Chartering for our first cruise in the Caribbean

Spokey Doke

New member
48
17
Idaho, USA
My wife and I would like to take our first cruise in the Caribbean in January of 2023 and are looking for some guidance in terms of where to base/charter a boat and basic logistics/itinerary.

Length of trip: 7-10 days
People: 2
Boat: smaller single hull
General Priorities: Solitude, scenery/nature, sailing (over motoring), snorkeling.

More background: DW grew up sailing north of Boston and regularly cruised NE in the summers on her families’ Erickson 27. I learned to sail mostly in dinghy’s (and windsurfing) in the upper midwest and have only cruised on the ocean a handful of times. After many years landlocked in Idaho, we are looking to start getting back on the water.

Our current primary vacations are backpacking in high and remote wilderness areas of the Northern Rockies, so we are used to roughing it, and really value getting away from people and human development…so for cruising, we’d ideally spend as little time in marinas as possible; don’t care about shopping or going to restaurants or shore power; would like to minimize the travel time/logistics to/from the home port; smaller single-hulls that obviously can be short-handed, and have better than average sailing performance are what we would most like to charter (I don’t see much in the way of smaller boats, say <35ft in the charter fleets I’ve looked at so far). We love to snorkel as well.

Neither of us have been to the Caribbean before. To jump start our future sailing ambitions (and build some docking confidence) we just did the ASA charter certification program in the San Juans, and would now like to start chartering. Our best window to do so is when I close my business here in Idaho for the month of January, and we’d fly out of Salt Lake City.

Given all that (thanks for reading this far)…what are your recommendations/considerations for a first cruise in the Caribbean chartering a smallish single hull?
 
No better place than the BVI for your first (or 100th) Caribbean charter. All line of sight navigation, multiple charter companies, generally very reliable and moderate winds, some good snorkeling spots and all the anchorages have mooring balls so you don't even have to worry about anchoring. BVI is no secret though, you won't be alone so your wish for solitude will take a bit of a hit. Despite not being entirely alone it's still a beautiful location and if you can go during the low season it will be far less crowded. And even though you won't be the only person there it's such a fantastic place for your first charter (or 100th) it's the best option by far.
 
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NZK

Anarchist
907
657
Roaming
Totally agree with @psycho tiller - for a first cruise the BVIs are a solid choice.

I'd also recommend looking at options further South in St Vincent and the Grenadines - here you have Bequia and the Tobago Keys, which are some of my favourite destinations in the Caribbean.
It's all a bit of trade-off though - BVIs are much simpler and usually more 'protected' cruising but due to their popularity will likely be busier and are somewhat more commercialised. The Grenadines, Bequia etc offer more chances of finding solitary anchorages and are less developed/commercialised but they are a bit more widely spaced so will require slightly longer passages between locations that can be more exposed to the trade winds...

If your trip was closer to the 10 day range than 7 then I think Bequia and the Keys would be totally accessible - allowing a day at each end to/from the chartering port would still plenty of time for actual cruising...
 
Ditto BVI
There are places to avoid people:
Benures Bay on Norman Island
White Bay on SW side of Peter Is
Lee Bay on Great Camanoe Island
No shore side establishments in these spots
Cool trail on Norman from Benures

....pretty welcoming reception this place is giving, didn't used to be like this.
 

hdra

Anarchist
651
145
You can't go wrong with the BVI - the reef health isn't great, but the sailing is great, the anchorages are sheltered, and it's easy to get to. Think it would be a good choice for a first time charter of that length, and there are definitely places to get away from people as long as you're willing to do it.
 

CCruiser

Super Anarchist
1,510
13
The BVI is a good spot, one issue has been raised and that is crowds, you will not be alone shall we say, especially in January, which is "high season" One other issue is going in January, when you will experience the Winter Trades, which can be quite strong, in the 20's, even the 30's on occasion. if you can go in May/June the winds will be lighter and the crowds diminished. Last time I was there it was in June, sailed over from St Maartin, to Soper's Hole, spent some time at the Bight at Norman, where there were very few boats. Have been in the Bight when there was a constant stream of 90 or so boats per day. As mentioned, there are number of more secluded spots. some a little challenging to get into, but definitely less visited.
 

Spokey Doke

New member
48
17
Idaho, USA
....pretty welcoming reception this place is giving, didn't used to be like this.

Indeed (thanks!)...And what's with the relative consensus?

So let's assume BVI is it...other do's and don'ts? I guess the first big decisions are just how to get there, who to charter with (and what boat) and where to get supplies from for the week...then it seems to be more about where to go/avoid...

Still open to additional quieter alternatives...it looks like less popular places can be a bit more work to get to (and I'd rather avoid spending too many days getting there and getting back).
 
Indeed (thanks!)...And what's with the relative consensus?

So let's assume BVI is it...other do's and don'ts? I guess the first big decisions are just how to get there, who to charter with (and what boat) and where to get supplies from for the week...then it seems to be more about where to go/avoid...

Still open to additional quieter alternatives...it looks like less popular places can be a bit more work to get to (and I'd rather avoid spending too many days getting there and getting back).
Regarding the welcoming reception, I feel terrible, please forgive me. My mother taught me better than this, where are my manners and respect for traditions? Fuck off newbie and show us some deuces!:p

If at all possible, even if it takes moving heaven and earth try to go during low season since one of your wishes is solitude. Much, much cheaper and way less crowds. If you have no other option it's still worthwhile going at busier times. It will be more crowded but there's places to avoid the crowds if you have to.

I haven't been there in a few years and not since the hurricane devastation but we flew from the West Coast to Atlanta, then a direct flight to St Thomas USVI. From there it's an easy ferry ride to the BVI. The other option is to fly into BVI, I think there's an airport on Beef Island for the BVI but unlikely you'll get a direct flight to BVI from mainland US. And by the time you transfer planes it might not save you much time vs. ferry from St Thomas.

Any of the charter companies should be fine, we used "BVI Yacht Charters" and have no complaints. They're a smaller operation than the moorings, sunsail, and most other companies. I personally prefer a smaller company. The other ones I'm sure are fine though.

Most (all?) charter companies will deliver food and provisions to your boat for a small fee. They'll give you a list of items, send them what you want and it's all onboard the boat when you arrive. A huge timesaver and convenience, especially because you'll probably arrive at the boat in the evening after a long day of traveling and stay onboard the night before your actual charter begins. Nice to have some food and drinks chilled in the fridge waiting for you. There are grocery stores within walking distance if you need to pick up some last minute things the next morning before you leave the dock. Plenty of other little shops on most of the other Islands during the week if you need to replenish supplies too.

Maybe we're just soft and lame but shore power air-conditioning is really nice to have if you can get a boat with that. (IMHO air-conditioning at sea/anchor is a bit much though, might as well stay in a hotel at that point. That's just me though.) Shore AC is especially nice if you live in a place with a really dry climate like we do. I can deal with 100 degree dry heat 24/7 but 80 degrees and humid is rough 24/7 if you're not used to the humidity. Like all tropical locations it's humid in the BVI. Air-conditioning at the dock for the first night you arrive after traveling all day and also the last night before you fly out early morning to go home is huge. We've also been known to grab a slip for one night in the middle of the trip in Spanish Town, Virgin Gorda for one night of AC too. Yeah yeah yeah I know, we should probably just suck it up but that one night of good sleep with AC is just too tempting and convenient. Spanish Town is an interesting place to spend some time as well. Although it has the standard tourist style restaurants and shops it also has some local culture and flavor mixed in, more so than some of the other stops in the BVI. Good grocery store there for replenishing too.
 

ChrisJD

Member
254
169
Boston, MA
A second (fourth? fifth?) the recommendations for BVI, but if you're really looking for solitude, another possibility to consider is flying into and chartering from St. Thomas, and heading west to Culebra. Ensanada Honda, Cayo Norte and Culebrita are all gorgeous, there are some of the best beaches in the world, Culebra is a lot less developed than the USVIs and BVIs, and the sailing isn't really any more challenging.

Just a thought.

image3.JPG
 

slug zitski

Super Anarchist
6,179
1,208
worldwide
My wife and I would like to take our first cruise in the Caribbean in January of 2023 and are looking for some guidance in terms of where to base/charter a boat and basic logistics/itinerary.

Length of trip: 7-10 days
People: 2
Boat: smaller single hull
General Priorities: Solitude, scenery/nature, sailing (over motoring), snorkeling.

More background: DW grew up sailing north of Boston and regularly cruised NE in the summers on her families’ Erickson 27. I learned to sail mostly in dinghy’s (and windsurfing) in the upper midwest and have only cruised on the ocean a handful of times. After many years landlocked in Idaho, we are looking to start getting back on the water.

Our current primary vacations are backpacking in high and remote wilderness areas of the Northern Rockies, so we are used to roughing it, and really value getting away from people and human development…so for cruising, we’d ideally spend as little time in marinas as possible; don’t care about shopping or going to restaurants or shore power; would like to minimize the travel time/logistics to/from the home port; smaller single-hulls that obviously can be short-handed, and have better than average sailing performance are what we would most like to charter (I don’t see much in the way of smaller boats, say <35ft in the charter fleets I’ve looked at so far). We love to snorkel as well.

Neither of us have been to the Caribbean before. To jump start our future sailing ambitions (and build some docking confidence) we just did the ASA charter certification program in the San Juans, and would now like to start chartering. Our best window to do so is when I close my business here in Idaho for the month of January, and we’d fly out of Salt Lake City.

Given all that (thanks for reading this far)…what are your recommendations/considerations for a first cruise in the Caribbean chartering a smallish single hull?
Boat size and type …Hard to say

not to small or you run out of fresh water

the Caribbean is about wind and waves….perhaps 16 knots true , ocean size waves

Fast sailing …go easy, plan short distances between anchorages and chilling out

for the evening anchor arrive early…get a good spot, use plenty of chain
 

Spokey Doke

New member
48
17
Idaho, USA
A second (fourth? fifth?) the recommendations for BVI, but if you're really looking for solitude, another possibility to consider is flying into and chartering from St. Thomas, and heading west to Culebra. Ensanada Honda, Cayo Norte and Culebrita are all gorgeous, there are some of the best beaches in the world, Culebra is a lot less developed than the USVIs and BVIs, and the sailing isn't really any more challenging.

Just a thought.

View attachment 534216
My brother is not a sailor, but loves to travel...he speaks highly of Culebra and its been on my list for some time
 
A second (fourth? fifth?) the recommendations for BVI, but if you're really looking for solitude, another possibility to consider is flying into and chartering from St. Thomas, and heading west to Culebra. Ensanada Honda, Cayo Norte and Culebrita are all gorgeous, there are some of the best beaches in the world, Culebra is a lot less developed than the USVIs and BVIs, and the sailing isn't really any more challenging.

Just a thought.
The Spanish Virgin Islands are on our list for sure. I wonder if you could charter out of Puerto Rico instead of USVI? For a first trip, should stay with BVI because right now it's about the sailing and learning boat related issues and having support from your charter company nearby. Regarding that, I highly recommend Conch Charters. Reasonable prices and great service and support.
 

hammonegg

Member
64
0
BVI is the way to go for first charter. It's not practical to go from Puerto Rico as you are heading directly into the wind.
Spanish VI"s are wonderful, but keep in mind there are few services (no water for instance) available. Maybe save that for a second or third trip.
Agree with avoiding High Season, also that January often still has the "Christmas Winds".
St Vincent/Grenadines are also great, but you are much more exposed/greater distance between anchorages.
Benures Bay on Norman Island is my favorite spot in the BVI's.
Have Fun!!
 

nibj

New member
We took our first charter in the BVI and thoroughly agree it’s a great place for all round fun. But you can charter on Puerto Rico for the SVI. We have booked a week long bareboat charter with SailCaribe in Fajardo next May. So far so good: they have been helpful and communicative. June 1, 2023 I will be able to report more!
 

Alaris

Super Anarchist
1,438
318
Maryland
I did a cat charter in the USVIs in October ‘21 and it felt like we had the place to ourselves. The choice of US over British was due to covid closures being uncertain. I don’t regret it, and now we can go back for a BVI trip.

Charter company was Navigare. They were good to deal with.
 

penumbra

Member
88
29
WLIS (ish)
We were in this exact position 15 years ago. I had an Ericson 27 I sailed all over the Great Lakes in my early 20s, dragged it to NYC and sailed around the Sound for a season. She had no experience before that season. We chartered a 32' Jeaneau in the BVI and had a blast. We've been back a few times since - two more as a couple, two with groups on big cats.

All the charter companies are about the same. Consider using a broker to find a deal - we used Ed Hamilton Co multiple times.

As noted above, have the groceries delivered. Dealing with provisioning made day 1 way more effort than it needed to be. Having said that, even the delivery services was a pain in the ass as they didn't have their act together on the delivery. Good awakening to the proverbial island time.

Given the experience on the Ericson, we didn't forecast how much easier it was to put in miles on a bigger boat. I raced buoys and distance on bigger boats, but never really grokked the exponential improvement to get out of a 3.5kt shit box. Take a lap around Tortola going counter clockwise (one of our mistakes the first time was going clockwise). Anegada and the north end of Jost van Dyke will give you sufficient quiet time.

Also, don't think there are really "crowds" in the BVI. Yes, it's busier than Maine or PNW, but you won't be hoarded upon like many tourist destinations. Newport, Block Island, Put-in-Bay, Mack Island and a thousand other cruising destinations are far busier than most of the harbors in the BVI.

Maybe to put the cherry on top: we're leaving for a year+ sabbatical on our latest boat at the end of June. I guess the whole thing stuck.
 

Peter Andersen

Anarchist
532
121
Yes BVIS for a first timer. Def get to Anegada for lobster dinner on the beach as well.
2nd time I would do St Vincent/Grenadines/Bequia/Tobago Cays.
You will have some 40-60 mile jaunts on 2 - 3 days in Grenadines but worth it to get up early and much
less crowded than BVIS. A bit more secluded and natural but still all the amenities.
BVIS be prepared to pay NY prices at restaurants etc. Lots of breakfast and lunch stuff on
board you will have dinner out most nights. And rum. Lots of rum its cheaper than water
And dont be in a hurry for service.
And dont pack anything more than some swimsuits, shorts, teeshirts, golf shirts, sun dresses, flip flops
First time we took steamer trunks and it will arrove two dasy after you do. Later trips it all fit in a backpack.
Get to destinations by mid morning and you will find a mooring. Anchoring is fine but you are on vacation and
dragging is one less worry. You dont need a slip and you dont need AC really .
Navigation is super easy and all line of sight except Anegada (about 20 miles) and most destinations are Flying into STT and taking
a ferry works well and is a nice ride especailly if you charter out of Sopers Hole. I think easier than PRico and Beef Island
Cruising forums have tons of info on the hot spots to hit. Its hard to get to all of them in 7 days. The snorkeling is excellent.
As far as USVI's, I believe the crime rate in BVIS is about half of USVIs. Its very safe
 




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