Cuba is incredible with much to offer. This Cuba travel itinerary is designed for first-time visitors. It includes Havana, Viñales, Varadero, Trinidad, and Cienfuegos. This is a day-by-day travel guide, including must-see cities, monuments, incredible day trips, and bucket list experiences. There is much to see and do in Cuba; this outlines a 9-day trip. The trip is easily shortened by eliminating day trips.
Save time by reviewing my Cuba travel guide for the best time of year to visit, currency, budget, language, safety matters, public transportation, what to pack, food to eat, and travel tips. I suggest printing this itinerary and plugging your dates into each stop. Then print the linked itinerary for each stop and supplemental things to do. Make adjustments to personalize your trip. Use the search box at the end of the post to find accommodation in your price point for the number of nights indicated. Prepurchase organized day tours to ensure everything goes as planned.
READ Complete Cuba Travel Guide, What You Need to Know
READ 100 Things to Do in Havana Cuba, a Bucket List City
What is the best way to travel around Cuba?
US citizens should plan to fly into Havana from Miami. The international airport is Havana José Martí International Airport (HAV). American Airlines, Delta, and Southwest Airlines all provide direct service between the United States and Cuba. The airport is located about 30 minutes from the city center of Havana. A taxi ride from the airport is a fixed price of $30 per car, not per person. You can ask your casa particular host to arrange a taxi for you. I found it easiest to stay in Havana throughout the trip and book day trips from there. I stayed in Old Havana and found it to be walkable.
What is the Best Time of Year to Visit Cuba?
The dry season is from November to April; the weather is cool, and there is low humidity. Tourist season is between December and March. The wet season is from May through October; the heaviest storms and hurricanes in September or October.
Where Should I Stay in Cuba?
US citizens are required to stay in case particulars. You can rent a room in a family’s home and interact with them or choose to rent an apartment on Airbnb. Both will satisfy the Support of the Cuban People requirement. I booked a 2-bedroom apartment in the old town with 2 king-size beds.
How Do I Build an Itinerary That Meets the US Support for the Cuban People Requirement?
Spend the night in a casa particular
Eat at paladars (small, family-run restaurants)
Shop and book activities through privately owned businesses
Interact with locals, artisans, musicians, and your casa hosts
Contribute to and learn about the culture and society of local Cubans
Create an itinerary for doing the above for at least 6 hours per day
Keep all your itineraries and receipts for 5 years
Do not visit the list of restricted entities published by the US government
How many days in Cuba are enough?
Havana and Vinales: 4 days
Havana, Vinales and Varadero: 6 days
Havana, Vinales, Varadero, Trinidad and Cienfuegos: 9 days
This Cuba Travel Itinerary is for 9 days. Keep reading for how I made the most of my time in Cuba.
Cuba Travel Itinerary Day by Day Guide
Duration: 9 days
Cities: Havana, Playas del Este, Viñales Valley, Varadero, Trinidad and Cienfuegos
Highlights: Classic car ride in Havana, enjoy Havana’s Malecon at sunset, smoke a Cuban Cigar, relax next to turquoise water, learn to salsa dance, see the Tropicana show
Day 1 Travel Day
This itinerary includes an overnight flight. It begins and ends in Havana Cuba. Fly to Havana via Miami and take a prearranged local taxi to your casa particular to meet your in Support of the Cuban People requirements.
Head to Central Park and take photos of the nearby National Capitol of Cuba. Enjoy a rooftop drink at Hotel Inglaterra and stop at El Floridita Bar for a photo with Hemingway. Have dinner at Cafe El Dandy paladar.
Day 2 Havana City Tour
Take a city tour in a 1950s convertible tour from Parque Central. Tours run $30 per hour. Provide the driver with this list of attractions and expect the tour to run about 4 hours. Attractions to request:
- Photograph the Cuba sign from the gas station below the Hotel Nacional de Cuba
- Take a short walk through the Havana Forest and eat a donut from the vendor
- Tour the mosaics at Flusterlandia
- Take a photo with John Lennon’s sculpture at John Lennon Park
- Walk through the Cristóbal Colón Cemetery
- Stop in Revolutionary Square to take photos of the murals and in the classic car
- Drive down Reina Street y Carlos III Avenue to see the crumbling buildings
- Ask to be dropped off at Iberostar Selection Parque Central for a late lunch with a rooftop view
Visit the Museo de la Revolución in the afternoon, followed by dinner at La Guarida (reservations required). The restaurant is known for its confit suckling pig with orange reduction honey, boniato frito (fried sweet potato), and pie de limón con almendras (lemon pie with almonds). It wasn’t my favorite meal in Havana.
Day 3 Playas del Este/Santa Maria Beach
Take the Blue (T3) air-conditioned Transtur bus from Parque Central at the curb directly across from Hotel Inglaterr. Buses depart daily every 40 minutes 9AM – 6PM. The ride costs $5 round trip and takes about 30 minutes. Alternatively, use a taxi or collectivo. Rent a chair and umbrella for a few dollars and relax on the beach and have lunch at a paladar. Return to Havana in the late afternoon.
Grab a taxi from the cars located around Central Park and head to the Tropicana for dinner and a show. Arrange for the driver to return to pick you up after the show. Tip: Do not purchase the front row seats; the view is not good.
Day 4 Vinales Valley
Take a 12-hour tour booked through Civitatis to ensure it meets US travel requirements. The tour includes a visit to a tobacco farm, a traditional Cuban lunch, and a boat tour through a cave. Return to Havana in time for dinner at a local paladar on Obispo Street.
Day 5 Old Havana
Spend the day exploring Old Havana on your own. Visit Plaza Vieja and Saint Francis of Assisi Plaza before having lunch at Los Mercaderes paladar. Order the lobster in mango sauce, it was amazing! Next, visit Plaza de Armas, Havana Castle of the Royal Force, and take a photo of the Christ of Havana across the water. Stop in La Bodeguita Del Medio, birthplace of the mojito. Continue to Plaza de la Catedral and Palacio de los Marqueses de Aguas Claras. Check out the view of the Malecon from the roof of the Royalton Habana.
In the evening, watch the sunset at the Malecon and open-air dancing at Paseo del Prado before dinner at San Cristobal. I ordered the grilled lobster and it was very good.
Day 6 Varadero
Take a 12-hour tour booked through Civitatis to ensure it meets US travel requirements. This tour includes a traditional Pina Colada tasting, a visit to Saturno Cave, and time at Varadero Beach. Return to Havana in time for dinner at a local paladar on Obispo Street.
Day 7 and 8 Trinidad & Cienfuegos
Take an organized two-day tour of Trinidad and Cienfuegos from Havana by minibus through Civitatis with meals in a paladar and an overnight homestay.
On the first day, visit Zapata Swamp crocodile farm, Cueva de los Peces (natural pool full of tropical fish), Museo Girón (museum of the Bay of Pigs invasion and weapons). The overnight visit will be in a guesthouse in Trinidad. It is arranged by the tour and includes dinner with the host family. This evening, go to the steps of Casa de la Música to listen to music and watch salsa.
The second day begins with breakfast in the homestay, followed by a 3-hour tour of Trinidad. In the afternoon, enjoy a 3-hour tour of Cienfuegos before returning to Havana in time for dinner at a paladar on Obispo Street.
Day 9 Travel Day
Due to longer check-in lines, security screening, and mandatory passport checks, it is strongly recommended to arrive at the airport in Cuba 3 to 4 hours before departure for a return trip to the US. Boarding gates close 1 hour prior to departure; arriving early is crucial to avoid missing flights. There is an inexpensive lounge at the airport with a smoking section.
Have more time? Check the Havana Board of Tourism website for upcoming festivals, special events and what’s happening during your scheduled visit.
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