Classic Cuba Tour

9 Days / 8 Nights

Miami | Havana | Playa Larga | Cienfuegos | Trinidad


Cuba’s most famous cities, Havana and Trinidad, stir visions of brightly painted Colonial buildings, pounding mambo rhythms and barrios that bustle well into the night. 

With U.S. travel to Cuba long forbidden until recently, these images may seem hazy, like paintings unfinished. Alongside insightCuba, you are finally able to complete the picture. 

Your nine-day Classic Cuba Tour begins in the boisterous harbor city of Havana and ends in the artistic enclave of Trinidad, with a stop in Cienfuegos, a jewel of a city known as “the pearl of the South,” along the way. At each destination, a generous Cuban spirit unfolds as the locals open their hearts and shed light on their colorful and often complex way of life.

As your first morning in Havana breaks, set out with your Cuban guide through the historic corridors of Old Havana. The UNESCO heritage area is spangled with 16th and 17th century buildings and cobblestone squares animated by the impromptu blare of trombones and lilt of guitars. Linger in the company of musicians. This is true city rhythm. It’s the beat of life as the Cubans themselves know it.

As you journey on to Trinidad, outlying sugar cane fields give way to an urban playground juxtaposed by modest red-tiled residences and rambling Colonial mansions and museums. Here, you can expect heavy doses of culture and history. Talk with local residents about the influence of African traditions and religion on society and culture and meet the professional singers, dancers and musicians of Ballet Folklórico de Trinidad, who regale you with the history of Afro-Cuban folkloric dance. 

Scroll down to see what's included, the sample itinerary, departure dates, and pricing

What's Included

  • One night at the Pullman Hotel & Resort Miami Airport, including breakfast and airport transfer

  • Private welcome reception and pre-tour briefing

  • Superior accommodations at the Meliá Cohiba Hotel in Havana

  • Standard accommodations in provincial hotels or casa particulares in Trinidad or Cienfuegos

  • InsightCuba exclusive-guided programming, including; unique handpicked people-to-people activities; insider access to Cuba's famous places and those rarely seen; and private visits and lectures with Cuba's renowned experts

  • Experienced insightCuba tour leader

  • Expert Cuban guide

  • All meals while in Cuba, except for two paladar evening dining experiences on your own

  • Certification of travel to Cuba under the U.S. Department of the Treasury general license

  • Small group size (usually 16 or fewer guests; never more than 24)

  • All entrance fees to scheduled activities and events

  • Flight package (cost additional) including; round-trip charter air from Miami to Havana, Cuban visa, priority check-in at Miami International Airport, and baggage fee for first checked bag

  • All in-country ground transportation and airport transfers via luxury motor coach

  • Private Cuban Driver

  • Travel health insurance, emergency medical evacuation, and trip cancellation coverage (up to $1,000)

  • Fresh bottled water while touring

  • InsightCuba travel guidebook

  • 24 hour emergency customer service hotline

  • Gratuities for luggage handling, restaurant service, and programmed activities throughout tour*

*Customary end-of-tour gratuities for the Cuban guide, driver, and tour leader are left to the guest’s discretion and should be based on your satisfaction with the level of service received.

Sample Itinerary

*A significant portion of your in-country programming is customized for each group to maximize your cultural experience. Many of the places we visit are not tourist destinations and are thus not always available. Therefore, this program should be considered as a sample only – please keep in mind that your particular tour may vary. Final itineraries are sent to guests one to two weeks prior to departure.

Days 1-2: Miami / Havana

Your trip begins at the Pullman Hotel & Resort Airport Hotel, where your small group will gather for an early evening briefing and reception. Following breakfast at the hotel on your second day, you’ll board the charter flight to Havana. After you clear immigration and customs, your insightCuba tour leader and Cuban guide will accompany you to your hotel in the heart of Havana. Get your first taste of Cuba with an afternoon orientation.

Meals Day 1 | Enjoy dinner on your own, at your leisure

Meals Day 2 | Breakfast, Lunch, Dinner

Day 3: Havana

Start your day by meeting an expert in Cuban architecture, who will discuss Old Havana’s rich architectural heritage and UNESCO designation. After lunch, you’ll visit an incredible organization to learn about Afro-Cuban art, music, and dance. Later, meet with university students and professionals for candid discussions about daily life in Cuba, before visiting an artist in his studio. You’ll end the day with dinner at La Floridita, one of Hemingway’s favorite spots for drinking daiquiris.

Meals | Breakfast, lunch, dinner

Day 4: Havana

Today, you’ll visit a local historian at the Colon Cemetery. Then, meet with an internationally recognized dance group for backstage access to a dress rehearsal. After lunch, you’ll have a riveting meeting at the Literacy Museum about a historic moment in Cuban history when the island’s youth mobilized across the country to teach rural inhabitants how to read. Later in the day, you’ll have the special privilege of meeting performers from La Colmenita, a children’s touring group that performs locally and internationally. In 2012, they performed at the United Nations.

Meals | Breakfast, lunch, dinner

Day 5: Havana

This morning, you’ll visit a local farmers market, where you’ll experience firsthand Cuba’s dual currency at work. Before lunching at a local paladar in Old Havana, you’ll meet with an organization that teaches trade skills for the new economy. After lunch, you’ll meet with an art specialist for an insightful tour of Havana’s Museum of Fine Arts. Tonight, dine on your own at a paladar, a private, family-owned restaurant. Your tour leader, a dining-scene expert, can make outstanding recommendations.

Meals | Breakfast, Lunch

Days 6: Havana / Playa Larga / Cienfuegos

Today, you’ll leave Havana for Playa Larga, where you’ll visit Korimacao Community Project, a respected school of the arts, known for developing musicians, dancers, poets, and actors. From Playa Larga, you'll continue your journey to the charming island town of Cienfuegos.

Meals | Breakfast, Lunch, Dinner

Days 7: Cienfuegos / Trinidad

We’ll stop at the Museum of Architecture to learn about Trinidad’s architectural and historic preservation and UNESCO designation. Afterwards, meet a world-renowned local artist who recently had her work displayed at the United Nations.
After lunch you’ll have an exclusive visit with the singers, dancers, and musicians of the Ballet Folklórico de Trinidad. Then, you’ll have an exclusive visit with our friends in their home for a taste of Cuban hospitality, warmth, and a chance to get to know them surrounded by their families and community. Later, you’ll visit a casa particular, a bed-and-breakfast-like accommodation in a private home. Tonight, dine on your own at a paladar, a private, family-owned restaurant. Your tour leader, a dining-scene expert, can make outstanding recommendations.

Meals | Breakfast, Lunch

Day 8: Cienfuegos / Havana

This morning, you’ll visit a cooperative artist center and then meet the singers and artistic director from the internationally acclaimed Coro del Cienfuegos (AN ALLTIME GUEST FAVORITE). After lunch, you’ll travel back to Havana. In the evening, share your favorite stories during a farewell dinner.

Meals | Breakfast, Lunch, Dinner

Day 9: Havana / Miami ¡Adios, Cuba!

After breakfast, bid farewell to Cuba as you board your flight home.

Meals | Breakfast

Tour Dates & Prices

Classic Cuba Tour

DateDouble Occupancy (per person)Status
Oct 10, 2015 – Oct 18, 2015$4,495  Sold Out
Oct 31, 2015 – Nov 8, 2015$5,295  Sold Out
Nov 7, 2015 – Nov 15, 2015$5,295  Sold Out
Nov 14, 2015 – Nov 22, 2015$5,295  Sold Out
Nov 21, 2015 – Nov 29, 2015$5,295  Sold Out
Nov 28, 2015 – Dec 6, 2015$5,295  Sold Out
Dec 5, 2015 – Dec 13, 2015$5,295  Sold Out
Dec 12, 2015 – Dec 20, 2015$5,295  Sold Out
Dec 19, 2015 – Dec 27, 2015$5,595  Sold Out
Dec 26, 2015 – Jan 3, 2016$5,595  Sold Out
Jan 9, 2016 – Jan 17, 2016$5,295  Sold Out
Jan 16, 2016 – Jan 24, 2016$5,295Only 3 spots left! Book Now!
Jan 23, 2016 – Jan 31, 2016$5,295Only 7 spots left! Book Now!
Jan 30, 2016 – Feb 7, 2016$5,295  Book Now!
Feb 6, 2016 – Feb 14, 2016$5,295  Book Now!
Feb 13, 2016 – Feb 21, 2016$5,295  Sold Out
Feb 20, 2016 – Feb 28, 2016$5,295  Book Now!
Feb 27, 2016 – Mar 6, 2016$5,295  Book Now!
Mar 5, 2016 – Mar 13, 2016$5,295Only 4 spots left! Book Now!
Mar 12, 2016 – Mar 20, 2016$5,295  Book Now!
Mar 19, 2016 – Mar 27, 2016$5,295  Book Now!
Mar 26, 2016 – Apr 3, 2016$5,295  Book Now!
Apr 9, 2016 – Apr 17, 2016$4,995  Book Now!
Apr 23, 2016 – May 1, 2016$4,995  Book Now!
May 7, 2016 – May 15, 2016$4,995  Book Now!
May 21, 2016 – May 29, 2016$4,995  Book Now!
Jun 4, 2016 – Jun 12, 2016$4,895  Book Now!
Jun 18, 2016 – Jun 26, 2016$4,895  Book Now!
Jul 2, 2016 – Jul 10, 2016$4,895  Book Now!
Jul 16, 2016 – Jul 24, 2016$4,895  Book Now!
Aug 6, 2016 – Aug 14, 2016$4,895  Book Now!
Sep 10, 2016 – Sep 18, 2016$4,895  Book Now!
Oct 1, 2016 – Oct 9, 2016$4,895  Book Now!
Oct 15, 2016 – Oct 23, 2016$4,895  Book Now!
Nov 5, 2016 – Nov 13, 2016$5,295  Book Now!
Nov 12, 2016 – Nov 20, 2016$5,295  Book Now!
Nov 19, 2016 – Nov 27, 2016$5,295  Book Now!
Nov 26, 2016 – Dec 4, 2016$5,295  Book Now!
Dec 3, 2016 – Dec 11, 2016$4,995  Book Now!
Dec 10, 2016 – Dec 18, 2016$5,295  Book Now!
Dec 20, 2016 – Dec 28, 2016$5,595  Book Now!
Dec 27, 2016 – Jan 4, 2017$5,595  Book Now!

Single Supplement: For single-occupancy pricing, add $600.

Group Rates: 5% off land for groups of 5 - 9 guests. 10% off land for groups of 10 or more.
Direct bookings only. Not combinable with any other offer or a custom group. Will be applied at final payment.

Flight Package

Classic Cuba Tour

  • Round trip air from Miami to Havana
  • Cuban visa
  • Baggage fee for first checked bag
  • Priority check-in at Miami International Airport
  • Cuban airport departure tax
Jan 8 - Dec 19$645
Dec 20 - Jan 7$745

-Flight Package prices are subject to change unless accompanied by confirmed booking

  • “The trip insightCuba offered that included Havana and Trinidad was exactly what I was looking for. I liked going to the various schools and museums to get a real feel of the country.”

    Barry M.

    Classic Cuba Tour
  • “We had so much fun at the block party in Trinidad. The kids were adorable and we loved dancing and joining in with all the Cubans. It was definitely a high point for the trip.”

    Janet T.

    Classic Cuba Tour
  • “ The music was fabulous. Loved the paladar we went to one night. Also had two rides in vintage 50's cars. People were extremely warm and welcoming.”

    Patricia S.

    Classic Cuba Tour
  • “ Thought this trip was one of our best and we have been lucky to travel a lot! ”

    Janice M.

    Classic Cuba Tour