Pearl of the Caribbean with Commodore Travel

Bienvenidos! Upon arrival, you’ll be greeted by Daniel Pérez, our trusted Destination Manager, and transported in comfort to the privately owned Tribe Caribe Cayo y Hueso Boutique Hotel, located in the heart of the music area once known as Spanish Harlem.

After check-in and time to settle in, we gather for a special welcome dinner at the eclectic and internationally celebrated Al Carbón. Tonight, we raise a glass to the journey ahead—with flavor, rhythm, and the warmth of new friends all around us.

After breakfast, we head into town for a guided walking tour of its four historic plazas—beginning at Plaza de la Catedral, then on to Plaza de Armas, Plaza San Francisco, and Plaza Vieja where each one offers a different experience from souvenir shopping to amazing architecture dating back to the 1500’s. 

Lunch is at Chacón 162, where each guest receives their own custom-made Cuban Sandwich, made by Cubans in Cuba—fresh, authentic, and full of heart. Let’s top it off with a drink at the original Sloppy Joe’s, recently reopened after 60 years with a beautiful renovation  of this iconic Art Deco bar.

Tonight, we’re hosted at the beautiful home of Nerea Vera, who has lovingly restored her 1916 mansion, now called Social 1916. Enjoy a stylish cocktail party with Eminente Rum, appetizers, and a great pianist on her restored 1908 Steinway.

We begin with rhythm and energy at Habana Compás Dance, where founder Eduardo Córdoba fills the painted halls with explosive percussion and creativity.

Next, we journey to Finca Marta, a stunning organic farm run by Fernando Funes-Monzote. We'll tour the grounds and enjoy a fresh farm-to-table lunch straight from the land.

Tonight’s dinner is prepared by the world-renowned Chef Alberto González, Cuba’s only Michelin starred chef. This exclusive dining experience blends traditional Cuban ingredients with elevated, global techniques.

We start at Finca Vigía, Ernest Hemingway’s serene estate outside Havana. We’ll toast his legacy with a cocktail at the Estate bar before heading to Muraleando, a community art and culture hub in Lawton where we will enjoy a lively salsa lesson followed by an authentic home-cooked lunch with local artists and dancers.

Classic car tour around Havana stopping for cocktails! 

Dinner tonight is served on the rooftop of Tribe Caribe, where Chef Daniel creates a soulful, celebratory meal. We’ll dine under the stars with live Cuban music—a perfect night of connection and culture.

We begin with a stop at the Museum of the Revolution where we view historic vehicles including the Granma yacht, tanks, and planes central to Cuba’s revolutionary history.

Two things that are very important in the Cuban culture are cigars and rum. Today we will tour a working cigar factory witnessing the skilled artistry of Cuba’s cigar rollers and visit the Havana Rum Factory for the story of how rum got started in Cuba along with a tasting at the end! Lunch will be served at Cha Cha Cha, one of our favorite places in Old Havana!

Dinner is on the Rooftop of the renowned La Guarida, one of Havana’s most cinematic and elegant restaurants. Afterward, we sneak away to Ley Seca, a hidden speakeasy with live music and creative rum cocktails—an intimate and stylish Havana nightcap.

It’s beach day at Tarará, a quiet retreat along Cuba’s northern coast. Spend the day at a privately owned home with a private beach, open bar, and lunch prepared by hotel staff. Swim, sip, nap, and relax—this is your Caribbean pause.

In the evening, we gather for the ViHumos Sunset Celebration, hosted by our dear friend, Vivian Acosta Meléndez, Cigar Master and Sommelier, at the stunning Mansión Castillo. With fine cigars, Cuban rum, dancing, and dazzling cultural performances, it’s a festive finale you won’t forget.

For those still energized, we’ll head to Espacios, where Big Bros, one of Havana’s most beloved bands, delivers a powerhouse show of American Classic Rock hits—from Led Zeppelin to Tom Petty. There is something very satisfying hearing a great Cuban band sing the Beatles! 

We enjoy one final breakfast at Tribe Caribe, then take a quick visit to the iconic Hotel Nacional de Cuba, where Hollywood stars and American legends once stayed. Enjoy a stroll through the lobby and gardens, take in the Malecón views, and maybe savor one last Cuban cigar.

Then we head to José Martí International Airport to return home—grateful, inspired, and forever connected to the Cuban spirit.

Hasta pronto, amigos. Nos volveremos a ver.