If you've got 2 weeks, you'll be able to hit all the highlights mentioned above, as well as some others, including Cuba's second city Santiago, a side trip to the gorgeous mogotes (limestone formations) and tobacco farms of the Viñales valley, and visits to Cienfuegos and Baracoa, two underappreciated Cuban cities. And, you get to do all this at a slightly more relaxed pace to boot. This itinerary starts off very similar to the 1-week version above, but soon diverges.
Day 1: Arrive & Settle into Havana
Arrive and settle in to your hotel. Spend the afternoon walking along the Malecón and have a sunset cocktail at the Hotel Nacional. After sunset, head over for dinner at Los Doce Apóstoles in the Parque Histórico Morro y Cabaña. Stick around for the cañonazo (cannon-firing) ceremony.
Day 2: Step Back in Time
Start the morning off 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. After lunch, head toward Parque Central and visit El Capitolio, then either the Museo Nacional de las Bellas Artes, or the Museo de la Revolución. Finish up your afternoon strolling along the outdoor art exhibit that is Callejón de Hammel, but if your second day is a Sunday, arrive here earlier for the Sunday rumba sessions. If you have a spare half-hour, drive by the Plaza de la Revolución to see the José Martí memorial and the iconic iron sculpture of the face of Che Guevara on the Ministry of the Interior building. In the evening, head to the Tropicana for dinner and a show.
Day 3: The Viñales Valley by Day, Jazz at Night
Sign on for an organized day tour of the Viñales valley. You'll get to take in some of Cuba's best natural scenery, and also visit a tobacco farm and cigar-rolling facility. You'll probably also visit the Guayabitas liquor factory in Pinar del Río, and take a quick tour through La Cueva del Indio. This jam-packed day tour should still get you back to Havana in time for a dinner at one of the city's standout paladares (private home restaurants), followed by some hot jazz at La Zorra y el Cuervo or the Jazz Café.
Day 4: Cienfuegos, la Perla del Sur
Pick up a rental car and head for Cienfuegos, a bustling port city on the southern coast, with a compact, yet very attractive colonial-era core. Get to know the old center around Parque José Martí, visiting the Catedral de la Purísima Concepción and the Teatro Tomás Terry. In the afternoon, head out to the Punta Gorda district and have a sunset drink on the roof of the Palacio del Valle. For dinner, walk downstairs to the Moorish dining room or to the basement for the tapas bar.
Day 5: Trinidad
From Cienfuegos, it's a short hop to Trinidad, with some beautiful scenery along the coast. Stay in one of the glorious casas particulares right in the colonial center of this classic little city. Spend the afternoon touring Trinidad's colonial-era landmarks, including the Plaza Mayor, the Plazuela El Jigüe, the Iglesia de la Santísima Trinidad, and the Museo Romántico. For dinner, make a reservation at Paladar Estela or Sol y Son. After dinner, stroll the area around the Plaza Mayor and listen for where the action is. It might be a salsa or son band playing on the steps below the Casa de la Música, or it might be in any one of several clubs nearby, including the excellent Palenque de los Congos Reales.
Day 6: Checking in with Che
Spend the morning walking around Trinidad and shopping at the various little street markets around town. From Trinidad, head north to Santa Clara, Che Guevara's city. Your first and most important stop here is the massive and impressive Monumento Ernesto Che Guevara, set on the Plaza de la Revolución Che Guevara. In the early evening, head to Parque Vidal, the downtown heart and soul of Santa Clara. Stop in to tour the Teatro La Caridad, and then head to Hostal Florida Center for dinner. After dinner, see if there's anything happening at Club Mejunje.
Day 7: Remedios and Back to Havana
In the morning, drive to the nearby charming town of Remedios. This is one of Cuba's smallest and best-preserved old colonial-era towns. Tour the Iglesia de San Juan Bautista, with its intricately carved and ornate baroque altar, and stop for a cool drink or light lunch at the open-air Café El Louvre right on the town's central plaza. Allow yourself a little over 4 hours to drive from Remedios back to Havana, where you'll turn in your rental car before taking a flight for the rest of your trip.
Days 8 & 9: Head East to Baracoa
From Havana, take a flight (booked well in advance) to Baracoa, the oldest, and arguably most beautiful city in Cuba. You'll definitely want to stay in the Hotel El Castillo, with its commanding setting on a hillside over the city. Spend 1 day exploring the architecture and old-world charms of the city, and another hiking the lush forests around El Yunque or the Parque Nacional Humboldt. Despite its diminutive size, Baracoa is a bustling little burg with excellent nightlife.
Days 10 & 11: Sweltering Santiago
In Baracoa, you can arrange for a transfer, Víazul bus, or private taxi to Santiago de Cuba, the island's second-largest city. If you want to be in the heart of downtown, choose the Hotel Casa Granda, while if you're looking for more comfort, amenities, and facilities, you should book a room in the Meliá Santiago de Cuba or stay in some of the city's lovely casas particulares. You'll need 2 days to fully explore this colonial-era port city, with its host of historical and architectural attractions. Be sure to schedule at least 1 night at Santiago's fabulous Casa de la Trova or its even better Casa de las Tradiciones.
Days 12, 13 & 14: Hot Sun, Cool Sands, Clear Water
Finish your trip off with some downtime at an all-inclusive resort on Cayo Largo del Sur. You'll have to fly here from Havana, and you're best off just buying a 3-day/2-night package from any of the tour desks in Havana or Santiago. You should easily be able to arrange a flight from Santiago to Havana that connects with a flight to Cayo Largo; be sure that your flight back from Cayo Largo gets you into Havana in time for your international connection and flight home. If you have time pressures, opt for one of the top-end all-inclusives at Varadero. Or, head north to the wonderful beaches of Guardalavaca, a 4-hour drive from Santiago.