Weekend in Havana Tour

5 Days / 4 Nights



Our Weekend in Havana tour is far more than a mere brush with exotic culture – it’s a full-on immersive discovery allowing you to not only pay witness to Cuba’s dynamic rhythm and color, but to dive right in and become part of the canvas. 


After you arrive, you'll be throwing back the curtain on this vibrant city and discovering, at long last, how its jovial soul has the power to delight and inspire you.

Like the fiery salsa rhythms that can be heard rippling through its city streets, Havana springs to life with warmth and vivaciousness that never stops taking you by surprise. Removed from the quiet fields of sugar cane and mango trees that thrive further afield, Cuba's largest city is an urban metropolis – a place of rambling Colonial architecture, endless adventure and unfettered discovery. It's where a trip to this Caribbean country, long forbidden to U.S. travelers, truly begins.

Our weekend tour of Havana packs dynamic sights and sounds into a few activity-filled days, offering a widespread look at what this cultural mecca holds. Immerse yourself in the iconic sights and sounds of Havana and the people that are the rhythm of the city. You’ll live vicariously through the lenses of local Cuban photographers who understand the nuances of their surroundings and will share them with you. Experience Havana’s art galleries awash in brilliant colors, and meet the artists to learn about their inspiration. Through it all, discover Havana through the eyes of a Cuban guide who’s there to engage you and forge heartfelt connections with the people that make the city pulse. It’s a unique people-to-people travel experience that stirs the emotions, as well as the senses.

woman_dancing.jpgOur average group size is 16 guests with no more than 24 guests, ensuring individual attention and plenty of personal moments. We have a game plan, but your actual experiences are uniquely your own.  Imagine wandering down cobblestone walkways and catching up with a ballet troop during rehearsals in their studio. Catch some shade before heading to the Quisicaba Community Project where African tradition and religion rolls on. Think about turning the corner and encountering a cluster of street musicians, the sound of son (Cuba’s signature Afro-Cuban drumming) punctuating the stillness before you head into their venue with them. Get close. Get acquainted. Our guides are there to foster dialogues between you and the Cuban people who will continue to inspire you long after your trip.

We’ll also peel back several layers of Havana’s tourist surface, immersing you in the real places where Cubans live, work, learn and grow.

What's Included

  • One night at the Sofitel Miami Hotel, including breakfast and airport transfer

  • Private welcome reception and pre-tour briefing

  • Superior accommodations at the Melia Cohiba in Havana

  • Insight Cuba 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 Insight Cuba Tour Leader

  • Expert Cuban guide

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

  • U.S. Department of the Treasury license and Insight Cuba letter of authorization

  • 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 Cuba; priority check-in at Miami International Airport; and baggage fee for first checked bag

  • All in-country ground transportation, and airport transfers

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

  • Fresh bottled water while touring

  • Insight Cuba 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.

Day 1: Miami

Your trip begins in Miami at the Sofitel Miami Airport hotel, where your small group of traveling companions will gather for an important early evening briefing and cocktail reception.

Meals | Enjoy dinner on your own and at your leisure

Day 2: Miami / Havana

Following breakfast at the hotel, we’ll board our charter flight to Havana. After clearing immigration and customs, you’ll begin your experience right away with a visit to La Plaza de la Revolución (Revolution Square), one of the world’s largest city plazas, where the monument to Jose Marti overlooks the city.

Then, it’s off to lunch at La Bodeguita del Medio, a bar and restaurant made famous by Ernest Hemingway, and arguably the birthplace of the mojito, the drink he favored. After lunch, you’ll experience the artistic side of Havana with a visit to Callejón de Hamel, a unique street in Centro Habana featuring hundreds of art displays and public music performances. After, we’ll check in to our hotel in the heart of Havana, and meet up again for an orientation program. This evening, we’ll celebrate your arrival with a welcome dinner at the hotel.

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Meals | Breakfast, Lunch, Dinner


Day 3: Havana

This morning, you’ll meet with students and professors from La Escuela Taller Gaspar Melchor de Jovellanos to learn about the school’s effort to preserve Cuba’s cultural and architectural heritage. Later, get a snapshot into the lives and work of Cuban photographers at Fototeca in Havana, which houses one of the city’s few darkrooms and is a photographer hub.

On your way to lunch, you’ll continue your walking tour of Old Havana’s cobblestone streets and sixteenth-century Spanish colonial architecture. After lunch, you’ll have a very special visit in Centro Habana with a friend and self-taught Cuban artist who opens his home to teach neighborhood children the art of papier-mâché. We’ll wrap up the day by visiting the famous Abdala recording studio, where famous musicians, including Nat King Cole and the Buena Vista Social Club, recorded some of their best music. Tonight, you’ll dine on your own at a paladar, a private, family-owned restaurant. Your Insight Cuba tour leader, who is an expert in the dining scene, will make the best recommendations.

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Meals | Breakfast, Lunch, Dinner


Day 4: Havana

We’ll kick off the day by meeting the editor of a popular Cuban newspaper for a presentation on Cuban social issues, economic reforms, and the impacts of U.S.-Cuba policy in Cuba.

Afterwards, we’ll gather with Cuban farmers at Vivero Organopónico to learn how organic farming efforts provide food to urban areas and how Vivero is taking the lead in regarding farm-to-table dining. For lunch, we’ll enjoy an authentic Cuban sandwich at Sloppy Joe’s, a legendary bar in Havana. After lunch, you’ll visit with an internationally known choral group and finish the day at a local farmers market where you’ll see firsthand Cuba’s dual currency at work.

In the evening, share your favorite stories about your time in Cuba with your travel mates during a farewell dinner.

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Meals | Breakfast, Lunch, Dinner


Day 5: Havana / Miami ¡Adios, Cuba!

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

Meals | Breakfast

Tour Dates & Prices

Weekend in Havana Tour

DateDouble Occupancy (per person)Status
Mar 5, 2014 – Mar 9, 2014$2,695  Sold Out
Mar 12, 2014 – Mar 16, 2014$2,695  Sold Out
Mar 19, 2014 – Mar 23, 2014$2,695  Sold Out
Mar 26, 2014 – Mar 30, 2014$2,695  Sold Out
Apr 2, 2014 – Apr 6, 2014$2,695  Sold Out
Apr 9, 2014 – Apr 13, 2014$2,695  Sold Out
Apr 16, 2014 – Apr 20, 2014$2,695  Sold Out
Apr 23, 2014 – Apr 27, 2014$2,695  Sold Out
Apr 30, 2014 – May 4, 2014$2,695  CALL NOW
May 14, 2014 – May 18, 2014$2,695  CALL NOW
May 21, 2014 – May 25, 2014$2,695  CALL NOW
May 28, 2014 – Jun 1, 2014$2,695Only 2 spots left! Book Now!
Jun 11, 2014 – Jun 15, 2014$2,695  CALL NOW
Jun 18, 2014 – Jun 22, 2014$2,695Only 6 spots left!Save $100!Book Now!
Jun 25, 2014 – Jun 29, 2014$2,695  CALL NOW
Jul 2, 2014 – Jul 6, 2014$2,695 Save $100!Book Now!
Jul 30, 2014 – Aug 3, 2014$2,695  Book Now!
Aug 20, 2014 – Aug 24, 2014$2,695 Save $100!Book Now!
Sep 24, 2014 – Sep 28, 2014$2,595 Save $100!Book Now!
Oct 22, 2014 – Oct 26, 2014$2,495  Book Now!
Nov 12, 2014 – Nov 16, 2014$2,595  Book Now!
Dec 23, 2014 – Dec 27, 2014$2,795  Book Now!
Dec 29, 2014 – Jan 2, 2015$2,895  Book Now!
Jan 7, 2015 – Jan 11, 2015$2,895  CALL NOW
Jan 14, 2015 – Jan 18, 2015$2,895  Book Now!
Jan 28, 2015 – Feb 1, 2015$2,895  Book Now!
Feb 11, 2015 – Feb 15, 2015$2,895  Book Now!
Feb 25, 2015 – Mar 1, 2015$2,895  Book Now!
Mar 4, 2015 – Mar 8, 2015$2,895  Book Now!
Mar 18, 2015 – Mar 22, 2015$2,895  Book Now!
Apr 1, 2015 – Apr 5, 2015$2,895  Book Now!
Apr 15, 2015 – Apr 19, 2015$2,895  Book Now!
Apr 29, 2015 – May 3, 2015$2,895  Book Now!
May 13, 2015 – May 17, 2015$2,795  Book Now!
May 20, 2015 – May 24, 2015$2,695  Book Now!
Jun 3, 2015 – Jun 7, 2015$2,695  Book Now!
Jun 17, 2015 – Jun 21, 2015$2,695  Book Now!
Jul 1, 2015 – Jul 5, 2015$2,695  Book Now!
Jul 15, 2015 – Jul 19, 2015$2,695  Book Now!

Single Supplement: For single-occupancy pricing, add $400.

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Flight Package

Weekend In Havana Tour

  • Round trip air from Miami to Havana
  • Cuban visa
  • Baggage fee for first checked bag
  • Priority check-in at Miami International Airport
Jan 8 - Dec 19$595
Dec 20 - Jan 7$645

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

  • “I had the most pleasurable experience taking my 87 year old father back to Cuba. It was a trip of a lifetime for him and I thank you all so very, very much.”

    Robin W.

    Weekend in Havana Tour
  • “My thanks to the creator of the program for providing me with the opportunity to, once again in my lifetime, experience the culture of Cuba.”

    William S.

    Weekend in Havana Tour
  • “I liked the variety of activities we had with the result I believe I had an opportunity to really get to know Havana in a limited period of time.”

    David R.

    Weekend in Havana Tour
  • “It was all excellent. I enjoyed the mix of history, architecture and gaining insight into the day to day lives of the Cuban people.”

    Donna O.

    Weekend in Havana Tour
  • “It was a fascinating trip and we will always be glad we went!”

    Sue H.

    Weekend in Havana Tour