What To Expect Aboard on Sail Trips

“Happiness is not a station you arrive at, but a manner of traveling.”
 –Margaret Lee Runbeck

I've always been a traveler, as well as a sailor from childhood, but the two were separate diversions until I discovered that slow travel-- allowing one to remember what country they're in on a particular day-- is the best way to travel.  And for me, sailing became the best method: your transportation is your lodging is your recreation; and you're on the water!

I do a lot of research to find the best spots to visit, not just the most popular.  While I work to keep costs low, I splurge on yachts, chartering newer, and larger models than necessary for the number of crew.  I also charter at the ideal time for a particular place. Because I'm not tied to one location, I don't need to try to fill "off" weeks.  My planning allows you to relax knowing that your 'hotel' and transportation are arranged, yet still have a great deal of independence over your time.  We typically sail only a few hours a day, giving you time to spend hiking, snorkeling/diving, or just lying on a beach.  I'll take you on a great itinerary, but how much fun you have is up to you.

There is often a concern that you'll be 'cooped up' for a week with others you don't know well. First, it's hard for me to think of a sailboat as claustrophobic-- when not sleeping (and sometimes even then!), we're almost always topside.  And we're ashore more than we're aboard.  Others have addressed this below, but it's rare that we have someone who doesn't understand the nature of these trips.  While you may not know others in the crew, I think that's another plus-- I have interesting people from all over sail with me, and the crews tend to become friends.  From what I read, traveling with friends/family is more risky, as you're recruiting people based on something other than their inclination toward this type of adventure.  I have friends I don't recommend this to, as I know it's not for them.

You do have to be someone who wants to be sociable and works well as part of a crew. While not quite a 'working vacation', my trips are not 'catered-to' events, either.  They are adventure travel for people who are willing to give up a little pampering for access and experiences that would otherwise not be available.  The first rule of sailing is there are no passengers aboard, only crew.  Being an active participant rather than a passive observer I believe makes for a better vacation.  Everyone has something they can do.  You don't need to know how to sail, but you do have to stay aware and willing to follow the skipper's directions.  There are times such as docking where everyone can help with a line or fender, but a willingness to cook or clean is equally appreciated.

As long as you're willing to help out, conserve, be respectful of others and clean up after yourself, you'll have a great time and so will everyone else.

While this was written long ago about the more serious open-water solo sailor, I include it because I also believe an active vacation can be more refreshing than a lazy one:

"Remember now, keep the cabin simple with everything stowed where it won't get wet or shifted in a knockdown. Eat sensibly. Don't get sunburned, for no berth is comfortable under those circumstances. Make the whole cruise an interesting game where you have pitted your wits against the elements: try to do everything in the best and simplest way; try to improve your technique each time; rest and relax whenever you can, for there may be some occasion coming when you will need a well-rested mind and body. If you cruise this way for a week in a small sailboat you will be greatly refreshed and strengthened."
  -- L. Francis Herreshoff

The Yachts

I charter larger and newer yachts than the majority of those available.  We spend more than necessary on a yacht, balancing cost with comfort.   Charter companies will state that a yacht  "accommodates" more than I would put aboard in order to make the per person cost seem lower.  But that assumes two people sleeping in the saloon (table converts to a bed), something I don't do.  Where Sunsail, as an example, will suggest a 39' yacht for eight people, I'll charter a 50.

A 50' sailboat is only 1.4 times longer than a 35, but it has more than twice the space.  It costs twice as much, too, but it's worth it-- larger boats not only have more room, they sail faster and more comfortably.

While the yachts we charter are considered luxurious by sailboat standards, they're still modes of transportation designed more for safety than luxury.  It's about getting through the water, so boats are streamlined and cabins are small: a double berth is essentially a full-size bed (5.5' x 6.5').  But the saloons are roomy and the deck and cockpit have plenty of space.  I also look for boats with single berths so solo travelers won't have to pay a surcharge.  Bathrooms (heads) are often shared, with just enough room to shower.  There's usually plenty of hot water, but keep in mind we carry our water, so you will need to conserve. 

Here is how other skippers addressed what to expect:

'We can't count the number of times people have told us that this was their "best vacation ever", a "dream come true", it "totally surpassed expectations", and other such comments. 

BUT—sailing isn't for everyone—and maybe the reason why we get so many comments like this is that we are very down-to-earth in setting expectations. 

A sailing yacht is not a cruise ship; and if this type of vacation isn't going to suit you, it's better realised now—not in the middle of the Aegean with not a hairdryer nor ice cube in sight for miles! 

 We hope these notes will help. . .

Q.      A comment that we know our  sailors get all the time— "Wait a bit. . . you're going to spend a week on a boat with a bunch of people who you don't  know real well ??  "

A:     A good point! But—the actual fact is that 95% of the time, everyone on board gets on just great, and ends up good friends. How ??

1) A very effective self-selection process! By definition, anyone who would choose an adventure vacation like this generally is an independent, flexible type, with a sociable nature which enjoys the company of others at close quarters. 

2)—and just to be QUITE sure, we go on . . . and on. . . at great length. . . to make sure that everyone who books with us totally understands what life on a sailboat is all about! 

We DO tell anyone who we don't think is really suited that they should reconsider. We're not doing anyone any favors by not being totally honest about this.


This is not a cruise ship holiday. It is a hands-on adventure where guests participate in all aspects of life aboard ship: partaking in raising sail, practicing Med-Mooring, as well as helping prepare, serve and clean up meals aboard each day. We ask that you consider your expectations, physical abilities, psychology in staying aboard a small vessel, dietary requirements (as there are limitations on what is available) and how well you enjoy the company of others - before you decide to join the tour. 

Other considerations are sea sickness, sun stroke, lack of sleep and allergies. Guests must appreciate that they are only one member of a crew and that they may affect others. For the enjoyment of all crew members, it is imperative that guests maintain a ‘positive group dynamic’  throughout the charter. Guests must respect all crewmates and in particular, follow the direction of the Captain who is responding to the needs and safety of all guests on board. Excessive drinking and cattiness will not be tolerated. For safety and to maintain a good group dynamic: the Captain’s word is the law aboard.

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