Sample Itineraries
Get inspired with our sample trips below. You can have any trip tailor made for your private travel. Any number of days.
Any departure date. Any experience you want.
Immersive Cuba Tour: History, Culture, and People
Immersive Cuba Tour: History, Culture, and People
8 Day Custom Tour
From $2,595
Step back in time when experiencing the layers of Cuba’s unique and captivating history. Travel along a singular road surrounded by the sea on either side. Journey on a vintage steam train through the lush landscape at the heart of the country. Follow the scent of dried leaves during a private tour of a cigar factory. Classic cars cruise cobblestone avenues. Horses clop down the boulevard pulling antique buggies. The sounds of rumba and salsa emphasize the vivacious murals, embellishing the culture and the country’s past. Your customized Cuba tour brings history to life, with you at its center.
Heart & Soul of Cuba Tour: Discovering Its People and Culture
Heart & Soul of Cuba Tour: Discovering Its People...
9 Day Custom Tour
From $2,920
Cuba is like a time capsule recently opened that is trying to restore its former majesty. The contrast of crumbling colonial architecture alongside freshly renovated façades adds to the allure of the cities. The culture has inspired artists to submerge entire neighborhoods in art projects. Ernest Hemingway captured a fishing village in an award-winning novel. The effects of the Cuban Revolutionary War have shaped everyday life. The slave trade of the 18th and 19th centuries led to the mesmerizing Afro-Cuban culture. Your custom-tailored tour immerses you into the heart and soul of the changing landscape of Cuba through the eyes of the locals.
Enchanting Sites & Sounds of Cuba Tour: From Colonial Towns to Salsa Rhythms
Enchanting Sites & Sounds of Cuba Tour: From Colonial...
10 Day Custom Tour
From $3,245
Cuba makes you want to dance into the night, experiencing the entertainment and living history inside the cities and searching for colorful flora and fauna protected in the national parks. Locals laugh as they jump into the Atlantic Ocean near the waterside avenue of the Malecón. A Tocororo twitters in the jade forest canopy. Flamingoes catch your eye against the waters of a quiet lagoon. Guitarists and bongo players fill the streets with passionate songs from sunrise to well past midnight. Your custom tailored tour shows you the exciting life of Cuba, which at times feels like worlds away and years apart.
An Immersive Cuban Tour to Havana, Vinales, Soroa & Trinidad
An Immersive Cuban Tour to Havana, Vinales, Soroa &...
12 Day Custom Tour
From $3,895
The rhythms of Cuba are orchestrated by the musical notes of salsa, the captivating dances of Santeria, and the wholesome birdcalls of the jungle mountains. Your custom tailored tour immerses you in the purity of the island’s emerald-clad bio-reserves to the open embrace of locals, eager to impart an understanding of their culture through a slice of their daily life. Hummingbirds dip their beaks into freshly opened flowers. Kids fly kites on the rooftops of Havana. Glassy water reflects flamingoes’ pink feathers. The mixture of history and contemporary living on colonial streets is sure to captivate you.
Highlights of Cuba Tour
Highlights of Cuba Tour
8 Day Custom Tour
From $2,595
The colonial architecture will impress you, the music will stir you, and the people will inspire you on your custom tailored highlights of Cuba tour. The clapping sound of horse hoofs against cobblestone streets imitate the pulsing rhythms of the salsa bands performing in the restaurants across Havana. Pastel colored homes accentuate the variety of blue hues layering the Caribbean Sea. Powerful stone fortresses continue to guard the shoreline amidst the sweet aroma of sugar cane juice pressed before your eyes. Experience the lifestyle. Indulge in the culture. Enjoy the splendor of Cuba.
Retracing the Steps of Cuban History: Havana & Cienfuegos Tour
Retracing the Steps of Cuban History: Havana &...
8 Day Custom Tour
From $2,595
The trepidations of the Cuban Missile Crisis and the Bay of Pigs are tangible memories. The easing of regulations has opened up new doors between the United States and Cuba. Your tour is custom tailored to discover the people and culture of the island nation, at times contrasting the perception of the country only 90 miles off the coast of Florida. Artists paint murals capturing the spirit of Havana. Cienfuegos is filled with pearled French architecture. Colonial buildings in Trinidad harken back to a bygone era. Cuba’s streets tell many stories, each as captivating as the next.
An 8-Day Tour of Havana, Varadero & Camaguey
An 8-Day Tour of Havana, Varadero & Camaguey
8 Day Custom Tour
From $2,595
The Cuban experience touches your soul during your 8-day tour, specially crafted for adventurers and word travelers. Find comfort during your time in Cuba as you blend an active lifestyle with the grandeur of historic sites. Spend jovial time with gregarious locals and marvel at the significance of squares which marked a revolution that became world renowned. Meander through labyrinthine streets and ride in classic American cars. Listen to engaging musicians and engage in unforgettable discoveries on your custom Cuba tour.
Ernest Hemingway Cuba Tour: Following in the Footsteps of a Legend
Ernest Hemingway Cuba Tour: Following in the Footsteps...
8 Day Custom Tour
From $2,595
This custom tailored tour retraces the steps of Ernest Hemingway, giving you access to the unique, eclectic cultures of the Caribbean country brimming with rich soil and surrounded by the immaculate sea. The architecture and gregarious people of Cuba speak to a rich legacy spanning centuries. Dancing and music enrich every day. The sweet aromas of coconut and pineapple emanate from gardens and markets. Coffee trees grow lush and strong. Ernest Hemingway’s former home maintains an inspiring ambiance. Murals decorate the streets. Artwork acts as a form of urban expression. Spanish colonial influences shape contemporary life, creating the distinctive character of Cuba.
A People-to-People Tour of Cuba: A Journey Focused on Arts & Culture
A People-to-People Tour of Cuba: A Journey Focused...
8 Day Custom Tour
From $2,595
Your custom tailored “People-to-People” tour of Cuba immerses you in the true culture and lifestyle of Cuba. Deep educational exchanges between you and the locals leave life-long memories. Throughout this itinerary, you will be introduced to community leaders, artists, writers, and farmers keen on showing you their connection to their country and the surrounding world. Smooth the crinkled texture of a dried tobacco leaf, following instructions from a seasoned veteran on how to roll a cigar. Witness how artists in Havana represent the spirit of the city in a way only locals could express. Dance with a traditional company and sing with celebrated musicians each finding ways to articulate their passion for Cuba in their own way.
Treasured Secrets of Cuba Tour: A Private Experience
Treasured Secrets of Cuba Tour: A Private Experience...
9 Day Custom Tour
From $2,920
Let the wealth of Cuban culture reveal itself to you during your 9-day discovery tour of the island’s hidden splendor. The floral aroma of freshly opened cocoa beans fills the air. The turquoise sea splashes against powder white sand. The rainforest canopy carpets emerging mountains. Dance the night away with the salsa moves you learn. Sip a mojito you mix yourself. Taste chocolate brewed by your hand and indulge in fresh fish caught by your net. From small villages to bustling cities, farmers to fishermen, you will traverse the magnificent landscape of Eastern Cuba and connect with the people.
Family Friendly Cuba Tour
Family Friendly Cuba Tour
8 Day Custom Tour
From $2,595
Take the family beyond the façade of Cuba to experience the life of Havana and Valley de Vinales. The sound of strumming guitars moves through the streets of Old Town. The engines of classic cars roar above the sound of the waves splashing against the sea walls. Imposing fortresses inspire dreams of pirates. Hummingbirds as smalls as butterflies sip nectar from magnificent flowers. Farmers use oxen to plow the soil. Your custom tailored family friendly tour sets the family on an ineffable journey, introducing you to the people, culture, history, and mystery of Western Cuba.
Charm of Cuba’s West: Havana & Viñales Valley Tour
Charm of Cuba’s West: Havana & Viñales Valley Tour...
8 Day Custom Tour
From $2,595
Cuba is a shining pearl refined by the turquoise waters of the Caribbean. Your custom tailored tour shows you the elegant past and colorful present of a country once closed off to Americans and now finding its place in the contemporary world. Farmers chew on thick hand-rolled cigars as they plow their fields. Cabaret dancers radiate the tropics, wearing iridescent hues while performing vivacious moves. Turtles hatch in white sand and crawl out to sea. Classic cars take you back to a bygone era. Experience the former grandeur of Cuba and let the contemporary culture captivate you.
Christmas in Cuba Tour: A Celebration of the Oldest Festival in Cuba
Christmas in Cuba Tour: A Celebration of the Oldest...
12 Day Custom Tour
From $3,895
Experience exceptional holiday festivities with an exclusive tour of Cuba during Christmas and New Years. The pulse of salsa music complements the rhythmic sounds of crashing waves on the coastline. Antique sugar mills give way to gorgeous manors reflecting the former prominence of agricultural barons. Pig roasts signify the importance of family gatherings for holiday feasts. Firework displays create an illuminating spectacle of a friendly feud between neighborhoods. Whether exploring galleries at the Museum of Fine Arts or relishing the colors of the sky on a sunset cruise, your time in Cuba provides a perfectly tailored and culturally immersive celebration.
A Private Group Tour of Cuba from Havana to Havana
A Private Group Tour of Cuba from Havana to Havana
8 Day Custom Tour
From $2,595
Whether traveling with your own small group or your extended family in comfort, explore the trails of rural Cuba. Wander through the rainforest in search of orchids and waterfalls, lounge on white sand beaches at the secluded edge of the country, witness a tobacco farmer roll a perfect cigar, with each moment accentuated by the pleasure of good company. Legends of pirates and plantation owners strike similar tones of mystique. Restaurants hum with live music spilling out onto the cobblestone streets. Your group tour is custom tailored to take you off the beaten path and soak up the splendors of Cuba with your private group.
Judaism in Havana: A Tour of Jewish Cuba
Judaism in Havana: A Tour of Jewish Cuba
8 Day Custom Tour
From $2,595
Jewish communities have traveled far and wide for hundreds of years, settling in countries open to trade and closed off from the rest of the world. Your custom tailored tour takes you through the stunning landscape of Cuba and immerses you in the Cuban Jewish lifestyle. Light the Shabbas candles with a local family to celebrated the end of another week. Peruse the library of one of the oldest synagogues in the country. Visit the only kosher butcher on the island. Learn about the heritage of the Cuban people and experience the unforgettable sensation of the Jewish community.
Festive Cuba: Jazz & Culture Tour of Havana
Festive Cuba: Jazz & Culture Tour of Havana
8 Day Custom Tour
From $2,595
Listen to the natural rhythms of Havana and the passionate pulse of jazz spilling into the streets on your custom tailored musical tour of Cuba. The rich history of the island shapes the melodic connection of people across the landscape, from the beach to the rainforest. Crashing waves and chirping tropical birds inspire instrumentals. Rural rivers and urban art spaces shape intangible expression. Colonial architecture and exposed stone fortresses cause sounds to echo throughout the streets. Listen, discover, and enjoy the powerful way music articulates emotion and the Cuban experience.
Uncovering the Artistry of Cuba Tour
Uncovering the Artistry of Cuba Tour
12 Day Custom Tour
From $3,895
Uncover the elaborate artistry of Cuba draped in murals and glinting with captivating neighborhoods; pastel colored homes and sweeping emerald rainforest. Classic cars cruise along the cobblestone streets of Old Town Havana. Baroque churches rise above the open plaza in the labyrinthine lanes of Santa Clara. Wild palm trees shade the edges of thriving tobacco fields. The aroma of sugarcane fills the air with indulgent sweetness. Your custom tailored tour guides you on a unique perspective of the Caribbean island, connecting you to the culture, history, and people creating and preserving Cuba.
Cuba Adoration: A Kid-Friendly Tour through Cuba
Cuba Adoration: A Kid-Friendly Tour through Cuba
8 Day Custom Tour
From $2,595
Indulge in the modern relics of city living during your custom tailored kid-friendly tour of Cuba. Stroll along the cobblestone streets of a preserved colonial town. Trek through the jungle for a panorama of a secluded waterfall. Absorb the endless majesty of historic buildings, ineffable culture, and the seductive rhythms of salsa on your customizable Cuba tour.
Cuba on Wheels: Cycling Tour from Havana to Trinidad
Cuba on Wheels: Cycling Tour from Havana to Trinidad...
9 Day Custom Tour
From $2,920
From the pulsating music encouraging you to speed along cobblestone streets to the refreshing salty aroma of the Caribbean Sea, your cycling tour of Cuba is unlike any adventure you have ever experienced. Colonial mansions in the cities highlight former grandeur while antique plantations in the countryside speak of similar past opulence. Images of Che Guevara harbor a spirit of revolution. Pristine beaches provide moments of tranquility. Undulating peaks divide the opposite shores. You will traverse the cities and countryside, shorelines and mountain ridges conquering the landscape as you immerse yourself in the authenticity of Cuba’s culture.
Trekking in Cuba Tour: Nature & History on Foot
Trekking in Cuba Tour: Nature & History on Foot...
14 Day Custom Tour
From $4,545
The landscape of Cuba tells stories of the island, from its indigenous peoples to the Cuban Revolution. Your custom tailored tour leads you on an outdoor adventure through the valleys and into the mountains for an immersive trekking experience. A bust of the father of Cuban independence welcomes hikers at the peak of Cuba’s tallest mountain. Colonial churches cast shadows over antique cobblestone streets. Tobacco fields thrive in the red soil near natural limestone caves. Traverse the three distinct mountain ranges of Cuba for an ineffable journey along the island’s natural and manmade history.
The Off the Beaten Track Tour of Eastern Cuba
The Off the Beaten Track Tour of Eastern Cuba
12 Day Custom Tour
From $3,895
Eastern Cuba offers an escape to a different world. Your 12-day adventure takes you on a journey unique even to Cubans, in the distinctive, unfettered cities and towns along the country’s east coast. Rainforest drapes across the mountains. The indigo sea splashes against the secluded town of Baracoa. The gems of Santiago de Cuba rise out of the bustling streets of the second-largest street in the country. Immerse yourself in the true culture of the island, from the Taino tribes to the Cuban Revolutionary War, to discover the endless splendor both natural and manmade.
Cuba Photography Tour: Havana & Trinidad
Cuba Photography Tour: Havana & Trinidad
8 Day Custom Tour
From $2,595
Take your time discovering the true Cuba and saving it in photographs for later. Historic fortresses frame the edges of Old Havana. Mountains rise above the red-tiled rooftops of the colonial town of Trinidad. Tobacco farmers puff on thick hand-rolled cigars while oxen plow the fields. Indigo water laps at white sand beaches. Plantations tell tales of barons and slaves. Classic American cars make the cities look frozen in time. Friendly locals smile and wave at the camera. Capture the country in perfect light during your custom tailored tour meant for amateur and seasoned photographers alike.
Getaway to Cuba: Havana, Cienfuegos, Trinidad, and More
Getaway to Cuba: Havana, Cienfuegos, Trinidad, and...
8 Day Custom Tour
From $2,595
Cuba shines like a pearl in the Caribbean Sea, a tropical paradise perfect for a getaway. Your custom tailored tour takes you along secluded islands, remote peninsulas, and energetic cities, incorporating both privacy and vibrancy. Feel the ocean breeze blow against your cheeks. Watch the sunlight glint off the crystal-clear water. Move to the captivating rhythms of rumba and salsa. From a French settlement to aboriginal archaeological remains, sensational panoramas to exciting wildlife, indulge in the experience of a lifetime in the passionate warmth of Cuba.
Best of Cuba Tour in Seven Days
Best of Cuba Tour in Seven Days
7 Day Custom Tour
From $2,270
Witness fine cigars rolled before your eyes and a majestic waterfall hidden in the Escambray Mountains during your 7-day Cuba tour immersing you in the island’s heart and soul. French architecture and Cuban heroes decorate Cienfuegos. The forest canopy protects radiant hummingbirds. Classic American cars add to the soundtrack of Havana. Cuba provides endless excitement and tangible splendor gathered into your week-long adventure filled with an endlessly uplifting spirit.
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