9-Day Ultimate Luxury Escapes Route in Cuba
Cuba is a land where time seems to stand still, yet its luxury scene is evolving rapidly for the discerning traveler. This 9-day itinerary is designed for those who want to soak in the vintage atmosphere of the 'Classic Route' while enjoying the island's finest comforts, from the rooftop pools of Havana to the pristine sands of Varadero.
Forget the crowded tour buses; your journey involves private transfers in mint-condition 1950s American convertibles and modern luxury SUVs. You will dine in the island's most acclaimed 'paladares' (private restaurants) and stay in historic boutique hotels that offer a level of service as warm as the Caribbean sun.
The Itinerary
Day 1: Havana, Cuba - Arrival & Grand Entrée
Luxury Check-in at Gran Hotel Manzana Kempinski
Arrive at Havana's José Martí International Airport where a private chauffeur awaits. Check into the Gran Hotel Manzana, Cuba's first true five-star luxury hotel, located in the heart of Old Havana.
Sunset Walk through Plaza Vieja
Explore the restored beauty of Plaza Vieja with a private historian. Learn about the city's baroque and art deco architecture while avoiding the tourist traps.
Gourmet Dining at La Guarida
Experience Cuba’s most famous paladar. Located in a weathered palatial building, this restaurant offers world-class fusion cuisine and has hosted celebrities from across the globe.
Nightcap at El del Frente
Enjoy artisanal gin cocktails on a chic rooftop terrace, overlooking the bustling streets of Havana Vieja.
Day 2: Havana, Cuba - Classic Heritage & Arts
Vintage Convertible City Tour
Cruise the Malecón and the leafy streets of Miramar in a meticulously restored 1950s Chevrolet Bel Air. Visit the Plaza de la Revolución for iconic photos.
Lunch at Otramanera
A sophisticated culinary spot in the Miramar district, offering a modern twist on Cuban ingredients in a minimalist, high-end setting.
Private Tour: Museo Nacional de Bellas Artes
Enjoy an exclusive guided walkthrough of the Cuban Art building with a local curator, focusing on the evolution of the island's vibrant visual history.
Legendarios del Guajirito Performance
Experience the soul of the Buena Vista Social Club in an intimate, upscale venue with world-class musicians and premium rum service.
Day 3: Viñales, Cuba - Tobacco Valleys & Eco-Luxury
Private Transfer to Viñales Valley
Depart Havana in a luxury SUV for a 2.5-hour drive to the Pinar del Río province, famous for its limestone mogotes and world-best tobacco.
Exclusive Cigar Masterclass at Finca Montesino
Visit a private tobacco farm to learn the secrets of the Habano from the farmers themselves. Enjoy a cigar rolling demonstration and a fresh farm-to-table lunch.
Mogote Lookout & Cocktails
Visit the Jasmines lookout for the most iconic view of the valley, followed by a sunset cocktail at a private boutique estate.
Dinner at El Cuajani
One of the region's finest dining experiences, focusing on organic ingredients grown on-site, served with an incredible view of the mogotes.
Day 4: Cienfuegos, Cuba - The Pearl of the South
Travel to Cienfuegos
A 4-hour luxury transfer takes you across the island to the French-influenced city of Cienfuegos. Enjoy the scenic views of the Zapata Peninsula along the way.
Seafood Lunch at Palacio de Valle
Dine in a stunning architectural marvel that blends Gothic, Venetian, and Moorish styles. The rooftop offers sweeping views of Cienfuegos Bay.
Bay Cruise by Private Yacht
Charter a small private vessel to explore the bay and see the Jagua Castle from the water as the sun begins to set.
Evening Stroll on Paseo del Prado
Walk the longest tree-lined boulevard in Cuba, taking in the neoclassical architecture and local evening life.
Day 5: Trinidad, Cuba - Colonial Elegance
Arrival in Trinidad
A short 1.5-hour drive brings you to the UNESCO World Heritage site of Trinidad. Check into your luxury villa or the Iberostar Heritage Grand.
Lunch at Museum 1514
Eat among antiques in this restaurant-museum that offers some of the best traditional Caribbean cuisine in a high-end setting.
Cobblestone History Tour
A private guide will lead you through Plaza Mayor, explaining the history of the sugar barons who built this wealthy city.
Canchánchara Tasting
Visit the famous Taberna del Pintado to sample the city's signature honey and rum cocktail in a private courtyard.
Day 6: Trinidad, Cuba - Nature & Escapism
Topes de Collantes Excursion
Take a private 4x4 into the Escambray Mountains. Hike the Salto del Caburní trail to reach a secluded waterfall and natural pool.
Coffee Plantation Lunch
Visit a mountain hacienda for a traditional lunch and a tasting of locally grown, high-altitude Cuban coffee.
Afternoon at Playa Ancón
Relax at the most beautiful beach on the south coast. Enjoy a private beach setup with refreshments and premium sun loungers.
Fine Dining at San José
Enjoy a final Trinidadian dinner at this top-rated restaurant known for its exquisite lobster and international wine list.
Day 7: Varadero, Cuba - Pristine Sands
Transfer to Varadero
Enjoy a comfortable 4-hour private transfer north to the Hicacos Peninsula, home to Cuba's most famous white-sand beaches.
Luxury Resort Check-in
Enter the world of all-inclusive luxury. Settle into your Royal Service suite with personalized butler service.
Sunset Golf at Varadero Golf Club
Play a round at Cuba's premier 18-hole course, located on the grounds of the historic Mansión Xanadú.
Dinner at Mansión Xanadú
Experience an elegant dinner in the former Dupont estate, featuring French-inspired cuisine and one of the island's best wine cellars.
Day 8: Varadero, Cuba - Private Waters
Private Catamaran Charter
Spend the day on the turquoise water. Sail to Cayo Blanco for snorkeling on the coral reefs and a private seafood lunch on the deck.
Dolphin Encounter
Enjoy a private, respectful interaction with dolphins in their natural enclosure at the Varadero Delfinario.
Spa & Wellness
Indulge in a signature Cuban rum and honey massage at the resort's premium spa center.
Farewell Beach Dinner
A private, candlelit dinner arranged on the sand, featuring local langoustines and premium Moët & Chandon.
Day 9: Varadero/Havana, Cuba - Final Flavors
Morning at Leisure
Enjoy a final dip in the Caribbean or a walk along the 20km stretch of pristine beach.
Artisanal Shopping
Visit the Taller de Cerámica Artística to purchase high-quality, local handmade ceramics and art pieces before you leave.
Private Departure Transfer
A luxury vehicle will transport you back to Havana's José Martí International Airport (2 hours) or Varadero Airport for your flight home.
Departure
Board your flight with memories of an island that is as complex as it is beautiful.
Best Time to Visit Cuba
The best time to visit Cuba is during the dry season, which runs 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 relaxation. May and June are also good but can be more humid, while the hurricane season (August to October) is best avoided for luxury travel.
Currency & Money
Cuba currently uses the Cuban Peso (CUP). However, for luxury travelers, it is vital to know that the economy is heavily cash-based for small purchases, while many high-end hotels and restaurants accept international credit cards (excluding those issued by US banks). It is highly recommended to bring Euros or USD in cash for tipping and private paladares. Tipping is customary and very much appreciated; 10% is standard in restaurants.
Getting Around Cuba
For a luxury itinerary, the best way to get around is via private transfers. While there are domestic flights between Havana and Santiago de Cuba, they are often unreliable. Private cars with professional drivers offer the most comfort and flexibility. For the 'Classic Route' vibe, hiring a vintage car for city tours is a must, while modern air-conditioned SUVs are preferred for longer intercity drives like the journey to Viñales or Varadero.
