Havana Luxury Weekend Tour

Tour Overview

Designed for the traveler seeking an elevated escape, this all-inclusive 4-day private Havana Luxury Weekend Tour delivers a seamless, 5-star experience of Cuba’s iconic capital. On this fully hosted private journey, you'll indulge in the absolute best of Havana’s rich culture, fine dining, and world-class nightlife—giving you an authentic glimpse into Havana as it was during its golden age.

From the moment you arrive, your dedicated professional guide and private driver accompany you every step of the way, providing 24-hour private classic car transportation and attentive care so you can relax and enjoy an effortless getaway.

What Makes This Journey Unforgettable

• Intimate Old Havana Walking Tour: Uncover 500 years of living history on an up-close-and-personal guided walk. Discover hidden plazas, landmark architecture, and intimate stories that unfold the captivating mystery of the city through the lens of your guide and local friends.
• Classic Convertible City Tour: Cruise along the Malecón and through iconic historic neighborhoods in a beautifully restored classic convertible. As you visit legendary landmarks and awe-inspiring viewpoints, your guide unfolds the stories behind 500 years of Cuban history, giving you a captivating, wide-angle perspective on the island's past while connecting you personally to its living culture.
• Cigars, Mixology & Coastal Relaxation: Go behind the scenes on an exclusive Cuban cigar factory visit, master traditional mixology during a private cocktail lesson with drinks included, and unwind along the white sands of Havana’s top beach.
• 5-Star Fine Dining & VIP Performing Arts: Savor full-service dining at Cuba’s highest-rated restaurants before taking in world-famous performances with VIP seats at both the Grand Theatre and the legendary Tropicana Cabaret.
• Professional Photography Package: Relax and stay fully present in every moment while your private guide candidly captures your journey in the background—hardly noticed. After your tour, you’ll receive a beautifully curated gallery of professionally edited photos to remember your trip forever.

Itinerary Highlights at a Glance

• Havana (3 Nights): Three nights hosted in premier 5-star luxury accommodations, surrounded by historic elegance, fine dining, 24-hour private transport, and iconic nightlife.

Experience Cuba Hosted by Gardner Tours

Discover the 500-year history, warm hospitality, and timeless romance of an island frozen in time—all wrapped in effortless private care and 5-star luxury accommodations.

Experience high-end, romantic Cuba on this ultimate 4-day getaway. Select your travel dates above and book your private tour today!

Day One: Arrival in Havana & Classic Car Tour

When you arrive at the José Martí International Airport in Havana, your professional guide will be waiting for you at your final customs exit. Your guide will take you to your 5-star accommodations, where you’ll have a few minutes to get settled. Once you are ready, you’ll kick your tour off with a bang on a two-hour Classic Car Tour of the city.

On the Classic Car Tour, you will visit Havana’s most remarkable sites such as the Christ Statue overlooking the city, the Morro Castle, Revolution Square, the Capitol and the Vedado neighborhood. You’ll finish with a breezy cruise down the Malecón (seawall) at sunset. 

After your Classic Car Tour, you will be dropped off at our favorite restaurant in the city to experience its mouth-watering cuisine and the live music that the alley offers. Following dinner, your guide can drop you off at your accommodations, if you prefer. But if you’d like to explore the nightlife of Old Havana on foot or visit some of Havana’s famous night clubs in the 24-hour transportation that is available to you, your guide and driver will ensure that you have an exciting and safe night out on the town.

Day Two: Classic Havana

Day two will include an incredible Cigar Factory Tour, a Cuban Cocktail Lesson, a show at the world-famous Grand Theatre of Havana, and dinner at an outstanding restaurant with live jazz. Your guide will meet you at your accommodations at your chosen time in the morning and then drive you to one of Havana’s famous cigar factories, where you’ll receive a complete education on the process of creating Cuba’s world-renowned tobacco.

Following your visit to the cigar factory and Habanos store, your guide will take you back to Old Havana for lunch at one of our partner restaurants. After a quick siesta, your guide will take you to one of our favorite places in Old Havana -- a quiet, private location in the heart of the city where you will receive a private lesson on how to make Cuban cocktails. And yes, of course you get to drink the cocktails after you make them! Each traveler is able to become the bartender himself for a time and put his cocktail-making skills to the test.

After your Cocktail Lesson, you will return to your accommodations where you’ll put on your finest attire. Your guide will drive you to one of our partner 5-star restaurants to taste its immaculate cuisine. After you have satisfied your appetite, your guide will drive you back to Old Havana where you’ll experience one of the best shows that Cuba has to offer -- at the Grand Theatre of Havana, home of the world’s largest ballet company!

Following the show, you’ll have the opportunity to get your dancing shoes on and explore Cuban nightlife. However, if you’d prefer to retire for the evening, your guide will transport you to your accommodations.

Day Three: Cuban History, Culture, Blue Waters, & A World-Famous Show

Day three is the icing on the cake, as you step even deeper into Cuban history and culture. Your guide will meet you at your accommodations at the time of your choosing, and together you’ll begin your Old Havana Walking Tour.

On the Walking Tour, you will receive a comprehensive education of Cuban culture, history and folklore. Your guide will walk you through the old city to some of its most historic and romantic sites such as the Castle of the Royal Force, Plaza de Armas, Plaza Vieja, the Havana Cathedral, and La Bodeguita del Medio (one of Hemingway’s hangouts). You will meet local artists at their shops and might even bump into a few of Havana’s vibrant personalities. Who knows, you might even find yourself dancing to traditional Cuban music with locals in the street!

Following lunch at one of our favorite partner restaurants, you will have the opportunity to extend the walking tour into the Capitol Area, visiting locations like an artisan’s market, Central Park, the Capitol, the Original Partagas Cigar Factory, and the Museum of the Revolution. [Alternatively, you can head straight to the beach, the next portion of the day, to catch more rays.]

After your walking tour, you will return to your accommodations and prepare for an afternoon at Havana’s most pristine beach. Your driver and guide will pick you up from your accommodations at the time of your choosing and take you to the beach for some time of rest and relaxation.

Upon your return from the beach, your guide will accompany you to another one of our favorite 5-star partner restaurants to dine on its fine cuisine. This will be the perfect opportunity to sit back, relax, and take it all in as you wind down your final evening in Havana.

But before you begin to think about returning home, you will experience one more exceptional show -- this time at Cuba’s most famous nightclub and cabaret, the Tropicana! The Tropicana Cabaret offers an unforgettable two-hour live show with music, dancers, and acrobats. The show has been held every night at the Tropicana Cabaret since 1939 and is the model for Las Vegas’ show girls. Following the show, your driver will return you to your accommodations in Old Havana to rest and prepare for your departure the next day.

Day Four: Final Taste & Departure

Most of our travelers like to take the morning easy, especially after an incredible night at the Tropicana. But if you wish to get out and about on your last morning in Old Havana, your guide will meet you at your chosen time to explore and get your final taste of “the city frozen in time.” You can spend your time purchasing any last-minute souvenirs from local artisans and taking any photos that you may have missed.

Three to four hours prior to your flight, your guide will accompany you in private transportation to the airport to say your final goodbyes and send you on your way.

Included

• Professional Guide*
• 5-Star Luxury Accommodations*
• Three Nights in Havana
• Airport Pick-up & Drop-off
• 24-hour Transportation*
• Breakfasts (3), Lunches (3) & 5-Star Dinners (3)*
• Old Havana Walking Tour
• Cigar Factory Tour*
• Classic Car Tour (convertible)
• Cuban Cocktail Lesson + Drinks
• Afternoon at Havana’s Best Beach
• Big Show at Grand Theatre*
• Big Show at Tropicana Cabaret*
• Classic Cuban Souvenir Package*
• Detailed Itinerary & Tour Packet
• Seasonal Packing List
• Emergency Support

Not Included

• Airfare
• Cuban Visa

More Information

* See the What to Expect tab for details on starred items.

WHAT TO EXPECT ON YOUR TOUR

The draw of this all-inclusive Havana Luxury Weekend Tour is that you don’t have to worry about a single thing. Forget about struggling to read maps, slogging through hotel recommendations, and wading through countless restaurants for a decent meal. Prior to your arrival, you’ll receive your complete itinerary, from 5-star accommodations to 24-hour transportation to ticketing to 4-course dinners. A Gardner Tours professional guide, educated on Cuban culture, history, and hospitality, will accompany you for your entire tour. All we ask of you is to simply enjoy yourself! In the event that something changes or doesn’t go as planned, please be patient and courteous; it is our guarantee that your guide will handle any challenges with timely grace. Our goal is to ensure that you are taken care of and receive the authentic luxurious Cuban experience you desire.

Your Tour Guide

Each of our guides are experienced and able to answer almost any question that you may have during your tour. Though we plan everything for you, you will have complete freedom to take your tour at your own pace, stopping as often as you like for a rest on your walking tour, returning to that one famous bar for the fifth time, or simply enjoying your dinner just a little longer than you normally would. Your guide will give you the time and space to enjoy each experience as you please. Your guide will meet you at your accommodations at your desired time each morning to begin the day, and he/she will also ensure that you are home safely at the end of each night.

Our travelers often comment that the experiences that they receive on their tours are top-notch, but our guides are what make the tours so special.

Havana Luxury Tour Accommodations

We provide 5-star Cuban accommodations with classic Cuban antiques, colonial architecture, comfortable furniture and beds, as well as privacy to help you properly wind down your evenings. Each room is equipped with an air-conditioner and a private bathroom. The service often includes a 24-hour butler onsite. If you desire to share a room with your travel companions (up to two persons per room), please specify in the details of your booking.

24-Hour Transportation

You will have 24-hour transportation available to you during your entire tour. Most of your transportation will already be arranged according to your itinerary, however if you desire to take a trip outside of your itinerary, feel free to arrange it with your driver, and he will be sure to take good care of you and your travel companions.

Luxurious Dining Experiences

We don’t want you to worry about anything on your tour, especially dining well. Our owner, Colby, is a foodie and has vetted about one hundred restaurants in Havana to identify the restaurants that offer exceptional experiences based on atmosphere, service, taste, and hygiene. Due to his extensive research and formed partnerships, we guarantee that you will enjoy each and every food experience, from breakfasts at your accommodations to your arranged lunches and dinners at Havana’s most sought-after restaurants.

Cuban Cigar Factory

Cigar Factories in Cuba are closed on the weekends as well as two longer holidays during the year. If you book during these times, we will adjust to ensure that you experience the cigar-making process.

World Famous Shows

Your first world-famous show will be at The Grand Theatre of Havana, which takes random breaks from shows at certain times in the year. Your second show will be at the Tropicana Cabaret (since 1939), which has shows every night. If these venues do not offer a show during your tour, we will make adjustments and ensure that you experience another amazing show, such as the renowned Cabaret Parisien or the Buena Vista Social Club.

Classic Cuban Souvenir Package

We desire our travelers to experience the best souvenirs that Cuba has to offer without the hassle of going to get it. We do the grunt work for you. Each of our travelers receive our “Classic Cuban Souvenir Package,” with 1kg of Cuban Coffee, one box of Premium Cuban Cigars, and one bottle of Premium Cuban Rum. We might even throw in a few other goods for you to ensure you remember the great taste of Cuba when you return home.

Our Guarantee To You

Gardner Tours is committed to delivering you the most hospitable and entertaining tours offered in Cuba! If you would like to adjust this tour in any way, please contact us so we can accommodate you.