sailing with family

Sailing With Family – Learn From Our Mistakes

As soon as we purchased our sailboat Curiosity we had family and friends lining up to visit.  Considering we hadn’t completed sailing school and we had months of service work to be done we pushed everyone’s visit to the holidays, which was a great and horrible idea at the same time.

Our thinking was we’d be done with sailing school, have some sailing under our belts and be in the Bahamas settling into sailboat life by that time.  All correct but there was no way our newbie selves could possibly have any idea what we had just committed to.

The holidays have come and gone, as has our first big group of guests as live aboard sailors. We learned heaps through the experience about our comfort level as hosts, sailors and what we should do differently in the future.  If you have any intentions of bringing guests on board for the first time or just curious how our first big visit went, this one is for you.

Sure, we made a lot of rookie mistakes but having everyone together for the holidays was a blast and such a rare occasion.  To be able to share a slice of our new lifestyle with family was a big deal for us and for them.  It is well worth the effort…and lessons learned.  Plus, the gourmet gifts from everyone totally made our Christmas! We’re still enjoying the stash.

We Have Commitment Issues

Schedules put sailors in a pickle and it’s a big deal.  Committing to a schedule is like choosing to set your hair on fire.  It’s just not a good idea.

We’ve mentioned many times before that as travelers, we are not fans of schedules.  They snuff the opportunity for spontaneity and serendipity and we avoid them like the plague.  This still applies as sailors but there is a new factor in play.

Mother Nature.  Our comings and goings are all dictated by weather and mother nature is on no one’s schedule but her own.

We realize that under certain circumstances schedules are a necessary evil.  As a 9 to 5er, life is all about planning and schedules.  If you want a vacation, especially a Christmas vacation it must be scheduled months in advance. This is a challenge for us as it’s incredibly hard to say months in advance where we will be.

I remember this summer’s conversation clearly between Jason, his mom and aunt: “I can get a condo pretty cheap in Freeport and there’s a major airport for us to fly into.”  It sounded simple enough.  And just like that, they were off to the races booking lodging, flights and planning the tropical family holiday.

This is where things started to go wrong…we made a commitment for six months into our very undetermined future. As travelers and especially now as sailors, we have major commitment issues.  Planning to a visit to us requires flexibility.  One month advance is about as much notice as we can give.

Hindsight is 20/20

Don’t get us wrong we were excited about having family on board, however we made a lot of mistakes that made for a more challenging experience than needed.  Since hindsight is 20/20 we thought it’d be good to share our experience.  Perhaps it will help a fellow newbie sailor and we’ll gain a few pearls of wisdom from the old salts following along.

Know Your Personal Sailboat Max Capacity

There is a saying in the RV world when it comes to guests that people love to say, “Drinks for six, dinner for four, sleeps two”.  I think we’ve learned our boat version.  Drinks for ten, dinner for eight, sleeps six.

A quick look at the numbers and we knew we were in for a little chaos.  In total, we had nine different family members coming in and out over a 3-week period (12/15 – 1/6).  With everyone coming and going at different times and overlapping some days…it was going to be a lot of coordinating and obvious we couldn’t accommodate everyone.

  • Our boat is best suited for five but can comfortably accommodate six. A day sail with our boat quoted max passengers of ten is doable if we prepare well with snacks, drinks and so on.
  • Dinghy holds 5 people max (another reason for the “best suited for five” comment).
  • To save money we planned on cooking in as much as possible. Cooking in small spaces for lots of people daily becomes challenging. Even when people help with the meals it’s still chaos and more time in the kitchen cooking and cleaning than anyone wants.  We probably should have eaten out a few more times to keep things simple.
  • We Have No Desire to Run a Charter – At times it almost felt like we were running a charter business since there was so many people on board that had never been on a sailboat. It’s a lot of responsibility to keep up with the boat, give everyone an orientation (because they all arrived at different times), cook, clean and still find time to hang out.

The big takeaway – The perfect guest sailing trip would be a minimum of 7-10 days with 5 people on board.  Everyone provisions together, spend a day or two on land, enjoy the town, then go sail and anchor out the rest of the trip to share the sailboat life.

Choose The Destination Carefully

Being the super green sailors at the time the trip was planned, we made the mistake of not properly looking at the charts for acceptable anchorages and marina options.  To be perfectly honest, we didn’t know how to at the time (we hadn’t gone through sailing school yet).  Vetting the location should have been our priority before anyone booked anything.

Long story short, there are very few anchorages around Grand Bahama and they are fair weather only.  Marinas were slim pickings and even more so because of Hurricane Matthew.  We found only one marina that could accommodate us.  The marina was a 45-min drive from the condo my aunt booked.  Which means we all spent less time together and more time driving expensive rental cars.

The Big Takeaway – We were so eager to say “yes” and make things easy and accommodating that our lack of understanding of how to properly vet the location accomplished neither in the end.  In the future, the planning will will start with where we can park the boat.  We will all need to stay together in the same area, near stuff to do.  Somewhere like Hope Town would have made for an overall better experience.  The boat could have been anchored out close by, public dinghy docks are plentiful and everything is within walking distance.

guests on sailboat

Flights to Small Airports

Flight pricing is all over the map so everyone arrived on different days and departed on different days.  This all means multiple days of taxi rides and rental cars which is less than ideal.

More than half the people flying in had issues with their flights either being changed or cancelled the day of.  Let’s just say it made the start of people’s vacation less relaxing than they’d prefer.  I guess when it’s a small island airline they will fly when they want and cancel or move flights without explanation.

Guests Cost Money

We’ve been living gloriously cheap…as in the least amount we’ve ever spent in our seven years as full time travelers.  We have been sipping on fuel because we’ve sailed 90% of our nautical miles traveled since leaving Florida.  All our days have been anchored out which has saved us literally thousands of dollars.  Having guests and schedules with various plans changed all that.  We needed to be at a marina and had to motor much of our day trips (because we were on a schedule).  Luckily, they are a very thoughtful bunch who graciously chipped in on expenses and helped with the boat any chance they had.  I can see how less thoughtful guests could leave a sailor feeling dried out.

What we did right

  • Setting expectations – We sent a sort of pre-boarding email to everyone with information on the boat, what to expect, what to pack and so on. This helped set the tone for the trip.  We never once had to ask for help, they were always ready and asking, “what can I do”.
  • Arrival orientation – Giving everyone a quick orientation on the boat and safety protocol, like what you experience boarding a plane or a cruise ship, ensures everyone stays safe and if something were to go awry, they all have an idea of what to do.
  • Experienced Crew – Having my brother on board for nearly a week before everyone else arrived was awesome. We taught him the ropes (literally) and he could take the helm and raise sails when we had the larger groups on board.
  • Book A Nice Marina – Because we were at a nice marina/hotel the people staying on board could use the showers and bathrooms at the marina instead of on the boat. If people wanted to lounge at the beach, use the hotel amenities or have a walkabout it was easy for them to escape the boat.
  • Go Sailing – Getting out of the marina, snorkeling shipwrecks, spearing lobster, harvesting coconuts, raising sails, waves crashing over the bow…it was all the stuff long lasting memories are made of. It was an experience that won’t soon be forgotten.


Stay tuned for more on pre-boarding and guest orientation checklists and a rundown of what to do on the island of Grand Bahama.

I am sure there are some points we’ve missed.  If you have pro tips for having guests on board, please share! 

Hello there! I honestly don’t know what to say, so I am going to tell you a bunch of random facts instead. I'm a fish eating vegetarian who hates spiders and loves snakes. I almost never took vacations growing up. I wanted to be Pippi Longstocking (still do). I misspell about every other word I write and still struggle with grammar. I love splurging on a good high tea (which is really hard to find these days). And whatever you do, don’t tell me I can’t do something, because then I'll HAVE to do it!

Comments (66)

  • Richard wishing at sailing

    Hi, my sister has purchased a new boat delivery sometime in 2025/6 and I want to get the most out of a visit to wherever I get a chance to drop in on their sailing life on board around the world. Where would you suggest flying into from the USA for a 2-1/2 weeks of sailing and exploring? Caribbean suggestions? Pacific side N. American? And maybe as far as Australian? For example, what was the Marina you stayed at?

    • Curious Minion

      Way too many variables here! Talk to your sister & see what there plans are. Where will they take delivery of the boat? What are their plans after that? Then you need to factor in how fast they’re going to be traveling, how much stuff breaks, etc. etc. etc. I’d start by getting what she sees as “the big picture” for the first year of boat ownership and then see if something along that route spikes your interest. Because spending time with your sister and enjoying boat life should be the larger goal, and you can do that most anywhere.
      Curious Minion

  • Dr. Glenn

    I’ve just stumbled upon your enjoyable videos, and thank you.
    I am however unable to find your pre-boarding and guest orientation checklists. Are they posted somewhere?

  • Jeremy

    I stumbled across your videos while surfing videos on marine surveying, as that’s my next career target. As a former sailing instructor, it was really cool to watch your progression from boat buyers, to students, refitting, and then going off and enjoying the cruising lifestyle. Impressive learning skills, outstanding videos – so fun and informative!! Also really incredibly reassuring regarding the practicality of a work / travel existence, which my wife and I are targeting in the next few years with her doing marine canvas fabrication and sail repairs, while I do Marine Surveying. Your videos reinvigorated my motivation and assured me that a parallel track is the right direction for us!!! Thanks for spending all the effort to share your travels and experiences – your videos are the most fun I’ve ever had on YouTube!! It’s slow season at work for me, so just like a canoe, it’s not a question of if I’ll tip, just when.

  • Eric & Monica Brown

    Hello you happy shiny people! My wife and I found your youtube channel by accident while searching for catamaran blogs. We have been soooo excited to follow you that we have been binge watching your episodes! We are interested to see your pre-boarding checklist but can’t seem to find it anywhere. Can you point me to the right place?
    Also, we didnt realize that you guys benefited from us hitting the like button and commenting on the video so we went back through ALL of them today and did just that! Thanks so much for letting us share with you.

  • Lessons learned the hard way sink in deeply. Sounds like overall though things turned out OK. I look forward to continuing to follow your new adventures. Fair winds and following seas.

  • aunt cindy

    I enjoyed the video. It was a great trip. I’m sure you will continue to learn something new every day/trip. Despite what you delegate … it’s always work when a group comes into you’re space. Staying closer would have ideal. We will make it a point next visit. But despite the hiccups we had a blast that ended to fast . You guys were ridiculously accommodating host!!! We love you and thank you for so many great memories!!! Can’t wait for the next one!

  • Irv

    You mentioned that you’ve prepared a guidance document that can be shared with guests prior to arrival. I’m unable to find it on the website and would like to see what you came up with. Please feel free to send via pm as well. We have been cruising in the Pacific Northwest for the past 30 years where things are pretty predictable for us and guests. Starting in July we will be full time cruisers on the east coast and Caribbean and are anxious to see your learnings in writing. Thank you and enjoy the blog and YouTube channel. Irv

    • Curious Minion

      The checklist isn’t out yet – stay tuned!

  • Sue Goetzinger

    It was refreshing to hear things we have often experienced whether in our RV or offshore sailing!

  • Barbara Ford

    It had been a few weeks since I “checked in” to see what you both had been up to lately. I found the checklist and honesty about the great holiday time refreshing. I do enjoy your writing and reporting style interesting and enjoyable.
    On a side note….I am heading out to Florida in my RV for the first long distance trip. Yay!

  • T C Spencer

    Jason – Are you older or younger than your brother or sister?

  • John Lochaby

    Greetings and Valentine’s Day love from North Texas
    TIP: Cpt. Rick Moore (SSL) says the fastest internet uploads in the Caribbean are found at “Off-the-Hook Bar at Paradise Beach”, Caricou, Grenada. This is a small off the beat island with very few boats on hook and NOT a high end tourist trap.

  • Andrea Clerkin

    It requires alot of planning and effort but it’s so worth it when you see the smiles on their faces. Watching the sun go down across the water with your loved ones .. Doesn’t get much better than that! Amazing videos as always 🙂

  • Jim Deatsch

    My eyes hurt after your shirt. 🙂

  • Bruce Claflin

    You can be at a place on a boat, at a time on a boat, but you CANNOT be at a place AND time on a boat.

  • RHI

    The simplest rendezvous strategy is:
    (1) Guests pick the location – you pick the date & time
    (2) Guests pick the time – you pick the location

    With a sailboat, guests who want to pick both will be either sorely disappointed or drive the sailboat owners/crazy trying not to disappoint their guests by buffering the pickup date for all timing contingencies.

  • Gina

    Jeff and I absolutely love watching your videos! You guys are an awesome team!

  • Randy

    Hi Nikki and Jason!
    We tell guests that they can pick the time or they can pick the place. They can’t pick both.
    If they have a fixed time, we tell them at the last minute where to come. If they tell us where they want to visit, we give them a rough date. We confirm when we get there. Sometimes we don’t make the intended destination and they have to rent a car to catch up with us. The thing about traveling by boat vs. car is that what takes a day by boat can be driven in an hour by car.
    Guests sometimes enjoy meeting the boat in one location and departing from another. Our niece met us in Ottawa and traveled to Montreal with us. We got to Ottawa a few days early so,we knew the lay of the land. After a couple days we had a nice multi-day cruise to Montreal. We had a ball!

  • Michael

    I wanted to mention that I found it interesting how much fuel you folks have saved. You are the exact opposite to the Bumfuzzle crew. I’ve also noticed that one young family is deciding on motoring instead of sailing because it gives more room. But I know that the cost of fuel is what scares me, so knowing that one can get by in that department relatively cheaply is a big boost to that lifestyle choice.

    Thank you.

  • Fred

    Hi Guys-Great videos and I have followed you for quite a while. We have done it in reverse of your logistics. We owned an Island Packet mono hull while the kids were growing up and after my wife was diagnosed with a melanoma we eventually sold the boat and got a fifth wheel. Now I am following vicariously back to sailing and loving it. One tip that I have is that as you now know, safety is in reality of primary importance and I know you emphasized that with your guests. While there are (and were) fortunately very few incidences when things get hairy from a safety perspective, what I would do on my introduction to the boat was tell folks that when I say the words “This is the captain speaking” the expectation is that all crew would stop what they were doing immediately, freeze, and look at me for further instructions or an explanation on why things are “tense”. You can of course come up with your own phrase, but as you now know there can be times where you need everyone to pay very close attention and they need to know that there is an elevated level of their engagement that is required at that moment. The hope of course is that you will never need to use that phrase and tone of voice but if we were having guests for 5 or more days I would “drill” it by using the phrase and throwing a life jacket overboard to then practice our man overboard drill. Keep up the good work and know that my wife and I over 45 years have been through the boat, the RV, and grandchildren and we still love each other and treasure our time and memories we made together. You all are headed in that direction so godspeed.

  • Kelley

    Always love watching your posts! I saw where you will be talking about security soon. That is the one thing my husband and I have been wondering about! Safe travels 🙂

  • Dania

    We take at least one bare-boat sailing vacation every year and always seem to have at least one couple who are not sailors or have never sailed before. I find getting them to understand that you do not need a lot in the way of clothing, shoes, and hair products/items is one of the hardest things to get across. It is such a change in perspective. Once they have been on one of our trips, they get it and are fully on board and jumping at a chance to get invited again! I like your idea of a pre-trip checklist. I usually send an email, but will probably develop a checklist to save time and make sure I do not miss anything.

    As for the cooking when more are on board, we modify what our meal expectations are. We eat simpler and do not do lots of “cooking” like we might when it is just us or we are at home. We grill and make enough for lunch or another dinner the next day. If we do cook, we make and serve things that are easy and filling and not a lot of prep when we have larger numbers on board. It takes awhile to change the mindset, but decreases stress enormously. Have not had any complaints yet and everyone thinks the food tastes great!

    Fair winds and hope to meet you guys on the sea someday 🙂

  • Gene Smith

    Hi you two! Love, love, love your videos! I share with my wife. Have a question.. You are always asking to have us “like” your videos but can not find a place on your videos to do that ? Finally got to see you catching some fish! Oh and Jason what was with you throwing that one back??? Want to see you clubbing it and Nikki cooking it. One more thing you could make a video, or two or three or four of just catching lobster, and spear fishing, and Nikkis recipes. Love you guys, Gene & Nansea

  • Dennis

    Interesting video and family time. Thank you for letting us share your family adventure. Now the concerns…LOL one of the ultimate goals for you when you bought your boat was charters for extra income. It sounds a bit on the low side now. (sad face) I think you saw that large charters are not worth it as a private enterprise but a small intimate charter could be very fun and profitable for you; i hope, at least that is your new thoughts. A family of 4 or less ( 1-2 kids depending on age could be challenging) but a couple for a week might be very good and give you a decent profit for your time. You have learned a lot and are fun and adventurous, i think most of your follows would love a week sailing and adventuring and pay a reasonable cost for the experience. At least that is my hope for your future from a income point of view. Four to eight weeks out of a year are not a lot of impact to your overall personal adventure and could be worth the planning. I do agree a pre-board check list for your guest and their responsibility on your boat is a great idea. If people cannot respect your property and rules, better to not have them on board. The sea is unforgiving but beautiful and a great adventure when planned and respected. Good luck in the new year and always look forward to seeing your videos. Stay safe

  • George

    The two of you just fill me with joy. I love remembering my sailing days in St. Thomas and you help me reminisce about those adventures.

  • I have been meeting up with family on boat vacations for years (Dad is the skipper). We usually sit down with some charts and discuss timing and length of stay first. Plot out a few routes and then eventually confirm closest airport. We figure out how to get to the boat (once had to talk the ferry boat chef into driving us across the island as none of the promised cabs existed). We always arrive early as possible in the day and have an emergency hotel identified in case the boat is delayed. Don’t rule out a local seaplane for drop off or pickup. Cooking a few meals, doing lots of dishes and carrying in missed items typically pays our room and board. Always great memories!

  • Nancy Fernandez

    How nice for your family to be all together. It may have been tougher the first time but we all learn as we go. I can imagine what great hosts you were. Another great time watching you two. Until next time have fun and Happy Sailing!

  • Changing Z

    Family reunions are always dramatic for me. I think y’all are more than just brave. Y’all are very brave to invite that many people to your boat.

  • Donna

    You two do the BEST travel videos! Kudos to you! And thank you for sharing with us, it’s so enjoyable to watch and live vicariously for we dry-land folks. We’ve had several boats but have switched to RV travel. We only had motor boats and stayed on fresh water = weekend warriors. But all of that makes me realize how fearless you are compared to us! Also never realized the space that a catamaran has and the possibilities for guests. Two staterooms and two heads are the most we had on a monohull cruiser. Much more limiting obviously, but still a lot of fun. We wish you continued safe sailing and smooth seas.

  • Deborah Kerr

    Pictures looked like a lot of family fun making memories – there’s a saying though, something about family visits are like fresh fish, it’s only good for 3 days!! lol I totally agree about the commitment phobia! I work a 9 to 5 M- F job, but when it comes to my free time or RV vacations, NO schedules so I can fiddle fart down the road and just stop or make a turn whenever and wherever!! Safe travels!!

  • mary

    Please pass on to Martin. I froze all types of meats over dry ice and did not have an issue bringing them into the country. Jacob carried beer (you can only have less than $100 but would they really know the cost of craft beer?) and hard chees and chocolate. Lauren and Gabe got shut down with fruits and vegetables and had to toss a lot of the stuff they brought in. I’m so glad we did because the meat selection was pretty bad in the grocery stores and 3x as costly. Be sure to ice all down in case you are delayed with the airlines – most everyone was in our group!!

    OK, 2 weeks notice works! Love you bunches!!! Mom

  • mickey

    Wonderful!! You both are AMAZING. Thanks so much for sharing.

  • mary

    I haven’t looked yet, and I am almost afraid to now that I have seen your tag line. Should I?? Mom

  • darlene sullivan

    I love your hair nikki I have enjoyed watching you two for years be safe

  • Heather Stewart

    Great video, respectfully and realistically honest! I am not a cruiser, I’m primarily a day sailor bareboat skipper & overnighters/weekender here in SF. I’ve done a couple of “travel to” bareboat trips and coastal trips…but pretty much all of what you said rings true for even “simple” day sails… even when you’re not the boat owner! The money, the timing, the skill sets, the space, the flexibility, the consideration by the guests as well as of and for the guests…and above all, the responsibility and safety. I often have a boat full of newbies, and therefore, I find myself in perpetual teaching mode. I love sharing the passion and introducing others to the sport. However, it’s *much* more fun & relaxing for me if I’ve got a boat full – or at least half full! – of knowledgeable sailors who “get it”…. and that’s when I really have to work at shutting up…I don’t have to teach them! ? I’m looking forward to you sharing your completed “pre-board” list for some ideas and comparisons. The idea of an organized orientation that encompasses your own “ways” that were observed by Jason’s brother are also informative! ? A few comments on YouTube had some good additional suggestions too. Your “takeaway” from the max capacity discussion sounds perfect to me, sign me up…I’ll be watching for when you’re ready to put out that call for crew! ??⛵️✌?

  • Sorry, follow up question from my better half. We’re off to the Bahamas soon too and were intrigued by your box of groceries brought for you by your brother. Are there any food stuffs you couldn’t bring into the Bahamas?

  • Looking forward to seeing your checklist. Did you tell them bring soft luggage instead of hard suit cases? No where on a boat to store big old suit cases.

  • Roger

    Hi guys, how about sending out a training / info video with the ‘pre boarding checklist’. That way you only ever have to explain all the important things once. Also it provides consistency with the same information for each person. It’s got to be the best option. Cheers for now.

  • sven

    I just saw you guys in my dream where I was having an argument with a friend and got kicked in my groin for welcoming you ashore because you were supposed to be her guests, not mine.

  • I’ve always found it important to remind everyone pre-trip that we will be in close quarters and to expect at some point (usually around Day 4) everyone will get on your nerves and you’ll be craving personal space. It’s important that they recognize that is normal and that grabbing a book and quiet spot on the deck or going for a hike alone ashore is a great cure.

  • James

    I love your capacity rule for boat. I never thought of that but it is so right. Thanks.

  • Such a wonderful insight into your plans. Dh would love to get a boat but I think we’d need a bigger one for our family! Or perhaps just the two of us instead… now there’s an idea…

  • Claudio

    I could imagine with my 6 y.old triplets in such a holidays mission. Congrats!, you are amazing.

  • Mike

    Great info. Lots of lessons learned! We are headed to the show in Miami this week for strictly sail. Gonna check out the new cats, as what’s new now will be a used boat hopefully in our budget by the time we are ready to make the move haha!

  • Brian

    Just watched your last two videos and as always enjoyed them both. Thanks for sharing your adventures. I do have a question for you. Do you have concerns when you leave your sailboat anchored and travel to town to shop? Is thee much of a chance of burglary or worse yet someone taking the boat? or is this very rare?

  • George Hofmann

    Thank you, Thank you, Thank you. And still you have kept up publishing our entertainment! What awesome people are The Wynns. Your commentary was done so well…….all the pertanent facts and no finger pointing!
    Here’s wishing you calm, solace and the gravy train.
    Love always, honor and respect. George

  • Ursula

    Hope Town marina?


Post a Comment