Havana Luxury Weekend Tour

Duration: 4 days / 3 nights

Number of Travelers: 2 Persons: $4,084 per person

Number of Travelers

$8,167.00
$6,941.95
15% off
Desired Tour Start Date:

Frequently Asked Questions

Can American citizens legally travel to Cuba, and do I need a visa?

Yes! US citizens can legally travel on this tour under the authorized Support for the Cuban People category. Gardner Tours handles all legal paperwork, itinerary compliance, and 24/7 emergency support. Plus, we’ll guide you step-by-step through obtaining your official Cuban e-visa–making the process quick, simple, and completely worry-free, so you can focus on making unforgettable memories.

What is included in the Havana Luxury Weekend Tour?

This all-inclusive 4-day / 3-night luxury weekend includes 5-star accommodations, 24-hour private transport, curated dining, and VIP entertainment:

  • Accommodations & Transport: 3 nights in 5-Star Luxury Accommodations, airport pick-up/drop-off, and 24-hour private chauffeured transportation.
  • Curated Gourmet Dining: All breakfasts (3), lunches (3), and dinners (3) at Havana’s top-rated, hand-vetted fine dining establishments.
  • VIP Shows & Cultural Highlights: Grand Theatre Big Show, Tropicana Cabaret Big Show, Classic Convertible Car Tour, Old Havana Walking Tour, Cigar Factory Tour, and Cuban Cocktail Lesson + drinks.
  • Excursions & Souvenirs: Afternoon at Havana’s best beach, and a Classic Cuban Souvenir Package.
  • Extras: Detailed itinerary & tour packet, seasonal packing list, and 24/7 emergency support.
How are meals and restaurant reservations handled on this luxury tour?

We take dining very seriously. Our founder, Colby Gardner, has personally vetted over 100 restaurants in Havana to select places that meet strict standards for atmosphere, service, hygiene, and world-class taste. All 3 breakfasts, 3 lunches, and 3 dinners are completely covered and pre-arranged at Havana’s most sought-after paladares and fine dining venues.

Is this a private luxury tour or will we be with a group?

Every trip we host is 100% private and built around your group. You won’t share transportation or guides with strangers—instead, you’ll enjoy a dedicated host, driver, and guide (often Colby Gardner himself!), providing an unhurried, VIP experience tailored entirely to your group's schedule.

Can our luxury weekend tour be fully customized?

Absolutely. While this luxury package includes our premier dining and entertainment options, we can add private events, extra nights, spa treatments, or specific cigar tastings. To curate a tailored luxury experience, visit our Custom Design page or give us a call, and we will design a once-in-a-lifetime trip with you.

Can I bring Cuban cigars and rum back to the United States?

U.S. travelers often purchase Cuban cigars and rum for personal consumption, but import regulations have evolved over time. Prior to returning home, we strongly recommend checking the latest official guidelines on the U.S. Customs & Border Protection (CBP) website for updated allowance limits and duty regulations. Ultimately, bringing items back is at your own discretion.

Have more questions? Visit our Cuba FAQs

Looking for a more Custom Experience?

Tell us how you'd like to travel and we will create a tour according to your desires. Build your Custom Tour now!

Tour Information

Designed for the luxurious-long-weekend-traveler, this all-inclusive 4-day / 3-night Luxury Havana Long Weekend Tour delivers the most splendid experience of Havana, allowing you to experience Havana like it was in its golden years. On this tour, you’ll enjoy 5-Star Luxury Housing, 24-hour classic car transportation (with air conditioning), an educational Old Havana Walking Tour, an extensive Cigar Factory Tour, an afternoon at Havana’s most magnificent beach, the city’s most historic and breathtaking sites on a two-hour Classic Car Tour, mouth-watering four course dinners at Havana’s finest restaurants, a Cuban Cocktail Lesson, a world-famous show at the Grand Theatre and the Tropicana Cabaret, alcoholic drinks, and much more! (Please see the “Itinerary” tab for more detail.) Your professional guide will walk you through Havana’s great history, cuisine, 500-year-old stories, rich arts, folklore, and famous nightlife, ensuring that you travel safely and efficiently. At night, you will encounter a more intimate, laid-back Havana with artsy expressions of the culture on every corner, including dinners at Havana’s highest-rated restaurants. After each evening of world-class entertainment, you will be free to further explore the city as you please or retire to wind down at your private 5-star accommodations.

We guarantee that you will experience Cuban culture at its finest. Even better, you’ll gain a true understanding of what this island, “frozen in time,” was like in its golden years.

Book now to experience romantic Havana over a long weekend on this unforgettable Luxury Havana Long Weekend Tour!

Gardner Tours Airplane Arriving over Blue Waters and Lush Lands in Havana, Cuba

Preparation

After booking, you will receive an email with a detailed itinerary and tour packet. Those documents will guide you through the entire process of preparation (purchasing flights, visas, packing list, etc), what your arrival will look like, the details of your tour (duration), and how your departure will be handled.

Our team is committed to serve you with the utmost hospitality, so we are honored to serve you and ensure that you are prepared in the most comfortable way that suits you.

Be assured that if you need help, we will be here to personally guide each step of the way.

A middle aged white couple kiss in front of a pink 1950 Chevrolet convertible under the shade in Havana Cuba

Arrival

Based upon the time your flight arrives at José Martí International Airport in Havana, your Gardner Tours Professional Guide will be waiting for you at your final customs exit.

Following a quick meet and greet, you will cruise into Old Havana in a privately arranged taxi, get settled into your BnB, then kick your tour off with a bang!

It won't take long before you're kicking back in luxury!

A handsome latino man runs Baywatch style in the water of the Playas del Este in Havana, Cuba

Duration

Your Gardner Tours Professional Guide will accompany you the entire way, guiding you through all four days of your luxury tour. That includes three nights in one of Havana’s awe-inspiring 5-Star BnBs.

You will have complete freedom to take your tour at the pace you please, deciding to sit and enjoy the view as long as you desire, asking that local artist as many questions as you want, or simply enjoying your dinner just a little longer than normal. Your guide will serve you along the way and ensure that you are well taken care of during your entire stay.

Gardner Tours is committed to delivering you the most hospitable and entertaining tours offered in Cuba!

Gardner Tours Havana Luxury Tour Hospitality with Elderly Couple Posing by their Maroon 1957 Chevrolet Bel Air in front of Restaurant Casa Miglis in Central Havana Cuba

Departure

Depending on the departure time of your flight, you might have the opportunity to relax and enjoy your last few hours in Havana. If so, you will have time to purchase any last-minute souvenirs from local artisans and/or take those photos that you may have missed.

At an appointed time, you will be picked up by your private transport, escorted directly to the José Martí International Airport, and dropped off three hours prior to your departure for an ample amount of time to purchase any last-minute souvenirs, check your bags, go through security and customs, and arrive at your gate for a safe flight home.

Your guide will accompany you all the way until the end.

Private Garden Sitting Area at La Bodega El Vedado Restaurant in Vedado Havana, Cuba

An Intimate Luxurious Experience

On our Havana Luxury Weekend Tours, we want you to kick back and relax in a manner that you don’t get to back at home. Not only will you enjoy our hand-picked intimate 5-star accommodations, 5-star dining, and 24-hour private transport, you will also get the full cultural experience from the big shows to the best beaches.

Throughout your private luxurious tour, you will experience the classic cars, the soul-moving music, big show atmosphere, the mouth-watering cuisine, and so much more!

It’s guaranteed that you will leave Cuba relaxed and in awe, knowing that you couldn’t have made a better choice than our Havana Luxury Tour.

Two men sharing a Cuban Coffee early one morning on a balcony in Old Havana as the sun rises

A Culture of Hospitality

Whether you're cruising down the seawall at sunset in a 1950s classic American car, learning how to smoke your first cigar, or sitting back and enjoying your third Cuban cocktail of the evening, you will find that you are being embraced with genuine hospitality, welcomed as an honored guest in a foreign land.

From the classic cars catching your attention as they cruise the streets to the rich aroma of Cuban espresso found as you stroll past every doorway, each moment truly invites wonder. And those are the moments of curiosity and connection that have inspired comments like, “We got to experience the very best while getting immersed into the culture in a very personal way.” and “These are the things that made me remember why I love traveling so much!”

It is our honor to deliver you with the most hospitable experiences, to ensure that you truly unwind and enjoy yourself like never before on this Havana Luxury Tour.

Man and Woman Cruising down the Malecon at sunset in Havana on Classic Car Tour in Classic American Car

A Perfect Private Experience

Traveling with Gardner Tours means that you travel in private, no strangers! Each and every tour is tailored to you and your travel desires and needs. You will only travel with the people in your booking, allowing you to have the most amazing and memorable time possible in the setting that you choose with us!

There's nothing like traveling in your own private group and it is our honor to ensure that your time with us is world-class.

After all, we are a hospitality company!