cuba
11 nights/12 days: February 2025
Detour with dean
As soon as you think you know Cuba, it changes. This small country is in a constant state of flux and contradictions. New currencies, rules, political landscapes, and foreign relationships make it difficult to label and fully grasp in a moment. It takes slow travel to appreciate its beauty, elegance, and nuance. When I first visited Cuba in 1997, I was seduced by the tough-as-nails spirit of its people. I felt the powerful salsa of energy that bounces off every street, mural wall, and alley. The rich scents of fresh coffee, fine rum, hand-rolled cigars, and the salty Caribbean etched their way into unshakeable memories for me. I love Cuba and I think you will too. If you’re willing to detour away from western certainties, briefly open yourself to a communitarian mindset, and expect the unexpected, then rich rewards in Cuba awaits.
highlights include
Learn the local customs, folklore and beliefs behind Afro-Cuban religion as you’re welcomed into the homes of devoted residents on a colourful and unconventional Urban Adventure in Havana.
Savor a garden-to-plate experience at an urban organic farm in Alamar.
Receive a fascinating insight into the rise and fall of the charismatic and highly celebrated Cuban revolutionary Che Guevara
Experience Cuban hospitality and old-world charm in the coastal town of Trinidad.
“If you tremble with indignation at every injustice, then you are a comrade of mine.”
Cuba is an island pulsing with contrasts. Classic Chevys rumble past horse-drawn carts under Havana's crumbling grandeur. Salsa rhythms ignite smoky clubs while guitars strum in rural villages to the setting sun. Education and healthcare shine, a testament to revolution's ideals, yet scarcity lingers, a reminder of life under an embargo's grip. Cuba, a land of contradictions, cradles both resilience and longing, its beauty etched in weathered smiles and sun-bleached flags. We’ll embrace the island’s rhythm of revolution and romance on this detour through Cuba’s contrasting communities.
itinerary
day 1: arrival in miami
Saturday, September 28, 2024
Our journey begins in Miami, where we will rendezvous at our hotel around 5:00 for a welcome reception to review our detour together and get to know one another. You’ll have the evening free to enjoy dinner and Miami on your own.
Hotel: TBA | Meals: Happy Hour | Activity Level: Light
day 2: ¡Bienvenidos a Cuba!
Sunday, September 29, 2024
We’re off bright and early to catch our flight to Cuba. Upon arrival, our coach will collect us and take us to visit the Plaza de Revolucion—an iconic symbol of Cuban history and politics. We’ll check into our accommodation with plenty of time for a siesta before meeting for an orientation walk en route to enjoy mojitos at the Hotel Nacional Gardens, followed by a dinner together of Cuban specialties. We’ll cap our night at a rooftop bar to savor Havana’s cityscape and musical pulse.
Hotel: TBA | Meals: B, D | Activity Level: Strenuous
day 3: colonial havana
Monday, September 30, 2024
This morning we enjoy new discoveries on a tour of Old Havana. This UNESCO World Heritage Site houses a labyrinth of cobblestone streets lined with colorful buildings showcasing Havana’s Spanish colonial and Baroque architecture. After lunch together, we’ll visit the National Museum of Fine Arts showcasing diverse artistic movements from colonial times to the contemporary era. The remainder of the evening is yours to explore Havana’s cuisine, music, and dance.
Hotel: TBA | Meals: B, L | Activity Level: Strenuous
DAY 4: Guevara & Hemmingway
Tuesday, October 1, 2024
Apart from their first names, Ernesto “Che” Guevara and Ernest Hemmingway had two things in common: a deep affinity for Cuba, and a love of the written word. Today we’ll get to know them both on a visit to Guevara’s Commanding Post and Hemmingway’s Finca Vigia. Our morning begins with a visit to the Morro-Cabaña Fortress, housing the Cuban revolutionary’s headquarters during the Cuban missile crisis. After lunch, we’ll visit Hemmingway’s Havana home, where he wrote some of his most famous works, including The Old Man and the Sea. This evening we’ll get our groove on over dinner and dancing at the Muraleando Community Art Center.
Hotel: TBA | Meals: B | Activity Level: Moderate
Day 5: farm to table
Wednesday, October 2, 2024
Cuba is a leader in organic farming not by choice, but necessity. After the dissolution of the Soviet Union, and loss of their main trading partner, organic farming became an economic imperative to ensure food security. We’ll spend the morning at an organic farm in Alamar, getting our hands dirty learning about sustainable agricultural practice before we enjoy a farm fresh lunch of organic produce together. This afternoon we’ll visit the bustling Old Havana Market with its narrow lanes brimming with stalls selling traditional Cuban wares. Tonight is free to enjoy jazz, dancing, or even the Copa Cabana show!
Hotel: TBA | Meals: B, L | Activity Level: Moderate
day 6: alley of rumba, bay of pigs
Thursday, October 3, 2024
Callejón de Hamel is a vibrant alleyway renowned for its celebration of Afro-Cuban culture and Rumba, a traditional dance deeply linked to Cuban religions of African origin. Every Sunday this colorful corridor comes alive with musicians, dancers, and locals partaking in this rhythmic and energetic dance and we’ll join them this morning. After dancing up an appetite, we’ll enjoy lunch together at the house of Salvador Gonzales Escalona, painter, muralist, & founder of Callejon de Hamel. We’ll then board our coach for the Bay of Pigs where we’ll unpack for the night.
Hotel: Hotel Agamemnon | Meals: B, L | Activity Level: Strenuous
day 7: seaside bliss in nafplio
Friday, October 4, 2024
The day is yours to explore Nafplio. Stroll through the narrow streets of the old town where Venetian and Ottoman influences blend seamlessly into a vibrant mix of cultures. Explore Syntagma Square, graced by elegant buildings and charming cafes, or wander along the waterfront promenade for breathtaking views of Bourtzi, a small fortified island. If you're feeling sporty, climb the 1000 steps to the Venetian fortress (or take a taxi directly to the back entrance) and be rewarded with stunning views of the Aegean Sea. After your day of exploring (or relaxing), we'll gather for a group dinner of sumptuous seafood!
Hotel: Hotel Agamemnon | Meals: B, D | Activity Level: Your Choice
day 8: trinidad
Saturday, October 5, 2024
If you’re feeling unwell, Epidaurus is good for what ails you. Dedicated to the god of healing, Asclepius, this site was home to a healing center where pilgrims sought remedies and solace through sacred rituals and sacrifices to Asclepius’ father, Apollo . Renowned for its spectacular theater, an architectural marvel famed for its near-perfect acoustics, Epidaurus is a symbol of artistic and engineering mastery. After a sing-a-long in the theater, we’ll detour to Corinth for a lunch stop en route to catch our afternoon flight to Santorini, where our island odyssey continues.
Hotel: Volcano View Hotel | Meals: B | Activity Level: Moderate
day 9: stunning santorini
Sunday, October 6, 2024
There’s good reason Santorini is the most famous island in the world. Apart from its breathtaking sunsets, iconic blue-domed churches, and unique volcanic beaches, Santorini was home to a thriving civilization whose remains at Akrotiri, often referred to as the “Minoan Pompeii,” offer a glimpse into the ancient life of the island. Today we’ll dive into Santorini’s past with a visit to Akrotiri, savor lunch seaside at Kamari’s black sand beach, sample the fruit of the vine at a local vineyard, and toast to our first night in Santorini over sunset in seductive Oia.
Hotel: Volcano View Hotel | Meals: B, L | Activity Level: Moderate
day 10: cruising the volcano
Monday, October 7, 2024
The morning is yours to meander Fira's serpentining walkways with their colorful shops, cafes, and sea views. We will gather mid-afternoon to descend the caldera by cable car, boarding our boat for an island tour. We’ll cruise along the volcano’s interior, swimming in the Aegean’s crystal waters, soaking in the volcanic hot springs, and exploring the most significant sights, including Red Sand and White Sand beaches. We’ll ready our cameras for Santorini’s famous sunset, paired with dinner and drinks on board.
Hotel: Volcano View Hotel | Meals: B, D | Activity Level: Your Choice
day 11: mykonos: island of the winds
Tuesday, October 8, 2024
This morning we bid Santorini farewell and ferry to Mykonos. Nestled in the heart of the Cyclades, Mykonos is known as the "Island of the Winds," welcoming us with its sun-kissed beaches, wave-lapped buildings, and iconic windmills standing sentinel over the azure horizon. We’ll spend our mid-day in cooking school, learning the craft of the Greek kitchen before making our way to our hotel. This evening we’ll stroll through the labyrinthine streets of Mykonos town, where pristine white buildings with vibrant blue accents create a postcard-perfect backdrop. The evening is yours to explore the charming boutiques and open-air cafes.
Hotel: Porto Mykonos | Meals: B, L | Activity Level: Moderate
day 12: delos: island of appollo
Wednesday, October 9, 2024
After a leisurely morning, we’ll travel by boat to “Apollo’s island." Delos was believed to be the birthplace of Apollo, the god of the sun, and his twin sister Artemis, the goddess of the hunt. As a result, it became a major religious center and a bustling hub of trade and commerce. Today, Delos stands as an open-air archaeological museum, showcasing the remnants of its rich past. We will explore well-preserved ruins of temples, sanctuaries, theaters, and intricate mosaics, offering a fascinating glimpse into the island's former grandeur. The evening is free for exploration, relaxation, or dancing the night away at one of the island's famous beach parties.
Hotel: Porto Mykonos | Meals: B | Activity Level: Strenuous
day 13: to beach or not to beach
Thursday, October 10, 2024
Our last day together is a choose your own adventure. Get lost with your camera in the town’s labyrinth, satisfy your souvenir list at the myriad boutiques, savor the day away in the open air cafes, or visit one of Mykonos’ stunning beaches. Whatever you choose to fill your cup, we’ll gather together to fill our collective cups over our final mythical happy hour at our hotel, followed by dinner together where we’ll toast to our odyssey and plan our next detours!
Hotel: Porto Mykonos | Meals: B, D | Activity Level: Your Choice
day 14: detour over
Friday, October 11, 2024
Our odyssey concludes after breakfast. Mykonos is a quick, 45-minute flight to Athens, where you can catch your return flight home, or you may choose to continue your exploration of the Greek isles by ferry. Knowing this won’t be our last detour together, don't say goodbye; instead say tha se tho syntoma ("I'll see you soon")!
$4,995 per person (double occupancy)
$5,695 per person (single occupancy)
$4,295 (triple occupancy)
$500 deposit