Half the charm is just the drive out to his old home, Finca Vigia, and the view it commands of Havana. The house itself is showing the years of neglect, and you are not permitted inside. You are allowed, however, to look through the windows, but you'll be under constant surveillance. A squad of militant librarians hiss and snap their fingers at you if you even look like you may be thinking about looking closely at something. Here you'll also find the true original Pilar, Hemingway's fishing boat, despite the claims of some tackle shop in Fort Lauderdale to have the original.
A small fishing village just east of Havana, where Hemingway kept his boat, Pilar. This was the backdrop to his book The Old Man and the Sea, and, until recently, the home of Gregorio Fuentes, his boat captain. Many claim that Fuentes was also the inspiration for the protagonist in the book. Before he died, Fuentes was still available to talk about "Papa" and marlin fishing (he used to tell me that the big numbers of fish came in June but the biggest marlin were caught in September). The Terraza restaurant is right on the water and has some nice of photographs of Cojimar back in Hemingway's day.
Playas del Este
A beautiful beach, protected by sand dunes, and dotted with little ranchos where you can sit, listen to live music, and get a bite to eat with a cold beer. Heaven. Hire a gypsy cab in Havana and head out here to spend a great day. You'll need to sneak past the guards at the tunnel east of Havana (cigarettes and crumpled dollars at the ready!), but once you get past them, it's clear sailing. Your driver will park with all the other gypsy cabbies in a makeshift parking lot, where they'll spend the time comparing cars with the other drivers and taking a siesta.
Located just off Plaza de la Catedral, this is another great spot for a cold drink and something to eat in the afternoon. Avoid the temptation to try the seafood and stick with the Cuban staples (chicken or pork chops). While it may not be the finest dining you will experience the atmosphere of the old city makes everything taste better. The owners usually have live music and will do their best to keep the beggars, as well as others trying to separate you from your money, at a distance.
It's touristy, it's overpriced, and the service is surly (especially the old guy with the glasses and all the goofy buttons on his vest), but after a day of walking around the amazing streets of Havana on a warm day, there's nothing, absolutely nothing on Earth, like a daiquiri at La Floridita. This was a favorite haunt of Hemingway, and there is even have a stool roped off in what was his favorite place to sit. Don't worry about having to decide what flavor of daiquiri you want because there's only one kind: a cool and zesty lemon. If you are thinking about getting a meal here, forget it. Have another daiquiri (one makes you lopsided anyway) and another bowl of salted plantains instead.
If you too live by the adage "You can't put a price tag on a good time," then you'll want to make sure to stay at the Hotel Nacional. Once the playground of gangsters and movie stars, the Hotel Nacional is the culmination of everything you could imagine about the heyday of Cuba. With elegant gardens and stunning ocean views, the Hotel Nacional still attracts the "A" list of entertainers and international dignitaries. If you want to make sure you blend in with the other "stars," men should make sure to don their guayabera shirts and slacks (shorts are for little boys), and women should put on their finest summer dress. While money may not be plentiful in Cuba, it's no excuse for not dressing properly, especially when strolling through the lobby of the Hotel Nacional.