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Cuba

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.

 

Check dates and availability
Trip Dates Availability Price Payment
January 21-28, 2023 0 spots left $3499 USD SOLD OUT
Reserve this trip with a non-refundable deposit, or pay in full. The balance of your tour is due 60 days before departure.
Day 1: Arrival to Havana

It’s arrival day! Please aim to arrive to Havana before 5 p.m. today.

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.

Tonight’s welcome dinner at 7 pm will be a fun way to kickoff our time together!

Meals: D

cuba tour with damesly
Day 2: Classic Car Tour + Havana Walking Tour

Explore La Habana and all of its magic as we immerse ourselves in Cuban history, lessons from the past, and how Cubans are looking towards the future. We’ll take you on a driving tour in classic convertible cars, before a short walking tour of the historic center stopping at all major plazas and points of interest.

This day provides you with a good lay of the land for independent exploration, as well as a general overview of the island’s history and current political and economic climate. We will also point out some of our favorite hidden gems such as shops, bars, cafés, galleries, and restaurants. At lunch, we will enjoy classic dishes with a modern twist at one of our favorite restaurants, Antojos, where we’ll dine al fresco.

After lunch, we’ll have some downtime because tonight we’re going out!

Dinner in Vedado Dinner at El Cocinero

Dinner tonight is in the Vedado neighborhood. Located adjacent to one of the coolest venues in La Habana, La FAC, El Cocinero is an old cooking oil factory that has been transformed into a stunning rooftop terrace and lounge. El Cocinero is an incredibly hip and modern establishment, especially by Cuban standards, and offers an extensive menu with everything ranging from freshly caught seafood, veggie dishes, and mouthwatering desserts.

La Fabrica de Arte Cubano

It’s hard to put into words just how incredible of a place La FAC is. You will view everything from photography to sculptures, fashion to architecture, as well as film, live music, and much more. This mixed-medium art space contains multiple galleries, stages, dance floors, and social areas for eating and drinking and is frequented by both locals and foreigners on a nightly basis.

Meals: B, L, D

cuba tour with damesly
Day 3: Horseback riding (Vinales)

After breakfast at our casa particular, we will begin the 2.5-hour 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.

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.

vinales cuba valley
Day 4: Drive to Trinidad

Roadtrip to Trinidad

Today we will travel in a comfortable, modern van with AC to Trinidad! This day can be a bit long (roughly 6 hours) but we will make stops along the way to use the bathroom, stretch our legs and grab a bite to eat.

Trinidad Walking Tour & Pottery Class

Once we have arrived in Trinidad and get settled into our new casas particulares, it’ll be time to hit the street. We will get to know this small town with beautiful colonial architecture and rich history of art and culture. During our tour, we will discuss the colonial period in Cuba, social classes and the economy, religious diversity, and of course, art! We will even finish our tour with a visit to the Santander family, heirs of a long tradition of pottery, where we will have fun creating a piece of pottery, guided by a pottery master.

Dinner at La Redacción

After working up an appetite on our walking tour and getting our hands dirty in our pottery workshop, it’ll be time to head to dinner! Tonight we will dine at La Redacción. Situated in an 1800s home this restaurant was inspired by the printing press. They also work closely with a select group of suppliers who include local fishermen, farmers, and butchers, as well as bake their own bread and grow their own vegetables and herbs to give you a healthy, natural, and local dining experience!

Meals: B, L, D

womens tour of cuba
Day 5: Trinidad Exploration + Salsa Lessons (Trinidad)

Today we will be exploring stunning Trinidad. We’ll start our day by traveling outside of the colonial center of Trinidad to explore the countryside, learning about the history of this area and how it’s shifted over time.

Once a major sugar-producing region of the island, we will visit a sugar mill and even learn how to use a “trapiche” to make fresh sugar cane juice.

Then, we’ll head back to town for lunch and we’ll do a short walking tour of Trinidad before allowing you free time to either rest, or continue exploring (and shopping) Trinidad.

Siesta

Take some free time to relax, rest or explore independently.

Salsa Class

It’s time to bust out your dancing shoes! Learn the basic steps of salsa with a private teacher in our one-hour dance lesson. Post lesson we will grab dinner and then head over to the local plaza to catch nightly live music and dancing.

Meals: B, L, D

womens tour to Cuba
Day 6: Beaches + Cooking Class + Cave Club (Trinidad)

Beach Clean Up & Barbecue

After quite a few days of adventuring, today we will take things just a bit slower. After a leisurely breakfast and some early morning free time, we will head to Playa Ancón. Here we can show some love and leave things better than we found them, by coming prepared to do some beach clean-up on or near our beach area.

You’ll then have time to relax and go for a swim or you can decide to hang with your local guides as they put together a picnic lunch for us to share as a group!

Siesta

Take some free time to relax, rest or explore independently.

Cuban Cooking Class

Today we will learn more about how the food production and distribution system works in Cuba and discuss the challenges that Cubans faced due to both internal issues and external factors, including the US embargo. We will discuss traditional Cuban dishes, and food-related issues on the island both pre and post-the 1959 revolution, as well as innovative solutions, because after all Cubans are nothing if not resourceful. After discussing these important topics, we will get our hands dirty as we make a traditional Cuban dinner and share it alongside our hosts and local guides.

Music & Cave

After a little post-dinner cafecito to perk us back up, we’ll head to an impossibly cool cave bar for music, drinks, and dancing! Note: getting to the cave requires walking in the dark over cobblestone and slick stones, often times uphill. If this is not in your ability, please sit this one out.

Meals: B, L, D

womens tour to Cuba
Day 7: Return to Havana

Final activities

Once back in Habana we will have time for one final activity and we want to make sure you make the most of your final hours in Cuba so we can break into subgroups if needed. We will discuss optional activities with folk early on in the trip and make decisions by the morning of Day Four in order to coordinate. Possible options are:

  • Pamper yourself the Cuban way: Get your hair or nails done, or even get a tattoo to remember your time in Cuba while supporting a small, privately owned business.
  • Learn about female entrepreneurs making artisanal soaps, honoring their roots, and fighting for a better future.
  • Visit Clandestina, Cuba’s first-ever privately owned fashion brand that upcycles old garments into fresh new pieces using 100% Cuban designs
  • Get your heart rate up in a personal training session along the malecón
  • Take a street art tour!

 

tour of havana cuba
Day 8: Departure

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. Please ensure your flight home departs today before 5 p.m.

Cost includes:

  • All meals
  • Accommodation in a shared room
  • Transportation
  • Private tour guide and driver
  • All activities including horseback riding
  • Airport pick-up and drop-off
  • Salsa lessons

Does not include:

  • Airfare
  • Visas
  • Travel insurance
  • Gratuities for guide and driver
  • Alcohol

What to pack:

  • Comfortable shoes for walking tours
  • Bathing suits for beach and waterfall days
  • Camera
  • Clothing for tropical weather
  • Small backpack for personal items
  • Beach towel

Additional Info:

Legal Questions Is this trip compliant?

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.

Money How much should I bring?

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 What's the deal with that?

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.

Visa How do I get a visa?

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.

Trip Minimum How many people are needed to run this tour?

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.

Reviews

  1. J

    Jill Hunt

    Cuba was a complex and fascinating country. The people are wonderful, the food delicious and the saying,
    “Don’t try to understand Cuba” holds very true. I jumped on this trip last minute due to a cancellation so went fairly unprepared. The Damesly team had a very packed schedule but it did have time for chilling out or going shopping, rum tasting (in my case) or checking out museums. The city and it’s people are extremely photogenic. Take a good camera. Our Cuban guide, Lidyz was AMAZING! She was extremely knowledgeable and answered any and all questions. She has a great network of people she works with in Cuba to help you have an excellent experience. The packing list was a bit light of information, in my opinion and make sure you get lots of coins for the toilets. I would go with a very open mind, drop the need for your creature comforts and enjoy the lack of internet. Salute!

  2. Laurence Holyoak

    I just returned from a week in Cuba and all I can say is WOW. The country is so vibrant and unique… it truly is like traveling back in time. We experienced things on this tour that most people will never get to see. And to do it with such an amazing group of women was icing on the cake. We formed friendships that will last a lifetime. My stomach still hurts from laughing so much. The trip itself was very well organized and fit so much into a week while still allowing for free time. Our trip guides were the best. They transferred money for us and translated the language for us. It would have been really overwhelming without them! They made everything easy so we could sit back, relax and enjoy every minute of the trip. I would highly recommend this trip. Can’t wait for my next trip with Damesly!

  3. S

    Sonya LaMere

    I recently returned from the latest Cuba trip, I had an AMAZING time. Cuba honestly was not on my short list for vacations but the price, dates and itinerary convinced me. I am so glad I did, I had the time of my life! We were so lucky to have such wonderful guides to include a local guide, these women made the trip! I embraced all this trip had to offer, horseback riding threw incredible country, swimming in the Caribbean sea,and an incredible waterfall to cruising in classic cars threw Cuba and all with an incredibly fun group of women. I would highly recommend this trip and Damesly they were so organized and helpful it allowed me to relax and enjoy the trip. Just a bit of advise for packing for this trip comfy shoes, wet wipes, change for bathrooms and an open mind!

  4. B

    Beth Esip, Van Atten

    Thanks to the generosity of my son-in-law and the remarkable research skills of my daughter, “Damesly” was found and a long-time dream was fulfilled. My Damesly Tour to Cuba will be a cherished memory for the rest of my life. Experiencing, first hand, the Cuban culture, music, food, drinks, architecture, history, ecology, and the PEOPLE was more than I imagined…very enlightening, exciting, and FUN.

    The other eleven participants, women from all over the US, were young, enthusiastic, and savvy world travelers. I felt privileged to be among them. Our two local guides were extraordinary, providing us with information, both historical and immediate, responding to all questions about the revolution and current life in Cuba. Our two Damesly guides went beyond expectations of seeing to our needs and comfort.

    I had no idea how much fun I would have. At age 81, being on a tour with other seniors would have been interesting, but I would have missed so much. I had some anxieties being with a group so much younger. Would I be able to keep up? The unexpected delight with this group was the total non-judgmental freedom I experienced. I was enraptured by the music and the people, and felt completely free to express my delight. I laughed so hard. It was truly cathartic.

    James, Laurence, and Kelly you made a dream come true! Thank you.

    Beth Van Atten

  5. B

    Beth Esip, Van Atten

    Thanks to the generosity of my son-in-law and the remarkable research skills of my daughter, “Damesly” was found and a long-time dream was fulfilled. My Damesly Tour to Cuba will be a cherished memory for the rest of my life. Experiencing, first hand, the Cuban culture, music, food, drinks, architecture, history, ecology, and the PEOPLE was more than I imagined…very enlightening, exciting, and FUN.

    The other eleven participants, women from all over the US, were young, enthusiastic, and savvy world travelers. I felt privileged to be among them. Our two local guides were extraordinary, providing us with information, both historical and immediate, responding to all questions about the revolution and current life in Cuba. Our two Damesly guides went beyond expectations of seeing to our needs and comfort.

    I had no idea how much fun I would have. At age 81, being on a tour with other seniors would have been interesting, but I would have missed so much. I had some anxieties being with a group so much younger. Would I be able to keep up? The unexpected delight with this group was the total non-judgmental freedom I experienced. I was enraptured by the music and the people, and felt completely free to express my delight. I laughed so hard. It was truly cathartic.

    James, Laurence, and Kelly you made a dream come true! Thank you.

  6. M

    MaryKay Moyer

    I had the most wonderful time in Cuba! I had no idea what to expect and it turned out to be a true adventure. Retha was the best guide…her and Lydiz were so welcoming and enthusiastic to each and every one of us. I would definitely do it again. The itinerary was perfection. Thank you….and especially Retha, for a great trip.

  7. N

    Nicole DiGirolamo

    Loved it, both guides, Retha and Lidyz went above and beyond making us feel welcome and taken care of. The itinerary was eclectic, very informative and a true adventure, just what I was looking for. Our experience gave me an insight into the true Cuba, a perspective I might not have acquired on another tour. Thank you, an experience I’ll never forget.

  8. M

    Milet

    My recent trip with Damesly to Cuba was incredible! I had alot to learn about Cuban culture and history and I’m so ecstatic to share that I got that and much, much more. Where do I start? From our warm and gracious tour guide to the organized daily itinerary, it was truly an experience for the books. I loved being able to meet local Cubans (who are so kind and hospitable) and enjoy their delicious food as well as enjoy beaches, salsa dancing and art/history/music/nightlife! I definitely recommend to all adventurous female travelers to make time to visit this beautiful country but to also try join the Damesly group because it’s safe, fun, and organized so well. Thank you Kelly and everyone for creating fantastic memories that I will cherish for a lifetime.

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