We recently completed a 10 day cruise around Cuba on the Azamara Journey. This was our 4th cruise in total and our first on Azamara. We chose Azamara mostly because of the itinerary and that it's a small ship experience marketed as being more upscale and luxurious than the typical mega-ships. We have been wanting to visit Cuba since they opened it up to Americans and thought a cruise would be a great way to see more than just Havana.
After some initial snafus with our reservation that was graciously resolved by Bonnie over on the CruiseCritic discussion boards, we boarded in Miami for our 10 circle trip around the Cuban island with stops in Santiago de Cuba, Grand Cayman, Cienfuegos and Havana. The most appealing part of the itinerary was the promise of multi-day stays in port rather than the usual arrive-at-8am-leave-at-5pm schedules of other cruise lines.
Which leads me to our first big gripe with Azamara: it was only after plotting the arrival/departure times on the calendar that we realized that the "extended" time in port was very misleading. On the itinerary, it listed only 1 day at sea but in actuality we ended up with almost 4 full sea days. For example, days 3 & 4 were listed as in port in Santiago, however, we arrived at 8am on Tuesday and left at 6am Wednesday. That's not 2 days - that's one day + one night. Wednesday turned out to be really a sea day but that's not how it was shown on the schedule.
All in all it is a great outside cabin. The extra space is nice and the location is away from elevators and stairs so you don't get a lot of noise from the hallway. If you can't afford a veranda or suite then 6004/6005 are good options. 7006/7007 one deck up is probably even a bit better.
Miami is Miami. Don't venture too far into the city center. Book a hotel close to the cruise terminal the night before and Uber/Taxi to your ship.
2nd biggest city in Cuba. Not much to do in town. Shopping is limited and not much to buy anyway. We heard the excursion to the fort outside the city was the main attraction. We took a taxi to the National Cemetery and saw Fidel's grave, memorial to Jose Marti and watched the changing of the guard at the top of the hour. Then ate lunch at a rooftop paladar before heading back to the ship.
Georgetown is a major stop for most cruise lines and there were 4 other ships in port that day which is typical. The area by the docks is swarmed with tourists and souvenir shops selling cheap junk (or majorly expensive goods like Rolex due to no sales taxes).
Only thing really to do is go to the beach. Take a taxi or local bus up the main road about 2-3 km to Seven Mile beach. Doesn't really matter where as it will still be crowded. Bring a towel, sunscreen and beer.
We took a shore excursion up to the mountains about an hour away. Hiked up to El Nicho waterfalls which was spectacular. Great views and stunning scenery. Bring your swimsuit and you can take a dip in one of the crystal clear pools along the path. Had lunch at the small restaurant at the base which was pretty good. Live music too.