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Old 12-08-2019, 11:24   #1
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Chartering a skippered sailboat (first timers with questions)

Hi

first post here on the forum. as a start to pursuing a dream of someday owning our own sailboat and cruising around together we (wife and I) are entertaining the idea of chartering a sailboat the size we might someday want to own. thinking that means something in the 35-40 foot (monohull) range. something with a skipper since we don't have the experience to do so on our own. (Yet) we were thinking about trying to do so in Florida as a winter vacation. hoping this will give us some insight into whether we actually will like this (have not done so before) probably a week long trip

One of the questions though is. Given the small size and limited space on the boat is it unformattable as a couple having a complete stranger on board? I am sure the personality of the individual makes all the difference in the world but would hate to have a terrible experience early on in this endeavor.

any advice for us as we plan this?

thank you very much.
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Old 12-08-2019, 11:35   #2
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Re: Chartering a skippered sailboat (first timers with questions)

Personalities do make a difference, but the typical charter captain is quite comfortable w jumping on boats w strangers, after all thats normal in that line of work, and being friendly and professional. There are, unfortunately, exceptions of course.

Ive run plenty of charters w couples on boats in that size range. Boats in that size range, esp those in charter, typically have 2 cabins. Weather permitting, Ive often slept in the cockpit so the guests have more privacy.
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Old 12-08-2019, 12:03   #3
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Re: Chartering a skippered sailboat (first timers with questions)

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Originally Posted by Debmar View Post
Hi

first post here on the forum. as a start to pursuing a dream of someday owning our own sailboat and cruising around together we (wife and I) are entertaining the idea of chartering a sailboat the size we might someday want to own. thinking that means something in the 35-40 foot (monohull) range. something with a skipper since we don't have the experience to do so on our own. (Yet) we were thinking about trying to do so in Florida as a winter vacation. hoping this will give us some insight into whether we actually will like this (have not done so before) probably a week long trip

One of the questions though is. Given the small size and limited space on the boat is it unformattable as a couple having a complete stranger on board? I am sure the personality of the individual makes all the difference in the world but would hate to have a terrible experience early on in this endeavor.

any advice for us as we plan this?

thank you very much.
Charter/ferry/part time Skippers are a fun lot. Friend of mine bought a Lagoon out in Florida in a sweetheart of a deal, we got to one of those crew seeking websites and connected with someone who was as weird as us.

Back then, we explained to him budget constraints, he threw down $500, said "Give somewhere to stay and shower and a couple of meals, I'm here till you send me off". That guy is still cruising out there with my friend, 5 years later.

If you get a good skipper, learn everything, sailing can only be demystified with the sheets in your hand. The major thing about sailing is that it's actually a lot more hands on practical knowledge that comes into play, pay attention and you'll pick up a lot of knowledge.

My best future case scenario was once a motoryacht, now it's a sailing catamaran (nothing wrong witha monohull by the way).

Cheers!
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Old 12-08-2019, 12:12   #4
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Re: Chartering a skippered sailboat (first timers with questions)

Cruise Abaco in the Bahamas can put a captain/instructor on board your boat every morning and remove him every night in their cruising area.
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Old 13-08-2019, 09:12   #5
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Re: Chartering a skippered sailboat (first timers with questions)

With a good skipper, and with good references you will have no problem.
Small tip for your purposes, choose a skipper who is also qualified (with references) as sail instructor and long cruise instructor.
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Old 13-08-2019, 09:17   #6
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Re: Chartering a skippered sailboat (first timers with questions)

A good charter skipper will have a personality to go with the job -- he (or she) will be fun to be on board with, or he won't be able to do his job which is to give his clients a satisfying experience.


References are key here, but given consistent good references, you shouldn't have much to worry about, and on the contrary, you should have a lot to look forward to.


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Originally Posted by Black Eagle View Post
. . . Small tip for your purposes, choose a skipper who is also qualified (with reference) as sail instructor and long cruise instructor.

Yes!! And this is a common arrangement for inexperienced new boat owners or prospective boat owners, and a really great way to learn
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Old 13-08-2019, 09:25   #7
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Re: Chartering a skippered sailboat (first timers with questions)

Quote:
Originally Posted by Debmar View Post
Hi

first post here on the forum. as a start to pursuing a dream of someday owning our own sailboat and cruising around together we (wife and I) are entertaining the idea of chartering a sailboat the size we might someday want to own. thinking that means something in the 35-40 foot (monohull) range. something with a skipper since we don't have the experience to do so on our own. (Yet) we were thinking about trying to do so in Florida as a winter vacation. hoping this will give us some insight into whether we actually will like this (have not done so before) probably a week long trip

One of the questions though is. Given the small size and limited space on the boat is it unformattable as a couple having a complete stranger on board? I am sure the personality of the individual makes all the difference in the world but would hate to have a terrible experience early on in this endeavor.

any advice for us as we plan this?

thank you very much.
As someone who did a lot of charters and now does many owner-assisted deliveries. Your concern is valid.

Good charter "Captains" know how to disappear when a couple wants to enjoy a glass of wine alone or will let you take the dinghy (or let you take the dinghy) so you can swim alone (hint this is how they earn their tips).

Likewise on a delivery, at anchor I will sometimes "disappear". Look at charter boats like the Jenneau 44ds that have a forward and aft head. This gives the skipper an end of the boat and you&your wife your own end of the boat.
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Old 13-08-2019, 14:34   #8
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Re: Chartering a skippered sailboat (first timers with questions)

Quote:
Originally Posted by Peeew View Post
Cruise Abaco in the Bahamas can put a captain/instructor on board your boat every morning and remove him every night in their cruising area.
Beat me to it! I was going to recommend them as well. Much better than anything in Floriduh. Great, well run business.
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Old 13-08-2019, 20:41   #9
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Re: Chartering a skippered sailboat (first timers with questions)

I have a charter catamaran with me (as captain) in Pensacola, FL.
A charter captain is constantly adapting to the situation. My experience with couples, (my experience is limited) I keep the husband busy with conversation, learning (boat stuff), and talking about his daylife while the wife relaxes (it is all about the admiral). I cook meals, give them some drinks, and go for a kayak (leave them alone). Come back and go to bed without disturbing them. If I don't go kayaking, I go to my berth and read.
A family charter has the captain wearing many hats. Basically keep the husband entertained (good conversation), keep children engaged (water stuff, kayaking, swimming, etc.) and letting wife relax. It is all about the admiral!!
Meals are the biggest issue in my opinion. Trying to cook for every guest's palate is tough. The last charter, I couldn't find anything this 13 year old would eat until I brought out the whip cream. So, her meals were basically fruit, granola, and whip cream while everyone else was eating chipotle shrimp tacos and seared ahi tuna.
Charters are all about admiral (the wife).

Teaching how to dinghy or kayak is very empowering for the guests. As soon as the anchor hits the bottom, the dinghy comes down and the kayaks are dropped. If guests are hesitant to leave the mothership, I will take them exploring.
Most guests are alittle uncomfortable at first with the motion. As a charter captain, we forget how the water makes some people unsteady.
Sometimes the captain makes some popcorn and inspires a game of old maid. Surprisingly successful for the whole family.
The charter is about disconnecting with electronics and connecting with nature. Some resist it more than others.
One of the most interesting aspects of charters. I ask all guests if they want to be isolated or anchor in a busy area (nightlife, shopping, busy beach). To a fault all of them say they want to be isolated. Until I take them to deserted island (private beach on Gulf). Most want to go back to the busy areas within 1-3 days.
On a great charter, the guests are learning to run the boat systems and sailing the boat. I can't speak for all but most charter captains LOVE to teach.
A charter captain is a friendly tour guide that gives the guests alone time.
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Old 13-08-2019, 22:28   #10
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Re: Chartering a skippered sailboat (first timers with questions)

Quote:
Originally Posted by sailingchiro View Post
I have a charter catamaran with me (as captain) in Pensacola, FL.
A charter captain is constantly adapting to the situation. My experience with couples, (my experience is limited) I keep the husband busy with conversation, learning (boat stuff), and talking about his daylife while the wife relaxes (it is all about the admiral). I cook meals, give them some drinks, and go for a kayak (leave them alone). Come back and go to bed without disturbing them. If I don't go kayaking, I go to my berth and read.
A family charter has the captain wearing many hats. Basically keep the husband entertained (good conversation), keep children engaged (water stuff, kayaking, swimming, etc.) and letting wife relax. It is all about the admiral!!
Meals are the biggest issue in my opinion. Trying to cook for every guest's palate is tough. The last charter, I couldn't find anything this 13 year old would eat until I brought out the whip cream. So, her meals were basically fruit, granola, and whip cream while everyone else was eating chipotle shrimp tacos and seared ahi tuna.
Charters are all about admiral (the wife).

Teaching how to dinghy or kayak is very empowering for the guests. As soon as the anchor hits the bottom, the dinghy comes down and the kayaks are dropped. If guests are hesitant to leave the mothership, I will take them exploring.
Most guests are alittle uncomfortable at first with the motion. As a charter captain, we forget how the water makes some people unsteady.
Sometimes the captain makes some popcorn and inspires a game of old maid. Surprisingly successful for the whole family.
The charter is about disconnecting with electronics and connecting with nature. Some resist it more than others.
One of the most interesting aspects of charters. I ask all guests if they want to be isolated or anchor in a busy area (nightlife, shopping, busy beach). To a fault all of them say they want to be isolated. Until I take them to deserted island (private beach on Gulf). Most want to go back to the busy areas within 1-3 days.
On a great charter, the guests are learning to run the boat systems and sailing the boat. I can't speak for all but most charter captains LOVE to teach.
A charter captain is a friendly tour guide that gives the guests alone time.

Wow, you are truly Full Service!



Good on you. The OP shouldn't think that all charter captains do this much, but he can see from this post how a truly excellent charter captain thinks He wants to be sure that his guests have a good time in all respects -- that's how he builds his business. And will do a lot to make that happen, although in most cases not quite THIS much


Most of them will not be cooking, for example, on top of all the other work load. If you want full catering, then you usually would need to charter a larger boat with more than one professional crew, which is obviously a different price category.
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Old 14-08-2019, 06:54   #11
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Re: Chartering a skippered sailboat (first timers with questions)

Quote:
Originally Posted by Debmar View Post
Hi

first post here on the forum. as a start to pursuing a dream of someday owning our own sailboat and cruising around together we (wife and I) are entertaining the idea of chartering a sailboat the size we might someday want to own. thinking that means something in the 35-40 foot (monohull) range. something with a skipper since we don't have the experience to do so on our own. (Yet) we were thinking about trying to do so in Florida as a winter vacation. hoping this will give us some insight into whether we actually will like this (have not done so before) probably a week long trip

One of the questions though is. Given the small size and limited space on the boat is it unformattable as a couple having a complete stranger on board? I am sure the personality of the individual makes all the difference in the world but would hate to have a terrible experience early on in this endeavor.

any advice for us as we plan this?

thank you very much.
Hi and welcome. Our experience (my wife and I) was very good - many years ago we did the same thing, sailing with a skipper that slept in the quarter berth, leaving the forward cabin for us. We didn't sail at night (at least overnight) so the v-berth was no problem. Our week of sailing was in a remote part of the Bahamas, and we learned more during that relaxing, free-spirited cruise than we ever did taking traditional sailing courses.
This was aboard a 39' sloop and there was plenty of room & privacy.
I would carefully check reviews of the captain(s) you might want to sail with, as skippers that run such charters run the gamut when it comes to experience and personality.
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Old 14-08-2019, 07:19   #12
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Re: Chartering a skippered sailboat (first timers with questions)

Quote:
Originally Posted by Dockhead View Post
Wow, you are truly Full Service!



Good on you. The OP shouldn't think that all charter captains do this much, but he can see from this post how a truly excellent charter captain thinks He wants to be sure that his guests have a good time in all respects -- that's how he builds his business. And will do a lot to make that happen, although in most cases not quite THIS much


Most of them will not be cooking, for example, on top of all the other work load. If you want full catering, then you usually would need to charter a larger boat with more than one professional crew, which is obviously a different price category.
Thank you very much! That is a very good compliment. Showing others the cruising lifestyle is my goal.
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Old 14-08-2019, 07:34   #13
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Re: Chartering a skippered sailboat (first timers with questions)

"we learned more during that relaxing, free-spirited cruise than we ever did taking traditional sailing courses."

If I have an engaged couple, it is amazing how fast they learn during a charter. Some are actually running the boat at the end of a week.

I look for the most nervous guest as we are loading the boat. As we are heading out, I stop the boat, teach them how to stop and start the engines, and make turns to right and left with just the engines. Then teach them to plot a course on the chartplotter and head that direction with the autopilot. Knowledge is relaxing in an uncomfortable environment. I ask the previous nervous guest to teach another guest how to start engines and plot a course.
Watching them engage is the perk of the job.
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Old 14-08-2019, 10:12   #14
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Re: Chartering a skippered sailboat (first timers with questions)

Or....Find a full time liveaboard cruising couple who are doing it, and have done it for a while, and are willing to have the two of you on board for a limited time. That way you can see how it really works. How to save water, how to do laundry, storage of perishables, etc etc...the list is long, and this way, you can dive in at the deep end with two lifeguards on duty.
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