CUBA

A farmer gathers tobacco leaves during the winter harvest

A farmer gathers tobacco leaves during the winter harvest

Cayo Jutia beach in Vinales

Cayo Jutia beach in Vinales

Possibly the happiest car in Cuba!

Possibly the happiest car in Cuba!

Everyone is scrambling to visit Cuba, a diverse island paradise seemingly stuck in the 60s. Cuba has something for everyone, including: classic car tours through Old Havana, bike rides through tobacco country, scuba diving, flamingo watching, waterfall jumping, historical walking tours, visits to old sugar plantations, and more! While most travel to Cuba takes place in the West (Havana, Vinales, and Trinidad), Eastern Cuba offers some of the richest history and stunning natural landscapes, is the birthplace of salsa music, and is home to spectacular national parks, wildlife reserves, and white sand beaches.

Group Trips to Cuba

Join me to explore Cuban culture, history, religion, food, and music, and to get to know the kind, generous, and endlessly optimistic Cuban people. I offer two distinct trips to Cuba, detailed below. Both tours are fast-paced, action-packed trips, geared at curious travelers that enjoy non-traditional, off-the-beaten-path, local travel experiences. They are perfect for travelers who avoid run-of-the-mill big bus tours and who like to engage with locals and see and do a bit of everything. Click on each tour for more details.

Cycling, Cigars & Classic cars

During this 11-day off-the-beaten-path group tour, you’ll get to do a bit of everything: cycling, hiking, historic walking tours, and roundtable discussions with small business owners. You’ll visit tobacco farms, museums, old palaces, beaches, nightclubs, art galleries, former sugar plantations, and non-touristy areas that few travelers ever see. You’ll soak up tons of culture through private tours and one-on-one engagement with local journalists, artists, and personal friends of mine in Havana, Vinales, Trinidad, and Cienfuegos, who offer a fresh perspective on life in Cuba.

Photo Tour of Cuba

On this one-of-a-kind 7-day photo tour of Cuba, you’ll learn about the island’s culture, history, art, music, & architecture, all through a camera lens. Professional Cuban photographers will share tips to improve your own photography and will capture photos of you in both classic and largely unknown locations in Havana, Trinidad, and Cienfuegos. You’ll see a side of Cuba that few tourists encounter and create meaningful connections with locals and fellow travelers, all while capturing once-in-a-lifetime pictures.

I joined the 11-day trip to Cuba and had an excellent time. We went on a flamingo-watching boat ride in a nature preserve, jumped off waterfalls in the jungle, cycled through Old Havana, visited several beautiful beaches, and went salsa dancing. I had limited expectations of Cuba because I don’t speak Spanish and I’d never traveled to a “non-westernized” country. My expectations were absolutely exceeded.
— amy m, broooklyn, ny
I joined one of EscapingNY’s 10-day group tours and had an absolutely amazing time and I can’t say enough good things about the trip. I so much enjoyed meeting a variety of Cubans from different walks of life to learn about their daily life and culture.
— Susan V., Los Angeles, CA
Classic car tour through Central Havana

Classic car tour through Central Havana

Observing an artist at work in Cienfuegos

Observing an artist at work in Cienfuegos

Bike tour stop at Revolution Plaza

Bike tour stop at Revolution Plaza

planning your own trip to cuba

In addition to leading group tours to Cuba, I also help individuals, couples, and groups plan their own personalized trip to Cuba (among other locations). Instead of spending dozens of hours researching and stressing out over conflicting information online, you just tell me about your interests, budget, trip goals, and travel style, and I handle the rest. I have helped many solo travelers and couples travel through Cuba (you can find testimonials here) and I absolutely can help plan your trip.

I offer full-service packages that include booking accommodations, guides, drivers, and planning the full itinerary but I also offer basic consultations to help travelers figure out what cities to go to, how much time to spend there, what to do, and how to get around, etc. Contact me for more information on how to plan your own trip to Cuba.

EscapingNY helped me plan my own solo trip to Cuba, providing great tips for staying within my budget, and narrowing down the worthwhile places to visit based on my interests. As a result, I felt a lot more confident traveling alone and had a successful trip because of it. I recommend EscapingNY to anyone needing a trustworthy guide outside of a travel book.
— Marisa Stern, Detroit, MI
EscapingNY provided an extremely useful, very personalized service, matching us with a documentary film maker who served as an air traffic controller with an opinion. Cassandra is very knowledgeable about every place she travels to, so even when she isn’t accompanying you, she can guide you to see and do just what you want you do. She made this a very interesting travel experience and her recommendations for accommodations found us in very nice places with people she personally had vetted. You can’t go wrong with EscapingNY!
— Meryl M, Tuckahoe, NY
EscapingNY organized a fantastic itinerary for our family of 5 that included excellent lodgings, meals, and activities. We had so much fun in Cuba! Having a knowledgeable, engaged, organizer handling all the details and checking in with us and our hosts and drivers throughout the trip allowed for a more relaxed trip and gave us piece of mind as parents.
— Eric F, Rhineback, NY
EscapingNY customized a special travel plan for me focusing on an in-depth, authentic Havana experience. During my short stay, I made many interesting local friends, biked off-off-beaten paths, and learned about Cuban culture. I’d highly recommend EscapingNY to anyone interested in really getting to know a country. Thanks again!
— Wei C., New York City

Related Articles on Cuba

For more information to help you decide what places you’d like to explore during your time in Cuba, see my previous blog posts to get a feel for the day-to-day life that few tourists encounter, what to pack, what to expect, and what to know.

2019 Group Trips to Cuba

What to Know Before Booking an AirBnB in Cuba

How to Pack for Cuba

Tips for Solo Female Travelers in Cuba

Cuba’s Local Food Scene Isn’t What You’d Expect

Is it Still Legal to Visit Cuba?

Camping in Guantanamo

Cuba's Zero-Waste Recycling Like You've Never Seen it Before

Spaghetti with Mustard: Not What You Expected from Cuban Food

How to Be Vegan in Cuba


Bike touring through Vinales, Cuba

Bike touring through Vinales, Cuba

Daily life in Gibara, Holguin

Daily life in Gibara, Holguin

Sample Activities for a Solo Trip to Cuba

- Explore tobacco plantations, secret swimming holes, and caves with nature guides!

- Explore religious, political, and cultural history with Cuban journalists

- Visit the hottest night clubs, art galleries, and theaters

- Bike through the streets of Old Havana

- Explore Cuban street food with local chefs and foodies

- Schedule a professional photo shoot with a Cuban photographer

- Stay at the homes of local families

- Scuba dive and snorkel in the infamous Bay of Pigs

- Go horseback riding to hidden waterfalls in the forest in Vinales or Trinidad

- Visit Hemmingway's Villa in a classic American convertible

- Attend guided educational tours focusing architecture, mob life, or Santeria/Afro-Cuban religion

Santa Clara

Santa Clara

Old Havana

Old Havana

Havana's busy Malecon

Havana's busy Malecon