wild, blue yonder and the towns along the US Eastern Seaboard. And she’s here to tell us all about it!


Five years ago, when I was pregnant with my 2nd child, my husband and I made a commitment to begin putting the pieces into place to fulfill our dream of living and cruising on a sailboat.  Three years later, we cast off the bowlines and set sail with our two little girls, ages 3 and 4.  For the next year, we sailed the east coast of the US on our 37ft Hunter Legend sailboat, visiting almost every coastal town between Annapolis, MD and Key West, FL and making the jump across the Gulf Stream to the Bahamas.  We are now settled back into land life in Beaufort, SC and just welcomed our 3rd child into the world.


Turning a Dream Into Reality

When we made our dream of cruising a priority, we started saving every penny over the course of the next three years and arbitrarily set a departure date of June 2016.  Both of us worked in public education, so it took extensive effort and discipline to make sure we were putting away enough money to support ourselves over the next year or two with no income.  We began following the blog Mr. Money Mustache, which provided an overall philosophy of life and money that helped us meet our savings goals.  We also began downsizing and started to sell all of our “things” over the course of those three years and were able to sell our house within months of our departure time.

Since we lived in a coastal town, Beaufort, SC, we were accustomed to boats and life on the water.  Our weekends typically consisted of day sailing with a 25ft Catalina and we made sure to get the kids on the water when they were babies.  We also read numerous books, blogs, and talked first hand to people who had sailed with kids.  Surprisingly, there are a number of cruising families and their experiences became an invaluable resource.

After three years of preparation, we actually were able to depart Beaufort, SC, on schedule, in June of 2016.  We left Beaufort, with no house, no cars, no jobs, and no stuff.  Everything we owned fit onto our boat and we set out on our family adventure for the next year with an intentional uncertainty of where it might take us.


Cruising Life

Cruising life for our family was one of incredible growth, intense challenges, fulfilling relationships, breathtaking beauty, and living with no regrets.   We met some of the most kind, caring, and interesting people along our journey.  The cruising community is a very tight knit group of people and families cruising with kids will tend to seek each other out in online forums or Facebook groups, planning meetups at different ports.  We had the opportunity to meet people from around the world and share very unique and special experiences with them in the different places we visited.   We shared Christmas dinner with two families (7 kids between all of us) that we had only met the day before on Peanut Island in Florida and Thanksgiving lunch in St. Mary’s, Ga with hundreds of cruisers that convene there every year at that time.   We had a number of mishaps along the way like running aground in Shallotte, NC, which damaged the boat and delayed our sailing for three weeks, but unexpectedly presented an opportunity for us to travel to Vermont by rental car in the meantime.  We got stuck between bridges because of flood waters after Hurricane Matthew, ripped our sail traveling downwind through the Abaco, endured and remedied a broken head (the sailboat word for toilet), and burned up our starter in the middle of Norfolk, VA, leaving us under sail alone in one of the busiest ports in the world.  Through each of these experiences, we encountered people who lent us a hand and restored any doubt one would have in the overall goodness of people.

Simple and mundane tasks on land, like grocery shopping, present unusual challenges and require vastly more amounts of time when living aboard.  It might take the better part of a day to walk a couple miles to the store with two little kids in tow on a wagon, buy what you need for possibly the next several weeks, walk back and load all of this into a 10 foot dinghy, eventually making it back home to the boat to unload and store everything away.  Cocktails on deck for sunset never tasted so good after a day like that!

Through constant daily monitoring of battery voltage and water tank levels, we learned how much we take for granted the automatic luxuries we have in our country every time we flip a switch or turn on a faucet.  To maintain those water and power systems and conserve those resources required a lifestyle of very conscious decision-making.

Cruising allowed us to visit very small towns and major cities.  We participated in local events and festivals with local people.  We also visited just about every ice cream shop, library, and playground along the east coast!  It allowed both of us to be with our children during a precious time in their youth.  Parents of older children know how fast it goes by and we wanted to seize the moment totally.


Sailing with kids

Life on a boat with two little ones can be overwhelming at times, so I adapted and adjusted my expectations as we traveled based on their needs.  To keep them safe and entertained, they needed my attention pretty constantly while underway, often leaving my husband to single-hand the boat.  This worked for the most part, but occasionally I was also needed on deck and had to get creative with activities that engaged the girls independently.  This was especially true if we were going to have a long travel day.  We invented a “travel fairy” that would come the night before a long day and put out snacks, rearrange toys, and put out fun activities.  While neither of the girls were technically in school yet, we still created our own version of school and worked on literacy and math tasks with hands-on activities.  We also began making “Blessing Bracelets” which we would send to people upon request who needed a lift in their life or just thought they were cute!  We ended up making over 150 bracelets that were sent across the country as we cruised!

Safety was paramount with two little girls on board.  We had a very strict lifejacket rule, so whenever the girls were on deck they had to have on their lifejackets.  This calmed some of my fears of always being surrounded by water.  We were also always very cautious when deciding when to travel and when to stay put depending on the weather.  When you live on a boat, the weather drives most all decisions, so when the weather turned foul or even just uncertain, we pretty much stayed put.  Both girls were prone to seasickness, so we would only make longer or offshore passages when the weather window was perfect.

Once we were in the crystal clear waters of the Bahamas and the Florida Keys, it was an amazing time for the kids to explore nature.  We would dive for starfish, collect sea glass on the beaches, and swim in the water next to dolphins and manatee.  It was truly a magical time for our family.


What Does It Cost?

The cost of cruising is entirely up to you.  This may sound like a frustrating answer to the question “what does it cost” but there really is no definitive answer.  If there were 100 cruising boats moored in harbor, there would be 100 widely different budgets and almost as many methods of financing these budgets.

Some people cruise on small boats with few, if any, luxuries or conveniences, anchor out every single night (which is free), cook all of their own meals on board, do all of their own maintenance, and don’t succumb to consumerist tendencies when they enter a new port.  There are many examples of people who live and travel on boats and spend $1500 a month or less….TOTAL!  Others live on expensive yachts with all the modern conveniences, stay in marinas every night, eat in restaurants, pay others to repair and  maintain the boat, and indulge in all that a new destination has to offer.  There is, of course, no limit to what you can spend if you choose to do so. Others still, and this might represent the majority of cruisers, find a balance between these two approaches.

But for the person interested in cruising and curious about costs that are unique to this lifestyle, here are a few things to consider.  The cost of the boat, which can range from a few thousand dollars to multiple millions, depending on the age and size of the boat as well as how it is outfitted.  Many yachts are equipped with climate control, water makers, extensive high-tech communication and navigational equipment, refrigeration, flushing toilets and more, but all of these things bring an expensive price tag and require even more money in terms of maintenance.

Boat insurance, the cost of which varies widely based on your boat, your experience, and your cruising grounds.  Marinas, which generally charge per foot per night, and can range anywhere from less than a $1/foot to $5/foot and much more, plus a fee for the use of water and electricity.  Boat maintenance will be never-ending and can cost a lot.  The more that you can do yourself, and there are lots of resources out there to assist you with that, the more you can keep the unavoidable cost of maintenance down.   Pretty much all other spending (food, entertainment, etc) is a lifestyle choice and doesn’t really differ that much from life on land.


We had never set a firm timeframe on cruising and left the door wide open when we left. We never even knew if we would return to the same town, hence the reason we sold our house.  We decided to conclude our year of cruising based on a number of different signs, one of which was finding out I was pregnant with our third little girl!!

While we have closed the chapter on our cruising life temporarily in order to expand our family and pursue other adventures, I have no doubt we will be back on the water in the future with our girls when they are older.  One thing I have learned through this experience is nothing is impossible.

If you want to learn more about our year on the boat you can check out our blog at

Laura, thank-you so much for sharing your family’s experience aboard “All In”!

I have a confession, when I first reached out to Laura about writing this piece, I was almost more excited to read it myself, than to share it with you, my readers. Sailing with kids has always seemed so unrealistic and it’s so encouraging to see other young families out there, making it happen! Thanks again, Laura! I can’t wait to see where your next adventure takes you and your family!


Laura and her family spent a year on “All In” and documented their journey on the blog,  She currently lives in Beaufort with her husband, Bryan, and three little girls, Avery (5), Leslie (4), and Hunter (newborn).  Their family intends to travel again by boat one day but for now they have started their own company, All In Educational Services, which provides psychological and educational services to children and families.

For similar stories about families who are making travel happen check out Housesitting and Full-Time RVing

37 thoughts on “Sailing with Kids”

    1. I agree! I would love to give my kids that experience! We just have to remember that we’re all doing the best we can and our kids are going to be great because of it!

  1. this looks like such a wonderful experience with your adorable daughters! I take my niece & nephew to the shore every summer & they love it – they would lose their minds over this!

  2. It looks like such a fun adventure to go sailing with your children. It looks like you all really enjoyed it.

  3. I can’t imagine cruising and leaving everything behind. It’s such a good learning experience for parents and it will definitely strengthen your relationship with the kids. I’m so curious about how they managed it all that I couldn’t stop reading!

    1. I’m so glad you enjoyed the story! It’s amazing, isn’t it! It blows my mind that a family with young kids could do it successfully and it’s such an inspiration to see it actually happening!

  4. These pictures look so good, I want to go to the ocean right away! I’m planning a holiday and I think sailing is gonna be on my list for my next vacay!!

    1. Yes!! I agree, those pictures look incredible! I would love to hear about it, if you decide to really go for it. Good luck with the holiday planning and hopefully we’ll see you sailing the ocean soon!

  5. These pictures are fantastic. Sailing with the little ones is so fun. We went sailing with our family, including our niece and nephew in Nantucket. Everyone had a blast.

  6. Such a dream I am so jealous of you guys lol I bet your kids are learning so much and the experience they get out of this is so much more than anything they could get while in school

Leave a Reply

Your email address will not be published. Required fields are marked *