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Old 20-11-2019, 18:52   #1
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Help selling the dream

Hello all!
I'm a dreamer, wishing I would sail the seas and exploring new worlds. I have lurked in this forum for a while, gaining knowledge. I'm planning to sail/cruise in about 5 years ( kids out of high school then). I'm already retired, and financial able to sail.
I need the help and the wisdom of the forum in *selling* the dream to the Admiral. I have gently approached the subject and I was met with *resistance*.
The Admiral did book a vacation in the Southern Caribbean for Xmas/New Year aboard a Cruise-line.
I'm hoping to book a 2-3 hrs sailing aboard a 40-50 feet cat on one of 8 stops in the islands.
The sailing trip should function as a selling point to my wife (and me!). I'm not at the point to sail anything myself so a captain, which reinforces the *safety* and comfort of a catamaran will be needed.
I looked online for a sailing trip around the islands and I could not find anything suitable. There are plenty of day sailing trips, but they do take place aboard not *live about * cats and they are more geared towards schlepping folks to snorkeling places.
Any suggestions or help here ?
Our itinerary is as follow:
Dec 23 St. Thomas (VI); Dec 24 Antigua, Dec 25 St Kitts, Dec 26 Barbados, Dec 27 Martinique, Dec 28 Trinidad and Tobago, Dec 30 Curacao and Dec 31 Aruba.
Thank you for suggestions!
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Old 21-11-2019, 04:54   #2
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Re: Help selling the dream

Greetings and welcome aboard the CF, tzukulika.
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Old 21-11-2019, 07:10   #3
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Most short catamaran trips in the islands I have seen are just booze and loud music raves for the party crowd..
Definitely Not something to sway her opinion..
Might be better taking her away for the weekend to a boat show so she she can get 'touchy feely' with the boats your into... it helps to ease in gently and let her build her own picture and not feel pushed over much.
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Old 21-11-2019, 07:33   #4
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Re: Help selling the dream

I will offer up a couple of comments....
First - if you are retired now and planning to go in 5 years - that's too far out. We did our first cruising about 5 years BEFORE we retired, by taking a sabbatical. And that got us both hooked. We had the benefit of meeting several cruisers that had waited too long and regretted it - so that gave us the fuel and energy to figure out a plan to retire early and go. The one thing you cannnot predict with any certainty is your health, physical agility, and passion to do something 5 years out.

Second - don't waste your time and money with a passenger cruise. If you don't have a boat, do a charter; or better still, do some ASA courses.

Third - follow some people that are doing it. There are plenty on YouTube - its fun, and you can learn a lot about do's, don'ts, and destinations.. But don't get too sucked into the ones that have become "commercial video ventures" like Delos and Vagabonde. Their early stuff was great, but now they are popping out videos as a production rather than capturing the real moment. I personally like Trio Travels, early Drake Paragon, etc. And if you have any interest in how we got into a part-time cruising life, take a look at my blog and videos. I don't try to make any income from them, I posted them for friends and family, and anyone else that may get some benefit/interest out of watching them. https://www.youtube.com/channel/UCDC...DNf4eVA/videos

I hope this helps you to "sell the dream"!

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Old 21-11-2019, 07:36   #5
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Re: Help selling the dream

Quote:
Originally Posted by tzukulika View Post
Hello all!
I'm a dreamer, wishing I would sail the seas and exploring new worlds. I have lurked in this forum for a while, gaining knowledge. I'm planning to sail/cruise in about 5 years ( kids out of high school then). I'm already retired, and financial able to sail.
I need the help and the wisdom of the forum in *selling* the dream to the Admiral. I have gently approached the subject and I was met with *resistance*.
The Admiral did book a vacation in the Southern Caribbean for Xmas/New Year aboard a Cruise-line.
I'm hoping to book a 2-3 hrs sailing aboard a 40-50 feet cat on one of 8 stops in the islands.
The sailing trip should function as a selling point to my wife (and me!). I'm not at the point to sail anything myself so a captain, which reinforces the *safety* and comfort of a catamaran will be needed.
I looked online for a sailing trip around the islands and I could not find anything suitable. There are plenty of day sailing trips, but they do take place aboard not *live about * cats and they are more geared towards schlepping folks to snorkeling places.
Any suggestions or help here ?
Our itinerary is as follow:
Dec 23 St. Thomas (VI); Dec 24 Antigua, Dec 25 St Kitts, Dec 26 Barbados, Dec 27 Martinique, Dec 28 Trinidad and Tobago, Dec 30 Curacao and Dec 31 Aruba.
Thank you for suggestions!
I think you could charter a boat with a captain. Fitting into a 2-3 hour period might not be easy but work with a charter company and see what you can work out.

Long term, you both will need to log many more hours on sailboats before it becomes something you are comfortable with. Too many dreamers, when they finally get the boat of their dreams, find it is not what they expected and they are soon looking for a way out.

I hope you live in port city or nearby one. You can find ways to get on boats (the two of you) if you are resourceful. (you'll need to be resourceful to operate and maintain a boat of your own anyhow, so you might as well start now). I often urge people to start by crewing with other sailors. Even on a race boat which is excellent training, and free. If you sail frequently for 5 years you'll be skilled and knowledgeable.

Being a little athletic will help.
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Old 21-11-2019, 08:38   #6
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Help selling the dream

Id say the best way is a Caribbean charter with a skipper.
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Old 21-11-2019, 08:58   #7
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Re: Help selling the dream

If you are going to do a daysail, why not try a monohull? They usually only go out when conditions are benign and it gives you room to move over to a cat as a "better" option. Or you could book a cruise and learn and let her just come along for the rideI saw a Sailing Virgins video the other day where the female passenger ended the trip expressing regret that she didn't sign up for the course work... (great videos btw, geared to the younger crowd and full of upbeat info).

Maybe try a charter to someplace mild and beautiful? One of the bad things about sailing summers in the PNW is that the winds are low to nonexistant. Then again, that's one of the good things about chartering here if all you want is a pleasant cruise with relaxing days and minimal stressful sailing. I am sure there are other "bad" places in the world to sail

You could also try a power charter. My first cruise and learn way back when was aboard a powerboat as I wanted to learn (and get my potential crew on board with) the basics of life afloat, docking, anchoring etc. without all those ropes and flappy white things. Eventually the $500 fuel bill will push you over to sailboats

Anyway, just some ideas...
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Old 21-11-2019, 09:52   #8
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Re: Help selling the dream

Charter a boat with, say, Moorings, and hire a captain and a cook - speaking as the Admiral in this couple, the latter is key. Try the BVIs - great combination of civilization and natural beauty.
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Old 21-11-2019, 10:08   #9
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Re: Help selling the dream

Rule Number One:
Do not ever scare her.
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Old 21-11-2019, 10:08   #10
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Re: Help selling the dream

Hi,

I've been in your shoes, though not nearly as close to retirement. Dreaming for years, hatching the idea to the Admiral and being met with quite some resistance, buying a boat and now on the water, sailing and "living the life"!

It's not easy. Lots to learn: the boat maintenance and upkeep sucks up not only money but time not spent "having fun". This puts strain on the relationship in an already challenging environment. Reality is different to the pics in the brochure. I never thought I would be working so hard at it! Maybe I'm doing something wrong?

Tips: A week on a cruise boat is no closer than a tourist tour around Rome. That's not where its at. As others have suggested book a charter and focus on enjoying yourselves! Short sails, nice meals, warm waters to swim in, sunset drinks lying in the hammock. That is the dream (and not my reality most of the time)!

Then if some excitement is left after the honeymoon, buy a small dinghy, learn to sail, learn together, have fun on the beach without worrying about systems maintenance, big bills, big risks, big commitments. Just fun clean cheap sailing. Only then think of buying a cruising boat!

We are in the Caribbean and have met Sailing Britican. Lovely people who have been cruising for some years and now offer a charter with a twist. They focus on teaching and helping their clients experience whatever it is you need for your development into a cruiser. I have no relation to them other than having met them and believing that what they are doing works well for some (not cheap!). Check them out if so inclined.

Lastly, take care of the Admiral. I forget this at times. I am grateful that she has willingly allowed this to happen, she has put up with the risks and discomforts of this adventure. She may need water, or ice, or a freezer, or just plain feeling she is part of the team. She may not care for oil change schedules or upgrades to the chartplotter. Make sure you know how to handle the priorities. I remind myself how may strong men end up sailing solo after the mermaid stomped her foot down one last time and walked off the dock.

Best of luck!
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Old 21-11-2019, 10:49   #11
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Re: Help selling the dream

You've been getting good advice. I'd suggest you stop discussing a long range plan and start learning to sail via classroom, paid courses including, week long classes onboard, attending boat shows. After awhile, this will get both of you to a point of whether you actually like being on a sailboat. Do you have any non-racing buddies who can take you out for a short sail together. Ease into the whole dream by building a base to discover if this is a real, or merely a dream. And besides, the current 'Boss' might find there's something special in the promotion to "Admiral".
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Old 21-11-2019, 11:25   #12
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Re: Help selling the dream

I will repeat what mostly has been said. Avoid the day trip charters. Go to a boat show that has boats you like. Charter a boat that you would consider buying with a captain and chef in the BVI. Maybe have some good friends or the family come along. Gain experience yourself so she is seeing how much you want this. She will also be more confident with your experience, that you both will be safe.

It is a process. My admiral looked at me like I had two heads when I approached her with the Idea of sailing around for retirement. That was twelve years ago. We did all of the above. After the first charter on a Moorings 46 with a capt and chef, she was basically hooked. Next week we fly to BVI to sail our boat with friends for a week. In two years we will move on full time.

Take it slow and good luck. all the best

Lou
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Old 21-11-2019, 12:34   #13
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Re: Help selling the dream

You should learn to sail first. Maybe take some ASA courses. Once she sees that you are not only interested in learning correctly, she will see that you are also doing it for safety reasons.

I also bought a used Hobie Cat to practice with. I take it out on the lake often by myself.

I took some ASA courses then booked a week with Sunsail in the Bahamas with another family on a 40' cat for a week this past summer. No skipper or cook on our trip, I handled all the captains duties and had plenty of first mates to help when it came to docking, anchoring, navigating, etc (get everyone envolved in the activities). My wife is a lot more excited about it now that we have done a week on a sailboat and saw that I really knew what I was doing - most of the time
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Old 21-11-2019, 12:39   #14
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Re: Help selling the dream

As an excursion off of a Cruise line, the catamaran cruises very rarely put up sails.
A 12 Meter ride will scare her.

Take her sailing on a lake or wide river first, for a who;e season.
Charter between protected southern islands and non-rolly harbors next.
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Old 21-11-2019, 13:20   #15
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Re: Help selling the dream

Missing some info here, mainly knowing where the OP lives, i.e. near to decent sailing waters or not. If the former then he has basically 5 years to learn to sail while retired and while seeing his kids grow up. Couldn't be a better start in my view. Get a good sized open dinghy/daysailer, learn to sail well and slowly get the wife on board, or not...


As mentioned earlier, never ever do anything scary. I once misjudged a very short trip off Holland and it almost cost us our future cruising together as a couple. Now we're in the Med, sailing in easy conditions, anchoring, swimming, and slowly we're looking at becoming a bit more ambitious together.


The idea of a 3 hour sailing hop while on a cruise I think will not help much in preparing the 'ground'. Spending the money on chartering + skipper + cook seems the better primer, thereafter the hard but (hopefully) fun work of learning to sail & skipper a boat begins.
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