We've chartered through Sail Caribe twice in the past (both times on a 450F) and had positive experiences with them. They keep their boats in good condition and are responsive to any questions we had or any issues while on charter. On our first charter we did have a minor generator issue while in the SVIs and they were going to send a chase boat to us, but we figured it out before they got it dispatched. Also had an issue with the mainsail on St. John and they connected us with some local riggers and got it dealt with quickly. Both were things that could have happened with any charter company so I don't fault them. Second charter with them was flawless with no issues.

We have chartered several times with DYC, but not out of Puerto Rico so I can't comment on their base there. All else being equal it looks like SailCaribe's boats are newer and the prices are comparable.

I'll add that I do like the logistics of chartering out of Puerto Rico. We can easily get there in one day from the west coast, there are plenty of provisioning options (including a Costco near the airport and a couple large supermarkets near the marina), and we enjoy spending time in Puerto Rico before/after the charter. That said, a lot of people really like chartering with CYOA as well and they have a nice stable of boats to choose from. You just have to get the boat back to the USVI at the end of the charter which could potentially involve a few hours of grinding into the wind and swell. And you have to deal with customs upon entering the SVI from the USVI - but not on the return to the USVI.

Last edited by snmhanson; 10/01/2019 06:18 PM.