In many ways, Cuba is a cyclist’s delight. Many Cubans rely on bicycles for getting around. The scenery is magnificent, and the roads are relatively light on traffic. That said, cyclists face all sorts of hazards (potholes, errant vehicles, etc.), and refreshments (and sometimes accommodation) of any sort are often very far between.
You’ll want to come fully supplied with spare parts, including inner tubes, and stock up with plenty of snacks and drinks for each day’s journey. A mountain bike is essential.
Set out from Havana west along the coast road via Playa Baracoa and Mariel to Las Terrazas. Overnight at the Hotel La Moka.
Today head south via Soroa to the Carretera Central, then cycle west to San Diego de los Baños. Either overnight here, being sure to steep in the local thermal mineral baths, or if you have energy, continue uphill through Parque Nacional La Güira and San Andrés to Viñales.
Today you’ll want to soak in the atmosphere of the Valle de Viñales, with forays through the valley to Cuevas del Indio and other key local sights.
South to Pinar del Río, where the sights are few. Continue west to San Juan y Martínez to visit Finca El Pinar San Luís to learn the fine art of tobacco-growing from world-renowned farmer Alejandro Robaina.
Head east along the Carretera Central to Jovellanos, making a detour en route to see San Miguel de los Baños. Turn south at Jovellanos and cycle through citrus plantations to Jagüey Grande, where you can overnight at Motel Batey Don Pedro.
Today head south through the Ciénaga de Zapata. Sights en route include Museo Memorial Comandancia FAR, a small museum at the former Australia sugar-processing factory, and a crocodile farm at La Boca, where a pleasant restaurant serves decent meals. Passing through Playa Larga, you’ll arrive at Playa Girón (setting for the Bay of Pigs invasion of 1961) with time to explore the museum and relax on the beach.
Eastward, the road gives way to dirt as you pass Caleta Buena (good for snorkeling). Continue along the coast (you’ll need a mountain bike for the track) to Jagua, where you can catch a ferry across the mouth of Cienfuegos Bay. Head east a short distance to Finca los Colorados , a superb casa particular.
Follow the coast road (Costanera Sur ) east via Arimao and Guajimico. You can eat midway at Hacienda La Vega . The Sierra Escambray  loom to the north as the road runs along the shore. Eventually you’ll cycle the hill into Trinidad , your destination.
You deserve a rest today. Spend the day exploring the colonial plazas of Trinidad on foot.
Either cycle to Playa Ancón  for a day at the beach, returning via Boca , where you can spend beachtime among Cubans; or take a round-trip into the Valle de los Ingenios , with lunch at Hacienda Iznaga . This afternoon, return to Havana  on a Víazul bus .
Transfer to the airport for your departure flight.