13 days
6 places
3
Private Roundtrip
Juan Carlos
CUBA TRAVEL SPECIALIST
"Why freeze through the holidays when you could be dancing salsa in the Caribbean? This route is made for anyone who wants to celebrate instead of shiver, trade snow for palm trees, and say goodbye to 2025 with sand between their toes. From rooftop dinners on Christmas Eve to classic car rides and beachside fireworks – you'll experience Cuba the way locals do. With premium stays, insider access, and moments that no travel brochure can offer."
Imagine spending Christmas not in grey winter weather – but under palm trees, with live music in the warm evening breeze and a mojito in your hand. This 13-day Christmas and New Year trip to Cuba blends festive spirit with unforgettable experiences across the island: colorful streets in Havana, the lush Viñales Valley, colonial flair in Trinidad, and beachside bliss in Varadero. You’ll stay in handpicked private guesthouses and 5-star beach hotels, enjoy rooftop dinners, join local celebrations, and still have time to simply sit by the sea and listen to the waves. Whether it’s a cozy Christmas Eve dinner with Cuban hosts, an open-air New Year’s party with fireworks over the ocean, or a quiet moment on the beach on January 1st – this trip gives you memories that last far beyond the holidays.
This 13-day route takes you deep into the real Cuba – from colonial Havana and the lush Viñales Valley to UNESCO-listed Trinidad and two relaxed beach days in Varadero. You’ll celebrate Christmas with locals on a rooftop, dance salsa instead of shivering – and start the new year barefoot by the sea. Along the way, you’ll stay in handpicked guesthouses and 5-star resorts, experience Cuba through local eyes – and return with stories no travel brochure could ever tell.
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Your journey starts in Havana, where vintage cars cruise past colonial facades and music pours from every corner. You’ll explore the city with a local guide – from the cobbled streets of Old Havana to the panoramic rooftops where cocktails meet sunsets. Hop in a classic convertible to visit a local cigar factory and learn the craft from a real torcedor. On Christmas Eve, you’ll celebrate with Cuban hosts on a private rooftop: dinner, live music, and warm holiday vibes instead of cold winter nights.
Head southeast to Trinidad, a colorful UNESCO gem with cobbled lanes and pastel houses. Shake up your own cocktails on a rooftop at sunset, then enjoy a festive dinner in the historic center. The next day, wander the colonial streets and then venture into the Valle de los Ingenios – sugarcane country full of stories, viewpoints, and greenery. Lunch is served in the valley, with mountain views and homemade flavors.
Trade cobblestones for coastline. In Varadero, you’ll check into a 5-star all-inclusive beach resort. No schedule, no stress – just turquoise water, white sand, and optional spa time. After two days of full recharge, it’s back to Havana for a modern twist: rooftop vibes, live DJ, and “A Taste of Havana” with creative cocktails and local tapas.
It’s almost New Year’s – and time to cook like a Cuban. In a local cooking class, you’ll learn how to prepare a traditional holiday meal, before heading out for dinner and the lively Havana Queen Show. New Year’s Eve comes with live bands, dancing, and fireworks over the sea – no dress code, just good vibes. On New Year’s Day, you’ll join the locals at Tarará Beach, where the city relaxes with sun, music, and ocean air.
Your final day takes you into the green hills of Viñales – known for tobacco fields, limestone cliffs, and slow rural life. Visit a local farm, learn how cigars are made by hand, and enjoy a hearty lunch with a Cuban family. In the afternoon, head back to Havana – filled with sun, rhythm, and stories worth sharing.
We are travel specialists for individual trips to Cuba! From vintage car trips, family trips to diving trips, discover our travel suggestions here and ask us about your personal Cuba trip.
From $ 1490 per person
12 day round trip
