Essential Cuba Itinerary (9 days, 8 nights)

9 days, 8 nights. $2557.38 ($2,495 + $62.38). Become immersed in the vibrant Cuban culture & experience everything from the bustling & historic city of Havana to the rural & lush Vinales Valley, Cuba's tobacco country. Maximum group size 10.
Essential Cuba Itinerary (9 days, 8 nights)


Time is TBD
Havana, Havana, Cuba



  • Licensed Travel to Cuba
  • Cuba health insurance (included/free with air ticket
  • Cuba airport departure taxes (included/free with air ticket) 
  • Private transport throughout: mini-bus, micro-bus, or taxi depending on group size 
  • Airport transfers 
  • Lodging: Private residences (casas particulares) with breakfast 
  • Meals, as shown - All breakfast and some lunches/ dinners
  • Air-conditioned transportation 
  • Tours, experiences, admissions & fees on days 1,2 and 9 and as noted

DAY 1 USA – Havana Private Residence Meal(s): Lunch and Dinner

  • Welcome to Cuba - airport greeting by guide & intro to trip 
  • Check-in and rest up at your lodging, or start your adventures from these choices (depending on arrival time): o Classic vintage 1950’s American car ride o Cooking and Mojito lesson o Tour Vivero Alamar - an experiment in socialist community living through organic farming o Art and music at Fabrica de Arte Cubano Dinner at one of our favorite paladares (“paladar” – private, family-run restaurants that fuel rapid growth of Cuba’s middle class) Buena Vista Social Club show

DAY 2 Havana Private Residence Meals: Breakfast and Lunch

After breakfast, choose from these privately guided adventures: 

o Cigar factory tour o Private salsa dance lesson o Hemingway’s Watering Holes: Bar Floridita, Bodeguita del Medio 

o Tour Hemingway’s Havana Estate - Finca Vigia ("Vigil Farm") 

o Beach time at one of our favorite Havana beaches

At your private residence, travelers relax and meet and greet their fellow travelers on their trips into the Cuban countryside and towns, followed by an optional dinner

DAY 3-4 Havana - Viñales Private Residence Meal: Breakfast

  • Guided Walking Tour of Old Havana and it's 4 main plazas 
  • Depart Havana for Pinar del Rio and the lush Viñales Valley. On the way we usually stop for lunch. Surrounded by picturesque limestone pincushion hills (“mogotes”), Viñales is a small and culturally rich town with friendly and welcoming residents and a wide variety of available outdoor activities. 
  • Travelers can explore caves, hike, bike, horseback ride or simply enjoy the views of the valley and sprawling tobacco fields below. 
  • Viñales is one of the more agriculturally productive areas of Cuba boasting an abundance of local seasonal fruits and vegetables always on offer - enormous avocados and mangoes, pineapples, papaya, guava and several varieties of sweet potatoes. 
  • Viñales and its surroundings are some of the cooler areas of Cuba, a nice escape from the mostly warm country. The nightlife is very active in town, with local residents more than willing dancers to the local live music.

DAY 5 Viñales - Cienfuegos Private Residence Meal: Breakfast

  • We head back past Havana to the French-founded city of Cienfuegos through the densely vegetated Peninsula de Zapata swamp lands, and along the beautiful Bay of Pigs. This is where the landing of counterrevolutionary exile militia took place in 1961, the notorious “Bay of Pigs” invasion. 
  • A museum here (:30 film) recounts the events of this conflict that resulted in the first defeat of a U.S backed takeover in Latin America. We will also stop at a beautiful swimming hole (cenote) resembling a huge natural tropical fish tank, and if the conditions are favorable, we’ll stop at a nearby beach for snorkeling. 
  • Cienfuegos’s appeal lies partly in the European flavor as a colonial hub, with a wide Parisian-style boulevard and elegant colonnades, its ambiance inspiring Cuba’s most celebrated singer of the Son musical genre to croon, “Cienfuegos is the city I like best”. We think you’ll agree.

DAY 6-7 Cienfuegos - Trinidad Private Residence Meal: Breakfast

  • For many visitors to Cuba, Trinidad is their hands-down favorite destination. No other colonial city in Cuba is so well preserved, and the locals (“los locales”) are extremely friendly and festive. Trinidad is steeped in religiosity none the least of which is Santeria, Cuba’s predominant AfroCuban religion.
  • What most of our travelers love about Trinidad is the nightlife. No fewer than 10 musical venues swing forth within a short walking distance of each other, many with lovely outdoor settings in courtyards and within walls of old colonial ruins. 
  • Not far inland is the Valley of Sugar Mills, Cuba’s “lost economy”. This area of rich fertile soil is where the Trinidad colonists derived most of their abundant wealth. A 10-minute drive in the opposite direction finds us at the beautiful, calm Caribbean beach, Playa Ancón. If the weather cooperates, your tour guide might propose a dinner BBQ here to witness the sun set over the ocean. Other optional activities in Trinidad are snorkeling, scuba diving, and the travelers’ favorite trek to a beautiful waterfall where you can swim in the fresh springs

DAY 8 Trinidad - Havana Private Residence Meals: Breakfast and Dinner

  • On our return to Havana we stop in at the town of Santa Clara, a key city during the Cuban Revolution. Entering into Santa Clara we see a huge statue and mausoleum holding remains and commemorating the life and contributions to the Revolution of Ernesto Ché Guevara, and and the contributions of Cuba’s revolutionary heroes who died at his side in Bolivia. The feature film “Motorcycle Diaries” recounts his exploits. A museum here is also dedicated to Ché’s amazing life. 
  • After returning from the provinces, travelers check-in and freshen up at their private residence, following which your private Guide from Days 1 & 2 for a special Cuba Farewell evening 
  • Farewell Cuba(!) dinner at one of our favorite paladares 
  • 9:00 p.m. Cannon Ceremony at the El Morro Fortress, a Havana tradition 
  •  Tropicana Night Club show or musical evening club-hopping on the streets and in the plazas of Old Havana

DAY 9 Havana - USA Meal(s): Breakfast and Lunch

  • Depending on flight schedules, enjoy your final morning in Havana before the 30-minute drive to the airport for your trip home. Activity options: 
  • o Shop for souvenirs along the Prado in Old Havana or at Cuba’s largest indoor arts & crafts expo with hundreds of small businesses, Almacenes San Jose
  • o Walk along the broad, flat central sidewalk boulevard of Havana’s Fifth Avenue (Quinta Avenida) Embassy Row past dozens of colorful foreign embassies 
  • o Stroll the Malecon to the iconic Hotel Nacional, gathering place during Havana’s “Roaring ‘50’s”, tour the lobby and enjoy the views and drinks on the Veranda overlooking Havana Harbor 
  • Airport transfer (1:30 minimum before departure)
  • Essential Cuba Itinerary
    +$62.38 Service fee
    +$62.38 Service fee