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Explore Habana Vieja | Meet with a Rewnowned Opera Group | 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 Río, where 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

  • 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**

  • Travel health and emergency medical evacuation insurance***

  • Flight concierge service (flight cost additional) 

*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.

***Trip-cancellation coverage available for an additional fee through Allianz.


Legendary Cuba Tour
DateDouble Occupancy
(per person)
Cuban Visa
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 SAVE $500- CALL
May 6 – May 12, 2017$4,795$99  
May 20 – May 26, 2017$4,795$99 USE PROMO CODE: SPRING FOR $250 OFF PER PERSON
Jun 3 – Jun 9, 2017$4,595$99  
Jun 17 – Jun 23, 2017$4,595$99 USE PROMO CODE: SPRING FOR $250 OFF PER PERSON
Jul 1 – Jul 7, 2017$4,595$99 USE PROMO CODE: SPRING FOR $250 OFF PER PERSON
Jul 15 – Jul 21, 2017$4,595$99  
Jul 29 – Aug 4, 2017$4,595$99  
Aug 12 – Aug 18, 2017$4,495$99 USE PROMO CODE: SPRING FOR $250 OFF PER PERSON
Aug 26 – Sep 1, 2017$4,495$99  
Sep 16 – Sep 22, 2017$4,695$99 USE PROMO CODE: SPRING FOR $250 OFF PER PERSON
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  
Jan 20 – Jan 26, 2018$4,995$99  
Feb 3 – Feb 9, 2018$4,995$99  
Feb 17 – Feb 23, 2018$4,995$99  
Mar 3 – Mar 9, 2018$4,995$99  
Mar 17 – Mar 23, 2018$4,995$99  
Mar 31 – Apr 6, 2018$4,995$99  
Apr 14 – Apr 20, 2018$4,995$99  
Apr 28 – May 4, 2018$4,995$99  
May 12 – May 18, 2018$4,995$99  
May 26 – Jun 1, 2018$4,995$99  
Jun 23 – Jun 29, 2018$4,595$99  
Jul 21 – Jul 27, 2018$4,595$99  
Aug 4 – Aug 10, 2018$4,495$99  
Sep 8 – Sep 14, 2018$4,695$99  
Oct 6 – Oct 12, 2018$4,695$99  
Oct 27 – Nov 2, 2018$4,695$99  
Nov 24 – Nov 30, 2018$4,695$99  
Dec 22 – Dec 28, 2018$5,095$99  
Dec 29, 2018 – Jan 4, 2019$5,395$99  

NEW!! PREPAYMENT DISCOUNT: Pay in full at the time of booking and receive $200 OFF the full price! *Must book 120 days in advance of the departure date. This may not be combined with any other promotions. Normal terms and conditions apply. 

SINGLE SUPPLEMENT: For single-occupancy pricing, add $1300.

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.

*SPRING SAVINGS is $500.00USD per couple, or $250.00USD per person. Valid for new bookings only. Requires payment in full at the time of booking. Normal terms and conditions apply. This offer may not be combined with any other offer or discount. Available only on tours and dates as indicated on the dates and prices section of each tour page. Not available for cruises or Marathon tours. Offer valid while space is available. Discount has no cash value.

Legendary Cuba Tour

Once you have booked your tour, our flight concierge will gladly assist you with all of your flight needs. Call us at 914-380-8303 or click here for an air quote.

The recommended flight* for all guests on this tour is: 

American        1345    MIAMI-HAVANA (MIA-HAV)  

American        1334    HAVANA-MIAMI (HAV-MIA) 

Flight times may vary, please consult the airline's website for the most up to date flight information on your particular dates of travel.  

*Group airport transfers are included for recommended flights only.

Visit our Flights to Cuba page for important information on the best way to book your flights, non-recommended flights, as well as group airport transfersPlease note that the tour you have chosen is a land based tour only, flights costs and Cuban visas are not included in your tour package.

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