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

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.

  • 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

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

  • 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*

*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)
(per person)
Aug 11 – Aug 17, 2016$3,995$645  
Aug 18 – Aug 24, 2016$3,995$645  
Oct 13 – Oct 19, 2016$3,995$645 Plus Overnight in Miami
Oct 27 – Nov 2, 2016$3,995$645 Plus Overnight in Miami
Nov 3 – Nov 9, 2016$4,795$645 Plus Overnight in Miami
Nov 10 – Nov 16, 2016$4,795$645 Plus Overnight in Miami
Nov 17 – Nov 23, 2016$4,795$645 Plus Overnight in Miami
Nov 24 – Nov 30, 2016$4,795$645
Only 4 spots left!
Plus Overnight in Miami
Dec 2 – Dec 7, 2016$4,495$645  
Dec 9 – Dec 14, 2016$4,495$645  
Dec 16 – Dec 21, 2016$4,495$645  
Dec 23 – Dec 28, 2016$4,995$745
Only 3 spots left!
Dec 30, 2016 – Jan 4, 2017$5,195$745
Only 3 spots left!
Jan 6 – Jan 11, 2017$4,695$745  
Jan 13 – Jan 18, 2017$4,695$645  
Jan 20 – Jan 25, 2017$4,695$645  
Jan 27 – Feb 1, 2017$4,695$645  
Feb 3 – Feb 8, 2017$4,695$645  
Feb 10 – Feb 15, 2017$4,695$645  
Feb 17 – Feb 22, 2017$4,695$645  
Feb 24 – Mar 1, 2017$4,695$645  
Mar 3 – Mar 8, 2017$4,695$645  
Mar 10 – Mar 15, 2017$4,695$645  
Mar 17 – Mar 22, 2017$4,695$645  
Mar 24 – Mar 29, 2017$4,695$645  
Mar 31 – Apr 5, 2017$4,695$645  
Apr 7 – Apr 12, 2017$4,695$645  
Apr 14 – Apr 19, 2017$4,695$645  
Apr 21 – Apr 26, 2017$4,695$645  
Apr 28 – May 3, 2017$4,695$645  
May 5 – May 10, 2017$4,695$645  
May 12 – May 17, 2017$4,695$645  
May 19 – May 24, 2017$4,695$645  
May 26 – May 31, 2017$4,695$645  
Jun 9 – Jun 14, 2017$4,595$645  
Jun 16 – Jun 21, 2017$4,295$645  
Jun 23 – Jun 28, 2017$4,495$645  
Jun 30 – Jul 5, 2017$4,495$645  
Jul 14 – Jul 19, 2017$4,495$645  
Jul 28 – Aug 2, 2017$4,495$645  
Aug 11 – Aug 16, 2017$4,495$645  
Aug 25 – Aug 30, 2017$4,395$645  
Sep 8 – Sep 13, 2017$4,395$645  
Sep 22 – Sep 27, 2017$4,495$645  
Oct 6 – Oct 11, 2017$4,495$645  
Nov 3 – Nov 8, 2017$4,695$645  
Nov 17 – Nov 22, 2017$4,695$645  
Nov 24 – Nov 29, 2017$4,695$645  
Dec 1 – Dec 6, 2017$4,695$645  
Dec 8 – Dec 13, 2017$4,695$645  
Dec 15 – Dec 20, 2017$4,695$645  
Dec 22 – Dec 27, 2017$4,995$745  
Dec 29, 2017 – Jan 3, 2018$5,195$745  

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


  • Round trip air from the U.S. to Cuba
  • Cuban visa and required Cuban Health Insurance
  • Cuban airport departure tax

*Add $100 for depatures Dec 20 - Jan 7. Flight Package prices are subject to change unless accompanied by confirmed booking.

**If you choose to book round trip air on your own, please call a travel specialist at 800-450-CUBA (2822) with your flight details.

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