Cuba presents a number of priceless opportunities to explore. Its pristine waters and impeccable beaches are just the start of the welcoming attractions the island country has to offer.
Our 8-day cruise covers some of the best Cuban highlights. With our unique experience sailing Cuba, you’ll have the chance to navigate the waters of the Caribbean Sea and snorkel in some of the most beautiful underwater landscapes in the world. Discover how the reef and animal life interact, forming some of the most picture-perfect presentations of Cuba.
Your sailing tour comes complete with seven nights and eight days of accommodation onboard our 60-foot Catamaran vessel, including an open bar. You and your companions will be provided meals and evening entertainment in several of our chosen locations.
Comfortable rooms with a cozy double bed, air conditioning, and a full bathroom ensure your stay on the catamaran is to your liking while sailing the seas of Cuba. When it’s time to relax with friends, take a break from all the action and wind down in the lounge, listening to the sounds of the Caribbean waves.
One of our top-rated bilingual staff members will be your guide and is there to help you feel at home, answering any questions about your experience sailing Cuba. Also joining you on the expedition will be your own personal cook who will prepare delicious meals made from local produce. You’ll also have the chance to take advantage of on-land meals provided at certain destinations along your trip.
We begin the expedition after your ride from the airport, included in your 8-day excursion. Starting our voyage, we’ll set sail on the sparkling turquoise waters of Cuba, journeying through a perfect blend of history and nature. You’ll have the chance to explore above and below waters to see some of the best the country has to offer.
The team will sail you through the clear waters to the protected homes of natural flora and fauna, incomparable with that of the rest of the world. Cuba is a spectacle of its own.
Bright, white-sand beaches welcome you on land at many of our favorite destinations to highlight while sailing Cuba. But this island country isn’t just looks; it has a long history filled with fascinating stories spanning centuries. On your voyage, you’ll take a trip through the local traditions and the authentic history that made Cuba what it is today.
Day One – Settling In
On day one, you’ll have the opportunity to visit the Beatles Club, where you can see the homage Cuba pays to the Beatles. Situated close to the coast, the bar is complete with mementos and artifacts typical to the culture that the Beatles created back in the 60s. Plus, the Beatles Club offers live music, playing some of the greatest Rock n’ roll covers of all time.
Once you’ve had your fill for the day, it’s time to return to the boat and settle into your home for the next week. Your guide will answer any questions or concerns, making your stay as comfortable as possible.
Sit back and relax for a quiet evening enjoying the sounds and sights of the sea. It will be golden hour by then, something you don’t want to miss; sunsets in Cuba are magical. And with a Cuban Mojito or Cuba Libre cocktail, you’ll feel settled in paradise.
Day Two – The Caribbean and its Culture
The adventure won’t stop there. On the second day we’ll sail to incredible reefs, a stunning bay, and a port city rich with history, presenting a cultural backdrop to frame your unique experience sailing Cuba.
Cuba is home to some of the clearest waters in the world. Upon arrival at our first reef stop, named “Cabezo Amarillo”, we’ll don our snorkels and dive into the turquoise waters to see colorful wildlife. Sea turtles, starfish, lobsters, and other animals are among the sealife living in Cuba’s waters. You may even spot a friendly nurse shark or moray eel.
On our next stop, explore the shallow Bay of Cardenas, complete with its crystalline waters and soft white sand. Amidst the long stretch of beach, palm trees sway lazily in the light breeze coming across the Caribbean.
Sip on a cocktail while enjoying the pristine beaches and crystal clear shallow waters. Once you’ve had your fill of the beach, peruse the colorful streets of Santa Clara, the resting place of the late revolutionary leader Che Guevara. Memories of him and his fight are scattered throughout the city, making it a valuable cultural stop along your travels in Cuba.
Here, we’ll drop anchor, taking in the sights and a hearty meal before closing the day.
Day Three – Beach R&R
Our next day is full of more amazing beaches. In Western Cuba lies another spectacular bay full of clear waters, white sand, and historical attractions. The tropical weather, luxurious feel, and lively culture are just some of the great attractions of the Bay of Cadiz. Explore the vast beaches and head to the lighthouse, built in the 1800s, to experience a coveted piece of Cuba’s history.
The landscape of this bay is lush and filled with tropical flowers of hundreds of different types, the perfect compliment to the colors which lie underneath the sea. A great variety of birds flock to the flowers and populate the trees here, adding to the experience you’re sure to appreciate during your visit to the Bay of Cadiz.
Next, we’ll sail to Cayo Hicacal. Lined with rocky cliffs and filled with Cuba’s signature crystal clear waters, Cayo Hicacal is the perfect place to anchor for the rest of the day. Explore the waters or park it on a beach towel after lunch for an afternoon of relaxation under the sun. Birds are plentiful here, along with more incredible sea life to wander through.
We’ll top off the day with dinner and an incredible Cuban sunset, tucked away in a special corner of the key.
Day Four – The Center of Nature
On our fourth day sailing Cuba, we’ll pass Ensenachos Key; another island in Cuba which has little chance of disappointing. Ensenachos Key houses all the best a beautiful beach has to offer: warm and clear waters, soft white sand, and gorgeous vegetation.
This is a favorite of Cuba’s highlights, complete with beach-side service and iguana sightings.
Next, we head to Cayo Santa María. Yet another paradise of Cuba, Santa María key is filled with more fine white sand, calm and warm waves to wade in, and friendly locals. The small island is sure to impress, housing many protected animals native to the region. The wildlife refuge on the island is worth a visit if you get the chance, sheltering many birds and other unique animals special to Cuba.
Here, we’ll visit a reef known as “Los Diablitos” around lunch time. You’ll have the opportunity to swim alongside some of the most colorful reefs of the region, peering through pristine waters at an abundance of wildlife native to Cuba’s piece of the Caribbean Sea.
The reefs of Cuba are some of the healthiest in the world, due to several factors. Cuba’s trade embargo against American tourism and trade for some 50 years, the island country’s remoteness, and it’s smaller population gives the reef a higher chance of withstanding development. This means you’ll have incredible views of some of the most pristine natural reefs on the planet.
Later in the day, when you’re ready to go shopping for souvenirs, La Estrella is the perfect place to find your Cuban memorabilia. Grab a Cuban coffee and go for a walk through this little village, exploring the various gift shops full of authentic handmade Cuban crafts. Check out the Cuban cigar shops, where you can get your very own cigar hand-rolled by locals. Here, you also have the chance to choose from various entertainment options including a piano bar, restaurants, a bowling alley, gym and spa, and a disco.
Day Five – Historical Highlights of Cuba
The next day will be filled with the history and culture of Cuba, starting with breakfast and continuing with a bus tour exploring several museums and other tourism highlights of the region.
Grab lunch at Meson de Rosalía under the care of attentive staff and unique decor, not to mention delicious food options that are aimed to please all patrons.
After a meal in the city, we’ll find ourselves in the oldest Spanish settlement in Cuba, San Juan de los Remedios. This charming little colonial town has preserved a lot of its history throughout the years. Colorful and carefully-painted colonial homes line the streets, home to one of the oldest traditional festivals in the world, Parrandas.
The city’s history is long and full, giving plenty of opportunity for history buffs to learn about how Cuba’s colonization began.
After an exciting day touring the history of Cuba, we’ll take dinner on the catamaran for another night of watching the sunset and relaxing to the gentle waves.
Day Six – A Day On the Sea
On day six, more white sand beaches and crystal clear waters await you at the keys of Fragoso and Francés. Two of the lesser-developed keys of Cuba, some of the most spectacular views are offered here. It’s also home to the permanently-anchored San Pasqual, a ship with a unique history, attracting visitors such as Hemingway and the famous artist Leopoldo Romañach, who painted some of his most notable works from its deck.
Next, you’ll have opportunities to fish crystalline Caribbean waters at Cayo Esquivel, where you can see your catch swimming right up to the boat from several meters away. You may even spot a wild dolphin or two along your journey, not to mention other notable wildlife like sharks, turtles, and barracuda. You’ll end the day returning to the paradise that is the Bay of Cadiz.
Day Seven – Beach Time
On day seven, our next stop is Cayo Blanco, where you’ll have another chance to relax on the undeveloped beaches and take a dip in the clear warm waters. You might even have the chance to spot an iguana or two sunbathing on the sand. The charm here is the lack of development which gives the reefs a healthy environment to flourish. Reef life here is rich and includes many endangered coral species, making it our perfect final destination to snorkel in Cuba.
Day Eight – Cap Off to Cuba
Our last day exploring Cuba begins with a morning at the dolphin aquarium. Later, for lunch we’ll make a stop at El Floridita Bar and Restaurant, one of the most iconic places to eat and drink in all of Cuba.
Earnest Hemingway and other famous names of history visited El Floridita. This, combined with the historical memorabilia and old architecture inside and out, gives El Floridita its own cultural appeal, making it one of the most famous restaurants in all of Cuba. Experience the energetic atmosphere, enjoying incredible live music and a delicious daiquiri in what is claimed to be “The Cradle of The Daiquiri”.
After a visit to the bar, you’ll have the choice to take a city tour, exploring the famous plazas of Cuba, getting a taste of what it looked like centuries ago. For a window into Cuba’s past, Plaza Vieja, also known as “Old Plaza” in English, is a great place to begin wandering.
Born in the 1500s, this square was home to some of the wealthiest residents of Cuba. Back then, it hosted a number of parties, bullfights, executions, food markets, and more. Now, this square highlights its elegant European-style architecture and fountain replica of the original from the 1800s. It is now classified with Old Havana as a Cultural Heritage site by UNESCO; surely worth the visit while exploring Havana.
Next on the tour is Plaza de la Catedral. Home to Havana’s Cathedral, this plaza is another of Havana’s many town squares. It’s also one of its most beautiful.
What makes this square unique is its limestone and sea fossil architecture, along with its ancient-looking porticoes to provide shelter from tropical storms. Wealthier residents used to reside here, building mansions in the 1500s after its marshy infrastructure was made dry enough to build upon.
All of these features of the plaza, along with the classic feel of the cathedral give visitors a charming old-town feel. The towering cathedral represents some of the newer Cuban-style ornate architecture brought to the island country in the 18th century.
You’ll continue your tour reaching Plaza de Armas; you haven’t seen the true Havana until you’ve seen Plaza de Armas. Once known as the birthplace of Havana, this plaza is filled with incredible Spanish architecture and cobblestone streets.
The square was once used as a protective place for the military to parade in front of the governor’s palace, which now serves as the city’s museum. These days, it has been dubbed as the place to buy and sell local art of Cuba.
To get away from the crowds that may also find it a good idea to flock to this famous landmark of Cuba, head to the Ambos Mundo Hotel–the seven-year home of famous writer Ernest Hemingway–for incredible panoramic views of both the square and Old Havana.
Last on the tour of Havana is Plaza San Francisco of Assisi. The famous fountain centerpiece was crafted by an Italian sculptor in the 1800s and is surrounded by various buildings with significant historical background. In the 1700s, it served as a home for the city hall building, police station, jailhouse, and customs office, not to mention the Basílica Menor of San Francisco de Asís, a Franciscan convent also built in the 1700s.
The architecture of this plaza reflects the extravagant tastes of the Spanish during this period, complete with a restored fountain statue, religious structures, and wide arch ways. These days, bits of modern Cuban art have been sprinkled in.
For your cap off to Cuba, visit La Bodeguita del Medio which lays claim as the birthplace of the Mojito. Once a supermarket, this building was converted into a lively restaurant. La Bodeguita del Medio is another one of the most famous restaurants in Cuba due to its history. Many famous names walked through this restaurant, giving it an added cultural appeal. The food is great, the Mojitos are even better, and the ambience is one-of-a-kind; a must-see while in Cuba.
This final exploration will cap off what is sure to be an incredible 8-day voyage sailing Cuba, navigating the country’s famous waters, keys, and cities with your closest companions.
With a backdrop like Cuba, it’s not hard to stay present and appreciate the moment for all that it is. While the experience must end, we’re sure you won’t forget the incredible memories you’ll make. When the expedition is over, we’ll part ways after your transport to the airport.
Cuba is a natural masterpiece, with its incredible crude landscapes begging to be seen; its waters calling for attention. Experience the best of the island country when you sail eight days with us in beautiful Cuba. We’ll take care of you from the airport to the vessel and ensure that your experience is one you’ll want to hold forever.