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Two Week Cuba Travel Itinerary
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Havana Itinerary
Overview
This two week Cuba travel itinerary begins in Havana, Cuba’s bustling capital. It offers a unique blend of colonial history, vintage cars, and vibrant nightlife. This city is the perfect starting point to immerse yourself in Cuban culture.

How long to stay in Havana
3 days.
How to get to Havana
Fly into José Martí International Airport (HAV). Taxis to the city center take 30 minutes and cost $20–30 USD.
Best hotels to stay in Havana
- Hostel La Maestranza (Budget): Affordable and located in Old Havana. Book Here
- Casa Densil (Mid-range): Comfortable and centrally located. Book Here
- Iberostar Parque Central (Boutique): Luxurious colonial-style hotel. Book Here

What to do in Havana
- Stroll through Old Havana (Habana Vieja), a UNESCO World Heritage Site. (Free)
- Visit the Revolution Museum to learn about Cuban history. ($8 USD)
- Take a ride in a classic car around the city. ($30–50 USD/hour)
- Walk along the Malecón, especially at sunset. (Free)
- Explore Fusterlandia, a mosaic-filled art neighborhood. (Donation-based)

Where to eat in Havana
- La Guarida ($$$): Iconic rooftop dining (Google Review: 4.6).
- El Chanchullero ($$): Modern Cuban cuisine (Google Review: 4.5).
- El Dandy ($): Budget-friendly tapas (Google Review: 4.7).

Modes of transport in Havana
- Taxis and Colectivos: Convenient for getting around; negotiate fares.
- Walking: Ideal for exploring Habana Vieja.
- Public Buses: Affordable but crowded.
Havana digital nomad rating
3.5/5. Pros: Charming atmosphere, decent Wi-Fi in specific cafes. Cons: Limited coworking spaces. Nomadlist Havana
Viñales Itinerary
Overview
This two week Cuba travel itinerary includes Viñales, a lush valley known for its tobacco farms, dramatic limestone hills, and serene countryside. It’s the perfect destination for a tranquil escape into Cuba’s stunning natural beauty.

How long to stay in Viñales
2 days.
How to get from Havana to Viñales
- Take a Viazul bus (3–4 hours; $12 USD) from Havana bus station to Viñales. Alternatively, hire a taxi colectivo for a faster and more private journey (2.5 hours; $20–30 USD).
Best hotels to stay in Viñales
- Villa Paradiso (Budget): Cozy with mountain views. Book Here.
- Casa Nolo (Mid-range): Great hospitality. Book Here.
- Hotel E Central Viñales (Boutique): Central and charming. Book Here.

What to do in Viñales
- Visit a tobacco farm and learn how cigars are made. ($10–15 USD)
- Hike or horseback ride through the Viñales Valley. ($20–30 USD)
- Explore the Indian Cave by boat. ($8 USD)
- Take in the view at Los Jazmines Viewpoint. (Free)

Where to eat in Viñales
- El Olivo ($$): International and Cuban dishes (Google Review: 4.6).
- Paladar La Cuenca ($): Great local flavors (Google Review: 4.5).
- Balcón del Valle ($$): Stunning valley views (Google Review: 4.7).

Modes of transport in Viñales
- Taxis: Best for reaching attractions outside town.
- Bicycles: Rent for $10/day to explore locally.
Viñales digital nomad rating
3/5. Pros: Beautiful scenery, decent homestay Wi-Fi. Cons: Limited modern infrastructure.
Cienfuegos Itinerary
Overview
This two week Cuba travel itinerary continues in Cienfuegos, known as the “Pearl of the South.” With its French-inspired architecture, picturesque bay, and laid-back vibe, it’s a charming and elegant coastal destination.

How long to stay in Cienfuegos
1 day.
How to get from Viñales to Cienfuegos
- Take a Viazul bus (7–8 hours; $25 USD) with a transfer in Havana. Alternatively, book a taxi colectivo for a more direct route (5–6 hours; $40–50 USD).
Best hotels to stay in Cienfuegos
- Hostal Sol (Budget): Budget-friendly and central. Book Here.
- Casa de Valle (Mid-range): Comfortable and authentic. Book Here.
- Hotel La Union (Boutique): Colonial elegance. Book Here.

What to do in Cienfuegos
- Walk along Paseo del Prado and explore Parque Martí. (Free)
- Tour Palacio de Valle, a stunning Moorish-style palace. ($5 USD)
- Enjoy a boat trip to Jagua Castle. ($20 USD)

Where to eat in Cienfuegos
- Doña Nora ($$): Rooftop dining (Google Review: 4.5).
- Paladar Ache ($): Budget-friendly Cuban cuisine (Google Review: 4.6).
- Las Mamparas ($$): Great seafood (Google Review: 4.7).

Trinidad Itinerary
Overview
This two week Cuba travel itinerary includes Trinidad, a perfectly preserved colonial town and UNESCO World Heritage Site. Known for its cobblestone streets, vibrant culture, and proximity to stunning natural wonders, it’s a must-visit destination.

How long to stay in Trinidad
3 days.
How to get from Cienfuegos to Trinidad
- Bus (Viazul): 1.5 hours, $6 USD.
- Taxi colectivo: 1 hour, $10–15 USD.
Best hotels to stay in Trinidad
- Hostal Anita (Budget): Cozy and friendly. Book Here.
- Casa Colonial ($$): Traditional charm in a historic house. Book Here.
- Iberostar Heritage Grand Trinidad (Boutique): Elegant and centrally located. Book Here.

What to do in Trinidad
- Wander the Plaza Mayor and visit its surrounding museums like the Museo Romántico. ($5 USD per museum)
- Dance the night away at the Casa de la Música on the steps of Trinidad. (Free–$5 USD)
- Explore the natural beauty of Topes de Collantes National Park. ($15–20 USD)
- Visit Playa Ancón, a nearby white-sand beach. (Free, $10 USD for a taxi).

Where to eat in Trinidad
- La Redacción ($$): International cuisine with Cuban influences (Google Review: 4.6).
- San José ($$): Local and international dishes (Google Review: 4.7).
- La Botija ($): Affordable tapas and cocktails (Google Review: 4.8).

Modes of transport in Trinidad
- Taxis and Colectivos: Common for nearby attractions.
- Bicycles: Available for rent to explore the area.
Trinidad digital nomad rating
3.5/5. Pros: Picturesque, cultural hub. Cons: Wi-Fi only in hotspots.
Santa Clara Itinerary
Overview
This two week Cuba travel itinerary continues in Santa Clara, a city steeped in historical significance from the Cuban Revolution. Known for its ties to Che Guevara, it’s a destination rich in history and revolutionary landmarks.

How long to stay in Santa Clara
1 day.
How to get from Trinidad to Santa Clara
- Bus (Viazul): 2 hours, $10 USD.
- Taxi colectivo: 1.5 hours, $15–20 USD.
Best hotels to stay in Santa Clara
- Hostal D’ Cordero (Budget): Classic colonial house. Book Here.
- Casa Martha ($$): Great location with friendly hosts. Book Here.
- Hotel America (Boutique): Stylish and modern. Book Here.

What to do in Santa Clara
- Visit Che Guevara’s Mausoleum and Monument, a tribute to the revolutionary. (Free)
- Explore the Armored Train Monument, a pivotal site of the Cuban Revolution. (Free)
- Stroll through Parque Vidal, the city’s social hub. (Free)

Where to eat in Santa Clara
- El Alba ($$): Cuban classics in a central location (Google Review: 4.5).
- La Marquesina ($): Affordable and tasty (Google Review: 4.6).
- Sabore Arte ($$): Fusion dishes with a twist (Google Review: 4.7).

Varadero Itinerary
Overview
This two week Cuba travel itinerary continues in Varadero, Cuba’s most famous beach destination. With its pristine sands, crystal-clear waters, and numerous resorts, it’s the perfect spot to relax and unwind.

How long to stay in Varadero
2 days.
How to get from Santa Clara to Varadero
- Bus (Viazul): 4 hours, $15 USD.
- Taxi colectivo: 3 hours, $50 USD.
Best hotels to stay in Varadero
- Casa D’Os ($$): Comfortable and family-run. Book Here.
- Be Live Experience Las Morlas ($$$): Affordable all-inclusive. Book Here.
- Royalton Hicacos ($$$): Luxury beachfront resort. Book Here.

What to do in Varadero
- Relax on Varadero Beach, known for its powdery white sand. (Free)
- Visit the Cueva de Ambrosio, an ancient cave with petroglyphs. ($5 USD)
- Snorkel or dive in the Coral Beach area. ($20–40 USD)

Where to eat in Varadero
- Varadero 60 ($$): Modern Cuban dining (Google Review: 4.7).
- La Gruta ($): Budget-friendly seafood (Google Review: 4.6).
- Waco’s Club ($$$): Gourmet cuisine (Google Review: 4.8).

Cayo Santa Maria Itinerary
Overview
This two week Cuba travel itinerary concludes in Cayo Santa Maria, a pristine island in Cuba’s Jardines del Rey archipelago. Renowned for its turquoise waters, white-sand beaches, and luxurious resorts, it’s the ultimate destination for relaxation.

How long to stay in Cayo Santa Maria
2 days.
How to get from Varadero to Cayo Santa Maria
- Taxi colectivo: 5–6 hours, $80–100 USD.
- Bus (Viazul): Not a direct route; private transport is recommended.
Best hotels to stay in Cayo Santa Maria
- Melia Cayo Santa Maria ($$$): Elegant all-inclusive. Book Here.
- Iberostar Ensenachos ($$$): Luxury resort with private beach. Book Here.
- Villa Las Brujas ($$): Budget-friendly beach retreat. Book Here.

What to do in Cayo Santa Maria
- Relax on Playa Perla Blanca, a secluded white-sand beach. (Free)
- Snorkel in the clear waters of the surrounding coral reefs. ($20–40 USD)
- Take a catamaran tour of the nearby islands. ($50–80 USD)

Where to eat in Cayo Santa Maria
- Meals are generally included in all-inclusive resorts.
Cayo Santa Maria digital nomad rating
2/5. Pros: Stunning scenery. Cons: Limited connectivity.
Extend Your Trip by visiting Santiago de Cuba
If you have a few more days extend your two week Cuba travel itinerary and squeeze in a visit to Santiago de Cuba, Cuba’s second-largest city. It is a vibrant cultural hub known for its Afro-Cuban heritage, revolutionary history, and lively music scene. It offers a unique energy distinct from Havana and a deep connection to Cuba’s historical roots.

How long to stay in Santiago de Cuba
2 days.
How to get from Cayo Santa Maria to Santiago de Cuba
Take a Viazul bus from Santa Clara to Santiago de Cuba (10–12 hours; $35 USD). Alternatively, book a domestic flight from Santa Clara’s Abel Santamaría Airport to Santiago de Cuba’s Antonio Maceo Airport (1.5 hours; $150–200 USD).
Best hotels to stay in Santiago de Cuba
- Casa Colonial 1893 (Budget): Cozy and centrally located. Book Here.
- Hotel Casa Granda ($$): Iconic property with a rooftop bar. Book Here.
- Melia Santiago de Cuba ($$$): Modern amenities and a pool. Book Here.

What to do in Santiago de Cuba
- Visit the Revolution Square and learn about its role in Cuba’s history. (Free)
- Explore Castillo de San Pedro de la Roca, a UNESCO-listed fortress overlooking the bay. ($5 USD)
- Dance and enjoy live music at the iconic Casa de la Trova. ($5–10 USD)
- Pay respects at the Santa Ifigenia Cemetery, where Fidel Castro is buried. (Free)

Where to eat in Santiago de Cuba
- St. Pauli ($$): Delicious Cuban-German fusion (Google Review: 4.5).
- Compay Gallo ($$): Authentic Cuban cuisine (Google Review: 4.6).
- El Madrileño ($): Budget-friendly with traditional dishes (Google Review: 4.4).

Modes of transport in Santiago de Cuba
- Taxis and Colectivos: Convenient for city travel.
- Walking: Ideal for exploring the historic center.
- Public Buses: Cheap but crowded and irregular.
Santiago de Cuba digital nomad rating
3/5. Pros: Vibrant culture, good cafes. Cons: Limited internet.