Legendary Cuba Tour | insightCuba

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Legendary Cuba Tour

7 days / 6 nights

Viñales Valley
Pinar del Río
Las Terrazas

Explore Habana Vieja | Dance at the famous Callejón de Hamel | Tour an Organic Farm and Enjoy Lunch | See Hemingway's Home | Explore Cuba's Tobacco Fields & Viñales Valley | Meet an Artist in his Home | 2 UNESCO World Heritage Sites

map of cuba havana, vinales vally, pinar del rio, las terrazas
Steeped in mystique, Cuba creates legends.
Discover Cuba for yourself and uncover a history so rich, its legacy is memorialized in its architecture and its people. Learn why icons such as Hemingway, Churchill, and Sinatra felt an affinity for this rare place. Experience the music, which, for generations, produced global superstars who shook the world. Explore Havana, Cuba's first UNESCO World Heritage Site, where breathtaking Spanish-colonial buildings line cobblestone streets, and then the western province of Pinar del Rio, where miles of square miles of Cuban tobacco awaits its destiny.
Day 1

After clearing immigration and customs at the José Martí International Airport in Havana, you’ll take a short drive to the Meliá Cohiba for hotel check in and tour orientation.*

Meals | Dinner

*Check-in begins roughly at 3pm ET. The tour start time will vary slightly depending on flight arrivals. 

Day 2

After breakfast, we’ll hear a lecture by a local expert on contemporary Cuba. Guests will be encouraged to ask their most pressing questions. Then, enjoy the rare chance to see a dance demonstration of the different orishas, part of Cuba’s Santeria religion.

After, you’ll visit the Finca "La Yoandra," an organic farm that also provides afterschool programs for children and inspiration to the community. The variety of fruits and vegetables will spoil you! We’ll continue our organic theme with lunch at the farm’s own paladar, Il Divino, where many of their fresh fruits and vegetables are grown.

Next, we’ll meet the dynamic artists and musicians behind Muraleando, one of Havana’s groundbreaking projects, where artists converted an old water tank into an art-and-performance space.

Lastly, meet university students and business professionals by your hotel’s poolside, for candid discussions about daily Cuban life. Dinner tonight will be at the famed El Aljibe.

Meals | Breakfast, Lunch, Dinner

Day 3

En route to one of Cuba’s renowned photography organizations, Fototeca, we’ll stop to take in the colonial splendor of Old Havana: its cobblestone streets, vibrant dynamics and stunning architecture. For lunch, we’ll eat at a popular local paladar.

After lunch, we’ll soak up Havana’s nostalgia the Cuban way, by taking the ferry across the harbor to the town of Casablanca. The day’s highlight will be a visit to Hemingway’s home, Finca Vijia, where you may come to understand why the author chose to spend twenty years in Cuba.

Dinner tonight is on your own. Your tour leader will be happy to recommend the best local paladares.

Meals | Breakfast, Lunch

Havana / Pinar del Río
Day 4

After breakfast, we’ll leave Havana to begin a journey exploring the magic of Pinar del Río.

Along the way, we’ll stop for a visit at the Patio de Pelegrin community project, an organic farm, art space and coffee shop. There, we’ll enjoy a lunch prepared by community residents.

Next, we’ll meet a curator at a popular artist’s home and studio to learn about his artwork, displayed in galleries in the US and museums in Cuba. After checking in at the hotel, we’ll meet with the members of a remarkable opera-and-theatre group, who perform around the world.

Dinner tonight will be at paladar Café Ortuzar.

Meals | Breakfast, Lunch, Dinner

Pinar del Río / Viñales Valley
Day 5

On your second day in Pinar del Río, we’ll head north towards Viñales National Park to meet a local guide. At a tobacco-drying house, a tobacco farmer will teach you how to roll cigars.

For lunch, you’ll indulge in a delicious farm-to-table meal preparred with local ingredients from the near-by crops.

After lunch, we’ll wander into Viñales Valley, Cuba’s Yosemite-like habitat, and into Viñales city. You’ll walk on clay and admire up close the giant limestone rocks that make Viñales famous.

At the end of the day, treat yourself to a savory coco loco (honey, rum and coconut water). Take our word for it: you won’t be disappointed! Dinner tonight is on your own.

Meals | Breakfast, Lunch

Pinar del Río / Las Terrazas / Havana
Day 6

After breakfast at the hotel, we’ll check out, then visit a cigar factory in Pinar del Río, where you’ll see firsthand how these legendary cigars are made.

On our way back to Havana, we’ll stop for lunch at Las Terrazas, a quaint, wholly self-sustainable eco community that also acts as a nature reserve. Then, we'll watch a dance performance from a local dance company who combines classical training with contemporary moves.

In Havana, enjoy a farewell dinner at a delicious paladar.

Meals | Breakfast, Lunch, Dinner

Day 7

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

Meals | Breakfast

Activities in this itinerary should be considered a sample only. Final itineraries are sent to guests one to two weeks prior to departure.

  • Private welcome reception and tour orientation

  • Four nights superior accommodations at the Meliá Cohiba Hotel in Havana

  • Two nights standard accommodations in Pinar del Río

  • 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

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

  • Private Cuban Driver

  • Travel health and emergency medical evacuation insurance

  • 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**

*Transfers available for group blocks or recommended flight arrival and departure times.

**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.

Legendary Cuba Tour
DateDouble Occupancy
(per person)
Cuban Visa
Oct 7 – Oct 14, 2016$4,495  Plus Overnight in Miami
Nov 25 – Dec 2, 2016$4,995  Plus Overnight in Miami
Dec 28, 2016 – Jan 3, 2017$5,195   
Jan 14 – Jan 20, 2017$4,995$99  
Jan 21 – Jan 27, 2017$4,995$99  
Jan 28 – Feb 3, 2017$4,995$99  
Feb 4 – Feb 10, 2017$4,995$99  
Feb 11 – Feb 17, 2017$4,995$99  
Feb 18 – Feb 24, 2017$4,995$99  
Feb 25 – Mar 3, 2017$4,995$99  
Mar 4 – Mar 10, 2017$4,995$99  
Mar 11 – Mar 17, 2017$4,995$99  
Mar 18 – Mar 24, 2017$4,995$99  
Mar 25 – Mar 31, 2017$4,995$99  
Apr 1 – Apr 7, 2017$4,995$99  
Apr 8 – Apr 14, 2017$4,995$99  
Apr 15 – Apr 21, 2017$4,995$99  
Apr 22 – Apr 28, 2017$4,995$99  
May 6 – May 12, 2017$4,795$99  
May 20 – May 26, 2017$4,795$99  
Jun 3 – Jun 9, 2017$4,595$99  
Jun 17 – Jun 23, 2017$4,595$99  
Jul 1 – Jul 7, 2017$4,595$99  
Jul 15 – Jul 21, 2017$4,595$99  
Jul 29 – Aug 4, 2017$4,595$99  
Aug 12 – Aug 18, 2017$4,495$99  
Aug 26 – Sep 1, 2017$4,495$99  
Sep 16 – Sep 22, 2017$4,695$99  
Oct 7 – Oct 13, 2017$4,695$99  
Oct 28 – Nov 3, 2017$4,695$99  
Nov 11 – Nov 17, 2017$4,895$99  
Nov 25 – Dec 1, 2017$4,895$99  
Dec 9 – Dec 15, 2017$4,995$99  
Dec 23 – Dec 29, 2017$5,095$99  
Dec 27, 2017 – Jan 2, 2018$5,195$99  
Dec 31, 2017 – Jan 6, 2018$5,195$99  
Jan 6 – Jan 12, 2018$4,995$99  

SINGLE SUPPLEMENT: For single-occupancy pricing, add $600 for departures prior to October 31, 2016 and $1300 for departures from November 1, 2016 onward.

Want a Roommate?: Solo travelers wishing to pay the double occupancy rate may share a room with another guest.

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

Legendary Cuba Tour


Flights from October 1 - November 30, 2016:

$645 per person and includes Cuban visa, Cuban airport departure tax, required Cuban health insurance, and priority check-in at Miami international airport. 

All guests booking a tour departing Oct 1- Nov 30, 2016 are automatically booked on a scheduled charter flight from Miami to Cuba round trip. (Commercial flights are not yet available.) This flight departs in the morning from Miami and includes an overnight stay at the Hotel Pullman Miami Airport, private welcome reception, pre-tour briefing, breakfast and transfers.

Please note that the flight charge will be added to your tour fee, once you are registered on a tour.

Flights from December 1- 31, 2016:

$645* per person and includes Cuban visa, Cuban airport departure tax, and required Cuban health insurance. 

For guests booking a tour departing Dec 1- Dec 31, 2016 we have blocked seats on American Airlines from Miami to Cuba. This flight departs in the morning from Miami and requires an overnight stay in Miami not included in the tour price.

*Add $100 for departures Dec 20 - Dec 31, 2016.

Flights January 1, 2017 and onward:

Once you are registered on one of our tours, we will handle all of your flight needs.


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