Sailing into Havana, ships negotiate a narrow channel with the guidance of a local pilot. Local pilots board the ship prior to entrance of most any port so that part is standard procedure.
Coming into port is quite scenic with a historic fort on the port side and the historic buildings of old Havana on the starboard.
Looking at a map of Havana, it shows 3 piers at the cruise terminal. Arriving there you see that while the one where the ship docks is in good condition, the other two derelict terminals are partly roofless and rotting.
At most ports it’s recommended to take ID with you, but often you won’t have to show it to anyone to get back onto the ship. In Cuba you have to bring your passport. First thing you do when you get into the terminal when you get off the ship and last thing you do leaving the terminal to get back on is go through customs. You need your passport and visa to get off the ship. They take a photo of you in which you are not allowed to smile and stamp the passport at that time. They need to see it again when you go back. Their photos are the only ones taken inside the port building. Passengers are not allowed to take any there.
You’re not supposed to use American money in Cuba and Cubans don’t take credit or debit cards from American owned banks so even if all you are going to do is tip people it’s best to go to the money exchange after you get through customs. Or bring along cash from somewhere else like Canada that you can use to tip people with – though they then have the hassle of exchanging that money. The ship recommended exchanging money in $50 increments to make it easier and quicker getting through the line. They keep a 10% tax on US dollars on the way into Cuba as well as the 3% exchange rate. When converting leftover CUC’s back to dollars on the way back to the ship you again pay the 3% exchange rate, but not the tax. You do not have to pay the 10% exchange tax on anything other than US dollars, just the 3% exchange rate, another good reason to bring Canadian dollars, euros, or if you happen to have some left over from a previous port stop, Mexican pesos.
The exchange booths are only fully staffed until 8pm so if you return to the ship later than that the line can be quite long and slow assuming the exchange is still open. We came on a ship that goes to Cuba every week so we just gave our leftover Cuban money to our cabin steward as a bonus tip rather than wait through that long line because he could make good use of it. Some people got rid of their Cuban money by shopping at the gift shops in the port building because they had shorter lines than the exchange did. Another option would be to spend it all before returning to the port building and avoid the lines altogether.
Cuban citizens use Cuban pesos (CUP), but foreigners use the CUC or Cuban Convertible Peso. It takes 24 CUP to make one CUC. The CUC is supposed to be equivalent to the American dollar, but since they take both a tax and an exchange rate you lose money in the exchange process.
The ship docks right in old Havana so there’s lots of historic buildings within walking distance and great views right from the ship. Walk carefully though because the surface is often uneven whether due to being paved in old cobblestones or through wear and tear or lack of maintenance. The Malecón waterfront walkway is not far from the cruise ship dock.
If you are American or cruising to Cuba on a ship sailing out of an American port you have to fit into the criteria in which Americans are allowed to visit Cuba. Cruise ships use the people to people category, and set up excursions which fulfill the requirement. Anyone who booked their cruise after June of 2017 has to do an excursion through the ship which lasts at least 8 hours on a full day visit or 4 hours on a half day visit if they want to get off the ship. Once the required excursion is complete people can then explore on their own. If the ship stays overnight or visits a second Cuban port you have to fulfill the excursion requirement again to leave the ship on a different day. The good news is that the ship takes care of your visa and mountain of paperwork when you book their excursion – at least Holland America did.
If you are not American and sailing on a ship that did not go to Cuba from an American port then you have a lot more freedom just to be a tourist because other countries do not have all the restrictions on traveling to Cuba that the USA does. If you are American these non-American cruise lines are not likely to let you book their Cuban cruise.