Cuba

Day-by-Day Travel Plan

14-Day Cuba Itinerary

14 days
6 cities — Havana → Varadero → Trinidad → Santiago de Cuba → Cienfuegos → Viñales
Best in Nov, Dec, Jan, Feb, Mar, Apr

The ultimate two-week journey through Cuba. Cuba feels like nowhere else — a Caribbean island where 1950s American cars still cruise past crumbling pastel-colored colonial facades, live son and salsa spill out of every doorway, and daily life unfolds at a rhythm entirely its own. This itinerary takes you through the highlights — from iconic landmarks to local experiences.

Day-by-Day Itinerary

1

Day 1 — Arrive in Havana

Havana

  • ▸ Old Havana (Habana Vieja)
  • ▸ Malecón

Havana — Cuba’s vibrant capital, known for its colorful streets, classic cars, historic architecture, and lively culture

2

Day 2 — Explore Havana

Havana

  • ▸ El Capitolio
  • ▸ Museum of the Revolution
3

Day 3 — Explore Havana

Havana

  • ▸ El Capitolio
  • ▸ Museum of the Revolution
4

Day 4 — Arrive in Varadero

Varadero

  • ▸ Varadero Beach
  • ▸ Cueva de Ambrosio

Varadero — world-famous beach resort town with white sandy beaches, turquoise waters, and luxury hotels

5

Day 5 — Explore Varadero

Varadero

  • ▸ Josone Park
6

Day 6 — Explore Varadero

Varadero

  • ▸ Josone Park
7

Day 7 — Arrive in Trinidad

Trinidad

  • ▸ Plaza Mayor
  • ▸ Museo Romántico

Trinidad — colonial town with cobblestone streets, pastel-colored houses, and rich history

8

Day 8 — Explore Trinidad

Trinidad

  • ▸ Topes de Collantes
9

Day 9 — Arrive in Santiago de Cuba

Santiago de Cuba

  • ▸ Castillo del Morro
  • ▸ Céspedes Park

Santiago de Cuba — historic city known for its music, Afro-Cuban culture, and colonial architecture

10

Day 10 — Explore Santiago de Cuba

Santiago de Cuba

  • ▸ Santa Ifigenia Cemetery
11

Day 11 — Arrive in Cienfuegos

Cienfuegos

  • ▸ Parque José Martí
  • ▸ Palacio de Valle

Cienfuegos — coastal city with French-inspired architecture, a beautiful bay, and cultural charm

12

Day 12 — Explore Cienfuegos

Cienfuegos

  • ▸ Malecón Cienfuegos
13

Day 13 — Arrive in Viñales

Viñales

  • ▸ Viñales Valley Viewpoints
  • ▸ Tobacco Farm Tours

Viñales — a laid-back farming town in a UNESCO-listed valley of limestone mogotes and tobacco fields, and the heart of Cuba's cigar country

14

Day 14 — Explore Viñales

Viñales

  • ▸ Cueva del Indio
  • ▸ Mural de la Prehistoria