For the new sailor (which I am), island hopping has a steep learning curve. The weather reports can be wrong, like the day we left Des Haies, in the north end of Guadeloupe, for the short hop south to Pigeon Bay, about half way down the island.
This is only 10nm, an hour and a half to two hour sail normally. The reports from Passage Weather and Wind Guru both said waves were 1-2m and wind 15-20k. But you never really know until you are out there.
To our surprise, we found 30-35 know winds. The tops of the waves were being blown off. NOT planned. Luckily the sun was out and land was obviously always within site. But I was scared; my knuckles white from hanging on tightly. That said, every rough passage tests you, and tests your boat. You feel scared, then you realize afterwards that you made it through okay. Things on the boat break, then you fix them. And afterwards, you eat, sleep, do something fun and then set out to do it all over again at the next place.
Island hopping is certainly not like in the post cards, but it’s not a bad life.