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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
TBD$2450 USD
Reserve this trip with a $500 deposit, or pay in full. The balance of your tour is due in full 60 days before departure.

Day 1: Arrival to Havana

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.

cuba tour with damesly

Day 2: Classic Havana

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!

cuba tour with damesly

Day 3: Horseback riding (Vinales)

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.

vinales cuba valley

Day 4: Drive to Trinidad

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!

womens tour of cuba

Day 5: Waterfalls + Salsa Lessons (Trinidad)

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.

womens tour to Cuba

Day 6: Beaches + Cave Club (Trinidad)

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.

womens tour to Cuba

Day 7: Return to Havana

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!

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.

View full itinerary

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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