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Vintage Cuba Tour

7 Days / 6 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 seven-day trip takes guests on an extraordinary journey through Cuba’s colorful, complex history via the places and people who bring it to life.
Miami / Santa Clara / Cayo Santa Maria
Days 1-2

Your trip begins at the Hotel Pullman Miami Airport, where you and your travel companions will gather for an early evening briefing and reception. Following breakfast at the hotel, we’ll board our charter flight to Santa Clara. After clearing immigration and customs, begin your Vintage Cuba experience in charming Santa Clara, site of the last and most decisive battle of the Cuban Revolution in 1958. Get your first taste of Cuba while meeting the members of a piquete, who will demonstrate how these small bands once played behind silent movies. Then, we’ll head north to your hotel for the next two nights in Cayo Santa Maria, a nine-by-one-mile island cay. Known for its turquoise waters, mangroves, and indigenous wildlife, Cayo Santa Maria is a UNESCO Biosphere Reserve. Here, you’ll enjoy a welcome dinner at the hotel.

Meals Day 1 | Enjoy dinner on your own, at your leisure

Meals Day 2 | Breakfast, Lunch, Dinner

Cayo Santa Maria / Caibaríen / Remedios
Day 3

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 4

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 5

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 6

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

Havana / Miami
Day 7

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

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.

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

  • Private welcome reception and pre-tour briefing

  • 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)
Jul 7 – Jul 13, 2016$3,995$645  
Jul 21 – Jul 27, 2016$3,995$645  
Aug 11 – Aug 17, 2016$3,995$645  
Aug 18 – Aug 24, 2016$3,995$645  
Oct 13 – Oct 19, 2016$3,995$645
Only 6 spots left!
Oct 27 – Nov 2, 2016$3,995$645  
Nov 3 – Nov 9, 2016$4,795$645  
Nov 10 – Nov 16, 2016$4,795$645  
Nov 17 – Nov 23, 2016$4,795$645  
Nov 24 – Nov 30, 2016$4,795$645
Only 4 spots left!
Dec 1 – Dec 7, 2016$4,795$645  
Dec 8 – Dec 14, 2016$4,795$645  
Dec 15 – Dec 21, 2016$4,795$645  
Dec 22 – Dec 28, 2016$5,095$745  
Dec 29, 2016 – Jan 4, 2017$5,295$745
Only 7 spots left!
Jan 5 – Jan 11, 2017$4,895$745  
Jan 12 – Jan 18, 2017$4,895$645  
Jan 19 – Jan 25, 2017$4,895$645  
Jan 26 – Feb 1, 2017$4,895$645  
Feb 2 – Feb 8, 2017$4,895$645  
Feb 9 – Feb 15, 2017$4,895$645  
Feb 16 – Feb 22, 2017$4,895$645  
Feb 23 – Mar 1, 2017$4,895$645  
Mar 2 – Mar 8, 2017$4,895$645  
Mar 9 – Mar 15, 2017$4,895$645  
Mar 16 – Mar 22, 2017$4,895$645  
Mar 23 – Mar 29, 2017$4,895$645  
Mar 30 – Apr 5, 2017$4,895$645  
Apr 6 – Apr 12, 2017$4,895$645  
Apr 13 – Apr 19, 2017$4,895$645  
Apr 20 – Apr 26, 2017$4,895$645  
Apr 27 – May 3, 2017$4,895$645  
May 4 – May 10, 2017$4,895$645  
May 11 – May 17, 2017$4,895$645  
May 18 – May 24, 2017$4,895$645  
May 25 – May 31, 2017$4,895$645  
Jun 8 – Jun 14, 2017$4,795$645  
Jun 15 – Jun 21, 2017$4,495$645  
Jun 22 – Jun 28, 2017$4,695$645  
Jun 29 – Jul 5, 2017$4,695$645  
Jul 13 – Jul 19, 2017$4,695$645  
Jul 27 – Aug 2, 2017$4,695$645  
Aug 10 – Aug 16, 2017$4,695$645  
Aug 24 – Aug 30, 2017$4,595$645  
Sep 7 – Sep 13, 2017$4,595$645  
Sep 21 – Sep 27, 2017$4,695$645  
Oct 5 – Oct 11, 2017$4,695$645  
Nov 2 – Nov 8, 2017$4,895$645  
Nov 16 – Nov 22, 2017$4,895$645  
Nov 23 – Nov 29, 2017$4,895$645  
Nov 30 – Dec 6, 2017$4,895$645  
Dec 7 – Dec 13, 2017$4,895$645  
Dec 14 – Dec 20, 2017$4,895$645  
Dec 21 – Dec 27, 2017$5,095$745  
Dec 28, 2017 – Jan 3, 2018$5,295$745  

SINGLE SUPPLEMENT: For single-occupancy pricing, add $600 prior to October 31, 2016 and $1400 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.
Direct bookings only. Not combinable with any other offer or a private group. Will be applied at final payment.

Vintage Cuba Tour
  • Air from Miami to Santa Clara
  • Cuban visa
  • Air from Havana to Miami
  • Baggage fee for first checked bag
  • Priority check-in at Miami International Airport
  • Cuban airport departure tax

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

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