In Cozumel, be sure to make a stop at Margaritaville. You can listen to the music of Jimmy Buffet while eating good food and drinking a strong blue margarita!
In Grand Cayman, make sure to try some Tortuga Rum Cake. Of course, the highlight is the "try before you buy" attitude...and most shops have samples of every flavor available. Beware, the cake is strong and you don't want kids eating this. They pour the rum on after the cake is cooked, so it is not baked out.
In Jamaica, the most beautiful homes can be found in the hills. Keep your eyes out for these. There are also areas of extreme poverty. Be mindful and respectful...and go home appreciating what you have.
Quick Tips:
When in Cozumel, head straight to Margaritaville. From the pier, turn right after the DuFry shop. Walk less than five minutes. Margaritaville will be on your right. Be sure to bring your swimsuit, because you can swim in the ocean at the back of the restaurant after you eat or drink there. If you want a more party-like atmosphere, you can head to Carlos & Charlie's or Senor Frog's, but be prepared for typical teenage antics and drunks.
In Grand Cayman, take the Trolley Roger tour. If you are lucky, Steve from Canada will be your tour driver. He dresses as a pirate, which is great for kids, but he imparts a lot of knowledge of the local culture and gives a tour of the homes on the island.
Before headed to Jamaica, look up the driver Phil Lafayette. You can find his tours online and book them in advance. Phil has a great knowledge and love of Jamaica and will definitely show you a good time. Bring extra cash in case you decide to do any side tours with him (for example, you can experience a real Jamaican barbecue for less than after seeing Dunns Falls) in a beautiful setting.Best Way To Get Around:
When in Cozumel: walk or take a cab. If you are interested in shopping or going to the bars, everything is within five to fifteen minutes walking distance. If you want to go to the beach, take a ten minute cab ride to Playa Paradisa (for tranquility) or Playa Mia (if you want the crowds from the ship).
When in Grand Cayman, just walk! Everything worth seeing is within walking distance. Of course, if you want to go to Stingray City, you will need to take a cab or tour. Caution: the bus service in GC is very slow. They often make multiple stops to take people shopping (and waiting for them) or to work. They are not catering to tourists and a 15 minute ride to 7 mile beach took us almost an hour!
When in Ocho Rios, take a tour of the island. There is so much to see...but most of it is a bit away from the port. However, if you want to just go shopping, it is about a 5 minute walk to Island Village on the Beach, which I recommend.