Why: Cuba is one of the most unique countries on earth. No where else in the Americas has experienced the time-warp quite like Cuba has. Although the country is opening up more now, the old cars, warm weather, and Caribbean beats still make this a fascinating place to visit.
Flight and Car: Check on skyscanner.com for flights. I took the buses to get everywhere in Cuba. Renting a car is also a great option for the few days that you are outside of Havana.
Day 1: Land in Havana and check out Old Havana with its fabulous cobblestone streets and malecon. Give yourself a nice walking tour to get a lay of the land. Check out El Museo de La Revolucion for history on the city and also Plaza de Armas. In the evening check out the local salsa and music which is everywhere in Havana. Stay at Hostal Red.
Day 2: Head out walking again in Havana. Go over to Morro Castle and stop in at Bodeguita del Medio. Be sure to walk by the Gran Teatro de Habana. Try some of the local street food. In the evening cruise the streets of Old Havana and enjoy the music.
Day 3: Go down to Viñales. Stay at Casa Lucy y Bartolo. In Viñales rent a bike or a moped and get out to the Valle de Viñales. Go on a hike through the beautiful farmland and make your way up to any one of the many rolling hills above the town. In the evening come back to have some more local food and music.
Day 4: Go out and visit one or two of the tobacco plantations to see where the infamous Cuban cigars come from. Your hostel will help you out with planning this with information on where to go. If you are looking for another hike, also ask about which of the limestone mountains just outside of town would make for a good adventure. Santo Tomas Cave would also be another good option.
Day 5: Go down to Trinidad. This a fabulous laid-back town. Hang out in the Plaza Mayor and make sure to go to the Bell Tower to look down on this beautiful town. Go out to Topes de Callentes National Park to see some of the nearby waterfalls. Stay in Hostal Bella Vista.
Day 6: Rent a bike and head out to Playa Ancon. It is a few miles out of town and this gorgeous beach is worth spending some time at. In the afternoon get lost in the streets of Trindad. Talk with locals who often sit on the doorsteps in the late afternoon. In the evening head over to Casa de Musica where there are always people dancing in the streets. This a great place to feel the energy that is Cuba.
Day 7: Head back to Havana and have one last walk through this memorable city and the malecon.