Ready To Stare presents…

LGBTQuba

5nights | 6days |
2 locations
in magical Cuba!

Meet real Cubanos who live, breathe and bleed Cuba- the only experts on Cuban culture. Learn about Cuba's history including their revolutionary policies which promote inclusivity and protect the rights of its LGBTQ+ community while enjoying all the food, art and dancing of the famous Havana Nightlife before exploring the natural beauty and hills of the Viñales countryside.

If you missed us in 2023, you definitely don't want to miss us this round!

This trip is designed for travelers who are plus size and/or LGBTQ+ but open to allies of all genders and all sizes. 

Tour highlights:

  • Learn

    From Cubans living in Cuba about their realities resisting under a 60 year blockade.

    Salsa dancing with world famous gay cabaret dancers.

    From Cuba’s leading gynecologist about their free medical system and its policies that create inclusivity for Cuba’s LGBTQ community.

  • DINE

    At Havana’s hottest restaurants with the prettiest cocktails and mocktails and the most authentic Cuban cuisine you cannot find anywhere else.

    On the most authentic Cuban cuisine including Ropa vieja, Platanos and a very special Cuban tradition - Lechon!

  • EXPLORE

    The many sides of Cuba. Experience the heat and buzz of Havana with music, salsa dancing and art around every corner.

    The mysteries of the Afrocuban religion Santeria.

    The natural beauty of Viñales and the rolling hills of the Cuban countryside on Horseback or by horse-drawn cart.

  • STAY

    At a 200 year old colonial-styled mansion reclaimed by Cuban families.

    A farm stay in our tia’s house in Viñales where the community opens its homes and hearts to us.

    Stick with double occupancy pricing to get a roommate or book a private room!

Book Now

Embrace and celebrate diversity and inclusivity in every aspect!

Did You Know?

Did you know the Cuban government provides free gender-affirming surgeries to qualifying patients?

Day 1

Bienvenida a la Habana!

The Cuban heat greets you on touchdown! Set your bags down and join us for lunch! Our first professor is joining us to give an insightful look into the CUBAN MEDICAL SYSTEM. Learn how medical socialism works, what Cuba’s medical system offers trans people, the sexual and reproductive rights Cuba values, the difficulties presented with the blockade, and so much more...

Next, we have a lesson in the HISTORY OF THE CUBAN LGBTQ+ COMMUNITY. Our expert is a former representative from Cuba's leading agency which advocates for tolerance of LGBTQ+ issues on the island. We highlight the evolution of the community from Cuba's Indigenous People to present day and the introduction of Cuba's Family Code legislation.

Now that the stage has been set, we head out to one of Havana's hottest restaurants for your first taste of Havana's nightlife. Sip on mojitos served by some of the hottest bar tenders on the island and unwind after a lot day of travel. Up for more? Our night guide's got the hookup on Havana’s cabarets and drag shows!

Day 2

Salsa, Santeria and Solidarity

We hope you brought your dancing shoes because today we're getting a CUBAN DANCE LESSON you simply cannot find anywhere else in the world. Our teacher is on hand to instruct us on the basic steps of Cuba's most popular dance styles before we're joined by the plus-size baddies of Carnival for a special performance just for us!

After lunch, we head to our next lesson at la Casa de Africa where we learn all about CUBA-AFRICA SOLIDARITY from a living, breathing, former freedom fighter and veteran of the Angolan Independence War. We learn about the many links Cuba still share with Africa including their unique SANTERIA spirituality.

Friday nights in Havana are unpredictable and tonight, anything can happen! We start with dinner but be prepared to put those dance moves from this morning's lessons to use!

Did you know?

Did you know drag shows in Cuba are extremely popular late night? Don't expect the party to start until 2AM!

What our travelers are saying:

  • Mon

    “Traveling to Cuba with Reroot and Alysse was a trip of a lifetime. This was the first time I went on a LGBTQ+ trip and a trip that focused on regenerative tourism. i had an absolutely unforgettable experience! All of our activities were organized through a queer lens and we also had local Cuban tour guides who were also queer! Everything was so meaningful which made for such a memorable experience and as the only transmac person on the trip, I felt safe and affirmed the entire time. It’s SO clear that Alysse thoughtfully plans her trips with intention and makes sure everyone feels welcomed and comfortable. Our little group became a family to me and I’ll cherish these memories for the rest of my life!”

  • Celeste

    “ Going to Cuba through Reroot with Alysse was an incredible experience that I 100% recommend. I've never traveled with a group as an adult; I prefer to design my own travel and go at my own pace but I gave this a try because the itinerary looked amazing. Talking with a leading gynecologist about the state of queer/trans medical rights? Learning about the farming process for cigars and coffee/TRYING them right there?!? Riding horseback through the countryside which happens to be a UNESCO World Heritage site? Every activity and interaction was meaningful and compelling, and I have a richer view of Cuban life and history, as well as a new found community of queer friends.”

  • Danielle

    "Cuba has been on my dream destination list for years, but I was having trouble navigating the guidelines for visitors, and I kept putting off the trip. Reroot travel took care of all the logistics and told me exactly what I needed to know to get there. Traveling with Alysse was amazing since she always made sure we were taken care of, and she took everyone’s needs and abilities into account. The accommodations were beautiful and safe and our schedule was packed with sightseeing, education, and delicious food. I loved hearing from native Cubans and so appreciated the time they spent with us and the care taken.

    This is a trip I will never forget!”

Did You Know?

Did you know queer people were imprisoned in Cuba and now celebrate in the world's most progressive policies?

Day 3

Arte Cubano y la Playa!

You'll need: sunglasses, swimmies and suncreen.

We take a stroll through Havana to visit some of the best SHOPPING spots where everything is 100% Cubano. Today is a real showcase of the beauty in resilience of Cuba. Your guide will take you to specially curated locations where you'll be able to purchase art, fashion, accessories and general souvenirs all made by Cubanos right here in Cuba.

We couldn't bring you to the caribbean and not take you to the beach, could we?! For lunch today, we head to the white sand beaches for a special BEACH BBQ. This afternoon we work on our tans and soak in the warm, crystal clear waters of Cuba.We've got everything set up for you. All you need to do, is show up!

After a full day of relaxing, we head home for a chill night. It's an early night tonight because tomorrow we head out on the road to spend the remainder of the trip in Cuba's beautiful countryside.

Did You Know?

Cuba’s tobacco farms are protected UNESCO heritage sites and no machinery is permitted. The entire farm is plowed by oxen and accessed via horse, just like the old days.

Day 4

Viñales: Eco-farming & Horseback Riding

Pack your bags and say goodbye to Havana 'cuz we're hitting the road today and heading to your second location - Viñales!

The majestic Sierra de los Órganos and Sierra del Rosario hills will welcome you to this part of your Cuban adventure. On arrival, our guajiro guides will greet us to saddle up and head on HORSEBACK to the world famous farms of Cuba. Sip on some mojitos and try your own cigar while you learn about the all-natural ECO-FARMING practices which make Cuba's tobacco one of the world's finest and most sought-after products.

We move on for a little trot into the mountainside where we stop finally at a farm-to-table, woman-owned restaurant that has the best views of the valley. The restauranteur will explain her sustainable way of farming and how her family has survived and thrived in Cuba's countryside.

Day 5

Sunrise Hike & LGBTQ Farmers

Start your morning with a breathtaking sunrise at one of the highest points in Viñales National Park. Head out on your hike while it´s still dark and reach the summit of Los Acuaticos in time to watch the sun rise over the mogotes. This is a hike to remember. This is a 2-hour experience where you are hiking for about 1-hour total up & back. This is 100% optional. If you'd like to sleep in, we've got a hearty farm-style breakfast waiting for you!

For our final, official activity of this tour, we have something very special in store. You've been invited to dine on the farm of two gay farmers who have prepared an entire suckling pig, Cuban style! They will share about their lives in the countryside of Cuba over cervezas, and various delectable home cooked Cuban dishes. You’ll learn what it’s like being gay in the countryside.

The rest of today is up to you. Enjoy some free time for the remainder of your hours in this paradise!

Day 6

Farewell!

Our trip ends here but we know you'll back soon! Your transfer to the airport will pick you up at your farmhouse.

Tour Date: Sept 25th - 30th, 2025

Early bird PRICE: $3,195
(‘til december 2024)

All quoted prices are based on double occupancy (shared rooms).

Private rooms are available at an additional cost of $800

A $350 non-refundable deposit is required to reserve your spot.

What’s included:

  • All Reroot classes

  • All accommodations

  • Daily Breakfast, Lunch & Dinners

  • Airport Transfers

  • Ground Transportation for tour acitivities**

  • An English-Speaking Guide

    **For nights out, you’ll be responsible for your taxis home. Our guides will instruct you how to catch one.

What’s not included:

  • Airfare

  • Entrance/VISA fees

  • Souvenirs

Ready To Stare

Alysse Dalessandro is a queer plus size influencer based in Cleveland, Ohio. Her social media, Ready to Stare, and corresponding blog, readytostare.com, focus on creating inclusive fashion, travel and lifestyle content. Whether it's wearing a crop top, zip lining through the rain forest or searching for LGBTQ+ friendly themed hotels, Alysse shows that if she can do it, so can you!

Ready to Stare aims to be a place where plus size LGBTQ+ folks can feel seen while allies are welcomed to be informed and educated. NBC Out named Alysse one of their 2019 #Pride50 for her work as a contemporary change-maker, innovator and rising star in the LGBTQ community and GO Magazine honored Alysse one of their 100 Women We Love, Class of 2020. In 2022, Google named Alysse an "LGBTQ+ Creator Sparking Change and Inspiring Generations."