Two Week Cuba Travel Itinerary

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.