Wyoming 2010 -
My husband and I were on the Insignia Cuba cruise over Christmas last year and did all of the cuban ports on our own. The first day in Santiago we just walked "up" to the center of town, stumbled on this bar with music - "El Traguito" https://www.businesstimes.com.sg/life-culture/deep-in-the-birthplace-of-cuban-rum-and-the-daiquiri and hung out for the afternoon. The second day we hired a taxi from inside the port who took us to see the changing of the guards at Fidel's gravesite along with various stops (including a cigar/rum shop stop). Yes, the "accosting" was intense in Santiago, but only those first few streets outside of the port. Once you got past those first couple of streets and with being persistent with "no thank you!" (and keep walking, act like you know where you are going), you will be able to navigate the town on your own. Be prepared, town is "up hill"!
In Cienfuegos, our first day we hired a private tour to take us to Trinidad (a UNESCO World Heritage City). Gio was our tour guide (#2 in Trip Advisor). We hired him for the whole day which included a private car. We went to Casa del Alfarero for pottery gifts, a new brewery in Trinidad for a couple of beers, a cafe for a nice cuban coffee (with ice cream) and did lots of walking with great photo opportunities within Trinidad. The streets in Trinidad are cobblestone, so if you have mobility problems, it will be a challenge getting around. Gio also gave us a quick tour of Cienfuegos on our way back to the ship so that we could have an idea on what to explore the next day (on our own).
The second day in Cienfuegos, we started to walk into the center of town to "Parque Jose Marti" (not really far). Along the way, we were approached by a bicycle rickshaw driver for a ride to the "Parque" and back to the ship for $20 for an hour. Basically, he rode us into town, gave us a quick tour, showed us where to shop and where to find him in the "parque" after our "adventures". We were able to walk into the main shopping district which was quite lively for Christmas day, check out the Hotel La Union (for great photos from the rooftop) then walk back to the "Parque" to visit a store for last minute coffee and cigars for folks back home and caught part of Christmas mass at the Church. Our rickshaw rider took us right back to the port.
We did not go to any restaurants while we were on any tours in Cuba, only because we had excellent food on the ship and really needed to cut back a little during our land visits.
https://www.flickr.com/gp/gtnorton/jt9Thx - photos from our cruise