Experience Cuba and all of its magic on this 8-day adventure through Havana, Vinales and Trinidad.
Explore Cuba with us via the “Support of the Cuban People” category, which we qualify for because we are working with local operators on the ground.
This is one of the most fascinating countries in the world, and we bring you to it like no one else can.
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Kelly Lewis is the founder of Damesly. She leads fewer and fewer trips these days, so if you get her as your leader, consider it a score!
Upon arriving at the airport, one of our Trip Leaders will be waiting to escort you to our headquarters in La Habana Vieja. Once in La Habana Vieja, you will be checked into your casa particular (bed and breakfast) and be given a brief orientation of the city. If you need any assistance with any errands or visits to a nearby point of interest, your guides will be more than happy to accompany you. In the event you arrive early in the morning and would like to coordinate any specific activities during the day just let us know so we can accommodate your requests.
We’ll start the day with breakfast at our casa particular. Afterwards, we’ll take a classic car tour around Havana, which will explore several different neighborhoods and showcase different ways of life here.
This afternoon, we’ll try traditional Cuban cuisine for lunch, and then we’ll go on a walking tour of Old Havana, stopping in major plazas and points of interest. We’ll be discussing Cuba’s history and current political and economic climate today.
After some downtime, we’ll have dinner as a group before live music and dancing!
After breakfast at our casa particular, we will begin the drive to Viñales Valley, a UNESCO World Heritage site known as the heart of the tobacco and coffee growing region in Cuba.
Upon arrival, we will enjoy a light horseback ride through the valley, where we’ll learn more about tobacco processing and farming at a local farmer’s home. Here, you’ll be able to purchase cigars or local beverages that make for great souvenirs!
We’ll have lunch together at an organic farm with a beautiful view, where we’ll learn about sustainable food production in Vinales.
In the evening, we’ll check into our casa particular for some downtime, before having dinner as a group.
After breakfast at the casa particular, we will begin the drive from Viñales to Trinidad. This drive will take us all day, but the rewards will be worth it (Trinidad is amazing!), and we will be making stops along the way.
For lunch, we’ll stop at a local restaurant for fresh seafood prepared right in front of us. In the afternoon, we’ll visit the Museum of the Invasion, for an interesting look into Cuba’s perspective on this event in history.
We will arrive to Trinidad at about 6 p.m., and have some downtime at our casa particular before enjoying an evening walking tour of the city. Tonight’s dinner as a group is a real treat, as is the option for live music later!
Breakfast at the casa particular. Afterwards, we’ll go on a hike to a waterfall and natural swimming pools that are gorgeous and popular with the locals. We’ll have lunch today at a nearby restaurant before having some downtime to freshen up.
This afternoon we’ll have a salsa lesson! It will be lots of fun, and lots of laughs, and you’re sure to enjoy it even if you don’t like dancing. Afterwards, we’ll have dinner as a group.
After breakfast, we’ll take a morning walking tour of Trinidad and visits to museums.
When the sun starts to head up, we’ll head to Playa Ancón for a picnic lunch and some beach time.
We’ll have some free time to relax today, before dinner tonight as a group. This evening is one of our favorites, because we’ll be heading to a nightclub within a cave. Whether or not “clubbing” is your thing– this is a fascinating place full of stalagmites and there is nowhere else in the world like it.
After breakfast, we’ll visit a local market and what was once an old sugar plantation to learn more about Cuba’s history and economy. Here, you’ll have another opportunity to shop for some unique pieces!
Today we’ll begin the drive back to Havana, where you’ll have time to rest and shower before this evening.
Tonight we’ll gather for our farewell dinner before heading to La Fábrica de Arte Cubano (entrance included, beverages not included) for an incredible mixed media art and bar experience. You will view everything from photography to sculptures, to fashion to architecture, as well as film, live music and much more. There are no words to describe this incredible place popular with locals and visitors alike!
This is a perfect chance to meet and interact with people from Cuba and enjoy late night eats. Live music will start at 10:30pm. Basically, this is one party in Havana that many tourists will never experience, but once you do you’ll be dying to come back!
It’s departure day, and we’re bummed. We’re sad to see you leave, but so happy we had such an amazing time together! After breakfast together, we will begin airport dropoffs.
This tour is 100% legal and compliant with US and Cuban laws. We travel to Cuba under the “Support for the Cuban People” visa category. Our trip is intended to be educational and to offer a deeper understanding about Cuban life and history. We fully comply with all federal laws and regulations, and reserve the right to make changes to this itinerary if necessary.
This tour is all-inclusive, so you’ll only need money to tip your tour guide and driver (recommended $10/day or $5/day each).
But, you should also bring money for shopping or alcohol, should you choose. Public bathrooms will have attendants who also ask for tips (1 CUC/per).
ATMs are not available in Cuba, so it’s best to bring cash with you and then change it into the local currency (CUC). Our guide can help you with this.
As such, it’s better to bring too much than not enough. $500 for 8 days, in our experience, should be more than enough.
Travel insurance is mandatory in Cuba, and also mandatory on our tours. Luckily, insurance is covered by your airline as part of your ticket. Hold onto your ticket and info before, during and after your tour, just in case.
You will need to get a Cuban Tourist Card (also known as a visa), to enter Cuba. You will get this from your airline. Each airline has different requirements and different rules, so be sure to check in advance what is required.
We are traveling under the “Support of the Cuban People” category — as we are staying in casa particulars coordinated by a Cuban tour guide.
This trip will run with 4 participants, and will be capped at 12 total. We recommend waiting to book your airfare until closer to the date, we will confirm the trip has met participant requirement 30 days before departure.
Cancel 30 days before a tour and receive a full credit or a refund, minus your deposit.
Want your own room? We've got you! Request to upgrade to solo or make this tour private.