Itineraries

Day 1:

Check in to your casa

Your guest family is probably already waiting for you. Some families also offer a pick-up service from the airport. In case ususally a friend or family member will be waiting for you at the airport with their old Lada to bring you back to the city for 30 CUC (it used to be 25 CUC).

Obispo Street

Head straight to Obispo Street in Old Havana to experience the most exciting part of town — and also the area you’ve likely seen in all of the photos. Take in the colors, architecture, live music inevitably being played in the streets, and enjoy some churros or fruit from a cart to keep your energy levels high.

Lunch at El Chanchullero

Make your way over to this 3-level restaurant that serves up yummy versions of classic Cuban dishes. Depending on where you’re sitting, you’ll be in perfect positioning for a bird’s eye view of the comings and goings of the local crowd below.

Stroll the Plaza de Armas

Stroll around the Plaza de Armas for some souvenir and book shopping. If you want a little bit of Cuban film history, scope out one of the guys selling film poster/prints and prompt them with a few questions — just be warned, you may not get a swift exit from the conversation!

Mojito Break at NOA

Move towards the Malecon to NOA Bar Paladar for some mid-day mojitos — because those are required in Cuba! This spot is set in a cute little alleyway close to a wifi source with an ocean breeze, so you can cool down with a drink and check-in with life back home (although, when you’re in Cuba why would you want to)?

Rooftop Views From Hotel Ambos Mundos

Just before sunset, make a visit to Hotel Ambos Mundos, a pink hotel in the center of Habana Vieja (Old Havana) which has stellar rooftop views overlooking the entire city.

Dinner at Habana 61

For dinner, Habana 61 is a great modern option for fresh and healthy food (some of the best we had during our stay in Cuba).

Drinks at Ernest Hemingway’s Watering Hole

End the night at El Floridita, a must-do for Ernest Hemingway fans as the writer frequented this now 100-year-old bar.

Day 2:

Start the morning with breakfast and coffee at your casa (most casas provide this, so make sure to ask if this is included in the price when booking).

The Oldest Hotel in Havana

Pop over to the Hotel Inglaterra, which is the oldest hotel in Havana and a fun spot for pictures if you enjoy retro signage! Across the street is an easy stop for the Habana Bus Tour which will take you all around the city.

See The Sights Via the Habana Bus Tour

Ok, let’s get one thing out of the way. I’m not one to normally suggest doing the tourist bus, BUT I particularly enjoyed this one for a few reasons. First off, it’s a super cheap way to cover a lot of ground around the city in a place where public transport is not readily accessible. Also, after a day on foot walking all around Old Havana, we enjoyed resting our legs and getting a different perspective from above. As a photographer, I especially loved this because there are so many cool buildings with intricate details to shoot from a higher vantage point. You can hop on and off the bus whenever you please and they don’t talk over the loud speaker the entire trip, so it’s quite relaxing especially on a nice sunny day — wear a hat or sunscreen!

Stop for Pictures at Revolution Square

Along the Habana Bus Tour, make sure to hop off at Plaza de la Revolucion where the famous Che Guevara mural is located.

Coffee Break at Cuba Libro

At the Colon Cemetery stop, hop off for pictures and walk five minutes to Cuba Libro, my favorite coffee shop and bookstore in Cuba with hippie vibes and a great selection of English books and magazines.

Dine at One of the Privately Owned Paladares

Paladares are the non-government run restaurants in Cuba and typically have better food than the latter option. Take the bus back into town and hop off to make your way to Atelier for dinner, a beautiful restaurant in the newer part of Havana which is consistently listed as one of the top paladares in the city.

San Cristobal is also a famous locale (make reservations ahead). It didn’t blow us out of the water, but the history behind this place (the Obamas made it famous) and atmosphere alone is worth checking out.

Socialize at the Fabrica de Arte

Don’t miss Fabrica de Arte Cubano (FAC).. It’s a contemporary art gallery that has been turned into a party spot. Different rooms throughout the gallery have different setups, ranging from live EDM bands to movie screenings. The lines get pretty long so be prepared to wait. The FAC open 8 pm – 3 am Thursday to Sunday each week.

The Parisien Cabaret at Hotel Nacional

End the night at the Hotel Nacional for the Parisien Cabaret show, one of the highlights of my trip. Many people decide to see the pricier show at the Copacabana as it’s more reputable, but my friend and I decided to go with this show instead and I’m so glad we did. It was entertaining, hilarious, impressive and cheesy all at once. Loved every minute.

• Take some Salsa lessons
• Visit Copelia: Cuba’s ultimate ice-cream parlor

Day 4:

Check in to your casa

• Arrive in Viñales around 5 pm, and check into Villa Farner’s, a modest little casa run by Lisette and Jimmy that sits in convenient proximity to the main drag in town (see map for details). Plus, the breakfast and rooftop views are to die for.

Take a tour (on your own)

• A viewpoint: panoramic views of the entire Vinales valley, a UNESCO World Heritage Site.

Have some lunch

• Lunch at an organic farm: a true farm-to-table experience! The food was fresh and absolutely delicious. The meal included everything from fresh meat and fish, to fresh vegetables cooked in Cuban spices. Our table was in a little hut that overlooked the lush valley.

Explore the hood

• Cueva del Indo: an underground boat ride through historic caves of Vinales
• Viñales Mural de la Prehistoria: a large colorful mural painted on the side of a mountain. The mural represents evolution from early sea-organisms to humans. However, we just stopped here for 10 minutes.
• A tobacco farm tour: Vinales valley is known for its tobacco plantations. We had the opportunity to see a farmer roll a cigar live and also bought some Cuban cigars at a great price (~20-30 CUCs for 10 cigars).

Dinner

• Be warned, there’s not much (if anything) in the way of good food in the main center of town in Viñales, so expect very basic and you may be pleasantly surprised.

Take in the views of Viñales

• Head to the rooftop of your casa (many in the area have them) for a sunset viewing overlooking the Viñales Valley. We spent a memorable night drinking wine and chatting it up with our casa hosts on the roof while each sampling our very first Cuban cigar — not a regular thing for me, but when in Cuba!

Dance into the night

• Walk a few minutes to the main square of town for salsa dancing in the square and to mingle with locals.

Day 5:

Viewpoint at Hotel Jazmine

Start the morning off by hopping onto the local Viñales bus which has multiple stops at tobacco houses, the Hotel Jazmine (great views overlooking the Viñales Valley, but terrible food) and other local tourist attractions. It’s the most convenient way to get around and often cheaper than taking a taxi, so if you’re looking to explore the area outside the main square this is the way to go. You’ll find the bus stop right in front of the main square.

Lunch at Finca Agroecologica El Paraiso

Once you’ve worked up an appetite, head over to the best lunch in town at Finca Agroecologica El Paraiso, which is a family-run organic farm with incredible food. The views are unreal overlooking the Viñales Valley, but it can be quite the tourist destination as it’s the #1 rated restaurant in the area on TripAdvisor and surpasses everything else by a long-shot. Try to go when the tourist buses are gone for a more enjoyable meal. Also, word to the wise — these are the largest portions I’ve ever encountered in my life (seriously, ever) and they won’t wrap them up in takeout boxes for you unless you bring your own. Bring tupperware — you’ll seriously get three extra meals out of it!

Drinks at Palenque de los Cimarrones

For drinks and dancing, finish your night at Palenque de los Cimarrones which is another Cuban cave club (I preferred this one over the Disco Ayala in Trinidad). This club also comes with a history lesson, as the caves were a main escape for slaves. If you’re lucky enough to be in town on a Saturday night, you’ll witness a weekly performance here and chances are if you’ve met any locals around town, you’ll run into them here for a dance session!

Day 6:

First thing in the morning, pack up and get a car to Trinidad (about a 4 hour car ride) with a stop for lunch in Cienfuegos, a small seaside town along the way.

Find a Casa with Rooftop Views

In Trinidad, it’s easy to arrive and ask around for accommodation on the spot (such is the way in Cuba). We stayed at Casa Amparo (see map for details), which is a spacious home in central Trinidad run by two very sweet ladies (they don’t speak much English but are extremely accommodating) and it has gorgeous rooftop views.

Beach Bum it at Playa Maria Aguilar

Pack up a beach bag and grab a taxi to Playa Maria Aguilar which is only about 20 minutes by car for a couple hours of sunbathing and cooling off in the turquoise water. Just note: the food at the restaurants here is not great and there are no bathrooms, so just be aware going into it, but the beach is worth it!

Take a Salsa Lesson

Salsa dancing is a must while in Cuba. Call your casa ahead (if possible) to have them book a salsa lesson for you on the roof on the afternoon of your arrival.

Dinner at La Botija

Satisfy your hunger at La Botija for dinner, which is open 24 hours but commands quite a line around dinner time, so make sure to arrive before starvation sets in. They have quite a large selection of tapas style food — definitely one of the better meals we ate while in Cuba.

Salsa Dancing at the casa de la musica

After dinner, head to the Plaza Mayor to watch the salsa dancing commence. It costs about 1 CUC to get a seat inside the square. If you’re a lady, be forewarned that you will probably be asked to dance — so this is the perfect opportunity to put your new salsa skills to good use!

End the Night at Rincon de la Salsa

If you still haven’t had enough salsa, walk down the street to Rincon de la Salsa to get your groove on with the locals.

Day 7:

Explore the Streets of Trinidad

After breakfast at your casa, spend an hour or two wandering around the colorful streets of Trinidad (we spent most of our time wandering between the Plaza Mayor and Plaza Carillo).

After breakfast, walk around Plaza Mayor. The square takes on a different character in the day, when it is quieter and has less tourists, so we spent some time walking around the cobblestone streets. Make sure to climb the La Iglesia y Convento de San Francisco – a bell tower which had a bird’s eye view of the entire town. Probably one of the best views I’ve seen! Closeby, make sure to visit the souvenir shops for some local art pieces as well as funky magnets.

Horseback Riding Tour Through the Trinidad Countryside

Head back into Trinidad in time for an afternoon horseback riding adventure that the casa can book for you. We did a tour for about four hours that took us through the gorgeous countryside to a waterfall, however, it started storming heavily and we turned right back around soaked without ever going into the falls. Make sure to check the weather for the best outcome! 2-3 pm is a good time to set off on this excursion.

Dinner at La Raddicion

Get back into town for dinner at La Raddicion, which has great lobster and vegetarian options as well. Their service can be slow (an expectation in Cuba), so make sure you’re not on a tight schedule before dining here.

Dance the Night Away in a Cave

End the night at the Disco Ayala, a semi-cheesy but have-to-see-once kind of nightclub, inside a cave. Check with locals about the best night to go because sometimes they do a show earlier in the night as well.