In just six years, Havana will celebrate its 500th anniversary as a functioning capital city. The architecture is incredible. There are fortresses built in the 1500’s and 1600’s that now function as museums.
On your first trip to Cuba, I strongly encourage you to spend at least your first few nights in the area known as La Habana Vieja—Old Havana (or as close to it as possible). This is roughly the area from Havana Harbor westward to Central Park. Its northern curved boundary is the Malecon seawall walkway, built by the U.S. Army Corps of Engineers in the early 1900’s. The western boundary is roughly Paseo del Marti (del Prado), which runs from near the harbor entrance south to the area around the Capitol Building and Central Park. From there, it runs roughly eastward to the commercial and cruise ship terminals. This area of just a few square miles contains numerous historical sites, museums, plazas, restaurants, shops, and musical venues & groups. It would literally take weeks to see everything. If you stay at a hotel in Old Havana, you will likely be very entertained by just walking around the block. So whether you stay in a five-star facility, a former mansion that is now a boutique hotel, or a casa particular (bed-and-breakfast inn), try to stay in Old Havana. Commercial tours in Cuba sometimes change itineraries and switch hotels. On brochures and other forms of advertising, you may see statements such as “best hotel available” or “Hotel Florida (or similar).” I recommend to my friends on a first visit to Cuba stay at a 3-star hotel in Old Havana rather than in a 5-star hotel several miles to the west.
One possible exception would be the iconic Hotel Nacionál. It is located about a mile and a half further west from Old Havana along the Malecon on a hill facing the ocean. Built in 1930, it has been the Cuban home of numerous athletes, musicians, movie stars, and heads of state from all over the world, including the United States. The Celebrity Bar has a fascinating collection of photographs of these special guests, grouped by the decade of their visit. In the front of the hotel facing the ocean are bunkers and tunnels dug in preparation for an expected full-scale U.S. Military invasión following the Bay of Pigs fiasco. There is a display of newspapers from all over the world describing events during October 1962 at the height of the Missile Crisis. (This display is closed on Sundays.) The rooms at the Hotel Nacionál can be a little stuffy, but even if you don’t stay there, it is certainly worth a visit of several hours. In addition, I’ve heard many glowing comments about their evening cabarét show from travelers who really appreciate that type of entertainment.