November 2019 group trip to Cuba - Havana's 500th anniversary

Join me for this unforgettable, non-touristy, small group trip to Cuba during the 500th anniversary of Havana. This will be a once in a lifetime opportunity where you will connect with extraordinary people and enjoy life-changing experiences. We’ll visit off-the-beaten path places in Cuba that you won’t find in any guidebook and you’ll get to engage with local Cubans from all different walks of life.

Havana’s 500th’ Anniversary:

Cycling, Cigars & Classic Cars

With the ever tightening restrictions and confusing information about whether it's legal to travel to Cuba, I'm getting more and more requests for group tours to Cuba. This group trip to Cuba will be extra special and it is quickly selling out. Reparations on the Havana Capital building will be complete, new museums will open, special concerts and parades will fill the streets, and a new public bicycle system will be completed.

We’ll visit off-the-beaten path places in Cuba, including four different cities, each of which offering its own flavor and flare. This educational/cultural Cuba tour is not your typical group tour and includes lots of walking, hiking, and biking. This is a fast-paced, action-packed trip, geared at curious travelers that enjoy non-traditional, off-the-beaten-path, local travel experiences. It is perfect for travelers who avoid run-of-the-mill big bus tours and who like to see and do a bit of everything.

Throughout the trip, you will meet Cuban friends of mine who will share their experiences as artists, journalists, government employees, entrepreneurs, and documentary film makers. These unique experiences will explore a side of Cuba that few tourists see.

This is a non-touristy Cuba group tour for people who don’t usually do group tours.

I joined one of EscapingNY’s 11-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, Los Angeles, CA
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, NY
A Cuban classic car in Central Havana

A Cuban classic car in Central Havana

Revolution Plaza in Havana

Revolution Plaza in Havana

Zip lining through Viñales Valley

Zip lining through Viñales Valley

Note that some cultural activities haven’t yet been announced so the itinerary may change a bit to accommodate anniversary parades, festivals, and concerts.

November 16th - 26th (11 days)

7-day trip to Havana and Viñales offered November 16th-21st

Saturday, November 16th

  • Arrive in Havana, get settled.

  • Neighborhood orientation tour and stroll along the bustling Malecón, where all of Havana congregates at night.

  • Evening visit to an old factory converted into the country’s premiere art exhibition space and nightclub.

Sunday, November 17th

  • Full-day historical walking tour of the Museum of Revolution and surrounding Old Havana historic hotels, churches, plazas, elegant mansions of one-time wealthy merchants, and growing street art and graffiti scene.

  • Evening drive in a classic car to watch sunset from across the bay.

Monday, November 18th

  • Morning discussion with an American journalist who’s been living in Cuba for 17 years and operates a business there. We’ll learn about her experience as an American living and running a business in Cuba.

  • Afternoon history and culture bike tour of Havana (Revolution Plaza, Old Havana, “The Forest”, Cemetery, etc.). The ride will be led by local urban planners and architects, and will be about 10-15 miles at a relaxed pace, making frequent stops.

  • Evening free.

Discover Havana’s best graffiti

Discover Havana’s best graffiti

Walking tour of Old Havana

Walking tour of Old Havana

The birthplace of the daiquiri

The birthplace of the daiquiri

Tuesday, November 19th

  • Three-hour drive to rural Viñales, the heart of Cuba’s tobacco country.

  • Guided walk through the Valley of Silence to learn about local flora, fauna, and agriculture traditions. We will visit several small family farms, where you’ll take part in the family's lifestyle and traditions, learn about the traditional coffee making process, and taste old-fashioned, filtered coffee.

  • Dinner and cocktails at a farm-to-table restaurant while watching the sunset over the mountains.

Wednesday, November 20th

  • Enjoy stunning views of the mountains and tobacco valleys as we ride through Viñales’ countryside (approximately 15 miles at a leisurely pace). We’ll go zip lining (canopy), visit a bar housed in a cave that used to shelter refugee slaves, and stop for rum and coffee throughout the rural valley.

  • Afternoon visit to a tobacco farm to learn about the traditional cigar making process. You’ll learn how to hand-roll your own cigar and have an opportunity to purchase organic Cuban cigars directly from local farmers.

  • Feast on a home-cooked dinner at our “casa” overlooking the mountains.

Viñales tobacco farm

Viñales tobacco farm

Viñales cigar demonstration

Viñales cigar demonstration

Biking in Viñales Valley

Biking in Viñales Valley

Thursday, November 21st

  • Three-hour drive back to Havana.

  • 7-day participants have the evening free and leave from Havana the morning of Friday, November 22nd

  • 11-day participants are off to Cienfuegos (another 3-hour drive).

  • Sunset at a waterfront gazebo, followed by dinner in an old palace.

Friday, November 22nd

  • Morning visit to a wildlife refuge, where we’ll learn about local flora and fauna and take small boats to visit a flamingo population.

  • Afternoon guided city tour of Cuba’s only French-colonized city, referred to as the “Pearl of the South”.

Saturday, November 23rd

  • Morning visit to El Nicho, where we’ll hike to several natural pools and waterfalls to swim in. The hike is relatively easy and lasts one hour.

  • One-hour drive to the colonial city of Trinidad.

  • Afternoon culture, history, and religion tour of the city with local journalists.

  • Evening visit to enjoy a live Afro-Cuban music and dance performance.

Plenty of rides in classic cars

Plenty of rides in classic cars

Explore Cuba with fun & interesting people

Explore Cuba with fun & interesting people

History & culture tour of Trinidad

History & culture tour of Trinidad

Sunday, November 24th


  • Participants are free to explore local beaches and hiking trails, cycle around the city, or take salsa dancing or percussion lessons.

  • Private photo shoots with local professional photographers can also be arranged.

Monday, November 25th

  • Morning historical tour of former sugar refineries, plantations, distileries, and slave quarters.

  • Four-hour drive back to Havana.

  • Evening is free for live music, dancing, packing, resting.

Tuesday, November 26th

  • Morning free for last-minute shopping or a private photo tour with Cuban professors of photography.

  • Afternoon flight home!

Client Testimonials (more here)

I joined an 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, Brooklyn, 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, NY
Breakfast on the patio

Breakfast on the patio

Drinks at sunset

Drinks at sunset


Pricing includes all activity admission, round trip airport transfers, transportation between and within cities, guides, B&B accommodations, all breakfast, and either lunch or dinner each day. Travelers with special diets (vegan, vegetarian, gluten-free, Kosher) can be accommodated with advanced notice. Contact me for more information!

$2299 per person for the 7-day trip if booked by April 15th ($2399 by June 15th, $2499 by August 15th)

$3199 per person for the 11-day trip if booked by April 15th ($3299 by June 15th, $3399 by August 15th)

*Prices are based on double-occupancy. If you wish to have your own room, please add $399 per person for the 7-day trip or $499 per person for the 11-day trip. In the past, guests have enjoyed inviting friends and family to share a room, though I will try to pair up interested singles looking for a roommate.

A 50% deposit is required by the indicated date to reserve your spot. The remaining balance is due by September 15th, 2019.

What is included:

  • Round-trip taxi transfers to/from Havana airport

  • English-speaking guides

  • Transportation between and within cities to all activities on the itinerary

  • Accommodations in comfortable B&B homes

  • Breakfast every morning and either lunch/or dinner each day

What’s NOT included:

  • Airfare (though I will make airline/flight suggestions).

  • Tips/gratuities for guides

  • Travel insurance

  • Admission and transportation to activities not included in the itinerary

  • Meals not indicated in the itinerary

IMPORTANT: Proof of travel insurance is required for this trip. Read my article Why You Should Buy Travel Insurance to learn why it’s so important. You may chose your own travel insurance provider but I recommend World Nomad's. I've used their insurance for many years, as have many of my clients, and they offer comprehensive coverage and excellent customer service at a reasonable price. Additional terms and conditions can be found here.

Make memories in Havana

Make memories in Havana

Explore off-the-beaten-path Cuba

Explore off-the-beaten-path Cuba

Explore classic & modern Cuba

Explore classic & modern Cuba