Havana
(4 nights total split between start and finish)
So much to see, so little time. You're best to concentrate your focus on Habana Vieja, where the main plazas are chock-full of museums and historic sites. Don't miss Plaza de Armas, Plaza de la Catedral, and Plaza Vieja, where Taberna La Muralla serves delicious home-brewed beer. Around Parque Central, the Fábrica de Partagás tobacco factory will give you 'Tobacco 2001' on the cigar-rolling process. In many regards the entire island is a lived-in museum: the two-part Museo Nacional de Bellas Artes displays a stunning collection of art; be sure to visit both the international and Cuban sections. Sure, it's melancholic and occasionally gory, but for a profile on the revolution the Museo de la Revolución, nearby, is de rigeur. Next, stroll the Malecón and the tree-shaded streets of Vedado, taking in the Cemeterio Colón and Plaza de la Revolución - it's a long walk, deserving a refreshing ice cream at Coppelia and a mojito pick-me-up on the garden bar of the 1930s-era Hotel Nacional. Linger for an evening of entertainment at the hotel's Cabaret Parisien followed by some bolero at Gato Tuerto, nearby.
Now pick up a rental car. Before leaving town, visit Parque Histórico-Militar Morro Cabaña (you can safely skip the evening cañonazo) then follow the Vía Monumental south to Museo Ernest Hemingway (the author's former home) and nearby Iglesia de Santa María del Rosario.