Set in the heart of the Caribbean, Cuba is a mosaic of vibrant culture, music and colonial charm. Come discover this enchanting island nation, where its open-hearted people, vintage cars, the legacy of revolution, and live music truly set the rhythm of daily life.
Delight in white-sand beaches and lush landscapes, UNESCO listed towns, stunning colonial architecture, and a rich historical heritage. Explore the known highlights and uncover hidden gems that inspired some of Cuba’s most famous- Che Guevara, Ernest Hemingway and the sensational Buena Vista Social Club. Roll a Cuban cigar, dance the salsa, or raise your Cuba Libre, in celebration of a truly unforgettable travel experience.
You’ll be in good company the entire trip. Local guides with a wealth of knowledge will enhance your adventure. Your Byroads host will support you throughout the trip. And a small bunch of fellow wanderers will create meaningful memories alongside you.
Arrive at Havana Airport and transfer to your hotel | Settle in and meet up with your group in the evening.
Hotel Telegrafo (or similar) – This iconic, historical colonial hotel is brilliantly located at the start of Prado Street, with easy access to historic Old Havana. It also offers a terrace style café, perfect for watching Old Havana street life.
Take a guided walking tour and continue to explore Havana’s ‘Old City’ This evening enjoy a ride through the city in a classic 1960’s convertible and watch the sunset over the Malecon and its spectacular coastline. (B)
Hotel Telegrafo (or similar)
Investigate Cuba’s famous exports with a visit to the Havana Rum Museum and later, the Partagas Cigar Factory | Tonight visit the ‘La Bodeguita del Medio’, Ernest Hemmingway’s renowned watering hole, and enjoy a Cuban Daiquiri. (B)
Hotel Telegrafo (or similar)
After an early breakfast fly to Cuba’s first colonial capital, Baracoa | Take time to explore the old town and the Matchin and La Punta fortifications | View the Parra Cross, left by Christopher Columbus in 1492 | Enjoy a canoe ride on the nearby Yumuri River. (B)
El Castillo Hotel (or similar) – Built in the 1700’s as a Spanish fortress, it is located on a hill and was built to defend the city from the attacks of buccaneers and pirates. Two hundred years later it hosted the Village Guards until the triumph of the Cuban Revolution in 1959. Today it is considered the best hotel in Baracoa, with its comfortable rooms and swimming pool.
Time at leisure to explore the stunning natural beauty of Baracoa | Wander the old streets amongst the beautiful, preserved colonial buildings | Relax at the picturesque and tranquil Maguana white-sands beach | Sample its specialised cuisine – seafood, and its chocolate-based recipes. (B)
El Castillo Hotel (or similar)
A long drive today to Cuba’s second largest city, Santiago de Cuba | Enroute, stop at Guantanamo | Check in to Santiago de Cuba for your three-night stay | Be guided over the Parque Cepedes and the stunning World Heritage Site, San Pedro Castle which overlooks the bay. (B)
Casa Grande Hotel (or similar) – Beautiful colonial hotel in the historical centre of Santiago de Cuba, right next to Cespedes Parque. Offers comfortable rooms, personalised service, a fitness centre, live music, massage service and body treatments. Roof Garden Restaurant, La Terraza Snack Bar and International Restaurant.
Embark on a guided tour of the city which includes all the major highlights | Discover the Cathedral, and the near-by City Hall, where Fidel Castro declared the success of the Revolution | Immerse yourself in the music, art and cultural delights of the famous street, Calle Heredia. (B)
Casa Grande Hotel (or similar)
Ride a local ferry boat to the tiny island of Cayo Granma | Wander the island and witness its beautiful coloured wooden houses on stilts | Enjoy lunch, then hike to San Rafael church | Return to Santiago de Cuba for a final evening in the ‘city of music and dance’. (B)
Casa Grande Hotel (or similar)
Leave Santiago de Cuba and enjoy the rich geographical diversity of Cuba -starting in the coastal, mountainous region and transitioning to the flatter, more pastoral region of its centre | Stop to explore the historical town of Bayamo | Arrive in Camaguey and explore its pretty and winding streets by bicycle taxi. (B)
Casa Particular – (or similar) – Private family-run accommodations, offering travellers and authentic and intimate glimpse into Cuban life and culture.
Drive to Trinidad, one of Cuba’s most loved and photographed destinations | Take a walking tour and explore the colourful Plaza Mayor, the heart of Trinidad | Visit the Church of the Holy Trinity | Marvel at the colonial buildings which exemplify the city’s rich history and charm. (B)
Casa Particular (or similar) – A Cuban style bed & breakfast. They are run by local families which allows a more authentic Cuban experience. It’s a wonderful glimpse into Cuban life and culture.
Time at leisure today to enjoy the town | Enjoy a swim at beautiful Playa Ancon | Walk to the ruined sugar mills in the Valle de los Ingenos | Take a hike in the near-by Sierra del Escambray mountains | Sip coffee. Relax and enjoy the local’s warm hospitality and rhythmic music. (B)
Casa Particular (or similar)
An early start to drive to Santa Clara, site of the last battle in the Cuban Revolution | Stop to reflect upon the Revolution at the Che Guevara Memorial | Call in to see local artists at work in the trendy Casa de la Ciudad | Arrive in Cienfuegos, ‘The Pearl of the South’ and enjoy a walking tour of the town. (B)
Hotel La Reunion (or similar) – Located in the historic heart of the city this hotel is known for its elegant architecture and welcoming atmosphere. Beautiful inner courtyards and comfortable rooms inspire memories of the distant past.
Drive west and stop at the infamous Bay of Pigs, site of the failed 1961 American sponsored invasion of Cuba | Dive in, swim, snorkel or just paddle in the bay | Visit the local museum | Arrive and check-in to enjoy a special roof-top dinner over-looking Havana. (BD)
Hotel Telegrafo (or similar) – This iconic, historical colonial hotel is brilliantly located at the start of Prado Street, with easy access to historic Old Havana. It also offers a terrace style cafe, perfect for watching Old Havana street life.
Breakfast concludes your tour | Taxis to the airport are available, or Byroads can organise a transfer on request. (B)
Byroads tour host, national and local guides
Arrival transfer, private air-conditioned vehicle, flight Havana to Baracoa, motorboat
10 nights’ hotel accommodation (3 to 4-star average), 3 nights’ casa particulares
13 breakfasts, 1 dinner
Entrance fees to indicated sites
Ready for travel without logistical nightmares? Your trip host has got you covered.
Every Byroads tour is supported by Steve or Bronny – two experienced travellers with a genuine passion for people. They take care of all the nitty-gritty details to ensure your trip runs smoothly – and you can focus on enjoying the moment.
Steve heads up Byroads and has over 35 years of experience in the travel industry. He’s designed and operated holidays to some of the world’s most fascinating destinations.
Like her brother, Bronny shares a keen curiosity about the world. Independently, she has journeyed far and wide – and has worked as a tour leader throughout Europe, Asia and Australia.