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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)
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: 

  • Cigar factory tour o Private salsa dance lesson o Hemingway’s Watering Holes: Bar Floridita, Bodeguita del Medio 
  • Tour Hemingway’s Havana Estate - Finca Vigia ("Vigil Farm") 
  • 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)

*** Additional fees apply

* $200 airfare credit applied on CTAG-booked flights. Inquire for details.

See our Downloadable Itinerary here: Itinerary

Special Note: This itinerary is only one example of a CTAG Cuba travel adventure. We are happy to customize any Cuba travel experiences to your private friends’ family’s or affinity group’s own travel pace, energies and your unique interests much as we’ve done for travelers journeying with us “off the beaten track” on the Cuban isle ever since our beginnings in 2004. We promise to leave your group with indelible memories of your experiences in Cuba with us.

Booking Change / Cancellation Policy: Cancel or change your trip for another without charge to 60 days before departure for a full trip credit until December 1, 2022.

Change without Fees: If you book now but have to cancel your trip, you’ll receive a travel credit in the full amount you paid for your vacation that can be used for any CTAG destination or itinerary in the future.  If hotel or other lodging prices are higher at the time of rebooking, you will have to pay the difference. For further assistance, call 1-415-789-9398.

Cuba Far and Wide 2021 departure dates

  • Dec 26 - Jan 1, 2022 (10+ spots left)

Cuba Far and Wide 2022 departure dates

  • Jan 9 - Jan 15, 2022 (10+ spots left)
  • Jan 16 - Jan 21,   2022 (10 spots left)
  • Jan 30 - Feb 5, 2022 (10+ spots left)
  • Feb 13 - Feb 19,   2022 (10+ spots left)
  • Feb 27 - Mar 5, 2022 (10+ spots left)
  • Mar 13 - Mar 19,   2022 (10+ spots left)
  • Mar 27 - Apr 2, 2022 (10+ spots left)
  • Apr 10 - Apr 16,   2022 (10+ spots left)
  • Apr 24 – April 30,   2022 (10+ spots left)
  • May 8 - May 14, 2022 (10+ spots left)
  • May 22 - May 28,   2022 (10+ spots left)
  • Jun 5 - Jun 11, 2022 (10+ spots left)
  • Jul 3 - Jul 9, 2022 (10+ spots left)
  • Jul 17 - Jul 23,   2022 (10+ spots left)
  • Jul 31 - Aug 6, 2022(10+ spots left)
  • Aug 21 - Aug 29,   2022 (10+ spots left)
  • Sep 4 - Sep 10, 2022 (10+ spots left)
  • Sep 25 - Oct 1, 2022 (10+ spots left)
  • Oct 16 - Oct 22,   2022 (10+ spots left)
  • Oct 30 - Nov 5, 2022 (10+ spots left)
  • Nov 6 - Nov 12, 2022 (10+ spots left)
  • Nov 13 - Nov 19,   2022 (10+ spots left)
  • Nov 20 - Nov 26,   2022 (10+ spots left)
  • Nov 27 - Dec 3, 2022 (10+ spots left)
  • Dec 4 - Dec 10, 2022 (10+ spots left)
  • Dec 11 - Dec 17,   2022 (10+ spots left)
  • Dec 25 – Dec 31,   2023 (10+ spots left)


  • Essential Cuba Itinerary

    $2,495.00 per person. 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.

    +$62.38 service fee



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