Begin in the Old City
AM: Start your day in La Habana Vieja. Visit the Plaza de la Catedral, the Plaza de Armas, Plaza Vieja, and Plaza de San Francisco. Be sure to tour the Museo de la Ciudad, the Castillo de la Real Fuerza, and any other attractions that catch your attention. Have lunch at La Bodeguita del Medio.
PM: As the day cools down, take a stroll on the Malecón. La Fontana -- For dinner, visit the alfresco dining area of La Fontana, a paladar known for its parillada and creative dishes.
Pinar del Rio: Cuba's Natural Side
AM: Heading two hours west from Havanna is picturesque Pinar del Rio. This region is known for its natural beauty, and its tobacco. This region grows the best tobacco in Cuba; used to make its world famous cigars.
PM: Have your first game against a local Cuban volleyball team in the early afternoon and enjoy a friendly meal together afterwards.
Head to the Beach
AM/PM: Head to La Cayería del Norte, where you will find a handful of large, luxurious resorts on some of the finest beaches in Cuba. Be sure to stop for a bit in the tiny, colonial-era town of Remedios on your way. There's excellent snorkeling and scuba diving, as well as numerous opportunities to indulge in other watersports.... Or you can simply relax.