Two Weeks in Cuba: Perfect Itinerary for First Time Visitors

Here’s our two weeks in Cuba itinerary!

Hoping to visit Cuba independently (i.e., not on a tour)? Then, I’m your gal! Cuba is one of my favorite travel destinations. To me, there’s nowhere in the world like Cuba, and it warms my heart whenever I think of this amazing island.

And we recently spent a memorable two weeks in Cuba, we started in Havana and ended in Varadero before flying home to Whistler Canada.

Traveling to Cuba is like stepping back in time, there’s no McDonald’s or Starbucks here. Damn, you’d be hard-pressed to find a grocery store in the capital Havana. There’s either no internet or very slow internet. And the transport system sucks. It’s a country of vast contrasts, from the white sand and palm trees of Varadero to the steamy, dusty, colorful streets of Havana. But those quirks are exactly why we love Cuba!

So, what are you waiting for? Here’s our ultimate two weeks in Cuba itinerary. I’ll share with you how long to spend in each destination, tell you why each destination listed is worth visiting, and list the best hotels, restaurants and things to do in each spot.

Perfect Two-Week Itinerary for Cuba

This itinerary starts in Havana, the biggest city in Cuba, and also where the island’s main international airport is located – Jose Marti International Airport (HAV). You will start this adventure with 4 nights in bustling Havana, then head onto rustic Viñales (where tobacco is grown and you can go horse-riding).

Next, you’ll move onto Trinidad – a pretty, smaller version of Havana. And you’ll end the trip with 3 days in Varadero, a popular tourist resort that’s home to one of the best beaches in Cuba. From here you can fly home as the second-biggest international airport in Cuba is just 30 km from Varadero, called Juan Gualberto Gomez Airport.

Be mindful, though, that public transport in Cuba can be unreliable. So, you may find yourself paying for a private transfer between towns (which can be pricey!)

Havana (4 Nights)

Havana is the biggest city in Cuba and it couldn’t be more different from the other cities we’ve visited on our travels. Yep, the Cuban capital offers a delightful mix of old-world architecture, with its colonial buildings and classic American cars. Walking through Havana, you’ll feel as though you’ve stepped back in time to the 1950s.

I’ll be honest, I’ve been obsessed with Havana since I watched Dirty Dancing 2: Havana Nights. And since then, I promised myself I’d celebrate a milestone event in Havana. So, I visited Havana for the first time to celebrate my 30th birthday!

Havana’s magic. Havana’s not perfect; in fact, it’s kind of dirty and gritty. The buildings are grand but crumbling, and the light here is epic it’s honestly like walking through a very pretty Instagram feed. The Cubans leave their doors wide open. They sit on their front step, chatting with their neighbors. Their kids run barefoot on the street.

The Malecon at dusk is the best place in the world. There’s a passion, a resilience about the city, kind of like an eff you to the non-believers. Yes, our buildings are crumbling, our streets are dusty, but we’re here, and we’re dancing in the streets. I’ve thought about Havana every day since I returned.

As for the best restaurants in Havana, we dined at and loved San Cristóbal Paladar and La Guarida. These are two of the best and most famous eateries in the city!

P.S. It may be a good idea to split your stay in Havana into 3 nights and 1 night. That’s because to get from Viñales to Trinidad, you must go via Havana. And it may be nice to break the long journey up with an overnight stay in Havana.

Best things to do in Havana:

1. Party at Fabrica de Arte

Fabrica de Arte Cubano is so much more than a nightclub. Contained within an old cooking oil factory. ‘Fabrica’, as it’s known to locals, is an art gallery, a live music venue, a restaurant, and a street food stall. It has a variety of music rooms playing different genres.

The best thing is that you get a stamp card upon entry, and when you buy a drink or even food, your server simply stamps the card, and you pay for what you consumed when you exit. Brilliant. No unnecessary queues at the bar.

2. Watch the locals boxing at Rafael Trejo Gym 

The Rafael Trejo Gym is definitely a unique, off-the-beaten-path thing to do while in Havana. But we really enjoyed watching the locals (who were very talented) in the boxing ring. The locals were so friendly to us and we enjoyed spending the afternoon chatting with them. may not be an activity most people consider for a vacation in Havana. There’s a small fee payable to the receptionist before you enter.

3. Explore Old Havana (Habana Vieja)

A UNESCO World Heritage site, where you can wander through cobblestone streets lined with colonial architecture and lively plazas.

We recommend starting at Plaza de la Catedral, home to the iconic Cathedral of Havana, and then making your way to Plaza Vieja, where you can relax at a café and soak up the local atmosphere.

Don’t miss a visit to The Malecón, try to save a visit here for sunset, if you can.

For a taste of Cuban culture, stop by the Museo Nacional de Bellas Artes to admire the extensive collection of Cuban art, or catch a live performance at the Gran Teatro de La Habana.

4. Visit Fortaleza de San Carlos de la Cabaña

The Fortaleza de San Carlos was built by the Spanish in the 18th Century to protect against pirates. Today, it stands as a testament to the island’s strategic military importance. As you explore its massive walls and intricate architecture, you’ll find museum exhibits detailing Cuba’s colonial history and revolutionary periods. One of the highlights of a visit here is the nightly cannon ceremony.

5. Get driven around in a classic car

Ride along the Malecon in a beautifully restored classic car. The best choice of classic cars can be found at Parque Central. Some drivers speak better English than others and nearly all will take you to Revolution Square. Be sure to haggle the price, it cost us around 50 CUC for one hour.

Where to stay in Havana:

My recommendation is to stay at a Casa Particular instead of a hotel in Havana. A Casa Particular is when a local rents you a spare room in their home (usually with breakfast and/or dinner included).

Similar to B&B or Guest House. It’s a great way for you to save money whilst giving back to the locals. Each Casa displays the same symbol – a double-sided arrow – somewhere near the entrance.

As for the best hotels in Havana, the Iberostar Parque Central is a great option. This 5-star hotel is located in Parque Central and has an incredible outdoor pool and terrace area.

Viñales (4 Nights)

Hidden away in the lush Viñales Valley, this charming town is famous for its jaw-dropping views, featuring striking limestone hills called “mogotes” and green tobacco fields. One of the best things to do in Viñales is to go horseback riding through the stunning countryside and get a tour of a tobacco farm.

Viñales lets you dive into the heart of Cuban life with its cute colonial buildings and lively culture. You can get a real taste of the local vibe by visiting the central square in the evening, where locals dance and you can buy delicious Mojitos from pop-up stalls.

We reached Viñales by Viazul bus, which cost around $10 USD one-way. The journey took around 4 hours.  

Best things to do in Viñales:

We did a guided horseback riding tour through the Viñales Valley, a UNESCO World Heritage site, to the tobacco plantations, organized by our Casa Particular. The ride through this stunning landscape dotted with mogotes and unique limestone hills had us in awe. And the farm tour gave us a fascinating insight into traditional cigar-making processes.

The Cueva del Indio, an impressive cave with an underground river, is another fascinating thing to do in Viñales. We also got a driver to take us to Cayo Jutias, which is about an hour and 20 minutes drive away. This beach is so stunning, and because it’s secluded, it’s so peaceful.

On two out of the three evenings we were in Viñales, we hiked up to Hotel Los Jazmines for sunset. The view is stunning and the drinks from the bar were reasonably priced. Quite close to Hotel Los Jazmines is the Sunset Restaurant – we had dinner here one evening and the sunset views really are incredible. The food was good, too.

Where to stay in Viñales:

As I said, we stayed in a Casa Particular in Viñales, we arranged it through our Casa host in Havana, and it was a perfect, cozy stay.

Hotel Los Jazmines is an iconic hotel on the outskirts of Viñales, as I said, we came here two nights for drinks and to watch the sunset. The rooms are basic, but the views and the outdoor swimming pool are wow-worthy!

Trinidad (3 Nights)

Trinidad is another Cuban city that has you feeling like you’ve stepped into a time machine. It’s a UNESCO World Heritage site, known for its cobblestone streets and pastel buildings.

To get from Viñales to Trinidad, your best option is to go via Havana and spend the night there, and head to Trinidad by bus the next day. This will take 4 hours. Your next best option is to get a private minibus from Viñales to Trinidad, but this will take over 7 hours!

Be sure to wander around Plaza Mayor, the heart of Trinidad, which is surrounded by museums like the Museo Romántico. This small museum is well worth a visit as it provides a glimpse into the town’s opulent past. And Casa de la Música is the perfect spot to enjoy live music and salsa dancing.

Another of our favorite things to do here was to climb the bell tower at the Iglesia y Convento de San Francísco de Asís. The views from up here were wow-worthy!

You’ve also got the lush Valle de los Ingenios nearby, which is sprinkled with sugar plantations and sugar mills. Which were once the source of Trinidad’s wealth. And the gorgeous beaches of Playa Ancón, where you can kick back and relax, are a short drive away, too.

We actually spent a full day at Playa Ancón, we organized a tour in a classic car here through our Casa Particular. It was amazing, and the tour ended with a lobster dinner on the beach that our guide had caught and cooked over a BBQ for us.

Best things to do in Trinidad:

Our day trip to Playa Ancón was memorable, but actually our favorite thing we did in Trinidad was a guided tour of the Valle de los Ingenios (Valley of the Sugar Mills). During the full-day tour, we wandered around the ruins of San Isidro de los Destiladeros and climbed the watchtower at Manaca Iznaga (which had epic views of the surrounding valley).

My husband’s favorite part of the day, though, was riding the old diesel-hydraulic tourist train through the valley.

Where to stay in Trinidad:

We also stayed at a Casa Particular in Trinidad, we arrived with nowhere booked. So, my husband walked around the city asking if any Casas had available rooms while I waited in a Cafe. As I said, each Casa displays the same symbol – a double-sided arrow – somewhere near the entrance.

Luckily, the one that had a room free was cheap and the elderly couple who run it were adorable and so helpful.

If you’d prefer a hotel, then Iberostar Grand Trinidad, comes highly recommended.

Varadero (3 Nights)

Finally, we recommend ending your two weeks in Cuba in Varadero. A very popular tourist resort (home to lots of all-inclusive hotels) and also home to one of the prettiest beaches in Cuba. Yep, Varadero Beach has the whitest sand, the bluest water, and it’s never too busy. This is because most tourists tend to use the beaches at their all-inclusive resorts.

We spent our two full days in Varadero just relaxing on the beach (the weather was perfect). We also ate at a fantastic restaurant for dinner both nights – it was called Varadero 60.

If you don’t want to sunbathe the whole time, some other fun things you can do in Varadero include –

• Explore the Varahicacos Ecological Reserve to see diverse wildlife and ancient cave paintings.
• Go on a day trip to the nearby town of Matanzas – this small town is known for its unique Afro-Cuban culture.

Like I said, the second-biggest international airport in Cuba is just 30 km from Varadero, it’s called Juan Gualberto Gomez Airport. So, you can fly home from there, if possible. Or get to Havana Airport (HAV), which is a 2.5-hour drive away to catch your flight home.

Where to stay in Varadero:

We split our stay in Varadero up into two – we stayed at an all-inclusive hotel (called Hotel Sol Caribe Beach) for two nights and one final night at a sweet Casa Particular close to Varadero Beach.

Hotel Sol Caribe is a lovely 4-star property on Playa Azul. It boasts two large swimming pools and several bars and restaurants.

FAQ’s about traveling to Cuba:

Can Americans travel to Cuba?

Yes, Americans can visit Cuba, but there are specific restrictions and guidelines they must follow. Travel for tourism is not permitted under U.S. law, but Americans can visit Cuba under one of the 12 categories of authorized travel, such as family visits, professional research, educational activities, religious activities, and support for the Cuban people.

Travelers must also adhere to certain regulations, like maintaining a full-time schedule of activities that support their category of travel. Additionally, U.S. citizens are required to keep records of their travel activities and expenses for five years.

How much money do I need for 2 weeks in Cuba?

If you plan to follow the above itinerary, I’d budget for about $100 to $150 a day. That’s roughly $1,400 to $2,100 for the trip. This means you would be staying in a mix of Casa Particulares and mid-range hotels, have most meals out and do a few guided tours.

If you’re on a budget, and staying in only casas particulares, eating at local spots, and using public transport, you might spend around $50 to $80 a day. That adds up to about $700 to $1,120 for two weeks.

For a more luxurious adventure, with high-end hotels and exclusive activities, you’re probably going to spend at least $200 a day, which comes to $2,800 or more.

Is two weeks enough in Cuba?

Yes, two weeks is enough time to experience Cuba. However, it’s the minimum amount of time I recommend spending on this gorgeous island. Because of the size of Cuba and the limited public transport options, you will be limited to what you can squeeze into two weeks here.

What is the best month to visit Cuba?

November and March are great months to travel to Cuba. The weather is usually warm and comfortable, with less humidity and rain than the summer months. November is perfect because it signals the end of hurricane season and kicks off the dry season. March keeps up that warm weather trend (without the scorching summer heat). Plus, by visiting in these months you’ll dodge the big tourist crowds of the peak winter season.

What should I pack for two weeks in Cuba:

• A decent pair of walking shoes. I wore my Teva Hurricane Sandals most of the time; they are so comfortable and have sturdy soles.
• A cute shawl – will be handy to keep warm on bus journeys and you can use it to cover up in museums, churches if needed. I have this one and love it.
• An eSIM, if you’re coming to Cuba for two weeks, then I recommend getting an eSIM as that way you won’t need to change your number or remove the physical SIM from your phone. They are so handy and cheap, too.
• Travel pants, we love the brand Kuhl and always wear their travel pants when travelling. Check out the best women’s travel pants here and the best men’s travel pants here.
• A good book to read or a playlist to listen to on your travel days.

Thanks for Reading!

To put it simply, there’s no place like Cuba. It’s got an energy like no other place I’ve visited. It’s like stepping into a time machine and being transported back to the 1950s. But change is simmering below the surface; Cuba will change; it may not be tomorrow, it may not even be next year, but it will happen. I’ve said it before, and I’ll say it again  – visit Cuba NOW before it’s too late.

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Last Updated on March 27, 2025 by snaphappytravel