Cloudy days

Here in San Juan, maybe we've gone 2 days in a row in the past 2 years... there is always a little sun, and almost always a little rain

I will say, maybe during the rainy season you will see a few days where it's cloudy and no sun. For the most even on a rainy day the sun will shine at some point.

Sun always shine, we just don't see it. 
But seriously the worst I seen is 6 days of constant cloudy and rain, most of the time the sun always comes out for a bit. It also depends where you are, it rains in the east and it moves to the west leaving the east in sunshine. Unlike mainland where it goes from west to east and from south to north east.

The Caribbean is in constant flux due to water and air temperature fluctuations, and you are right next on the north to the Bermuda Triangle.

It can ruin a vacation but a day or two later it is perfect again.

Thank you all,

That was what I was hoping to hear!

Correct me please if I'm wrong here, but I relate it to the weather in Florida I experienced while working down there.
Rains everyday, for a short period then clears.

What I saw in Florida was every morning it was clear (from over-night), clouds built as the humidly gathered, down came the shower and released the moisture, clear again for the evening.
I could time the showers where we were.
Certain there are days of constant, as you have mentioned, but is it close to the same?

Very close to the same. It pays to carry an umbrella every day specially from mid afternoon on. But the tropics are always boiling with weather patterns that are in constant flux.
Clouds can only hold so much so they have to let go.

yes, similar.  rain most days from the central highlands moving down to the lower areas.

I would suspect then the winds/seas are the same way.
Typically calm at night into the morning and building for the afternoon and relaxing again.

Again, knowing there are those known Trades that build for a period.

Hey I am a good passenger but willing to learn boating. Looking forward to one day having a boat to fish from and to reach the nice places to scuba.

ReyP wrote:

Hey I am a good passenger but willing to learn boating. Looking forward to one day having a boat to fish from and to reach the nice places to scuba.

Oh my.. It's my main reason of the area!
I have two others in mine to retire to (well, semi retire).
This area has the best sailing, into regions, of constant wind/sea, depending on.. (which I'm researching) that I have found.

The other two (which go un-named for reasons of not driving up costs..) have better return for dollar, but not the sailing opportunities.

The drifts, above and below the SVI's & the USVI's create a unique area prone to large seas.
Also create a very interesting marine wildlife opportunity.
As I research and learn (and ask a bunch of questions), I'm prone to this area.
Then again, am I choosing the wrong season...
As another in another thread said, the Christmas Winds/Seas are there.
9 to 12ft seas, winds blowin' 20knots..
Not seas I wish to see anymore.

I will continue to research and ask.
Be ready my friends....
And thank you for all so far!

I don't know squat about sailing - but the surf  / ocean swells are big on the north side of PR in the winter, much calmer during the summer months in my limited experience. 

I suspect that any type of boating that time of year can be rough off shore.   I had  a 25'Glasply in Alaska and learned to respect the weather.  No more green water comin over the bow for me!

Caribbean side on the east and south are calmer. West and north are rougher and you need a bigger boat. When going island hoping one must be prepared to spend a few days at each location due to possible weather. But well worth it visiting all of those islands.

Glaspy aye.. Shame they stopped making them. Good big water design,

ReyP, been doing a lot of research of currents/winds and effects on wave height. The East Coast seems the best for conditions to me, all considered.
And yes, good advise, anywhere you sail (boat), weather means everything. Plan out staying put till it clears.

What I seem to be learning is that my planned early stay Sept/Nov leads to some real nice sail time, Nov/Jan seems a bit dicey unless the boat is big enough, Feb/April seems decent again.

I'm seeing myself as land-based (land-lubber, LOL) with opportunity.
I really need to get down there and walk-about.
Think about how "I'd" do this.
I can't be 'land-locked'.

This should be a fun trip!

If you can sail us from Fajardo to Vieques and Culbra, I have a few that are looking for passage.

It's been many years since I've sailed, but recently I did look into winds and currents in the West Indies/Caribbean.  My understanding is that the most common route to the West Indies is out of Miami, sailing a bit north of east out past the Bahamas.  There you catch the trades into the Indies, and ultimately into the east coast of PR.  Making your way back to Miami to start the route over seems to be the biggest challenge, and likely will put some hours on your inboard.

If I've got this right, seems to me that you want want a place to call home either on the east coast of PR or in Florida.  I'd choose the island in an instant.