Our first port of Key West was very enjoyable. There is no need for a taxi, with most shopping and sightseeing with in walking distance. Safe and easy to walk from the port and explore the town and all it has to offer. So much to see and very relaxing to tour Key West.
After a full day at sea our next port is Georgetown, Grand Cayman's. We didn't have an excursion arranged but there were plenty of well organized van/taxis at the port. We quickly boarded the van. On the 10-15 minute drive into town, our driver; a friendly and knowledgeable gentleman gave us passengers a brief history on Grand Caymans. We felt safe and comfortable exploring the jewelry shops, coffee shops and souvenir shops. I highly recommend the Guy Harvey Shop. Check out the "John Hardy" Jewelery in the Shops.
Our next port was Ocho Rios, Jamaica. Having never been to Jamaica, I was so excited and looking forward to it. I thought it would be the highlight of the trip. Unfortunately, Ocho Rios did not live up to my expectations....from the minute we stepped off the port, we were hustled and hounded by aggressive local entrepreneurs and 'so called' taxi drivers. If you do get a taxi; #1. don't trust them, #2 ask for a rate before you get inside and ask if that the total fare or "per person", did I say 'don't trust them'? Oh, and don't eat at Momma Marley's Bar, you'll be overcharged $5.00 for a tiny (single serving)Styrofoam cup of coffee and they have no cream or milk they serve it with powdered coffeemate.
Ocho Rios is such a scenic island and I believe it has a lot to offer. If ever I return, I'd highly recommend doing a guided excursion as the only comfortable and safe method to see the island.