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Old 04-25-2019, 05:38 AM   #1
thinkxingu
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Default Where to Start: Caribbean Boating

Dave's post about becoming a "looper" got me wondering: where would someone start if he wanted to do some boating in the Caribbean? I always see the photos in Boat US's magazine of people on deserted islands with extensive sandbars and want to be there.

PS Any info on expense for options would be welcome as well. Thanks!

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Old 04-25-2019, 05:55 AM   #2
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My grandfathers plans were to be a looper all around the country when he retired. He spent time in the Caribbean with paid captains learning on their boats, him being a Navy guy he was familiar and comfortable with being out to sea but he wanted the experience of doing it all alone not with an entire crew so he had the confidence. Plans were to chase the warm weather all year and enjoy sport fishing. Sadly after he bought his boat, fully rigged it up, set his plans for the next year and retired he passed away three days before leaving for his trip. His reality made me say if your thinking about doing it do it before its too late! Definitely would have been a life changing trip
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Old 04-25-2019, 06:39 AM   #3
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Default Great Loop

Becoming a "looper " is defined as someone who has cruised the Great Loop. That is the 5,000 to 7,500 mile trip mile trip on the water through the Eastern United States

The American Great Loop Association is comprised of a niche group of individuals with a passion for cruising the Great Loop.

By definition, The Great Loop is the circumnavigation of Eastern North America by water also referred to as America's Great Loop and the Great Circle Route, the trip varies from 5,000 to 7,500 miles (8,000 to 12,000 km) depending on route options and detours taken. It has been said to be the world's safest and most scenic continuous waterway. It is the boating adventure of a lifetime that will take you to shorelines from the Florida Keys to Canada. On the trip you will pass the Statue of Liberty by way of the Hudson River, journey through the Historic Erie Canal, across downtown Chicago, down inland rivers of the heartlands and finally to the Gulf of Mexico.
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Old 04-25-2019, 07:22 AM   #4
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Becoming a "looper " is defined as someone who has cruised the Great Loop. That is the 5,000 to 7,500 mile trip mile trip on the water through the Eastern United States

The American Great Loop Association is comprised of a niche group of individuals with a passion for cruising the Great Loop.

By definition, The Great Loop is the circumnavigation of Eastern North America by water also referred to as America's Great Loop and the Great Circle Route, the trip varies from 5,000 to 7,500 miles (8,000 to 12,000 km) depending on route options and detours taken. It has been said to be the world's safest and most scenic continuous waterway. It is the boating adventure of a lifetime that will take you to shorelines from the Florida Keys to Canada. On the trip you will pass the Statue of Liberty by way of the Hudson River, journey through the Historic Erie Canal, across downtown Chicago, down inland rivers of the heartlands and finally to the Gulf of Mexico.
Wow that is some awesome trip. Definitely adding it to my bucket list!
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Old 04-25-2019, 07:54 AM   #5
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Quote:
Originally Posted by TiltonBB View Post
Becoming a "looper " is defined as someone who has cruised the Great Loop. That is the 5,000 to 7,500 mile trip mile trip on the water through the Eastern United States

The American Great Loop Association is comprised of a niche group of individuals with a passion for cruising the Great Loop.

By definition, The Great Loop is the circumnavigation of Eastern North America by water also referred to as America's Great Loop and the Great Circle Route, the trip varies from 5,000 to 7,500 miles (8,000 to 12,000 km) depending on route options and detours taken. It has been said to be the world's safest and most scenic continuous waterway. It is the boating adventure of a lifetime that will take you to shorelines from the Florida Keys to Canada. On the trip you will pass the Statue of Liberty by way of the Hudson River, journey through the Historic Erie Canal, across downtown Chicago, down inland rivers of the heartlands and finally to the Gulf of Mexico.

That looks like a great trip!

I guess I should have bought a bigger kayak...
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Old 04-25-2019, 10:31 AM   #6
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I have some friends who have actually circumnavigated the world on their sailboat (the ultimate loop!)- took them about ten years, and they homeschooled their three children. It's been a blast following them, and getting random postcards from places like St Helena and Papua New Guinea.

They run a cool blog here- https://www.sailingtotem.com/ and make money via coaching people who also want to cruise full time. To hear them tell it, the Bahamas is the place to start because it's easy to reach from the mainland USA (you don't need to do a long passage to get there), and there are a ton of islands close together and it's easy getting supplies/repairs and you meet a ton of other cruisers. Most people apparently who are only cruising for a short period never even get further than the Bahamas for various reasons.

Personally my only issue with the entire thing is to paraphrase Kurt Vonnegut, I am a freshwater person and whenever I swim in an ocean I feel as though I'm swimming in chicken soup.
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Old 04-25-2019, 10:48 AM   #7
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Default Youtube!

Lots and Lots of people post their adventures on youtube, some are better than others, Many start out with high hopes but run into setbacks like running out of Money, loose interest, or worse, have major fails.

There are a few that I fallow, both Sail and Power,

Tula's Endless Summer
MJ Sailing
Sailing Delos
Searching for C-Shels
Lady K-Sailing
Barefoot Sailing adventures
Technomadia

It can be addicting once you start watching, at least for me, my wife thinks I'm crazy. I think she may be right.
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Old 04-25-2019, 11:17 AM   #8
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I love YouTube.

When you get tired of watching all the great boat trips that you and I will probably never have the opportunity to go on search "Boat Ramp Failures".

You will see hundreds of people making the mistakes that all of us hope we never make! Those trips also started out with high hopes!
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Old 04-25-2019, 11:26 AM   #9
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Quote:
Originally Posted by thinkxingu View Post
Dave's post about becoming a "looper" got me wondering: where would someone start if he wanted to do some boating in the Caribbean? I always see the photos in Boat US's magazine of people on deserted islands with extensive sandbars and want to be there.

PS Any info on expense for options would be welcome as well. Thanks!

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I have spent a lot of time in the USVI and BVI. Great place to start and not too intimidating.

St. Vincent and the Grenadines is also a blast
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Old 04-25-2019, 12:17 PM   #10
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Quote:
Originally Posted by thinkxingu View Post
Dave's post about becoming a "looper" got me wondering: where would someone start if he wanted to do some boating in the Caribbean? I always see the photos in Boat US's magazine of people on deserted islands with extensive sandbars and want to be there.

PS Any info on expense for options would be welcome as well. Thanks!

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It is very expensive, but you can charter boats pretty easily in the BVIs. Companies like Moorings will set you up with a boat and provisions and even provide a captain for the first day or two for instruction. We had always planned to do that until we bought a boat that we can "simply" cruise there...

Another option would be to crew on someone else's boat. You won't likely get to the Caribbean that way, but you can learn a lot by helping someone transport a boat between ports on a multi-day run. This time of year there will be tons of people headed north on the ICW and many may need help.

I've got years of boating experience, but have never handled a twin inboard, so my first cruise was a little worrisome. However a friend volunteered to join us for the first 400ish miles of our cruise home. He has years aboard his twin inboard cruiser and I will be learning a lot while he's there to teach. He's psyched to do the Eire Canal, a bucket list item for him, so it's a win-win.

If you really want to cruise long distances in your own boat, it's imperative that you become as self-sufficient as possible. If you have to pay someone to fix every little or big problem, it can be incredibly expensive. I hav been pouring over the manuals for all the system on my new boat all Winter and it's pretty overwhelming, to be honest. I love an adventure though, so...
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Old 04-25-2019, 12:54 PM   #11
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Did a few catamarans in the BVI. Great place to start and not much navigating as you sail pretty much by sight. Need to get back there and do that again. Each time we had 3 boats and had a blast.
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Old 04-25-2019, 12:55 PM   #12
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Default Carribean

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I have spent a lot of time in the USVI and BVI. Great place to start and not too intimidating.

St. Vincent and the Grenadines is also a blast
Have sailed in a crewed, sailing catamaran at many carribean locations for the last 14 years with friends. BVI, St. Maarten, St. Barts, Mustique, Guadaloupe, Antigua, St. Kitts, Nevis, Belize, Panama. Our favorite is the Grenadines and in particular Tobago Cays! They are awesome! In Tobago Cays you can swim with turtles, rays and all sorts of marine wildlife.
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Old 04-25-2019, 02:32 PM   #13
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If you just want to "go boating in the caribbean", fly to BVI and rent something. I've rented and taken some center consoles from Tortola to Peters Island, Jost Van Dyke, etc. Waters are pretty forgiving, for the most part, you generally have line of sight between islands, and other boaters are pretty helpful.

You can also rent some nice bareboat or crewed cat's out of Road Harbor marina, among other places, if you want to do some extended trips.

If you want to take your own boat down there, presumably from FL, then you'll want to spend a little more time getting used to your boat, and the waters. There are always people going back and forth, so some buddy boat trips on your first couple of crossings would be recommended. Start with some runs to the Bahamas, figure out max seas you (and/or your boat) can safely handle, ensure you have plenty of safety gear and a full tank of gas
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