Vintage Cuba Tour

7 Days / 6 Nights

Santa Clara | Caibaríen | Remedios | Cayo Santa Maria | Havana


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 Insight Cuba’s newest tour: Vintage Cuba. 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.

Highlights of the trip include performances by talented musicians in traditional bands called piquetes; touring the colorful town of Remedios via bicycle taxi; taking a historic ride via an antique steam locomotive between Caibaríen and Remedios; and learning about the soul of Cuba’s famous art form, dance, from a dance expert and personal friend of Insight Cuba.

At every step of the way, our extensive expertise and longstanding relationships in Cuba ensure unique experiences you won’t find anywhere else.

Scroll down to see what's included, the sample itinerary, departure dates, and pricing

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What's Included

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

  • Private welcome reception and pre-tour briefing

  • Superior accommodations at the Melia Cohiba in Havana, and Melia Las Dunas in Cayo Santa Maria

  • Standard accommodations in Santa Clara

  • Insight Cuba 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 Insight Cuba Tour Leader

  • Expert Cuban guide

  • All meals while in Cuba, except for two paladar evening dining experiences on your own

  • U.S. Department of the Treasury license and Insight Cuba letter of authorization

  • 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 Cuba; priority check-in at Miami International Airport; and baggage fee for first checked bag

  • All in-country ground transportation, and airport transfers

  • Travel health insurance, emergency medical evacuation, and trip cancellation coverage (up to $1,000)

  • Fresh bottled water while touring

  • Insight Cuba 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.

Sample Itinerary

*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.

Days 1-2: Miami / Santa Clara

Your trip begins at the Sofitel Miami Airport hotel, 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

Day 3: Santa Clara / Caibaríen / Remedios / Cayo Santa Maria

This morning, we’ll depart for Caibaríen, a coastal town called the White Village for its sugary sand beaches. We’ll meet the artists and organizers behind a pivotal community project involving plastics art. Then, it’s all aboard the train, a timeless mode of transit still used in certain areas, to Remedios, where Las Parrandas — street celebrations —have occurred each December since the 1700s. Later, we’ll tour the town via bicycle taxi.

Meals | Breakfast, Lunch, Dinner

Day 4: Cayo Santa Maria / Caibaríen / Santa Clara / Havana

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 director is locally famous and a friend of Insight Cuba. Next, you’ll visit a traditional printing house that still uses nineteenth-century machines. Then, it’s off to Havana.

Meals | Breakfast, Lunch, Dinner

Day 5: Havana

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: Havana

We’ll continue soaking up Havana’s nostalgia, starting with a visit to a remarkable community project that has created colorful murals from old facades and built public parks and artworks, such as an Arc de Triomphe from recycled materials.

Next, we’ll visit one of the city’s most beautiful churches in the Regla neighborhood, just across Havana Harbor. We’ll learn about the role religion has played in Cuba’s history and culture. We’ll lunch at a paladar in Cojimar, the setting for Hemingway’s Old Man and the Sea. Ever wondered how those ’57 Chevys stay on the road? You’ll have the pleasure of meeting Cuban mechanics who maintain these old-timers. This evening, share favorite moments with your traveling companions during a farewell dinner at a landmark Havana restaurant.

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Meals | Breakfast, Lunch, Dinner


Day 7: Havana / Miami

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

  • Meals | Breakfast

Tours Dates and Prices

Vintage Cuba Tour

DateDouble Occupancy (per person)Status
Mar 6, 2014 – Mar 12, 2014$3,895  Sold Out
Mar 14, 2014 – Mar 19, 2014$3,895  Sold Out
Apr 3, 2014 – Apr 9, 2014$3,895  Sold Out
Apr 17, 2014 – Apr 23, 2014$3,895  Sold Out
May 1, 2014 – May 7, 2014$3,895  CALL NOW
May 22, 2014 – May 28, 2014$3,695Only 4 spots left! Book Now!
Jun 12, 2014 – Jun 18, 2014$3,695Only 7 spots left!Save $200!Book Now!
Jul 3, 2014 – Jul 9, 2014$3,695  Book Now!
Aug 14, 2014 – Aug 20, 2014$3,695  Book Now!
Oct 16, 2014 – Oct 22, 2014$3,495  Book Now!
Nov 13, 2014 – Nov 19, 2014$3,695  Book Now!
Dec 11, 2014 – Dec 17, 2014$3,795  Book Now!
Jan 15, 2015 – Jan 21, 2015$3,895  Book Now!
Feb 12, 2015 – Feb 18, 2015$3,895  Book Now!
Feb 19, 2015 – Feb 25, 2015$3,895  CALL NOW
Mar 5, 2015 – Mar 11, 2015$3,895  Book Now!
Mar 12, 2015 – Mar 18, 2015$3,895  CALL NOW
Mar 26, 2015 – Apr 1, 2015$3,895  Book Now!
Apr 16, 2015 – Apr 22, 2015$3,895  Book Now!
May 7, 2015 – May 13, 2015$3,695  Book Now!
May 21, 2015 – May 27, 2015$3,695  Book Now!
Jun 4, 2015 – Jun 10, 2015$3,695  Book Now!
Jun 25, 2015 – Jul 1, 2015$3,695  Book Now!
Jul 16, 2015 – Jul 22, 2015$3,695  Book Now!

Single Supplement: For single-occupancy pricing, add $400.

Pricing From

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Flight Package

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
Jan 8 - Dec 19$595
Dec 20 - Jan 7$645

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