Cuba with The Emilies!

November 21-29, 2026
$2,999 (international flight not included)

Registration opens August 15, 2025

Trip Overview

We (The Emilies) visited Cuba in the Summer of 2016, along with fifteen teenagers, and we still maintain it was one of their favorite trips of all time. We are SO excited to bring more people to this historic island to explore its natural beauty and unique history. Keep in mind: traveling to Cuba is much more of an adventure than a vacation. 

*Important note: While our itinerary has planned everything to be as nice and comfortable as possible, Cuba has been fairly cut off from the rest of the world (for reasons we will definitely highlight on our trip.) Internet and phone access can be sparse in some places and some of the nicest tourist hotels are not quite as luxurious as they might be on other trips. What we're saying is, if you're looking for an all-inclusive island retreat, this may not be the trip for you. BUT, if you're excited to explore this historic island, get an other perspective on the ongoing U.S.-Cuba stare down, and get to know the Cuban people and culture, you're going to LOVE this trip.

What’s included?

  • Hotel Rooms

  • All transportation within Cuba, including airport transfers

  • Breakfast (7/8 mornings)

  • Lunch (6/7 days)

  • Dinner (6/7 evenings)

  • All entrance fees, tours and activities included on the itinerary

  • Group Tip for our local guide and drivers

What’s NOT included?

  • International Flights (to/from Havana)

  • Lunch (1 day - Day 7 in Trinidad)

  • Dinner (1 night - Day 2 in Havana)

  • Visas/travel insurance

Itinerary

Day 1: November 21, 2026
Arrive in Havana

Bienvenidos a Cuba! Welcome to Cuba! Upon arrival, soak in the decaying beauty of Havana and the surreal feeling that you have entered a bygone era. This is a very historic time to visit Cuba, as the gates finally creak open to a country so long forbidden, an opportunity has arisen to support the Cuban people and explore their incredible country. 

As there are no activities planned for today until your important welcome meeting at 6 pm – why not take a stroll to get acquainted with Cuba’s capital, where vintage cars, plumes of cigar smoke, Neo-Gothic churches and Art Deco theatres come together in a unique mesh of histories. After your welcome meeting, enjoy dinner at a local paladar, a privately-owned restaurant and a great example of Cuba’s incremental shift to a more free-market economy. Paladar means ‘palate’ but the popular usage of the word to describe this kind of restaurant references a Brazilian soap opera popular in Cuba in the 1990s.

Meals included: Dinner

Day 2: November 22, 2026
Explore Havana

This morning, find out more about the local customs, folklore and beliefs of Cuba’s Afro-Cuban religion from an insider on a colourful and unconventional tour with Urban Adventures. Be welcomed into private homes and take the opportunity to learn from the devoted residents as you explore one of Havana’s sub-cultures at a grassroots level, something not often experienced by tourists. Next, you’ll get to see outer Havana in a convoy of classic American vintage cars. Cruise via points of interest – such as the Malecon, Revolution Square, Avenida de los Presidentes and ending in Old Havana. 

Next, your leader will take you on a walking tour around the charming neighborhood of Old Havana (approximately 2.5 hours). The best place to start any Havana experience is in the Old City, which is one of the best-preserved towns and in 1982 was designated a World Heritage Site. The streets are lined with colonial architecture, 16th-century fortresses and countless churches. Visit La Catedral San Cristobal de la Habana, the Palacio de los Marqueses de Aguas Claras and the Plaza de Armas. After a full day of exploration, enjoy an evening at leisure.

Meals included: Breakfast, Lunch

Day 3: November 23, 2026
Havana-Las Terrazas-Viñales

This morning, head east to Vinales. En route stop by an outer-Havana suburb to see the passion project of Jose Fuster, an artist who has turned an entire neighbourhood into a lively and colourful series of mosaics. Known as 'Fusterlandia', the inspiring and whimsical scenery is a perfect spot for pictures. Continue your journey to a local community in Las Terrazas (approximately 2 hours). The village was built as part of a government reforestation project and has since received a UNESCO biosphere listing. Meet up with local community leaders who will share insights into Las Terrazas and how the society works. You’ll also visit the ecological research centre and take a guided walk around the complex. 

After lunch take a 2 hour drive to Vinales – situated in one of the most picturesque parts of Cuba, it’s a small and culturally rich village, with friendly and welcoming residents. On your way into the village, you may pass by the vibrant Mural de la Prehistoria at the foot of the verdant Sierra de Vinales. Take the short journey into the centre of town and arrive in time for a brief orientation walk before heading to a privately- owned organic farm to learn about sustainable farming in Cuba. Hopefully meet local farmer Wilfredo Garcia Correa or at least his family who will show us around the farm and explain the methods used to cultivate crops without the use of pesticides, then enjoy a deliciously fresh and diverse meal prepared by the family, a truly authentic farm-to-fork experience!

Meals included: Breakfast, Lunch, Dinner

Day 4: November 24, 2026
Experience Viñales

Today at 9 am, spend the morning (approximately 3 hours) finding out more about Cuban agriculture with a visit to a local tobacco farm to learn about the tradition of Cuban cigars. Get an insight as to how the communist system works, how much tobacco they keep, how much produce they give back to the government and how they make ends meet. Learn about the process of tobacco planting to rolling the final cigar. Share in the secret recipe of how they cure their leaves, which originated from one family and has been passed down through three generations – then drink some freshly roasted coffee from the farm while watching an expert roll a cigar. 

In the afternoon, get involved in a 1-hour salsa dance lesson, followed by a cooking demonstration from a local chef. Viñales is one of the more agriculturally productive areas of Cuba, so an abundance of homegrown seasonal fruit and vegetables are always on offer such as avocados, mangoes, pineapples, papaya, guava, and several varieties of sweet potatoes. Sit back, relax and enjoy the well-prepared meal while overlooking the lush scenery of Viñales.

Meals included: Breakfast, Lunch, Dinner

Day 5: November 25, 2026
Viñales-Ciénega de Zapata-Cienfuegos

Depart Vinales at 8 am and head to Cienfuegos – drive for approximately 4.5 hours before stopping for lunch. This afternoon you’ll visit the Korimakao Cultural Project in Ciénega de Zapata, an area famous for its wetlands. Founded in 1992, Korimakao is a project to bring theatre, music, and dancing to remote areas of Cuba. You’ll have the opportunity to meet a director of the project, who will talk to you about the importance of this venture and the number of students that have benefited from it. 

Continue along to the picturesque town of Cienfuegos, a slice of Paris in the Caribbean. Founded in 1819 by pioneering French immigrants – the elegant architectural influence that these settlers brought with them, earned the city a UNESCO World Heritage Site listing in 2005.

Meals included: Breakfast, Lunch, Dinner

Day 6: November 26, 2026
Cienfuegos-National Park-Trinidad

This morning at approximately 8.30 am, your leader will show you around the charming streets of Cienfuegos before getting back on the road around 10 am, heading towards the National Park of Topes de Collantes (approximately 2 hours). Here there is a stop for a swim in a waterfall and to have lunch at a small privately-owned family farm. 

Travel onwards to the beautiful city of Trinidad (approximately 1.5 hours). Located near the lovely Valle de los Ingenios (Valley of Sugar Mills) and Playa Ancón, Trinidad enjoys long stretches of unspoiled, white sand beaches and is home to numerous churches and well-preserved colonial buildings. After lunch, begin with a guided cultural tour of the city (approximately 3 hours) – this includes an opportunity to visit two museums such as Museo Nacional de la Lucha Contra Bandidos, Museo Romantico or the History museum. 

Later, visit the privately-owned pottery workshop of the Santander family. This family are well known in the Cuban cultural landscape for having produced pottery for generations as well as assisting in the restoration of sculptures that once existed in this UNESCO world heritage site. Support the Cuban economy by taking the chance to purchase your own pottery as a reminder of your time in Cuba. 

In the evening, perhaps seek out the dance scene in Cuba. You may wish to see the local Afro Cuban Folkloric dance group that perform shows at the club Palenque, which has cultural and social importance in this region. Nightlife in Trinidad is probably the most accessible and intense in all of Cuba, with numerous live music venues and many dance performances every day of the week.

Meals Included: Breakfast, Lunch, Dinner


Day 7: November 27, 2026
Explore Trinidad

This morning is yours to explore Trinidad by selecting one of the many optional activities on offer. Perhaps you’d like to hire a bike and cycle along the city’s colorful streets, past once-grand mansions, pastel buildings and wrought iron features – or instead you might choose to explore one of the excellent walking trails in the nearby Sierra del Escambray mountains. Your leader can suggest a lunch place at a local paladar. 

In the afternoon head to Playa Ancon for some beach time fun and maybe a little snorkeling, followed by a sunset picnic prepared for you by one of the privately-owned guesthouses.

Meals included: Breakfast, Dinner

Day 8: November 28, 2026
Trinidad-Santa Clara-Havana

Leave Trinidad around 9 am, head to Santa Clara, a key city in the Cuban Revolution to see the iconic statue of Ernesto Ché Guevara, built to commemorate his death and that of the revolutionaries. There will be time to explore the museum which honors Che's life. 

Drive back to Havana (approximately 3 hours) where there will be some time to freshen up before a final fun-filled night of music, dinner and dancing at Rosalia de Castro – where you’ll enjoy an ensemble of Cuban classics performed live by Buena Vista Social Club!

Meals included: Breakfast, Lunch, Dinner

Day 9: November 29, 2026
Depart from Havana

Your adventure ends today after breakfast. There are no activities planned for the final day so remember to say good-bye to your leader before you head back to the U.S. (or onto your next adventure!) 

Important note: 
Due to licensing restrictions, only one night’s pre-tour accommodation may be requested. Post-tour accommodation cannot be offered.

Trip Cost

$2,999
International flights not included

$1,000 deposit due at booking (non-refundable)

Final payment due by July 25, 2026

Cancellation Policy


Your down payment (due at the time of booking) is non-refundable. 

- If you cancel your registration more than 120 days before the trip start date, you will receive a refund of any amount paid beyond the non-refundable deposit. 

- If you cancel your registration between 60-120 days before the trip start date, you will receive a refund of half any amount paid beyond the non-refundable deposit. 

- If you cancel within 60 days of the trip start date, you will not receive any refund. 

Join the waitlist

Registration for this trip opens August 15, 2025. Let us know you’re interested and we’ll send you the link to sign up for the trip as soon as it’s available!