Spring 2017 trips to Cuba

My February 18-28 trip sold out, so I added the following dates. Shorter/longer trips are also available! Contact me for more details!

February 18 - 28 - Havana - Vinales - Bay of Pigs - Trinidad

April 12 - 19 - Havana - Cienfuegos - Trinidad

April 19 - 29 - Bike-Centered Havana - Vinales - Bay of Pigs - Trinidad

June 23 - July 3 - Havana - Bay of Pigs - Cienfuegos - Trinidad

June 30 - July 4 - Bike-Centered "Havana Highlights"

June 30 - July 10 - Havana - Vinales - Bay of Pigs - Trinidad

September 1 - 11 - Havana - Vinales - Bay of Pigs - Trinidad

September 8 - 18 - Bike-Centered Havana - Vinales - Bay of Pigs - Trinidad

January, February, and April, 2017 dates TBD...

Join me in Cuba this spring for an unforgettable trip. Now that travel has become much easier to the island, Americans are scrambling to get there before it changes (even more than it already has!). Join me to explore Cuban culture, food, music, and everyday life before it changes forever.

Some sample activities include:

- Ride in a classic American convertible

- Swim in crystal clear water and lounge on white sand beaches

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

- Explore tobacco plantations, secret swimming holes, and caves!

- Zip line across valleys in tobacco country!

- Bike through the streets of Old Havana

- Stay with local families, B&Bs, or hotels (prices vary)

- Scuba dive and snorkel in the infamous Bay of Pigs

- Go horseback riding to hidden waterfalls in the forest

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

- Longer and shorter trip options available

***For bike-focused trips, we will drive between cities and rent bikes to ride within the cities. Cuba is not yet set up for long-distance bike trips unless riders bring their own bikes, gear, and any equipment needed along the way. Bike shops are few and far between and are often very poorly stocked. A goal of the bike-focused trips is to also collect donated bikes and bike parts in the US to bring and donate to the Cuban people.


11-day trip
$1499/person ($400 deposit) by April 11th, 2017
$1599/person ($400 deposit) by May 8th, 2017
Prices based on double-occupancy. Single supplement +$199
Add only $100 more if you’d like to stay an extra night in Havana!
Flights range from $350-650, depending on when you book!

Trip includes:
B&B accommodations for 10 nights (hotels cost extra)
Breakfast every day, dinner 5 nights
Transportation between cities / bikes within cities
Admission to museums, night clubs, and snorkeling excursion

Trip does NOT include:
Gratuity for drivers, guides, porters, etc.

Other Random Activities:
Private salsa dancing or percussion lessons cost $15/hour
Massage costs $30/hour (plus tip)

Here are some references from previous group trips & travel consultations:

"Many people love to travel but few are actually good at it. Cassandra is one of these rare specimens that can pull it together wherever she's at. With a sense of adventure and also a keen idea of how to relax, she is capable of maneuvering in many situations. Cassandra is also completely bilingual in Spanish and English, which means she can help you achieve a truly unique experience - not just the touristy stuff. With her help, I was able to make the most of a week-long escapade to Cuba and I hope to be able to travel with her soon."

- Megan Frye, editor of Savoteur (Mexico City). May, 2016

"I joined one of Cassandra's 10-day group tours and had an absolutely amazing time and I can't say enough good things about the trip. She kept the group very small, 7 people, to ensure a comfortable journey and the flexibility to accommodate different group members' interests and trip goals. As I'm vegan and haven't used my Spanish since college, I had concerns about visiting Cuba alone but Cassandra speaks Spanish fluently and ensured we enjoyed vegan meals in every city, which gave me great peace of mind. I went snorkeling in and cycling around the Bay of Pigs, enjoyed petting a cuddly rodent of unusual size and jumping off waterfalls in Vinales, admired colonial architecture in Havana, Cienfuegos and Trinidad, and met many genuinely, lovely open-hearted people in every city. Cassandra invited her local friends to join us along the trip, including a documentary filmmaker, an actress, a paragliding instructor, and a man competing for the Guinness World Records title for tallest bike in the world. I so much enjoyed meeting a variety of Cubans from different walks of life to learn about their daily life and culture."

- Susan, New York City, February, 2017

"I traveled with Cassandra as part of a 10-day, small group tour through western Cuba and had an excellent time. We met in Havana where she had arranged airport pick up and accommodations at a centrally-located casa particular (homestay). Cuba is not known for its food, however in every city we traveled to, she found us an excellent restaurant. 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 in a hot nightclub built inside a cave. 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. Cassandra opened my eyes to much more adventure and culture then I was ever expecting."

- Amy M, New York City, December 2015

"Cassandra's service helped in planning my own solo trip to Cuba. She was able to give me great tips for staying within my budget, and helped narrow down the worthwhile places to visit based on my interests. I felt a lot more confident traveling alone after speaking with her, and had a successful trip because of it. I recommend her services to anyone needing a trustworthy guide outside of a travel book."

- Marissa Stern, Professional vagabond musician. (Detroit, Michigan). October, 2016

"Zip lining and scuba diving were great, I enjoyed the trip very much! We would not have done this many activities if we had gone on our own. Thanks!"


- Mei C., New York City, April, 2017