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Do you have to be naked to go bareboat sailing??

Do you have to bare it all to go barebutt sailing?  Oops! I mean bareboat sailing? Maaaaybe…

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Well…bareboat sailing just means that you or a close friend is certified and skilled enough in sailing prowess so that your group can charter a sailboat on your own without hiring a local professional skipper, or even better, sail your OWN boat! You sail wherever you want (within practical limits) seeking beaches, secluded coves, private islands, and untrampled snorkeling spots. So, actually that’s the beauty of it – being naked truly is entirely up to you (and your boat mates).


Where can you go?

The world’s sailing destinations are numerous and varied. It’s a great way to see some amazing places and get away from the crowds and souvenir shops at the same time. Some destinations are tropical (our favorite) and some are more cultural. Depending on your interests, (snorkeling, diving, archaeological, beach bars, private beaches, cultural, local cuisine, total seclusion, hiking…), you can customize your sailing itinerary to maximize your fun. So far, we have experienced The British Virgin Islands, Greece (Cyclades Islands), Belize, French Polynesia and Thailand. Our next destinations will be The Grenadines and St. Lucia in 2016, then hopefully The Whitsundays, Australia in 2017! We’d love your suggestions.

What kind of sailboat?

The answer depends on the group size, the experience of the skipper, the destination, and the boats available from the charter company. Our experience has been on 45 – 55 foot catamarans with 4 cabins and 4 heads, so a total of 8 friendly folks. Cabins are tiny (think of the smallest cruise ship cabin and cut it in half), but you don’t spend much time in them except to sleep and change clothes. There is also a shared kitchen, living room and outdoor dining/hanging out areas. We spend most of our time on the deck and trampoline areas, and in the water, of course! Relaxing on a trampoline at night with no light pollution to mar the intensity of the stars is glorious. It was kind of a jolt to realize we were looking at THE Southern Cross in Bora Bora.

What about food and drink?

Planning is key and a lot depends on the destination. Most sailing charter companies make arrangements with local provisioning companies so that you can pre-order and have food and drink delivered to your boat on arrival day. We always take advantage of this option for basics and bulk heavy items – it is easier than using local transportation to shop and schlep and it saves a lot of time. Beware of the language barriers when ordering; you can end up with drastically different quantities than you were expecting (12 large bunches of bananas, instead of 12 bananas :-). We stop into the local market for final items, deli and local specialties, then we’re set! It’s best to plan to re-provision at some point if you want fresh fruit and to check out the local markets. We almost always have breakfast and lunch on board, unless we’re near a small town with restaurants and shops to explore. For dinner, our favorite model (on a 10 day trip) is to eat ashore half the nights, then have each couple on the boat take a turn cooking for the group, and the last night is for leftovers. Storage space in the kitchen and especially the fridge and freezer is limited, so planning helps to keep each couple from duplicating all the basics. Also, it’s the skipper’s judgement on refueling and filling the water tanks; having enough water for showers is a perk we enjoy.

At home, while daydreaming about bareboat sailing trips, we order wine from Naked Wines! We found their Angel Program for independent winemakers by chance and it seems appropriate to mention them here. They’ll even give first timers $100 off. Visit NakedWines.com.

Who should I take with me?

This is the most important aspect of your trip planning – only sail with folks that you are confident you can enjoy for a week or more in tight quarters. The best traits to look for are flexibility, a laid back attitude and a willingness to jump in and get things done. On sailing trips, sometimes the weather changes or a boat part breaks, or someone gets sick or injured and that can mean changes to plans. It’s best to sail with friends who can cheerfully improvise and still have fun. Everyone has their moments, but one jerk with a bad attitude can ruin it for everybody so choose wisely.

What about seasickness?

If you’ve ever had a problem on a cruise ship, you’ll feel the motion far more on a sailboat. If you are prone to getting seasick, an extended sailing trip is probably not right for you, but honestly a few of our favorite sailing friends are extremely prone to seasickness.  They use a patch and do just fine. We have never had a problem, but we sometimes wear the wristbands as a precaution and if we know it’s going to be higher seas (like in French Polynesia) we’ll even wear the Transderm Scop seasick patch behind the ear (Rx from your doc). Better safe than sorry.

Reasons to own your own boat.

Most people who own or want to own a boat don’t need ANY reasons from us, but here’s what we think!  When we charter sailboats we’re limited to their inventory and dependent on them for how well each boat is maintained and furnished. We’ve had trip altering repairs needed and a variety of issues, including the worst: no coffee pot on board (they had parts of an old percolator!). Having your own boat allows you to choose (and furnish) the type of boat that truly fits your desires for speed, comfort, design, ease of sailing, navigation and more. We spent time on the amazing Rapier 550 by Broadblue and can easily imagine spending LOTS of time on a boat like that. It has the racing speed, high tech navigation and innovative engineering of a high performance design, yet it’s SO luxurious and comfortable inside that you can enjoy cruising, relaxing, cooking and entertaining as if it was a second home. “Home is Where the Anchor Drops!” Yes, Sheila dreams of charming sailors’ decor. We’ll write soon about our fun at Isle of Wight, England for Cowes Week, the world’s largest sailing regatta!

Hiring a skipper / crew may have advantages as well

If you’re sailing an area new to you, they are likely to be much more knowledgeable of the local geography and attractions and know what to avoid. They might even be a better cook than you. They are probably very familiar with the sailboat’s quirks. On the downside, you may not be comfortable sharing small living spaces with strangers or they could be set on a fixed itinerary and inflexible. Caveat: We have never hired a skipper, so we are merely speculating – we’ve been very confident with our sailing friends who have skipping credentials. Plus, doing the research necessary to plan the itinerary is part of our fun. Nonetheless, if we really want to sail somewhere that our friends don’t, we’d certainly consider hiring a skipper.

And YES, as a bareboat sailor, if you want to shed those pesky inhibiting clothes, GO FOR IT!

Just make sure your boat mates are fully accepting and prepared for the shock. Also, pack lots of sunscreen and it’s good manners to sit on a towel. Be clothed around other boats and at any ports.  Send pictures to [email protected] 🙂

So, he says “YES!” to being naked and she says “You go right ahead, darlin’”.

Sailing stories we’ve posted so far: The British Virgin Islands, Belize, The Greek Islands, French Polynesia, and Thailand.

A few more images…

?Do you sail? Where have you enjoyed sailing and why? What places are on your bucket list?


  1. January 19, 2016 at 11:33 AM — Reply

    Hi – Cool article with a lot of great content. I am a blogger that writes for a tech startup (like an Airbnb for boats). If you’d like to share more boating while traveling options with your readers, the site is boatsetter.com. Cool thing is you can rent any kind of boat (power,sail, big, small, etc) anywhere in the world…so if you are vacationing in Miami, you rent your boat which can even include a US Coast Guard-licensed captain and off you go to see the city from the vantage point of the ocean. (Best view ever, if you ask me!)
    Hope you find this information worth a share to your audience.

    • Avatar photo
      January 22, 2016 at 9:07 PM — Reply

      Hey Jen! Thanks, we LOVE boats and sailing and captains and marinas and SCUBA and snorkeling and pretty much all things aquatic 🙂 Haven’t tried Boatsetter yet, but it sure sounds intriguing!

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