14-Day Ultimate Luxury Escapes Route in Cuba
Cuba is a land where time feels suspended, but your experience doesn't have to be basic. This itinerary is designed for the discerning traveler who seeks the rhythm of Havana and the turquoise waters of the keys without sacrificing the comforts of world-class service. From the rooftop terraces of five-star hotels to private helicopter transfers and vintage car excursions, we have curated the ultimate Cuban odyssey.
Expect a blend of immersive cultural experiences and serene luxury. You will navigate the cobblestone streets of UNESCO World Heritage sites by day and indulge in the island's burgeoning private culinary scene (paladares) by night. This is Cuba seen through a lens of exclusivity, elegance, and deep historical appreciation.
The Itinerary
Day 1: Havana, Cuba - Arrival & Rooftop Elegance
VIP Arrival at José Martí International
Enjoy a seamless entry with a VIP meet-and-greet service that whisks you through customs and into a waiting luxury modern sedan.
Check-in at Gran Hotel Manzana Kempinski
Settle into Cuba's first true five-star luxury hotel, located in the heart of Old Havana with views overlooking the Capitolio.
Sunset Cocktails at Terraza Habana
Sip a premium aged rum mojito while watching the sun set over the city’s iconic skyline from your hotel’s rooftop.
Dinner at La Guarida
Dine at Cuba's most famous paladar, located in a stunningly dilapidated palace that served as the set for the film 'Strawberry and Chocolate'.
Day 2: Havana, Cuba - Colonial Grandeur & Classic Cars
Private Walking Tour of Habana Vieja
Explore the four main plazas of Old Havana with a private historian, focusing on the architectural restoration of this UNESCO site.
Al Fresco Lunch at Doña Eutimia
Enjoy traditional Cuban 'ropa vieja' in a hidden alleyway known for its celebrity clientele and high-quality ingredients.
Convertible Classic Car Promenade
Cruise the Malecón and the residential Miramar district in a meticulously restored 1950s pink Cadillac.
Tropicana Cabaret Show
Experience the 'Paradise Under the Stars' with VIP table seating and premium champagne at this legendary open-air cabaret.
Day 3: Havana, Cuba - Modern Art & Rhythmic Souls
Fusterlandia Art Immersion
Visit the studio of José Fuster, who has transformed an entire neighborhood into a Gaudi-esque mosaic masterpiece.
Lunch at El Cocinero
Eat at this trendy spot located in a former peanut oil factory, right next to the city's premier art space.
Fabrica de Arte Cubano (FAC) Exclusive Tour
Get a private afternoon tour of this multidisciplinary art space before it opens to the public, meeting local artists.
Private Salsa Lesson & Dinner
Learn the basics of casino-style salsa with a professional partner before enjoying a private chef's dinner at your hotel.
Day 4: Viñales, Cuba - The Tobacco Heartlands
VIP Transfer to Viñales Valley
Travel west in a private air-conditioned SUV through the lush Pinar del Río province.
Mural de la Prehistoria
Witness the massive cliffside painting depicting evolutionary history before taking a boat ride through the Cueva del Indio.
Organic Farm Lunch at Finca Agroecologica El Paraiso
Dine on 'farm-to-table' dishes while overlooking the iconic mogotes (limestone karsts).
Check-in at Hotel Ermita
Relax at this boutique property known for having the best sunset views in the entire valley.
Day 5: Viñales, Cuba - Premium Cigars & Horseback Riding
Private Tobacco Plantation Tour
Visit a 'Vegas' (tobacco farm) to learn the art of cigar rolling from a master and sample a farm-fresh Habano.
Valle de los Jazmines Overlook
Take in the most photographed view in Cuba before a private lunch prepared in the fields.
Luxury Horseback Trek
Ride through the valley floor, visiting hidden caves and coffee plantations away from the standard tourist crowds.
Traditional Creole Dinner
Enjoy an authentic 'lechon asado' (roasted pig) dinner at a private villa in the valley.
Day 6: Cienfuegos, Cuba - The Pearl of the South
Transfer to Cienfuegos
A scenic drive along the coast brings you to the 'French' city of Cuba, known for its neoclassical architecture.
Lunch at Club Cienfuegos
Dine in a stunning yacht club building overlooking the bay, specializing in fresh seafood.
Palacio de Valle Tour
Explore this architectural marvel that blends Gothic, Venetian, and Moorish styles.
Check-in at Hotel La Unión
Stay at this historic boutique hotel in the center of the city, featuring elegant courtyards and a pool.
Day 7: Trinidad, Cuba - Time Travel in Cobblestone
Walking Tour of Plaza Mayor
Step back into the 19th century as you explore the perfectly preserved colonial heart of Trinidad.
Lunch at Museo de la Arquitectura
Enjoy a light lunch followed by a visit to the museum to understand the town's wealthy past.
Pottery Workshop at Casa del Alfarero
Visit the Santander family, who have been creating traditional ceramics for generations, and try your hand at the wheel.
Live Music at Casa de la Musica
Settle into VIP seats on the steps of the plaza to watch world-class musicians perform under the stars.
Day 8: Trinidad, Cuba - Mountains & Waterfalls
Jeep Safari to Topes de Collantes
Ascend into the Escambray Mountains for a day of nature and exploration.
Hike to Salto del Caburní
A guided trek through coffee plantations leads to a spectacular 60-meter waterfall with a natural swimming pool.
Traditional Mountain Lunch
Eat at a rustic hacienda specializing in locally grown vegetables and charcoal-grilled meats.
Beach Sunset at Playa Ancon
Head to the nearby white-sand beach for a relaxing swim as the sun dips below the horizon.
Day 9: Sancti Spíritus & Transit - The Interior Route
Transfer to Sancti Spíritus
Stop briefly in one of the original seven villas founded by the Spanish, crossing the historic Yayabo Bridge.
Plaza de la Revolución
Stretch your legs and see the revolutionary monuments of this central Cuban hub.
In-Car Picnic Luxury Service
Enjoy a gourmet picnic prepared by your Trinidad hosts as you transit towards the northern coast.
Check-in at Royalton Hicacos
Arrive at Varadero’s premier adults-only luxury resort to begin the beach portion of your journey.
Day 10: Varadero, Cuba - Pristine Sands & Spa
Private Beach Cabana Experience
Relax in a reserved luxury cabana with dedicated butler service on the world-famous Varadero beach.
Gourmet Seafood Lunch
Dine at the resort’s specialty seafood restaurant, featuring fresh-caught lobster.
Couples Massage & Hydrotherapy
Indulge in a signature Cuban rum and honey massage at the world-class spa.
Fine Dining at Mansion Xanadu
Eat at the former Dupont estate, a 1920s mansion built on the cliffs with incredible ocean views.
Day 11: Varadero, Cuba - Private Catamaran Sailing
Private Yacht Charter to Cayo Blanco
Board a private catamaran for a day of sailing, snorkeling at the coral reef, and swimming with dolphins.
Lobster Feast on Cayo Blanco
Enjoy a private beach lunch on this uninhabited island, prepared by your boat crew.
Sunset Sail back to Varadero
Relax on the nets of the catamaran as you sail back to the mainland with an open bar of premium spirits.
Late Dinner & Jazz
Visit a local jazz club for high-quality live music in an intimate setting.
Day 12: Varadero, Cuba - Golf & Leisure
Tee Time at Varadero Golf Club
Play 18 holes at the only professional golf course in Cuba, which winds along the ocean cliffs.
Lunch at the Golf Club Terrace
Enjoy a light club lunch with views of the greens and the Caribbean Sea.
Mixology Class: The Art of the Cantinero
Learn the secrets of the perfect Daiquiri and Hemingway Special from a master Cuban bartender.
Farewell Beachside Dinner
Celebrate your final night in Varadero with a private table set up directly on the sand.
Day 13: Matanzas & Havana - Cultural Return
Stop in Matanzas: The City of Bridges
On your return to Havana, visit the Sauto Theater, one of the most beautiful neoclassical buildings in the country.
Lunch at Jibaro's
Experience innovative Cuban fusion in the heart of the San Isidro art district in Havana.
Check-in at Paseo 206 Boutique Hotel
Spend your last night in a Small Luxury Hotel of the World, located in the sophisticated Vedado district.
Dinner at Otramanera
Enjoy a contemporary culinary experience that is widely considered one of the best in Havana.
Day 14: Havana, Cuba - Final Souvenirs & Departure
Private Shopping: Rum & Cigars
Visit the Partagas factory shop for authenticated, high-quality Habanos and rare aged rums.
Brunch at El del Frente
Enjoy a trendy final meal on a stylish rooftop in Old Havana before heading to the airport.
VIP Transfer to Airport
Your private driver will ensure you arrive at the airport with ample time for your departure.
Departure
Board your flight home, reflecting on two weeks of Cuban luxury and history.
Best Time to Visit Cuba
The best time to visit Cuba is during the dry season from November to April. This period offers plenty of sunshine and pleasant temperatures ranging from 21°C to 27°C (70°F to 80°F), perfect for both city exploring and beach lounging. Avoid the hurricane season between August and October, and be prepared for higher humidity and heat if traveling in June or July.
Currency & Money
Cuba currently uses the Cuban Peso (CUP). However, the economy is dualistic; as a luxury traveler, you will often pay for hotels and government services with credit cards (excluding US-issued cards). Tipping is a vital part of the culture; 10% is standard in restaurants, and small tips for drivers and guides are highly appreciated. Always carry some cash in Euros or USD, as they are widely accepted in private businesses (paladares and casas).
Getting Around Cuba
For a luxury itinerary, the best way to get around is via private, air-conditioned transfers or hiring a dedicated 'car with driver' for the duration of your trip. Domestic flights are available between Havana and eastern cities like Santiago de Cuba but can be unreliable. For short distances in Havana, the iconic restored classic cars offer a stylish way to travel, while Viazul buses are the standard for budget travelers but are not recommended for a high-end experience.
