Have you heard of novelty bonding, Sunshines? It’s a thing. When you and your significant other share new experiences together you naturally feel more bonded and connected…your intimacy grows. On our Cuba Couple’s Trip you are literally sharing in moment after moment that evoke “Remember that time we…” memories that will become part of your shared story.

There are places that stay with you long after you’ve left and Cuba is absolutely one of those places. From the polished chrome of classic cars to the scent of hand-rolled cigars and the rhythm of Havana’s streets, our Cuba Couple’s Trip is about more than travel. It’s about connection with the Cuban culture and with each other.

January 10th-16th, 2026
Stories to last a lifetime: A Journey Through Vintage Cars, Rum, and Verdant Rolling Hills

Here are some of the amazing Trip Highlights:

Private visit to a vintage car repair shop – witness the passion behind Cuba’s iconic symbol.
Cruise down the Malecón in classic convertibles
Cuban rum & cigar pairing guided by a sommelier
Explore a centuries-old tobacco farm in the stunning Viñales Valley
Savor a farm-to-table Michelin-recognized lunch in a rustic paradise
Sunrise coffee and a hike through a breathtaking national park
Dine at some of Havana’s most sophisticated restaurants
Relax on a Caribbean beach with turquoise waters at your feet

Day-by-Day Journey

January 9th-Optional Early Arrival

Optional day to arrive early to explore the iconic and captivating city of Havana. (Many couples will choose to do this.)

January 10thth-Welcome to CUBA!

Official welcome to the enchanting city of Havana and to your incredible Cuban adventure. A private driver will meet you at the airport. Check into your boutique hotel accommodation in Old Havana. In the evening: Cuba welcome dinner! Enjoy an incredible welcome dinner with our new friends and get your first taste of the sights and sounds of vibrant Havana. We’ll dine at a restaurant with cult-like status that was the filming location for the revered movie "Fresa y Chocolate".

January 11th – Havana’s Timeless Charm

Start with breakfast on the tropical balcony of our boutiqe hotel and then set out to explore Old Havana via bici taxis and on foot. We’ll wind through the colorful, historic streets. Lunch is a Cuban fusion feast in a beautifully restored mansion, followed by a behind-the-scenes visit to a vintage car repair shop.

Later, ride in a classic convertible along Havana’s iconic Malecón, stopping for photos at Revolution Square and Parque Almendares. The evening brings a rooftop dinner with panoramic views of the sea, fortress, and city skyline.

January 12th – Tobacco Trails & Rustic Elegance

Early departure via the Tobacco Route to the greenest and most breathtaking of all Cuban provinces, Pinar del Río. The Viñales Valley is a stunning region with Jurassic era mogotes where time seems to stand still. We’ll stop at an incredible lookout for pictures before heading to lunch at Paladar El Cuajaní. Written up in Conde Nest, The Lonely Planet and even the Michelin Guide, El Cuajaní has a surprisingly elevated and sophisticated menu in a magical, rustic setting.

Next up is a tour of a naturally beautiful, working tobacco farm where we will have a true Cuban experience, learning from a farmer about their world-renown Cuban cigars.

January 13th – Sunrise in the Hills

Rise and shine! We will have a “to go” breakfast as we make our way for a sunrise hike to Los Acuáticos. We begin our hike in the national park, which is one of the most beautiful landscapes in the Viñales. Upon reaching the top we will enjoy a spectacular sunrise while enjoying a Cuban coffee (with a view!). The walk down from the magnificent look-out, keep your eyes peeled for all the birds, many of which are unique to this area. Arrive back to the town of Viñales and enjoy some free time to wander the cute, colorful streets.

Dinner: A driver will take everyone from their individual casas so that we can have dinner together as a group at the spectacular casa and restaurant of a renowned author and former expat, also featured in Conde Nest Traveler.

January 14th – A Taste of Giving & Gourmet Flair

After breakfast, we visit a rural community for a sustainable giving experience. Lunch at Finca Tungasuk features seasonal dishes prepared by a Peruvian-Nicaraguan duo who blend organic farming with culinary artistry. Return to Havana for a relaxing evening.

January 15th – Sun, Sea & Dancing in Havana

Enjoy a free morning to soak in the sights and sounds of Havana. In the afternoon we will spend a relaxing afternoon at a local playa where aqua blue Caribbean waters await. You can swim, sun read, snorkel or take a siesta on this white-sand beach. We will then enjoy a beautiful lunch in the garden of a local couple’s home.
We have a surprise evening in store! First up is dinner at a trendy loft-style restaurant in a former cooking oil factory on the banks of the Almendares River. We will then use our VIP tickets to go to Fábrica de Arte one of the most unique spots in all of Cuba. Experience art, music and dancing in one at this incomparable club and gallery. An amazing way to end a spectacular trip!

January 16th – Farewell to an Amazing Week

Breakfast at the hotel one final time. Say goodbye to our new Cuban friends as we depart for the USA. Private transfer to the airport.

Spend the New Year in this elusive, bucket list location with your loved one…

I get it. Most people only dream of going to Cuba and this is your chance to turn a bucket list trip into a reality.
Here is the full itinerary and when you are ready to book this is the link. ** I have to tell you there are only three spots left on this amazing, lifetime adventure.

We can’t wait for you to experience the magic of Cuba!
xo, Bree
Bree@Besomewheresunny.com

Cuba Couple’s Trip January 2026

Free Trip for a Single Mom!