How Solo Women Can See the ‘Real’ Cuba, From a Woman’s Perspective

by | Mar 31, 2024

Three women sit in a vintage red car on a tour with Cuban Adventures
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Last updated on April 3rd, 2024

Featured image: While Havana is a must-see, there’s lots to do in Cuba | Photo provided by Cuban Adventures

How to explore Cuba from a woman’s perspective 

by Carolyn Ray

With over 500 years of history and dazzling white sand beaches, Cuba is an appealing destination for many solo women. Not only is it an inexpensive place to visit, it’s also a relatively short flight for North American sun and adventure seekers.

While Cuba conjures images of Havana’s touristy vintage cars, the pastel hues and all-inclusive hotels, four women-led businesses from our JourneyWoman Women’s Travel Directory are eager to show solo women the real Cuba — the one that you miss if you’re staying in resorts. They also say it’s a good time to come to Cuba because tourism is desperately needed to boost the economy.  Americans may not be aware that they can visit Cuba, with the U.S. government’s ‘Support for the Cuban People’ requirements.  All visitors to Cuba must have a Cuban tourist visa, which can be purchased at the airline counter or online

According to Reuters, Cuba has fallen on hard times since the COVID-19 pandemic. Tourism – once a major source of foreign currency – has sputtered, with potential visitors put off by a lack of infrastructure, U.S. visa rules and news coverage of economic woes and unrest.  However, even with food shortages being reported at government-owned hotels and resorts, these trips focus on women, locally owned casas particulares and support women-owned businesses, including restaurants and markets, allowing you to can make a difference at a local level. Other experts I spoke with say that if you’ve been to Cuba before, it may be different, with less variety than you’ve come to expect but it’s stil safe and worth the trip.

According to Cuban officials, 2.4 million people visited the island in 2023, significantly less than expected. According to the national statistics agency ONEI, almost a million Canadians visited Cuba in 2023, representing 38 percent of all visitors. Other sources included Cubans residing in other countries (358,481), Russia (184,819), the United States (159,032), Spain (89,285) and Germany (69,475). 

Colourful and historic buildings on the streets of Cuba

Historic buildings around Cuba / Photo by Carolyn Ray

Is Cuba for safe for solo women?

“I have visited Cuba four times since 2016,” says Joy Sherman, founder of US-based JoyRide Charters. “The first year was fascinating enough! In subsequent years, I have observed the many changes the people have gone through.  Women are strong and resilient. Women there carry themselves with confidence.  Whether man or woman they must work with what they have both in business and personal. There are many women artists who make up the creative vibe in Havana and elsewhere. Cuba is extremely safe for women!”

Talek Nantes, Founder of Travels with Talek agrees. “Cuba is among the safest countries in the world where the tourism industry is protected as it is one of the country’s major revenue sources,” she says. “Women are highly regarded and respected within the Cuban culture and gender equality in all aspects is mandated by law.”

“Women played a strong and important role in the revolution,” says Clarita Dervent, COO of Cuban Adventures, a full-service tour company that has provided tours in Havana, Cuba since 2005.

“Prior to this, they had no rights to education, healthcare or equal opportunities for employment. Their participation broke the stereotype of tradition and challenged the patriarch. Meeting the younger generation of female entrepreneurs in Cuba who run micro businesses and who continue this tradition to push boundaries is inspiring. Seeing what the women of Cuba have achieved even under the longest blockage in history, is extraordinary. The strength of solidarity and female comradery that exists in Cuba society is the most impressive and lasting memory many will take home with them.”

Why solo women should visit Cuba

“Cuba provides a very welcoming and secure environment which you’ll encounter from the Cuban people,” says Gina Cambridge, CEO of Wanderlust Solo Women Tours. “Personally, I discovered this when I traveled there myself as a solo female traveler back in 2016. Combining its safety, sustainability, immersive and vibrant culture it is a highly desirable country for women travelers in 2024 and beyond.”

Travel with Talek’s Nantes says the political relationship with the United States has resulted in a lack of U.S. businesses and franchises on the island.

“There are few places on earth where you won’t find a McDonalds, Starbucks or Coke — Cuba is one of them,” she says. “The country seems to be frozen in 1959, the year of the Cuban Revolution. Classic American cars from the 1950s and before roam the streets and the worn symbols of a pre-revolutionary Cuba can still be seen on faded store signs and abandoned buildings.”

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There are nine UNESCO World Heritage Sites in Cuba, including the Convent of Santa Clara, the first women’s convent in Havana (founded in 1644). Other sites include the entire old section of Havana, as well as Trinidad, Camaguey, national parks and the Valley of Vinales. With its national parks, biosphere reserves, and thousands of miles of pristine coastline, visitors are never more than an hour’s distance from a powder-white beach or a spectacular waterfall.

“Believe it or not, Cuba is one of the top sustainable countries in the world,” says Gina Cambridge of Wanderlust Solo Women Travel. “Community projects, eco-tourism, and recycling/upcycling are an integral part of a Cuban adventure. Cuba also offers a unique blend of rich history, vibrant culture, and stunning landscapes, making it an ideal destination for those seeking truly authentic experiences (and don’t forget amazing salsa, art and music!)

Four experiences to support the women of Cuba

The Land & Sea Cuba Tour by Joy Sherman, JoyRide Charters

In January 2025, female captain Joy Sherman is offering a Land & Sea Cuba Tour for women that includes Havana, Trinidad, Cienfuegos, Vinales, Cayo Largo, Cayo Guano and Cayo Sal. Guests stay in casa particulares during the land portion, some of which are women-owned. All of the stays include breakfast.

“We spend the first part of the week on some local tours in Havana and then Trinidad,” Sherman says. “Then we have a week of sailing off the southern coast of Cuba.  People can experience and enjoy “island life” Cuban style.  Abundant seafood is available all week on board.  We have Cuban chefs who prepare the meals. When we return from sailing there are three more days of land tours which include Vinales.” Learn more about this tour here!

Women spotted the "pink Barbie car" in Cuba

The women spotted the “pink Barbie car” and we all piled in / Photo provided by JoyRide Charters

Cultural Tour of Cuba by Gina Cambridge, Wanderlust Solo Women

In November 2024, Gina Cambridge, founder of Wanderlust Solo Women plans to offer a different perspective of Cuba, with stops in Old Havana, Playa Alcon, Trinidad, Vinales and Saint Clara. Guests stay with local, women-owned “casa’s” (private homestays) that help build a connection with the people of Cuba and leave “Western” expectations at the door.

“With my tour, I offer 1:1 personal support, live Q&As, and pre-tour group chats that go beyond the normal tour booking experience,” Cambridge says. “Not only will we have our own local personal guide, and all guests also have me as their personal host for an extra layer of support. The emphasis of this tour is to support the women of Cuba, whether this is staying in women-owned casa particulars, visiting women-owned businesses, craftswomen and artists, the goal is to empower, both the women within the local community but also those guests that join us on tour.” Learn more here!

Women on a group tour in Cuba

Women on tour with Wanderlust Solo Women / Photo by Gina Cambridge

A group of women in a pink vintage car in Cuba

In a pink vintage car / Photo by Gina Cambridge

Cuba Cultural Tour, by Travels with Talek

In May 2024 and into 2025, Travels with Talek’s tours will go beyond Havana to fascinating locations including Cienfuegos, the only Cuban city founded by French settlers, the beautiful Vinales Valley, and Trinidad, the best-preserved colonial city in the Americas and the Valley of the Sugar Mills. All of these are UNESCO World Heritage sites. The tours are operated by Cuban-Americans who are very familiar with the country and visit unknown places including underground rivers, religious performances and off-the-beaten-path artists’ studios. All of the accommodations are in casas, Cuban B&Bs, or homestays, most of which are women-owned businesses.

“Our tours offer visitors to the island a culturally immersive experience in compliance with the U.S. government’s ‘Support for the Cuban People’ requirements,” says Talek Nantes of Travels With Talek. “As one guest said, ‘We not only visit Cuba, we KNOW it.’ The activities on our tour include dance lessons, cooking lessons, and meetings with farmers, musicians, teachers, shopkeepers, artists, students, women’s entrepreneurial cooperatives, and the Cuban people in general.” Learn more about this tour here!

A group of women on tour in Cuba with Travels With Talek

Talek and a local guide with their group touring in Cuba / Photo provided by Travels With Talek

Women-Only Tours by Cuban Adventures

In her tours, Clarita Derwent of Cuban Adventures focuses on Cuba from a Cuban woman’s perspective, focusing on the contribution that women have made to Cuba culture and society. Beyond the classic car drive around Havana, guests will walk through the lush Vinales valley, stop to learn how to roll a cigar; swim in the Caribbean sea at the Bay of Pigs and sip a cocktail at the organic farm overlooking the beautiful valley at sunset, There’s also Trinidad, a picturesque colonial town on the Caribbean sea, full of colour and heat, music and a deep history of old sugar plantations.

“We meet local businesswomen, learn about their challenges and also their achievements and meet local female creatives (artists, ceramicists or musicians),” Derwent says. “We’ll visit a female-owned and operated organic farm and enjoy an amazing meal and stay in female owned guesthouses. Everywhere we go we meet, stay, chat and interact with local women – this way hopefully you come away with an in-depth understanding of Cuban culture and life in general.

Exploring the Vinales Valley in Cuba on a tour with Cuban Adventures

Exploring the Vinales Valley  / Photo by Cuban Adventures

Travel Tips for Women in Cuba

Have the right mindset

Start your trip with no expectations – this makes travel in Cuba so much more satisfying.  Learn to embrace the natural Cuban calm and humour of dealing with daily struggles. — Clarita

The best tip for visiting Cuba is to go with an open mind. It is a poor country experiencing many challenges. However, these difficulties are offset by the country’s natural beauty, fascinating culture, and the warmth of the Cuban people.  — Talek

First travel with no expectations and then you’ll never be disappointed (do you research of course) and imagine what it was like to travel with no technology, which to be honest some of us will remember, traveling 20+ years ago! That’s what traveling in Cuba is like. — Gina

Expect the unexpected and remember that even the most difficult moments are all part of the “cuba experience”. This is how the Cuban people live every day under a blockade, much of what we take for granted in our own lives. — Clarita:

Learn a little Spanish, it will go a long way with the locals. — Gina

Safety in Cuba for solo women

Cuba is seen as a very safe place for women to travel in general. Petty crime is low compared to most other countries; women can walk alone at night; violent crime is rare, but don’t take unnecessary risks of course eg: don’t carry valuables or walk in areas locals would not! The Cuban people are always very friendly and helpful to everyone and do not abide by people mistreating any visitors to the island. — Clarita

Local scams on tourists do exist so don’t change money on the street. Street hustlers and wolf-whistling are both quite common in Cuba, just be aware of prices and ignore those whistles! None of this poses a danger to your safety. — Clarita

Check government travel advisories before you book a trip. Canadians here. Americans here.

You need to show proof of travel insurance upon arrival in Cuba – check rates here.

Bring what you need

There are food and oil/gas shortages in Cuba so don’t expect the same variety of food or services that you may be used to, particularly outside of Havana. In more remote resort areas, staff are usually bussed in from other regions so this may be affected as well.

Don’t expect to be able to buy any essentials in Cuba (come prepared with everything and more) you can always leave items behind to very grateful recipients. — Clarita

Take everything you may need, especially medications and period products, though the medical care is good, the resources are not. — Gina

Leave room in your packing to bring what you can in over-the-counter medicines and anything else, for the people. — Joy


Go to Cubacel phone store, and get a sim card for your phone. You can keep in touch the entire time you are there.  For years this was not the case! — Joy

Have multiple ways of accessing money. — Clarita

Do not rely on wifi (get that Lonely Planet guidebook), take cash, US dollars or EUROS, as ATMs are more than likely not to work. – Gina

The currency is CUP (Cuban Pesos). You must get them there. Sometimes you can pay with euros or US dollars. Your credit cards will not work there. – Joy

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Getting there

For Canadians: There are direct flights from Toronto and Montreal to Cienfuegos, Havana and Cayo Largo operated by Sunwing, Air Transat and Air Canada. Check Skyscanner for rates here.

For Americans: Travel to Cuba for tourist activities remains prohibited, but you can travel to Cuba under one of 12 categories approved by the U.S. government.  Flights are available from most US cities. Check Skyscanner for rates here. Most U.S. visitors choose the “Support for the Cuban People” category. This category is selected when purchasing an airline ticket from the airline, and it just involves checking a box.  — Talek

All visitors need to purchase a Cuban visaa. Pink for U.S. to Cuba travel, green for anywhere else to Cuba travel. Cost from $50 to $100, depending on your airline. Buy at the airline counter or online. Fill it in carefully. No scratch-offs accepted.  If you buy  it online, it will be mailed to your home so give yourself enough time to receive it. At passport control in Cuba, they will take half of your Cuban visa/tourist card. You must hand in the other half when you leave the country. Do not lose it. — Talek

Check out the visa process information to Cuba from your country of residence and if you plan to travel to the US in the future (if not a US resident) before booking anything. If after your holiday to Cuba, you plan to visit the US or transit through it you will need to apply for a B2 visa, US residents do not need to do this. — Gina

IMPORTANT, do not use the word “CUBA” as any reference code when paying for your Cuba experience via bank transfers, credit cards etc. US citizens might already be aware of this but it is applicable for all countries as you don’t want to be caught out like a New Zealand woman was recently (*not on my tour), use the word “holiday” or anything else as you might find your bank accounts have been frozen due to the current US sanctions with Cuba. Even though your country of residence might not have sanctions with Cuba. — Gina

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More to Discover from Cuba and the Caribbean

As the CEO and Editor of JourneyWoman, Carolyn is a passionate advocate for women's travel and living the life of your dreams. She leads JourneyWoman's team of writers and chairs the JourneyWoman Women's Advisory Council and Women's Speaker's Bureau. She has been featured in the New York Times, Toronto Star and Zoomer as a solo travel expert, and speaks at women's travel conferences around the world. In March 2023, she was named one of the most influential women in travel by TravelPulse and was the recipient of a SATW travel writing award in September 2023. She is the chair of the Canadian chapter of the Society of American Travel Writers (SATW), a member Women's Travel Leaders and a Herald for the Transformational Travel Council (TTC). Sometimes she sleeps. A bit.


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