Roads and Rhythms of Cuba
About the Trip
February 27–March 8, 2026 | 10 Days
Step into the soul of Cuba on a 10-day journey through its rich history, rhythmic streets and stunning coastlines. Wander through Havana’s historic plazas, sip cocktails in Hemingway’s favourite haunts and cruise Old Havana’s waterfront Malecón in a classic car. Discover Trinidad’s UNESCO-listed old town, where colonial charm and Cuban culture collide. Dance to the island’s infectious beats with a salsa lesson, savour authentic cuisine at a family-run paladar restaurant and visit Che Guevara’s final resting place in Santa Clara. End your adventure in Cayo Santa María, where white-sand beaches and turquoise waters offer the ultimate retreat.
CAA Premier Collection Tours
One-of-a-kind departures that offer immersive and intimate group journeys.
- Every detail matters: From the moment you're met at the airport to your farewell dinner, you'll experience best-in-class service wherever you go.
- Our CAA Hosts lead you on incredible adventures to iconic destinations. They will take care of every detail on each journey.
- Travel in style: Stretch out on spacious motorcoaches while exploring during the day and rest easy at night in the best hotels each destination has to offer.
- Memorable dining: Delicious local dishes and the season’s most flavourful offerings will have you savouring every bite.
Member Exclusive Benefits
We reward all our CAA Members on our Extraordinary Explorations® tours.
- Bon Voyage Gift†
- 100 CAA Dollars®^
- 25% savings on CAA Travel Insurance◊
Package Includes:
- Airfare from Toronto or Winnipeg to Varadero and return from Santa Clara to Toronto or Winnipeg
- 4-night stay in first-class accommodation in Havana
- 2-night stay in first-class accommodation in Trinidad
- 3-night stay in first-class accommodation in Santa Maria
- 7 breakfasts, 5 lunches, 1 snack, 4 dinners and 2 all-inclusive days
- Land transportation via first-class motorcoach
- Sightseeing and entrance fees as per itinerary
- Professional English-speaking tour director throughout
- Prepaid gratuities
- Destination transfers
- CAA Host
Roads and Rhythms of Cuba
Activity Level: Moderate. Discover Cuba’s rich culture on a 10-day tour that includes classic cars in Havana, salsa in Trinidad and sun-soaked shores in Cayo Santa María.
Day 1
Havana – Depart Toronto or Winnipeg for Varadero, where your Cuban adventure begins. Meet your guide and transfer to Havana. Check into your hotel and soak in the lively atmosphere. (S)
Day 2
Havana – Explore Old Havana’s historic plazas, grand colonial buildings and lively streets by foot. Visit the Rum Museum before enjoying lunch followed by a classic car tour. This evening, dine at an authentic paladar, a family-run restaurant offering a taste of traditional Cuban cuisine. (B/L/D)
Day 3
Havana – Enjoy a full-day tour highlighting Ernest Hemingway’s life. Visit Finca Vigía, his former home, and Cojímar, the fishing village that inspired The Old Man and the Sea. Enjoy a mojito at La Bodeguita del Medio and a daiquiri at El Floridita, two of his favourite spots, before a local lunch. (B/L)
Day 4
Havana – Start your day with an energetic salsa lesson led by professional dancers. The afternoon is at leisure to rest or explore Havana’s museums, sip coffee in a lively plaza and browse local markets. (B/D)
Day 5
Trinidad – En route to Trinidad, stop in Cienfuegos, the "Pearl of the South." Walk through Parque José Martí, lined with grand architecture, and visit landmarks like Teatro Tomás Terry. Continue to Trinidad, a city where cobbled streets, music and history converge. (B/L/D)
Day 6
Trinidad – Discover Trinidad’s UNESCO-listed old town on a walking tour. Visit La Canchánchara for a traditional cocktail, explore the Palacio Cantero Museum and watch artisans at a pottery workshop. After lunch, enjoy some free time. (B/L)
Day 7
Cayo Santa María – Travel to Cayo Santa María, stopping in Santa Clara to visit Che Guevara’s mausoleum and museum. See the Armoured Train Battle site, a key moment in Cuba’s revolutionary history. After lunch, continue to your all-inclusive beachfront resort. (B/L/D)
Day 8
Cayo Santa María – Enjoy a full day of relaxation at your resort. Lounge on the beach, swim in the turquoise waters and take part in optional excursions like snorkelling or catamaran sailing. (AI)
Day 9
Cayo Santa María – Savour your final day in paradise. In the evening, enjoy your farewell dinner. (AI)
Day 10
Transfer to Santa Clara Airport for your return flight to Toronto or Winnipeg. (B)
B - Breakfast | L - Lunch | D - Dinner | S - Snack | AI - All Inclusive
Terms & Conditions
*All CAA Member prices are per person, based on double occupancy, in Canadian dollars unless otherwise indicated and are subject to change without prior notice until final payment is paid. All prices are correct at press time and apply to new bookings only, based on availability at time of booking. To receive CAA Member-exclusive benefits, there must be one valid CAA Member travelling per booking. Non-members booking Extraordinary Explorations will not receive Member-exclusive benefits.
†Bon Voyage Gift is based on one per person.
^CAA Dollars awarded per adult Member. To earn and redeem CAA Dollars, you must be a current CAA Member in good standing (CAA Membership dues paid in full by membership expiry date). CAA Dollars will be credited at time of departure. For more information on CAA Dollars, please visit www.caasco.com/caadollars.
◊CAA Travel Insurance, an Orion Travel Insurance product, is underwritten by Echelon Insurance. Twenty-five percent (25%) Member savings is made up of a ten percent (10%) Member savings as well as a promotional fifteen percent (15%) savings when you purchase an Extraordinary Explorations tour through CAA Travel, applies to CAA South Central Ontario and CAA Manitoba Members in good standing (CAA Membership dues paid in full by membership expiry date). This promotional offer is valid until December 31, 2026. Ten percent (10%) Member savings applies to Members in good standing of all other CAA clubs. Savings apply to the total premium excluding applicable taxes. Minimum premium applies. Visitors to Canada Insurance is limited to the promotional savings. Certain exclusions, limitations and restrictions apply. Subject to change without notice. A Medical Questionnaire may be required to purchase travel insurance.
Extraordinary Explorations vacations are organized and booked by CAA Travel (South Central Ontario) Inc. and CAA Manitoba (“CAA Travel”) on behalf of CAA Club Group (o/a CAA South Central Ontario and CAA Manitoba). In the event of an increase in any of the cost factors, CAA Travel reserves the right to increase the price whereby the provisions of the Travel Industry Act shall prevail. CAA Extraordinary Explorations packages are 100% non-refundable at final payment. CAA Travel service fee for cancellation prior to final payment varies by program. For full payment terms and conditions, please ask your CAA Travel Consultant. CAA Travel reserves the right to cancel or re-schedule any tour departure in accordance with operating requirements (minimum number of participants) or circumstances beyond its control. Additional fees for checked luggage or other incidentals may be incurred and vary according to itinerary and airline. Air schedules with some tours are not available at press time and may include several connections or forced overnight at passenger’s expense. CAA Travel strongly recommends the purchase of trip cancellation and emergency travel and emergency medical insurance at the time of booking.
Please note: Participants must be able to embark and disembark cruise ships and coaches without assistance as well as have a good level of mobility for walking tours in destinations where stairs and traditional cobblestone streets can be challenging. International transportation vehicles and facilities may not meet accessibility standards.
Flight
IncludedTour Itinerary
Day 1
Havana
Depart Toronto or Winnipeg for Varadero, where your Cuban adventure begins. Meet your guide and transfer to Havana, a city where history, music and culture blend effortlessly. Settle into your hotel and take in the city’s lively atmosphere. (S)
Day 2
Havana
Step into the heart of Old Havana on a guided walking tour, where you’ll visit the historic Plaza de la Catedral, Plaza de Armas, Plaza de San Francisco de Asís and Plaza Vieja. Admire the city's architectural splendour, from baroque cathedrals to pastel-hued facades. Visit the Rum Museum, where you’ll learn about Cuba’s legendary spirit and perhaps enjoy a tasting. After lunch, relive the glamour of the 1950s in an unforgettable classic convertible car tour, cruising along the waterfront Malecón and past Revolution Square. This evening, experience an authentic Cuban paladar, a family-run restaurant in a restored home, where you’ll enjoy traditional dishes infused with local flavours. (B/L/D)
Day 3
Havana
Follow in the footsteps of Ernest Hemingway on a full-day tour dedicated to the writer’s time in Cuba. Explore Finca Vigía, his former hilltop home, where his books, fishing gear and typewriter remain untouched. Continue to Cojímar, the quaint fishing village that inspired The Old Man and the Sea, where Hemingway’s presence is still felt in the stories of the locals. Stop at two of Hemingway’s favourite haunts: La Bodeguita del Medio for a mojito and El Floridita for a daiquiri before a leisurely lunch at a local restaurant. (B/L)
Day 4
Havana
Feel the rhythm of Cuba with a salsa lesson led by professional dancers. Whether you're a beginner or experienced, this vibrant and energetic dance will immerse you in the island’s culture. The afternoon is yours to explore Havana at leisure and perhaps visit a local museum, sip coffee in a lively plaza, or browse local artisan markets. This evening, enjoy a relaxed dinner at the hotel. (B/D)
Day 5
Trinidad
Depart for Trinidad, stopping en route in Cienfuegos, known as the "Pearl of the South" for its elegant French-influenced architecture. Stroll through Parque José Martí, lined with grand 19th-century buildings, and visit Teatro Tomás Terry, Palacio Ferrer and Palacio de Valle, each telling a story of Cuba’s colonial past. Continue to Trinidad, where cobbled streets, colourful facades and lively music set the scene for an evening of cultural discovery. (B/L/D)
Day 6
Trinidad
Step into another era on a walking tour of Trinidad, a UNESCO World Heritage site where time seems to stand still. Wander through beautifully preserved streets, stopping at La Canchánchara, an 18th-century house where you’ll taste a traditional cocktail made with sugarcane and lime. Visit the Palacio Cantero Museum, filled with artefacts that bring the city’s history to life, and observe skilled artisans at a pottery workshop, where age-old techniques are still practised. After lunch at a local restaurant, take time to explore a craft market or relax in a leafy square, absorbing the slow-paced charm of this historic town. (B/L)
Day 7
Cayo Santa María
Travel to the pristine beaches of Cayo Santa María, with a stop in Santa Clara where Che Guevara’s legacy is immortalized. Visit his mausoleum and museum, reflecting on the revolutionary spirit that shaped modern Cuba. See the Armoured Train Battle site, a pivotal moment in the Cuban Revolution. After lunch, continue to your luxurious all-inclusive resort, where white-sand beaches and turquoise waters await. (B/L/D)
Day 8
Cayo Santa María
A full day of relaxation at your resort. Sink your toes into powdery sand, enjoy a swim in warm Caribbean waters and indulge in the resort’s world-class amenities. For those feeling adventurous, optional excursions such as snorkelling or catamaran cruises are available. (AI)
Day 9
Cayo Santa María
Savour your final full day in paradise, unwinding by the ocean or enjoying the resort’s offerings. This evening, gather with fellow travellers for a farewell dinner, reminiscing about the incredible experiences shared throughout your journey. (AI)
Day 10
Transfer to Santa Clara Airport for your return flight to Toronto or Winnipeg, taking with you the vibrant spirit and unforgettable memories of Cuba. (B)
B - Breakfast | L - Lunch | D - Dinner | S - Snack | AI - All Inclusive