Almost all you wanted to know about the Caribbean.. from someone there.

[magentawave]

If you could go to one island in the Caribbean and spend the entire time your visa would allow (90 days or so) what island has ALL of the following...

- lots of surf spots with consistent uncrowded waves
- decent internet for working
- simple cheap places to stay

And what time of the year would you go to get all of the above?

[Caribsurf]

wow so many to choose from...not sure if you are an American citizen or not, but PR has all that in the winter and you won't need a visa.  it does have crowds, but it's possible to find empty breaks too  caters to all sizes wallets.

St.Thomas (USVI) has a few good surf spots and it's a quick ferry to Tortola in the BVI where you can find some good surf (crowds too when its good) winter is best

Barbados..multiple breaks on every coast and great vibe. year round surf... Can get crowded on weekends and holidays as there are many local surfers and lots of tourist surfers.  There are SUP breaks where proners don't go.  can find some inexpensive eats and lodging if you want or 5 star luxury

St.Barts..small island but has some really good surf.  again weekends and holidays there can and will be crowded, but during the week during school hours, you can have it all to yourself  sometimes.  nothing cheap or simple here

St.Vincent & the Grenadines, my home breaks...the mainland of St.Vincent has lots of surf, some breaks never ridden. Some serious surf at times, and some nice reef break and point beaks too   noone surfs here but me and a couple of friends who work for their  yacht charter business. The Grenadines have some good breaks too and can be excellent..gorgeous flat water paddling  the Grenadine islands Bequia, Union and Canouan have some decent surf but not as good or consistent as St.Vincent.  St.Vincent is inexpensive compared to the Grenadines.  great kiting and wind surfing too
winter mostly but south swells in summer can be magical

Dominican Republic...north coast ..fly into Puerto Plata  Sosua, Cabarete areas all have good surf. Reasonable prices..not too crowded when I was there many times years ago, but I think popularity has increased especially for kiting.  Playa Encuentro in between Sosua and Cabarete has good surf...Playa Grande east of Cabarete has good surf (seen photos never surfed it)  Even the capital city Santo Domingo has a good break right in front of La Concha downtown area, but I wouldn't trust that water..seen many people out there.

Like I said before every island in the Caribbean has surf ..some world class...even Aruba, best known for windsurfing has now become a popular SUP destination and some really good surf.

just fly into one island and if you don't like it, jump a ride on a sail boat/mail boat heading north or south and get off at the next stop

[magentawave]

Thanks for all of that great info, Caribsurf. Point breaks in the tropics - nice! This is an awesome thread!