Cuba Tours

You are here

Vintage Cuba Tour - 6 Days / 5 Nights - Santa Clara, Caibarien, Remedios, Cayo Santa Maria, Havana

Explore Habana Vieja | Explore the town of Remedios via 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 delicious welcome lunch (guests arriving before or on recommended flight time only). 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

Our first stop will be a visit to the Che Guevara memorial and mausoleum. Then, 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 hairdressing salon that also acts as a museum, displaying antique tools and art inspired by the trade. 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 Cayo Santa María in Cayo Santa María

  • 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

  • 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.

Vintage Cuba Tour
DateDouble Occupancy
(per person)
Cuban Visa
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 USE PROMO CODE: SPRING FOR $250 OFF PER PERSON
Sep 8 – Sep 13, 2017$4,395$99  
Sep 22 – Sep 27, 2017$4,495$99 USE PROMO CODE: SPRING FOR $250 OFF PER PERSON
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  
Jan 19 – Jan 24, 2018$4,695$99  
Feb 9 – Feb 14, 2018$4,695$99  
Mar 2 – Mar 7, 2018$4,695$99  
Mar 23 – Mar 28, 2018$4,695$99  
Apr 13 – Apr 18, 2018$4,695$99  
Apr 20 – Apr 25, 2018$4,695$99  
May 4 – May 9, 2018$4,695$99  
May 25 – May 30, 2018$4,695$99  
Jun 15 – Jun 20, 2018$4,595$99  
Jul 6 – Jul 11, 2018$4,295$99  
Jul 20 – Jul 25, 2018$4,495$99  
Aug 3 – Aug 8, 2018$4,495$99  
Aug 31 – Sep 5, 2018$4,495$99  
Sep 14 – Sep 19, 2018$4,495$99  
Oct 12 – Oct 17, 2018$4,495$99  
Nov 9 – Nov 14, 2018$4,495$99  
Nov 23 – Nov 28, 2018$4,695$99  
Dec 21 – Dec 26, 2018$4,995$99  
Dec 28, 2018 – Jan 2, 2019$5,295$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 $1400.

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.

Vintage 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 flights* for all guests on this tour are:

JetBlue                        387      FORT LAUDERDALE-SANTA CLARA (FLL-SNU)           

JetBlue                        800      HAVANA-FORT LAUDERDALE (HAV-FLL)       

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, 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.

Twitter Feed

  1. Cuban farmers working hard in the tobacco fields of Pinar del Rio. #Cuba #TravelToCuba
  2. Planning to #travel in 2017? Add #Cuba to your Travel Wish List:
  3. A behind-the-scenes introduction to the thriving world of Cuban art and jazz:
Follow @insightcuba

Request your FREE Brochure!

Browse itineraries, check out photos, and learn more about upcoming trips with our FREE brochure.

Sign up for News & Offers