** Last Updated Nov 2018.

DAY 1 (Thursday) May 9
Mainstay Goes to Cuba begins early in the day, when our bus to Newark Airport** leaves at 4:30AM. After a 2.5-hour drive, we will begin the check-in process for our 10:15AM direct flight to Havana (duration 3.5 hours). After clearing customs and boarding air-conditioned coach bus, the group will arrive at our homestays around 4PM. Here we will meet Lily (our wonderful Hostess) and her family and check into our rooms. After a short walk (2 blocks) to Havana’s beautiful and iconic waterfront boulevard, the Malecón, we will enjoy our first of many home cooked meals. After dinner, we will take a short bus ride to the La Cabaña Fort high on the cliffs overlooking Havana’s large natural harbor to enjoy the “cañonazo,” a theatrical show during which actors dressed in full 18th-century military regalia reenact the firing of a cannon over Havana harbor – a ritual that used to signify the closing of the city gates. Our excursion to the fort will be led by one of our local established and knowledgeable guides.

 DAY 2 (Friday) May 10
This morning we will walk over to the Museum of the Revolution. Only a few blocks from our guest homes, you can actually see the façade of the former Presidential Palace while standing right outside our homes. After a 2-hour guided tour of this fascinating museum, you’ll have lunch on your own at one of the many restaurants that are in this area. Afterwards we will re-group and venture into Havana’s Old Town (Havana Vieja), where we will get a guided tour of Havana’s four main squares (Plaza de Catedrál, Plaza de San Francisco, Plaza de Armas, and Plaza Viejo). When this tour ends, you’ll have 1 or 2 hours to wander the old town at your leisure (and maybe do some shopping).  This is the most photographed part of Havana and is where all the cruise ships come in to dock. You’ll want plenty of time to explore this part of town and its shops. Music is everywhere in the old town…you won’t know which way to turn!

After touring the old town, you’ll make your way back to the homestays for a little rest and dinner. If the mile-plus walk seems a bit daunting, we’ll encourage/help you to take a taxi  – which are very easy to hail and negotiate.

In the evening, we will head to the Hotel Lincoln, where Septeto Nacional Cubano holds a weekly performance. Septeto Nacional is one of the most well-known and important Son groups in Cuba. A seven-piece group now, it started as a sextet in 1927, when it played the World Exposition in Sevilla (Spain) in 1933. Since the Cuban Revolution in 1959, the group which consists of trumpet, guitars, bass, percussion (claves, bongos, maracas) and vocals, has been playing continuously.

DAY 3 (Saturday) May 11
After a delicious home-cooked breakfast, several classic American Convertibles from the 1950s will pull up to our houses and whisk us away for a 2.5-hour tour of Havana’s most notable destinations, including the Plaza of the Revolution, the Forest of Havana, the Colon Cemetery, and an outdoor museum displaying missiles and other hardware from the 1961 Cuban Missile Crisis (it is a moving experience for anyone who lived through this frightening crisis). After the tour, we’ll have a late lunch together at one of Havana’s high end restaurants, El Atelier (http://www.lahabana.com/guide/el-atelier/).

After lunch we will walk one block to El Gran Palenque – Centro Cultural, where Cuba’s National dance troupe (El Conjunto Folklórico Nacional) gives a weekly performance from 3:00-6:00pm. The performance includes a wide variety of traditional music and dance from across Cuba by some of the nation’s most outstanding talent. Later this week, we will have an opportunity to meet intimately with some of the singers, drummers, and dancers from this troupe. Dinner will be served back at our homestays around 7PM. After dinner (and a long day) guests can relax, take a walk on the Malecón (oceanside promenade), or go to one of the bars near Central Park to enjoy some local music and drinks. There will be lots of options this evening to hear music in town!

DAY 4 (Sunday) May 12
After a delicious breakfast, guests will participate in a private salsa class offered by world-class dance instructors. After freshening up, we will depart via bicycle taxi (11:30AM), and wander through the streets of Centro Havana on our way to the world- famous Callejón Jamel, an alley known for its extensive murals and fascinating art, most of which have been inspired by Afro-Cuban culture and religions. Here we will have a chance to meet some local artists and then enjoy a portion of the rumba that draws large crowds of Cubans and foreigners every Sunday at noon.

After the Rumba (1PM), we will walk a short distance and enjoy lunch at Bicky’s, one of Havana’s most successful (and delicious) new private restaurants. Next, we will be joined by several Cuban tour guides (2PM) who will take us on a one-mile walking tour of the Vedado community, where we will see and learn about the Park of the Martyrs and the University of Havana, enjoy ice cream at the Coppelia Ice cream park (ice cream is a national obsession among Cubans), and the opulent Hotel Nacional – known for both its beauty and for its connection to American mobsters such as Al Capone.

After enjoying some refreshing mojitos (one of Cuba’s national drinks) at the Hotel Nacional, we will hop in taxis and head back to our homestays where we will have down time until dinner. Guests will be encouraged to relax (even nap) because it will be a late night! This is also a good time to pack your bags, because tomorrow we hit the road.

After a 7:30 dinner, we will leave our houses for a 10:00p.m. show at the Tropicana, the world famous Vegas-style stage show. An outdoor venue, the Tropicana features five stages and hundreds of musicians and dancers! It will be among the most memorable moments of your Cuban experience! After the formal show, you’ll be offered the opportunity to show off your newly learned salsa moves!

DAY 5 (Monday) May 13
Today we will start a little late (last night’s concert won’t wind down until midnight or even 1:00AM)! After a 9:30am breakfast, we’ll board an air-conditioned coach for a day-long excursion outside Havana, about 90 minutes to the west. Here we will visit the pioneering ecovillage of Las Terrazas. Today it’s a Unesco Biosphere Reserve, a burgeoning activity center and the site of the earliest coffee plantations in Cuba. Close by, in the picturesque whitewashed village that overlooks a small lake, there’s a vibrant art community with open studios, woodwork and pottery workshops. But the region’s biggest attraction is its verdant natural surroundings, which are ideal for hiking, relaxing and birdwatching.

We will arrive back Havana in time for dinner. This evening, we will head over to Havana’s premier Jazz Club, La Zorra y el Cuervo, which features both national and international superstars. Show starts at 10:00pm.

DAY 6 (Tuesday) May 14 & DAY 7 (Wednesday)
These are our last two days in Havana and there is still so much to do. Some clients will undoubtedly wish to head to one of Havana’s beautiful white sand beaches (Playas del Este). These pristine beaches are about 30 minutes east of Havana. We could go as one large group, or generate a few separate itineraries. During these days, we will tour a typical Cuban home, and learn much about the creative spirit of Cuban’s who have endured 60 years of heavy embargo by the United States. We will visit several artists’ communities, tour a Tobacco Factory, and visit Hemmingway’s home (Finca La Vigía) on the outskirts of Havana. No trip to Havana is complete without a visit the largest craft market in Cuba, as well! In the evenings we have several concert venues to choose from (see below). It is way too early to know what the best options are. But, we’ll will be sure to have fantastic options both nights! We can be flexible these days and develop our tour to match the desires of our clients. If we are lucky, we will also have the opportunity to witness an Afro-Cuban religious ceremony.

Possible Concerts: Buena Vista Social Club at Hotel Cohiba; Flamenco Nights with Reynier Marino at “Tablao” in Gran Teatro de La Habana; Jazz Café in Vedado; Traditional Son at El Jelengue de Areito; and many others! We’ll find the best.

DAY 8 (Thursday) May 16
Today, we will rise early and board an air-conditioned coach for the start of our two-day excursion to Trinidad de Cuba. Our first stop, about 4 hours into the trip, will be  Cienfuegos, known for its beautiful colonial buildings and even more beautiful bay, called by some “the pearl of the South.” During our short stay here, we will tour the town center (Parque José Martí) and the Moorish-inspired Palacio de Valle. The Palacio was built in 1917 on a dramatic piece of land that juts into the bay and is comprised of an outrageous jumble of tiles and turrets, crenellated edges and scalloped arches. In the mid-afternoon, we will leave Cienfuegos and make our way to Trinidad, a dramatic drive with towering mountains to our left and ocean views to our right.

Trinidad is a beautiful colonial city situated on the edge of the 2nd largest mountain range in Cuba and overlooking the Caribbean. Founded in 1514, it is the third oldest-settlement in Cuba. Full of wonderful restaurants and several music venues (most notably, Casa de Music, Casa de Trova, and El Palenque de Los Congos Reales), everything is easily accessible within 2-4 blocks of our homestays. Music is audible from our homestays 365 nights a year. Tour participants will have this night to independently explore Trinidad and have dinner at their personally selected restaurants.

DAY 9 (Friday) May 17
This morning begins with a tour of Trindad’s old town led by our local guide Yuder Ignacio. Following the tour, our group will split. Some of us will enjoy the 3-hour horseback ride that skirts the edge of Trindad’s sugar cane fields and ultimately ends up deep within a tropical mountain rainforest. Along the way, there will be opportunities to stop and drink locally grown and roasted coffee and (for the bravest among us) to hop into a crystal clear, refreshing mountainside swimming hole. Those who don’t want to climb on horses, will instead hop into local taxis (hopefully convertibles) to tour the beautiful countryside and learn about Cuba’s sugar history, while visiting plantations, mills, and historic mansions. After concluding these two tours, we will return to Trinidad where tour participants can independently experience the historic downtown where shopping is abundant, the food is wonderful, and the music is ever-present. For those interested in a different view, for an additional cost, trips to the local beach may be arranged.

DAY 10 (Saturday ) May 18
Today we leave Cuba. After breakfast in our homestays, we leave for the Santa Clara airport at 8:30AM. A two-hour drive, we arrive by 10:30AM for our 1:30pm flight. With a layover in Fort Lauderdale, we will arrive back at Washington DC’s Regan National around 10:00PM where we will take our private coach bus back to Chestertown.

* The itinerary here is tentative and subject to change. As a small tour we are able to adjust to conditions on the ground to ensure guests with the best possible experience. Weather is the biggest factor influencing our schedule, as many of the events we have planned are outdoors. Typically we monitor the weather several times a day, and make regular adjustments to our schedule. We are also subject to the availability of our artists, lectures and others, who schedules sometimes change at the last minute. Though we will try to follow the above schedule, please be patient when activities get moved or substituted.

** Flight information for May have not been completely released by all the airlines. Currently, the trip is designed around an outbound flight from Newark to Havana and an inbound flight from Santa Clara to Reagan National Airport near Washington DC. This might change in a few months, which would require us to modify portions of our itinerary.