Divergent CUBA

9 DAYS/8 NIGHTS

Divergent Travel Trips

JANUARY 24 – FEBRUARY 1, 2026

Price from $3,900

BOOK HERE

“This is an immersive journey to Cuba.“

Join Divergent Travel Trips for an incredible cultural adventure in Cuba! This will be our third visit (second group trip) and we can’t wait for you to join us.

Spend 9 days of full immersion in the natural, and cultural wonders of Cuba with us on this custom-built itinerary that you will not find anywhere else.

Havana Cuba
Trinidad Cuba Guide - Divergent Travelers

We offer this trip in partnership with THE BEST operator available. They are registered with the US Government and have all of the necessary permits to offer these incredible people to people trips to Cuba for Americans. 

Not only will you be shocked by the incredible natural beauty of the country, we will be completely immersed in the culture, too. You’re going to meet the real people of Cuba. 

We have a long-standing partnership with them, having traveled with them and also operated our previous Divergent Travel Trips with them. Our itinerary is custom built based on our previous visits and input from our partner on new and upcoming places.

We’re going to show you the best of Cuba but also get you off the beaten track, too. This experience is exclusive and beyond special. 

Daily activities include sightseeing, hiking, cultural experiences, and plenty of photo stops.

Something to note: While every trip we offer provides a photographic element, you do not need to be a photographer to join this trip. But, if you want to take photos, we’ll have amazing opportunities to do so.

If all you have is an iPhone, no worries! We can help you take great photos with it.

If photography is of no interest to you at all, that’s ok too.

Trip Itinerary

View the itinerary, pricing, inclusions, exclusions, & book!

Welcome to Miami, Florida!

Arrival at the Miami International Airport is at leisure. There are many options for hotels near the airport. We will arrange a meetup dinner.

Overnight: Miami Airport Hotel (not included)

Welcome to Cuba!

This morning we will meet at the Miami International Airport to take a morning flight to Havana, Cuba. We will be met at the airport and transferred to the city for a full day of sightseeing and activities.

Overnight: Local Casa Particulares in Havana (L-D)

Facts About Cuba Havana
Old Car Tour Havana Two Week Cuba Itinerary

After breakfast, we will leave Havana and make our to Vinales. We will have a full day of sightseeing and activities along the way and upon arrival to Vinales.

Overnight: Local Casa Particulares in Vinales (B-L-D)

Las Terrezas Cuba
Vinales Valley Cuba

Today we will enjoy a full day in Vinales. We’ll visit a tobacco plantation, learn about Cuban cigars, and meet some of the farmers.

Overnight: Local casa particulares in Vinales (B-L-D)

Cuba tobacco plantation
Tobacco Field Vinales Two Week Cuba Itinerary

After breakfast we’ll head back to Havana, where we’ll enjoy lunch. Afterwards, we’ll head to the Havana Old Town for the afternoon.

Overnight: Local casa particulares in Havana (B-L-D)

How to Visit Cuba Havana
How to Visit Cuba Havana Classic Cars

Today we’ll head to the south for a visit at the Bay of Pigs. We’ll enjoy a boat ride through the marshes, in search of crocodiles and pink flamingoes. We’ll learn the history of the Bay of Pigs and after lunch, we’ll make our way inland to Cienfuegos.

Overnight: Local casa particulares in Cienfuegos (B-L-D)

Bay of Pigs, Cuba
Bay of Pigs Cuba

Today we will make our way to stunning town of Trinidad. Upon arrival we’ll enjoy a walking tour to get familiar with the town.

Overnight: Local casa particulares in Trinidad (B-L-D)

How to Visit Cuba Trinidad
Square in Trinidad, Cuba

Today we’ll enjoy a full day of activities in Trinidad! This includes journeying to the Valley de los Ingenios to visit one of the old sugar mill plantations outside of the city. We’ll meet local families and learn about the sugar trade that Cuba was once famous for. In the afternoon, we’ll have free time to enjoy the street music and visit with the local artisan vendors.

Overnight: Local casa particulares in Trinidad (B-L-D)

Valley de los Ingenios 14 days in Cuba
artisan shops in Trinidad, Cuba

Waking up in Trinidad, we’ll have breakfast and then head out for an adventure to Topes de Collantes. We’ll learn about the history of the region, meet local artisans, ride in old russian trucks and then hike to a stunning waterfall for a refreshing swim. We’ll do some bird watching along the way in hopes of spotting the endemic Cuban Trogon, among other species.

Overnight: Local casa particulares in Trinidad (B-L-D)

Truck in Topes ed Collantes Cuba
Topes de Collantes Cuba

All good things must come to an end, and this morning marks the official end of our amazing time in Cuba together. We will be transferred from Trinidad to the Santa Clara Airport to catch our flight back to Miami, Florida.

(B)

Additional Trip Information

What’s Included:

  • International Flights MIA-HAV & SNU-MIA
  • Airport transfers – Arrival & Departure
  • Transportation by classic cars
  • 8 nights at local casa particulares
  • 8 breakfasts, 8 lunches, and 8 dinners
  • All entrance fees (HUGE value)
  • All National Park fees (HUGE value)
  • Daily activities (including extras)
  • Drinks at meals
  • Expert local guide
  • Local drivers
  • Gratuities
  • Cuba Visa
  • Photography instruction
  • Welcome gift
  • Your hosts (us)!

What’s Not Included:

  • Airfare to/from Miami, Florida
  • Travel Insurance (required)
  • Personal Expenses
  • Single Supplement (if requested)

Trip Perks

If you’re looking for a trip to Cuba that includes all of the highlights, along with some lesser-known gems, this itinerary is for you.

Our trips include ALL extra activities, day trips, and entrance fees. We’ve also hand-selected lovely local accommodations.

This trip starts and ends at the Miami International Airport (MIA) in Miami, Florida.

Your flights from MIA-HAV and SNU-MIA are included in the trip price and will be booked as a group.

Your Cuba visa is included with the trip price and will be issued at the Miami airport by our operator prior to boarding the flight to Havana.

Expect warm weather with highs in the 80s and lows in the 70s.

We have worked with our operator to hand-select each and every property that is used for our trips. Trust us when we say we only want the best for you! On this trip, we’ll be staying in a variety of local casa particulares, which are essentially home stay bed and breakfasts. They will offer prime locations across Cuba. They all offer private bathrooms.

Room sharing – if you are traveling solo and select the shared room option, we will do our best to pair you with someone of the same gender. We’ll do our best to pair you with someone we think you’ll click with based on your signup forms.

We cannot guarantee that you’ll mesh well with your assigned roommate. This is very rare, but it does sometimes happen.

Things to Consider – If you like your own space after a day of group traveling, are a light sleeper, or snore, sharing may not be a good fit for you.

In the event that you are incompatible with your assigned roommate and need to change rooms, your trip host will either swap shared rooming arrangements or work with the hotel to get you a solo room. Please note that if you have to switch to a solo room, you will be subject to a solo supplement.

If you sign up for a shared room and we are unable to pair you with another solo shared traveler before the trip starts, your booking may become a solo booking. If this happens, we will notify you and the single supplement will apply.

If you do not want to share, it is possible to have your own room with the additional fee of a single supplement.

Note: this option is limited.

It is possible to have a solo private room but this option is limited. The cost to have a solo private room for the whole trip is an additional $300.

This tour is rated Moderate. There will be some long driving days while on safari and some easy hiking. To really enjoy the tour you should at least be prepared for some long walks in outdoor settings.

Yes, we have some down time built into the schedule if you’d like to explore some on your own or just relax at the homestays.

There will be no cell service available. It will be possible to purchase WIFI cards, but please be aware that WIFI connection is typically only in the town squares. I would plan to be offline for the duration of this trip unless absolutely necessary.

Once you arrive in Cuba your airport transfers, accommodation, activities, and transport are included. You will need money to cover any personal expenses.

Diverge & Join This Adventure!

The dates of this trip are January 24-February 1, 2026.

The cost is $3,900 per person for a shared room.

This price is exclusive to our group and includes staying in beautiful local casa particulares, private local guides, all activities, all transportation on arrival, all meals & drinks, a welcome gift, and photography help from us, if you want it.

We’re offering you a custom-built trip that includes all the day trips, sightseeing, entrance fees, and extras at an insanely good price.

Additionally, this will be a small, private, and intimate group.

Solo-Share Option: If you are traveling solo and select the shared room option, we will do our best to pair you with someone of the same gender. If you sign up for a shared room and we are unable to pair you with another solo shared traveler before the trip starts, your booking may become a solo-private booking. If this happens, we will notify you and the single supplement will apply.

Solo-Private Option: If you are traveling solo and wish to have a private room, this is possible. The cost to have a solo private room for the whole trip is an additional $300.

BOOK HERE

A $500 non-refundable deposit is required to reserve your spot, and the remaining balance is due 120 days before departure. Payment plans are also available upon receipt of your deposit.

Departure is not guaranteed until the minimum number of guests is met. Please do not book flights or other non-refundable travel until we guarantee departure.

If the trip is full, email [email protected] and we will add you to the waiting list — also follow Divergent Travel Trips on Instagram to be the first to know when future trips are announced.

Divergent Travel Trips

Frequently Asked Questions

We live in a fast and ever-changing world these days, which is one of the many reasons we require travel insurance for all of our trips. This also means that if you cancel your trip due to covered reasons with your policy, you’ll be able to file a claim and be reimbursed.

Your travel insurance will also cover trip interruption or cancellation, should something happen like a natural disaster or political unrest.

Beyond that, this is our cancellation policy.

We can offer a full refund less the non-refundable $500 deposit up to 120 days before the trip departure date if you choose to cancel for a personal reason.

If you need to cancel less than 120 days before the trip, we are unable to offer a refund of any amount.

No, the $500 deposit to secure your space is non-refundable and the remaining balance is due 120 days before departure. If the trip must be postponed or canceled due to events beyond our control, you will be offered a full refund.

World Nomads and Allianz Travel Insurance offer travel insurance, required for the duration of this trip, at affordable rates. Travel insurance will also reimburse you in the case of flight delays, medical issues, and more.

International flights are not included. Some of our trips do include internal domestic flights and are noted within the itinerary.

We welcome anyone 18 years or older. Our groups are usually made up of both women and men. The ages typically range from mid 20s to mid 70s and everything in between.

We cannot predict the ages of those who sign up for each trip. That said, this range meshes surprisingly well and we’ve shared many great adventures!

If you are in good health, of reasonable fitness, have a good sense of humor, and a sense of adventure, you’re welcome to join!

There will be a waiting list on a first-come, first-served basis in case spaces open up or we decide to offer an additional departure for each trip.

If the trip is full and you’re still interested, email us at [email protected] to be added to the waiting list.

Absolutely not! While every trip we offer provides a photographic element, you do not need to be a photographer to join this trip. But, if you want to take photos, we’ll have amazing opportunities to do so.

If all you have is an iPhone, no worries! We can help you take great photos with it. If photography is of no interest to you at all, that’s ok too.

Still have questions?
 
 

Divergent Travelers- Adventure Travel Blog