Vintage Cuba Tour | insightCuba

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Vintage Cuba Tour

6 Days / 5 Nights

Santa Clara
Cayo Santa Maria

Explore Habana Vieja | Explore the town of Remedios on a bici-taxi | Ride on an Antique Steam Train | See Hemingway's Home | Visit a Dance Community Project | Enjoy a Concert with Piquetes, a 19th Century Band | 1 UNESCO World Heritage Site 

map of cuba, havana, santa clara, cayo santa maria, caibarien, remedios
It’s often said that visiting Cuba is like traveling back in time.

Indeed, the classic cars, weathered buildings, and unique history create an unforgettable experience in this enchanting country, one that stays with visitors long after they return home.

While Cuba is changing more than ever, its one-of-a-kind yesteryear is the inspiration for insightCuba’s Vintage Cuba tour. This six-day trip takes guests on an extraordinary journey through Cuba’s colorful, complex history via the places and people who bring it to life.
Santa Clara / Cayo Santa Maria
Day 1

After clearing immigration and customs, begin your Vintage Cuba experience with a visit to the Che Guevara memorial, then enjoy a welcome lunch. Partake in an exchange with musicians who play nineteenth-century Cuban music on 200-year-old instruments. They will be accompanied by the Alegrias de Vivir dancers, who will teach you their national dance.

Next, we visit Santa Clara’s town center and a local artist’s studio before departing for Cayo Santa María.

After checking in to your hotel and meeting for orientation, you’ll enjoy a sumptuous dinner with your traveling companions.

Meals | Lunch, Dinner

Cayo Santa Maria / Caibaríen / Remedios
Day 2

This morning, we’ll depart for Caibaríen, a coastal town called The White Village for its sugary sand beaches. First stop is a local print shop that still uses nineteenth-century machines. Then, meet the artists and organizers behind a pivotal community project involving plastics art. Next, it’s all aboard the train, a timeless mode of transit still used in certain areas, to Remedios, where residents have put on Las Parrandas—street celebrations—each December since the 1700s. 

Meals | Breakfast, Lunch, Dinner

Cayo Santa Maria / Caibarién / Santa Clara / Havana
Day 3

We’ll begin our journey to Cuba’s capital city on a musical note, with a toe-tapping performance by Caibaríen’s outstanding municipal band, whose locally famous director is a friend of insightCuba. We’ll stop for a light lunch en route to Havana.

Meals | Breakfast, Lunch, Dinner

Day 4

In the Cuban capital, we’ll explore enchanting Old Havana, whose cobblestone squares echo with memories. We’ll meet with a PhD from the university, who will share his insights on social equality in Cuba. After lunch, we’ll visit a craft community project led by women who teach children traditional sewing techniques. Tonight, you’ll dine on your own at a paladar, a private, family-owned restaurant. Your tour leader, an expert in the dining scene, can make outstanding recommendations.

Meals | Breakfast, Lunch

Day 5

We’ll continue soaking up Havana’s nostalgia the Cuban way, by taking the ferry across the harbor to the town of Casablanca. Next, explore Cuba’s colonial history with a visit to the third-largest fortress in the Americas. Then, depart for the seaside village that served as inspiration for one of Ernest Hemingway’s best-known novels, The Old Man and the Sea. Visit the acclaimed writer’s home after lunch at a local café.

Later, meet the talented jazz dancers who make up a local community organization. This evening, share favorite moments with your traveling companions during a farewell dinner at a landmark Havana restaurant.

Meals | Breakfast, Lunch, Dinner

Day 6

¡Adios, Cuba! After breakfast, bid farewell to Cuba and board your flight back 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

  • Two nights superior accommodations at the Meliá Las Dunas Hotel in Cayo Santa Maria

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

  • 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.

Vintage Cuba Tour
DateDouble Occupancy
(per person)
Cuban Visa
Oct 13 – Oct 19, 2016$3,995  Plus Overnight in Miami
Oct 27 – Nov 2, 2016$3,995  Plus Overnight in Miami
Nov 3 – Nov 9, 2016$4,795  Plus Overnight in Miami
Nov 10 – Nov 16, 2016$4,795  Plus Overnight in Miami
Nov 17 – Nov 23, 2016$4,795  Plus Overnight in Miami
Nov 24 – Nov 30, 2016$4,795 
Only 4 spots left!
Plus Overnight in Miami
Dec 2 – Dec 7, 2016$4,495   
Dec 9 – Dec 14, 2016$4,495   
Dec 16 – Dec 21, 2016$4,495   
Dec 23 – Dec 28, 2016$4,995   
Dec 30, 2016 – Jan 4, 2017$5,195 
Only 1 spot left!
Jan 6 – Jan 11, 2017$4,695$99  
Jan 13 – Jan 18, 2017$4,695$99  
Jan 20 – Jan 25, 2017$4,695$99  
Jan 27 – Feb 1, 2017$4,695$99  
Feb 3 – Feb 8, 2017$4,695$99  
Feb 10 – Feb 15, 2017$4,695$99  
Feb 17 – Feb 22, 2017$4,695$99  
Feb 24 – Mar 1, 2017$4,695$99  
Mar 3 – Mar 8, 2017$4,695$99  
Mar 10 – Mar 15, 2017$4,695$99  
Mar 17 – Mar 22, 2017$4,695$99  
Mar 24 – Mar 29, 2017$4,695$99  
Mar 31 – Apr 5, 2017$4,695$99  
Apr 7 – Apr 12, 2017$4,695$99  
Apr 14 – Apr 19, 2017$4,695$99  
Apr 21 – Apr 26, 2017$4,695$99  
Apr 28 – May 3, 2017$4,695$99  
May 5 – May 10, 2017$4,695$99  
May 12 – May 17, 2017$4,695$99  
May 19 – May 24, 2017$4,695$99  
May 26 – May 31, 2017$4,695$99  
Jun 9 – Jun 14, 2017$4,595$99  
Jun 16 – Jun 21, 2017$4,295$99  
Jun 23 – Jun 28, 2017$4,495$99  
Jun 30 – Jul 5, 2017$4,495$99  
Jul 14 – Jul 19, 2017$4,495$99  
Jul 28 – Aug 2, 2017$4,495$99  
Aug 11 – Aug 16, 2017$4,495$99  
Aug 25 – Aug 30, 2017$4,395$99  
Sep 8 – Sep 13, 2017$4,395$99  
Sep 22 – Sep 27, 2017$4,495$99  
Oct 6 – Oct 11, 2017$4,495$99  
Nov 3 – Nov 8, 2017$4,695$99  
Nov 17 – Nov 22, 2017$4,695$99  
Nov 24 – Nov 29, 2017$4,695$99  
Dec 1 – Dec 6, 2017$4,695$99  
Dec 8 – Dec 13, 2017$4,695$99  
Dec 15 – Dec 20, 2017$4,695$99  
Dec 22 – Dec 27, 2017$4,995$99  
Dec 29, 2017 – Jan 3, 2018$5,195$99  

SINGLE SUPPLEMENT: For single-occupancy pricing, add $600 for departures prior to October 31, 2016 and $1400 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.

Vintage 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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