Havana & Vinales
Cuba is an incredible, historic country filled with romance and timelessness. I urge you to visit soon, especially as the sanctions have been lifted. Personally, I know I will be back again. Here is a three day itinerary that I think highlights what I love about Cuba and takes you through meaningful areas and local scenes...
Day 1 - Arrive Havana in the late afternoon, check into your hotel and take a walk on the Malecon along the sea. Have dinner at Casa Miglis in central Havana, walk via Avenida Neptuno which connects Old Havana to Central Havana. After dinner, visit the Plaza Vieja in Old Havana for live music and mojitos.
Day 2 - Breakfast at your hotel, then take an antique taxi to the Museo de la Revolucion for a brief lesson in Cuban history. Have lunch at Castropol, with a view of the sea. Walk down Plaza de Marti from the Malecon, and take your time to explore the streets of Old Havana in the afternoon. Walk to Central Havana for dinner at La Guarida (reservations are a must). These walks are very short, safe and the best way to see what Havana really looks like (not to mention a photographer's dream).
Day 3 - After breakfast, find your way via water taxi to the Fortaleza and Castillo across the bay, there you will find the most beautiful view of Old Havana. Have a snack of grilled cheese at the historic Hotel Ingleterra and enjoy the beautiful old cars driving around the square. If you have time, take a vintage taxi to Vinales, which is two hours outside of Havana. The drive alone is worth it, but visit a tobacco farm and have your driver introduce you to some of the local restaurants too. Return that evening and rest up for your early departure the next morning.
Tips - There are many different places to stay in Cuba, we stayed at a Casa Particular which you can book from the states, but I would recommend doing your research and staying at a hotel. The hotels will be the only places with wifi but it will be expensive and limited. Bring extra cash in case you run out, you will not be able to use your US bank cards at all and it will be impossible to contact your bank with the limited internet. Try not to check your bags on the way to Cuba, it can take hours to retrieve them at baggage claim. Don't over pack but bring what you need, there's not much "shopping" in the traditional sense. Remember, you're going to have an amazing time!