Newbie needs EXPERT advice about how to get started.

[jojobead]

Thank you sincerely for your time and for reading this. I am 38 years old and have a dream of sailing (within 5-10 years) with my family (wife and two boys ages 4 and 6). I want to sail the Mediterranean, Caribbean, the world, stopping at small islands and ports and places I've never heard of, and do this for about 2 weeks every year. I want to skipper myself. But, I've never had any sailing course and I don't live (very) near the ocean. I am however starting to put my vision and dream into an achievable goal and for that I want to kindly ask you for advice.

* How do you recommend I start? What education is required and what is the best way to get it?
* Financially, buying a sailboat is not within my 5-10 year future, but renting one for 2 weeks a year very much could be. Is this a recommendable option? What brokers / websites do you recommend?
* What books should I read?
* What else should I have asked or should know?

I can't thank you sincerely enough for your valuable time. I hope you know I appreciate it and I hope to repay it back to others someday. I hope you have a great day.

Sincerely,

Jeff from Virginia

[two-rocks]

Welcome, this forum needs a dreamers section.

I am not an expert. Search works. Look into chartering.

2-weeks is barely enough time to unpack and repack to fly home. This is my expert part, as we only have 2-weeks a year - buy a boat and sail locally.

[GordMay]

Greetings and welcome aboard the CF, Jeff.

[steve77]

Find a local sailing club that offers instruction. OR join the local Power Squadron and take classes. OR find an ASA instructor who offers instruction coupled with a week long sail through the Florida Keys. I did all of these and they all helped me build skills and confidence before gaining experience chartering.

Cheers!

Steve

[JimsCAL]

Some suggested steps.
1. Buy a small daysailor to learn the basics. Or join a sailing club that lets you use their boats.
2. Take a couple of courses to learn how to handle larger boats and be able to charter.
3. Charter boats for your two week vacations.

[fahtcha]

Welcome aboard Jeff.

I do not claim to be an expert, but here is my experience.

I took ASA101, 103, and 104 in 2016 and sailed a bit at Annapolis that summer. We then chartered (me as skipper) in the BVIs, Exumas, and Grenadines in 2017, 2018, and 2019. These were all one week charters. Too short for me, but my wife is short on vacation.

Not living near the ocean, this could be a good path for you as you could probably do the classes in a week long visit to Annapolis or somewhere else with a school. A friend took a class in the BVIs and then chartered there; however, I do not think he chartered since.

For reading, I suggest staring with The Annapolis Book of Seamanship.

[jojobead]

I just wanted to sincerely say thank you to those who have responded. This helps me more than I can say and I appreciate you.

[Flagman101]

Has a sailing instructor I would sugest training. Do invest on your training.
Training will provide a Learning structure that will make it easier and faster for people to learn.
This also will make you more competent and charter companies will like seing formal training on you CV.
2 weeks a year fits a bareboat charter profile.
Rule of thumb, most charter companies will let you book a boat about 10 feet longer then you have experience on has skipper.
Do keep in mind that even if they rarely check if your CV is accurate, if they have any Reason to beleive you do have have the abbilities to skipper the baot you will be left with two choices. You stay at the dock the whole charter on you hire a skipper for about $150 a day.
Makes the 2 weeks a bit ore expensive
They will not refund you.


Also has a crewed charter skipper I would suggest your first time to be with a skipper.
Even better with a licenced instructor.

The biggest difficulties in your first bareboat charter will be dropping the hook, picking up a mooring in a crowded bay and manoeuvering the boat in and out of the marina.
Sailing is the easy part.
Charter skippers also know a few local secrets spots and tricks. Even who makes the best BBQ lobsters.

One of the cheapest way to charter a boat is to rent a cabin. But this implies you live on a boat with strangers. I would rather recommend that you build your own group. 2 or 3 couples that know each has a better chance at making it a succes.. Even if they know Nothing about sailing.
Some of my best crewed charters experiences have been with groupes of friends who hire me.


Choose you destination according to your objectives.
The BVI's are coming back from hurricanes and offer a much different experince then say Martinique or Guadeloupe or the Grenadines

Has for books, sailing books tend to be very thecnical. Unles you catch on very fast to the principles of sailing, they provide a very dry reading experince to inexperienced readers.
Sailing for dummies is good.
Dont get into the technical stuff to much at first.


Beam winds to you and your familly

[anacapaisland42]

Jeff,

How much do you weigh?


Buy the smallest sailing dink with a jib and main (e.g. CL 11/12 or Hobie 14) that will carry your weight. Initially a craft like an Albacore/CL 16/*.16 etc will be too much and scare you/put you off sailing

Learn to sail on that in complete (if often wet), security

You will learn pretty much everything needed to sail any boat..big boats are easier/slower to sail.
Bill
(who has sailed on boats from a 55 foot MFV to a CL 12 but the most exciting is a Hobie 16)





* How do you recommend I start? What education is required and what is the best way to get it?

[StuM]

Once again we see someone who has ambitions to cruise in a keelboat being told to buy a dinghy. I disagree. The required sailing skills can be learnt just as easily on a keelboat as on a dinghy. The required seamanship skills cannot be learnt on a dinghy (anchoring, mooring, manouvering under a motor in a marine, pilotage etc, etc.).


As others have said - If you are not close to the ocean, courses (ASA/Power Squadron in the US) and chartering.

[JPA Cate]

Everyone has been right, so far. Now, I am going to add a twist.

My Jim started with a 15 ft. O'Day, iirc, and then worked his way through a progression of boats. He had 2 small children and his first wife at the time. The boats were always something fun to do together. He took the boat to lakes and they sort of camped out with sailing fun in the daytime.

You have 2 sons and a wife you want this to be fun for. They can all learn by doing, and remember, some form of child care is necessary, best the two of you share it. Also, if it doesn't come naturally for your wife, then I suggest separate lessons for her--there are learn to sail programs for women, and are highly confidence building. I'm not an "expert," either, just a person with a fair number of sea miles. I learned to sail as an adult, by doing. There were modest, low level race boats, and a woman friend of mine got me on a couple of crews.

Anyhow, I'd suggest something like a Catalina 22 that you can sail in local waterways, and start learning about looking after the boat. Play with it on weekends. In a couple of years, get a 30 footer, a real keel boat. If you still think you might want lessons, take them now that you've some experience to relate them to.

Eventually, you might want to charter different places in the world, or you might decide to buy a bigger boat and really go cruising, which cannot be done in 2 wk. chunks. You can only go popular places, that have been visited for a very long time. Which is fine, not everyone really takes to sailing, anyway, and many are drawn to other pursuits.

One caveat, and it is based on something I read here on CF. The intensive training holiday kind of deal in the Caribbean worked better for the husband than the wife. For her, it was a little too much--she had not had time to do all the reading beforehand, and her "vacation" was a bit of a struggle, no free time at all, studying and practicing, at a time when she could have used some time off. This came as a surprise to them. Her husband had done the reading, and had a good time.

So, welcome aboard CF.

Ann

[sailingchiro]

Take ASA 101-104 for fundamentals. Crew on boat such as Carib 1500 or the like. Crew on local yacht club boats. Charter boats with captain.
My boat charters with Master Captain for $3300 per week. Might be able to charter in the Bahamas, BVI, etc. for more than that.
Having a captain on board, increases the learning curve. We absolutely love to teach. Buy a 30' boat to learn systems and maintenance. Take boat out at least 12 times a year. I like the 30' Catalina for many reasons. THen in 5 years grow to your big boat.

[Zzmeyer]

OK. So you are 38 years old. Want to start in 5-10 years. Sail 2 weeks a year and sail the world. Figure it takes about 150 weeks to sail around the world if your are sort of quick it will take about 75 years. Starting at 43 you better hope for dramatic increases in life expectancy.

[DockDoc]

Where are you in Virginia?

We keep our cat in Deltaville, which is nice, but Annapolis is fantastic. Get to Annapolis, take some classes ASA 101-104. Get on a catamaran and a monohull. Annapolis has tons of opportunity.
Charter somewhere easy, the Keys, the Abacos, the Bay in fall. The Caribbean can be a ball buster don't let the turquoise water fool you. If you charter in the Caribean pay for a captain, tell him or her just to be the safety net. We did this a few times, well worth the money, education, and peace of mind.

Yea you can grasp the physics behind wind, shear, and force in a small boat, but you can get the same education sticking your hand out the window at 10mph and 50mph. Sailing is a sheet and strings on a stick with a semi-buoyant tub attached.

Skippering is navigation, weather interpretation, anchoring, sail reefing, battery management, water management, fuel management, sleep deprivation avoidance, crew management, time management, crisis management all with back up plans when Sh1t goes wrong and plan A isn't working. That's the hard part of sailing.

Two weeks a year? Out of all your plans, this seems the least likely to succeed. I have done 3000 NM since buying our boat in April, and I don't think I am out there enough!

[knot smart]

Originally Posted by jojobead

Thank you sincerely for your time and for reading this. I am 38 years old and have a dream of sailing (within 5-10 years) with my family (wife and two boys ages 4 and 6). I want to sail the Mediterranean, Caribbean, the world, stopping at small islands and ports and places I've never heard of, and do this for about 2 weeks every year. I want to skipper myself. But, I've never had any sailing course and I don't live (very) near the ocean. I am however starting to put my vision and dream into an achievable goal and for that I want to kindly ask you for advice.

* How do you recommend I start? What education is required and what is the best way to get it?
* Financially, buying a sailboat is not within my 5-10 year future, but renting one for 2 weeks a year very much could be. Is this a recommendable option? What brokers / websites do you recommend?
* What books should I read?
* What else should I have asked or should know?

I can't thank you sincerely enough for your valuable time. I hope you know I appreciate it and I hope to repay it back to others someday. I hope you have a great day.

Sincerely,

Jeff from Virginia

Good morning, where are you in VA?. I was raised in Lynchburg, and know my way around a bit. Depending on where you're located, Smith mountain lake comes to mind. Otherwise, how far are you from the Chesapeake?