Questions about a prolonged trip in the Caribbean

[Cheechako]

Pearson 323
Bayfield 32
Morgan 30/32
Dufour31
Alberg 30
CapeDory 30
Watkins 30
All come to mind and can be decent boats. All under probably $18k

[westsail374]

For your limited electrical needs, solar and a wind turbine should be fine. If you have an efficient and well-insulated small fridge, that should be taken care of by such a rig as well.

Consider a Westsail 32. They aren't fast, but they are tough. The boats have been very well loved, and many are available as real bargains - well maintained and loaded with good cruising gear. My brother and I sailed one from MD to the Grenadines and back 30+ years ago with no problems at all. Many have followed the company's motto to "Westsail the World" very happily. There is a great group of mutual supporters.

Find used Westies here:

WESTSAIL - CRUISING BOATS FOR SALE

[Highland Fling]

I wont give you boat advice nor will I suggest or criticise your 'partner' this will be your choice.

"Most" modern production boats will be "tougher" than you I am NOT an Island Packet fan.

For sure the thorny passage is a bind and NOT as easy as the book suggests unless you are going to take a few months to get to the USVI's

I would suggest some solar and a 'good' wind generator (a KISS one) as your main power generators.

Have you thought about 'cheating' coming down to St Martin or the BVI's and buying your Caribbean Cruiser there......that would make a lot of sense to me.

Hopefully you don't think Caribbean cruising is an easy broad reach from island to island in 15 knots of trade winds whether you are going down the chain or up the chain......IF ONLY

Me I would buy in the BVI or USVI and get my feet wet in the USVI's until I had a better idea of what I wanted to do and was capable of doing. At least in the VI's your not going to get severely beaten up by the weather. Then when you feel you are up to it, it is a day or overnight sail to St Martin chose your weather window carefully and you will 'hopefully' enjoy the Anegada Passage. Once in St Martin you will find BIG waves BIG seas and BIG winds......at least you would have this year, just now it is blowing 25 knots. Of course buying in St Martin is also a sensible option. One thing you have not said and is rather (very) important is how many $'s are you going to spend on your Caribbean Cruiser. PLUS how are you going to finance a 7 year wander around the Caribbean...what is your skill set?

[Joe Brown]

Most of my experience is in the Bahamas, and while some would say never to go anywhere except in a large heavy boat, I am not one of them. My experience is mostly on a Morgan Out Island 37 ketch, a Crealock 37 yawl, and an Ericson 28.

I would say you should be alright on the Catalina 30 if you make sure she is sound and watch your weather windows on crossings. I met several cruisers in smaller boats (27 - 30) who were doing just fine in the Bahamas and loving their cruises.

Seems the fleet is getting larger and larger these days. Doesn't mean you must have a large boat to cruise successfully.

Someone mentioned the Van Sant book. Good one. The title is "The Gentlemen's Guide to Cruises South"

[ThomasWeiss]

One thing you have not said and is rather (very) important is how many $'s are you going to spend on your Caribbean Cruiser. PLUS how are you going to finance a 7 year wander around the Caribbean...what is your skill set?

All good points and questions! I'm looking to spend around $20k on the boat. If I had to I could spend a little more but I would rather have the money on hand to repair and upgrade the boat as needed rather than spend a ton of money on a boat that very possibly will need the same repairs and upgrades. As far as the how, I have a decent amount in my savings account and my line of work only requires an internet connection (and a weak one at that).

Like I said on the first post I primarily have sailed in lakes and very close costal daytrips so I'm absolutely going to take my time between purchasing the boat and starting the trip. I have thought about flying down to the VI's but I'd much rather to shakedown in Florida and remedy any major issues in the states. There is also a certain level of familiarity about Florida so I feel it would be wiser to stick to waters I know versus jumping in a boat with no one to guide me should I need a bit of help.


-Thomas

[Hard Rock Candy]

My first boat was a trailer sailer and I trailered it to Belize and stayed on it with a friend for 6 weeks. we sailed it from Belize to Honduras and all the stops in between. Then I sold the boat and came home and daydreamed about my next boat for four years. I retired, sold my property and came to Florida looking for a 30 ft Morgan Outisland. It is one of the sturdyest, roomiest toughest little boats you can by. I bought a 78 ready to go for 17,500.00 Then I put another 5.000.00 Into it. It had 6 ft. of headroom, It has a thick insulated ceiling so it was cool on the sunnyest days. It was named Slo-n-ezy and it was. But I was just retired, I was looking for slow and easy. I've Had 13 people partying in it at one time with dancing in the salon. It is very roomy. It was also tough. It only drew 3 ft but with the long wide keel Iv had it aground about 20 times at least, especially in the Bahamas. I never damaged the keel at all other than scraping the blue ablative off a little bit. Whatever you get, Try to get one with a shallow draft, You can go so many places that you can not go with a deep draft boat. Mac

[sailsw00]

Thomas:
As someone mentioned above, almost any boat will do it. I took a 33' Moody from Rio to teh UK many years ago, and teh biggest boat we cruised in company with was 46', and it seemed massive! What's too big or too small changes with time, not with safety standards.
As for singlehanding, I love it! "He travels fastest who travels alone."
-Steve (Catana 431)

[ThomasWeiss]

Steve,

Do you find it difficult to manage the boat during docking and tough to navigate through reefs singlehanded? Those are some of the biggest concerns I have about going at it alone, but I suppose it's simply a matter of going out and doing it..

[sailsw00]

Thomas: there aren't a lot of reefs that block entrance to harbors, and where they do exist, they are either well marked on the charts or well marked with buoys, or both. Yes, there are a few exceptions, but you will learn about them at the last bar you went to.
Docking? What's that? Why would you want to dock? It's expensive and that's how boats get most of their scratches, and how stuff gets stolen from boats. You will anchor out most of the time, and use jerry jugs to get water and fuel. I did use a dock once, in my 42', when I was single-handing, due to a transmission taht gave up transmitting, and I found friends who helped me move the boat into a slip by using two dinghies tied alongside.
That said, a dinghy will get more use than your main boat: get a good one.
-Steve

[Sandero]

30' seems a bit on the small side for many reasons... but I've seen smaller sailed by 2 in the Caribe.

You def want a good dink and OB... you will use it constantly.

$20k seems too little. But I don't know what that can buy or what it will take to prepare the boat for the task.

Since you have a lot of time you can choose the most favorable weather for passages... but the trades are what they are... heading east is no fun in a small boat.

You want an SSB to communicate and get weather... probably alt charging sources. I did a engine drive refer... and got bat charging and hot water ever time the refer cooled. High output smart regulator alternator is mission critical for live aboard sailing boats.

You'll need some sort of awning, a dodger and a bimimi.... no way around that. Some places like English Harbor you can anchor and almost everything you might need to work on the boat... but no West Marines. Point a Pitre had a pretty good chandlery...

There's so much more to know... ask... read.. school of hard knocks... where there is a will there is a way.

[Cheechako]

Originally Posted by Hard Rock Candy

My first boat was a trailer sailer and I trailered it to Belize and stayed on it with a friend for 6 weeks. we sailed it from Belize to Honduras and all the stops in between. Then I sold the boat and came home and daydreamed about my next boat for four years. I retired, sold my property and came to Florida looking for a 30 ft Morgan Outisland. It is one of the sturdyest, roomiest toughest little boats you can by. I bought a 78 ready to go for 17,500.00 Then I put another 5.000.00 Into it. It had 6 ft. of headroom, It has a thick insulated ceiling so it was cool on the sunnyest days. It was named Slo-n-ezy and it was. But I was just retired, I was looking for slow and easy. I've Had 13 people partying in it at one time with dancing in the salon. It is very roomy. It was also tough. It only drew 3 ft but with the long wide keel Iv had it aground about 20 times at least, especially in the Bahamas. I never damaged the keel at all other than scraping the blue ablative off a little bit. Whatever you get, Try to get one with a shallow draft, You can go so many places that you can not go with a deep draft boat. Mac

if you are going small and simple there is a lot to be said for shallow draft, you can do the Caribe with 6 ft draft, no problem, but going slow and easy there are a lot of off the path places available with shallow draft!

[belizesailor]

Re single handing:

Normal small boat handling under sail or power is not hard single handed after you've built some experience doing it. You develop a routine on a given boat for how you do things single handed and you think things out in advance.

I also find I am more cautious and conservative when single handing.

One of the most difficult things Ive ever done single handed was getting the anchor up in bad conditions without a windlass. Forecast went wrong and actual conditions made the anchorage untenable. That was a bitch.

Eyeballing reefs. Its handy to have crew who can get the best vantage point, but not absolutely necessary. Buy a pair or two of good quality polarized sun glasses just for this purpose. I keep a pair of Maui Jims in a hardshell case and only wear them for eyeball navigation. I have a pile of cheap ones for normally daily use.

Learn how your boat heaves-to (whichever boat it ends up being)...this can make many things easier when single handing, like reefing sails, shaking out a reef, making repairs underway, etc. Heave-to behaviour is another reason to consider an older mono with a fuller keel shape...it will heave-to better than newer fin/shoal draft hulls.

[Highland Fling]

Originally Posted by ThomasWeiss

All good points and questions! I'm looking to spend around $20k on the boat. If I had to I could spend a little more but I would rather have the money on hand to repair and upgrade the boat as needed rather than spend a ton of money on a boat that very possibly will need the same repairs and upgrades. As far as the how, I have a decent amount in my savings account and my line of work only requires an internet connection (and a weak one at that).

Like I said on the first post I primarily have sailed in lakes and very close costal daytrips so I'm absolutely going to take my time between purchasing the boat and starting the trip. I have thought about flying down to the VI's but I'd much rather to shakedown in Florida and remedy any major issues in the states. There is also a certain level of familiarity about Florida so I feel it would be wiser to stick to waters I know versus jumping in a boat with no one to guide me should I need a bit of help.


-Thomas

Well 20K is rather light for my taste in boats and I am not sure what you can get for that.

I still think buy in the VI's or St Martin and learn down here......getting to the VI's from Fl is a RPITA and could easily put you off Caribbean cruising BIG TIME.....and for life. No matter where you start from you are going to be on your own......BUT down here you will be surrounded by friendly helpers who are living the dream. I somehow think in FL you wont get the help and support you need to move from novice to being confident in your abilities and plans.

have a wee read here

Caribbean Compass - The On-line Magazine

and here

Home - ALL AT SEA

BUT after saying $20K wont get you a good boat....
LOOKY HERE>>>>>>> - Bargain Yacht for Sale Camper and Nicholson 38 Year 78 She's a Classic and with young enthusiastic skilled hands can be restored to her former glory. Great Yanmar Engine, Center Cockpit with separate Aft Cabin. I will not accept offers as she is worthy every dollar at $6,950. Laying BVI. Phone Harry 1-284-342-8209

enjoy

[osirissail]

I have recently - 3 years ago - finished a decade of cruising the Caribbean. About two-thirds of the time as a single-hander. So here are some reminisces about my experiences that may be relevant to your questions.
First, boat size is not really a major factor as I have met cruisers on 20 footers and others on 60+ footers. All manage to successfully deal with their experiences with probably the only major differences being the speed at which they get from one place to another and the amount of "necessary" or "excess" stuff they can cram into their boat. So a 30 footer for a single hander or a young couple is quite fine and it can also be a blessing when it comes to getting in and out of some of the smaller "gunkholes" here and there in the Caribbean.
Next, money - - the old saying "nothing is free in this life" applies to cruising/wandering around the Caribbean or any place else. You either have to have a steady income from someplace or other or a significant savings account. Getting into and out of countries costs money, food costs money, boat fuel and even water costs money, and most importantly beer, wine, and rum costs money. The smaller the boat the more economical it generally is as there are less things to fix or replace. But you need a definite "revenue stream" to support such an adventure.
The biggest factor in the success or failure of your dream is first - your attitude towards dealing with some tough times, adverse weather, and foreign cultures and bureaucrats. The "rest of the world" does not adhere to USA or North American customs and ideas of things should or need to be done. Flexibility is a key to success.
Then your experience level with the boat and the types of waters and weather patterns of the Caribbean is very important. That is I would suggest spending significant time cruising the Bahamas to build up your confidence in both the boat and yourself before heading out to see the rest of the Caribbean.
There are always "other ways" but generally the Caribbean is done in a clockwise circle heading east from Florida down the islands to the most eastern islands then south to the bottom of the Windward Islands and finally westward along the northern coast of South America to Panama. Then either choosing to head to the Pacific or completing the circle up Central America and back to Florida.
The "circum-navigation" has been done in as little as two years and generally in 4 to 6 years maximum. That is, if you don't take out time to "settle" in one island or place for longer than one or two seasons.
Thousands of people have sailed around the Caribbean and back so everything is well documented and what I find is the main variable to either having a positive experience or having a rotten experience - is - your attitude towards others and other cultures and your willingness to learn and build your experience level over time so that you don't go rushing in where fools fear to tread.

[ThomasWeiss]

Thanks for posting that listing! I'd definitely be interested in looking at what is being offered, and once again, I have a little bit of time to figure all of this out. I'm a firm believer in the 7 ps so maybe a quick flight to the VI's would be in order after all. I'm also looking at a trip to Jamaica for the same purpose as well. With that in mind, is it harder to find a reputable surveyor?

Also osirissail made a bunch of good points as well, the biggest being that I did not factor in rum into my endeavor . Seriously though, having spent a bit of time in Jamaica (and off the resorts with the locals) I absolutely understand and appreciate the change in the definition of 'now' in that part of the world and how we, as Americans, tend to place so much emphasis on rushing through our lives rarely getting a chance to enjoy them. That's a big reason I chose to do this at all. I'm 27, I have the resources to make it happen, I'm not married (she gets seasick), my mother suddenly passed away at 50 about a year ago (never saw it coming), & I don't care to stay to pour money into a big house and car for the rest of my life. I've been on that side of it and found that it really doesn't thrill me.

Sorry for the long post just felt the need to clarify a few things.


-Thomas