Roots Rails & Rambles Roots Rails & Rambles

Cuba, November 2024

Rumba and Rambles: Cuba, November 11-20, 2024

Forget everything you thought you knew about Cuba and prepare to have your mind and heart expanded by this fascinating place! This trip dives deep into Cuban culture – spending time with accomplished artists, musicians, and entrepreneurs, gaining a first-hand understanding of real life in Cuba today. Many of our previous Cuba travelers have reported being overwhelmed by the warmth and generosity of the Cuban people we’ve met there, aexperiencing a real shift in their understanding of Cuba’s history and relationship with the rest of the world.

This trip expands on our previous offerings by spending the bulk of our time in Havana, with side trips to Matanzas and two days in the utterly magical valley of Viñales, a quiet farming community that offers a striking contrast to the frenetic (but amazing!) pace and vibe of Havana.

Our base in Havana is a lovingly restored, privately owned Casa right on the fabled Malecon – vintage car enthusiasts will have a ball watching the endless parade of 1950’s era American cars that survive by the sheer ingenuity of Cuban mechanics. Comfortable air-conditioned rooms, each with private bath, and daily delicious breakfast prepared by our casa hosts are part of the package

So how much for all this wonderfulness?

$4589 per person, shared occupancy. ALL ROOMS HAVE PRIVATE BATH

$6500 per person, solo occupancy (only 2 of these spots available) . ALL ROOMS HAVE PRIVATE BATH

Please keep in mind that we are always happy to take a deposit then set up a monthly interest-free payment schedule. Just ask Sarah for details.

What’s included?
  • Airport transfers
  • 8 nights’ accommodation (1 Pre-trip night in Tampa, 5 nights in Havana and 2 in Vinales)
  • All transportation while in Cuba
  • All excursions
  • Guide services – although “guide services” doesn’t really capture the depth of knowledge, passion and completely unique experiences our guides bring to the table. We’ll be going places and meeting people that most tourists never do, giving us a unique appreciation of this fascinating and complicated place.
  •  Most meals (breakfast is served each morning at our casa, and most lunches and dinners are included as well. We’ll give you a few opportunities to venture out on your own once you’ve got your bearings.

What is NOT included?
  • Your air travel. We’ll be gathering in Tampa on the evening of November 11 and traveling over to Havana on Southwest the next day. You’ll receive notice about which flights to book to and from Havana.
  • Your Cuban Visa – purchased at the Tampa airport for about $85
  • Travel Insurance -- We strongly suggest that people purchase comprehensive travel insurance that covers: Cancellation for Covid-19 illness or other medical reasons, Trip Cancellation, Trip Interruption, Emergency Medical Care, including coverage for Covid-19, and Medical Evacuation
  • Tips for our guides, housekeepers, and drivers
  • Alcohol
  • Souvenirs etc.

So, if you’re ready and excited to commit before we open the trip up for general sale, here are the links through which you can secure your spot(s):

$500 per person deposit to hold your spot. Within 30 days of deposit, you’ll set up your payment schedule with Sarah

$4497 per person: Discounted fare for paying in full at the time of booking.

$6370 per person solo occupancy: Discounted fare for paying in full at the time of booking.

Our itinerary and activities are curated and led by our legendary Cuba Concierge, Carol Steele* and an established Cuban travel agency – giving us access to more reliable transportation while in Cuba. With everyone arriving in Havana together we’ll be able to hit the ground running! Sarah, who is an experienced hand at negotiating Cuban Customs, will be traveling with you from Tampa, so you’ll be in good company negotiating the Havana arrival process.

For those wishing to arrive in Tampa a day early, we can arrange an add-on group hotel the night before (Nov. 10) for those who want it.

Our itinerary will look roughly like this, allowing for the inevitable Cuban “eventualities” that always occur, and leaving room for some wonderful new experiences that Carol always has up her sleeve.

Monday, November 11, Arrive Tampa: We’ll have a hotel set up in Tampa near the airport to make for an expeditious transition. Meet and greet that evening to go over last minute questions and details.

Tuesday, November 12: Fly from Tampa to Havana. We’ll be picked up at the airport and transported to our accommodations We’ll have a chance for some initial exploration and a welcome dinner at one of Havana’s exciting new restaurants, before retiring to our lovely casa right on the legendary Malecon.

Wednesday, November 13: Morning presentation by retired Havana architect and city planner, Miguel Coyula to get an overview of the history of the city and thoughts about its current challenges and possibilities. Followed by a walking tour of Havana Vieja and lunch. Afternoon activity may be anything from private dance rehearsals, artisan studio visits, fine arts museums, old fortresses, and churches – we never quite know what adventures Carol will have in store for us, but it’s always amazing! Dinner will be at another one of Havana’s up-and-coming delicious and creative privately-owned restaurants.

Thursday, November 14: Another full day and evening of Havana activities—perhaps a trip out to the wacky world of Fusterlandia with lunch at artist Jose Fuster’s house and a chance to learn about the inspiration for his massive neighborhood-wide art installation. We’ll schedule time on one of these days for a visit with Roberto Chile, Fidel Castro’s personal photographer and videographer, have coffee and rum in his lovely backyard and see a beautiful presentation of his portfolio and whatever is currently inspiring him to create.

Friday, November 15: Following breakfast at the casa we’ll be taking a day trip east to Matanzas, the center of Afro-Cuban music, dance, and religion. We’ll be having a home cooked lunch and a house party with rumba royalty who are basically the keepers of the flame of Afro Cuban Folklore in Cuba. The group will be comprised of musicians, dancers, and singers, from the two top Rumba groups – AfroCuba de Matanzas, and Los Muñequitos. We’ll return to Havana in the evening for another fabulous dinner.

Saturday, November 16: More Havana-based activities. Maybe a private concert with Cuba’s premier women’s acapella choir – in the beautiful apartment of a family of Cuban artists – overlooking the sea and the Hotel Nacional, where we may retire for a few cocktails on the breezy patio before heading to a private performance of Raices Profundas – an amazing fokloric dance group.

Sunday, November 17: Morning departure for Viñales – it’s about a three hour drive through some of the beautiful countryside of western Cuba – up into the Sierra de los Órganos mountains before descending into the virtually pre-historic looking Viñales Valley. We’ll have a chance to rest and refresh at our expansive casa at the edge of town before heading out to explore the amazing landscape and then dinner at one of the local farm-to-table restaurants.

Monday, November 18: A full day of Viñales activities – visiting tobacco farms and talking to local growers about the history and process of making the legendary Cuban cigar, as well as their re-building efforts following the 2022 hurricane We’ll have a chance to poke around the little town of Viñales – explore the local church and botanical garden, art galleries, and shops and hopefully stumble into some live music and dancing at the Polo Montanez Cultural Center.

Tuesday, November 19h: We leave Viñales and head back to Havana, with a stop en route for a birding walk with a local naturalist, visits to local artists’ studios and a fabulous lunch and private concert in the middle of the jungle. We’ll be back in Havana in time to freshen up and head out for our final night on the town.

Wednesday, November 20th: After another breakfast at our lovely casa, we’ll head for the airport for our charter flight back to Tampa.

We’re very excited about this trip and hope you are too!!!! We’re happy to discuss any questions you may have and we LOVE talking about Cuba, so feel free to contact us anytime.

For those who may have heard us talk about Carol Steele, you should know a bit about her.

Carol has been traveling to Cuba for over 30 years, introducing the island to fellow travelers for the last 25. Carol’s enthusiasm is contagious, as is her love of Cuba, its culture, its history, and most of all, its people. She’s had an incredible career as a percussionist, performing and recording with the likes of Peter Gabriel, Steve Winwood, Joan Baez, Tears for Fears, Bette Midler, and many other well-known artists. She’s got great stories! Carol was the first American woman to play with Los Muñequitos de Matanzas, one of Cuba’s iconic folklore groups, and she toured the United States with Lazaro Ros and Amelia Pedroso, two of Cuba’s most popular and beloved Folkloric singers. Carol’s second passion, besides music, is the study of Cuban Religions of African Origin. She loves to share her knowledge of the history of these spiritual practices, of their survival through music and art, and of how deeply entwined they are into the fabric of everyday Cuban life.

Since the advent of Covid-19, and its impact upon travel, we feel purchasing travel insurance has gone from wise precaution to fiscal necessity. Going forward, we are strongly suggesting that all patrons carry trip insurance that provides, at a minimum, coverage for the following:Cancellation for Covid-19 illnessTrip CancellationTrip InterruptionCancel for Medical ReasonsMedical Coverage for Covid-19 (often included under Emergency Medical Care)Emergency medical careMedical EvacuationAfter doing extensive research, we feel a product such as AXA USA Assistance Silver or Nationwide Essential provides robust coverage for all those items at a very fair price. Both of those products (and many more) can be purchased through our affiliate, Squaremouth. Because travel insurance is such a highly personalized product, when you click on the link and are directed to the Squaremouth landing page and the "Compare and Buy Travel Insurance" calculator, you’ll have to enter your own demographic information – age, state of residence etc. -- after which you'll be presented with a number of options to consider. Among them will be the AXA and the Nationwide products. You are certainly not limited to those two products – we are merely outlining the elements of coverage that we are strongly suggesting going forward and a convenient way to access them. If you purchase the policy through that link to Squaremouth it does not cost you anything more than purchasing the product directly from the vendor, but we receive a small commission.

Our customers are extremely important to us, and when travel disruptions occur, we are committed to working with you to minimize the financial impact. In the event that you need to cancel a trip for whatever reason, we will work with you to try and find a buyer for the space you are needing to give up. Often this works out well for all: the person needing to cancel recovers most, if not all, of their investment, and a person who might have been on a waiting list gets to go on the trip - however, there are no guarantees.
We understand that the new realities of travel are such that we need to be more flexible than ever before. We are also an extremely small business with many fixed costs that can't always be recovered if a trip needs to be postponed or cancelled due to health and safety concerns. We will be completely transparent if a scheduled trip looks like it needs to be adjusted in any way that might impact your enjoyment of the experience. Please read through our cancellation policy carefully and feel free to reach out to us with any questions or concerns.

Cancellation policy: Deposits, whether paid separately or as part of a full payment up front, are non-refundable. Outside of deposit and credit card fees, full refund will be given up until 90 days prior to start of trip. 50% refund 60-89 days. No refund less than 60 days prior to start of trip. Reservations are fully transferable to another person.The payment of a deposit or any part or full payment for a reservation shall constitute consent to all the provisions contained herein. Roots, Rails and Rambles shall not be held responsible for property loss or damage and/or any damages resulting from illness, personal injuries or death which may be sustained by reason of, or while engaged on, any trip or tour whether due to the ownership, maintenance, use, operation or control of any vehicle, hotel, common carrier or any other conveyance used in carrying out these tours. We can assume no liability due to any cause whatsoever whether caused by failure or delay or other irregularity, acts or omissions occurring during a tour under which the means of transportation or other service thereby is offered or supplied by owners, operators or public carriers for whom Roots, Rails and Rambles acts only as agent. Roots, Rails and Rambles reserves the right (at its discretion) to alter or omit any part of the itinerary, or change any reservation, feature and/or means of conveyance without notice or for any reason whatsoever and without allowance or refund and with extra costs, if any, resulting therefrom paid by the passengers. We reserve the right to cancel any tour prior to departure, in which case payment will be refunded without further obligation on our part. Roots, Rails and Rambles shall not be responsible for any injury to person (whether or not resulting in death) or damage to property.Baggage is at the owner's risk entirely. The transportation companies concerned are not to be held responsible for any act, omission or event during the time passengers are not aboard their carriers or conveyances. The passenger contract in use by the carriers concerned (when issued) shall constitute the sole contract between the transportation companies and the purchaser of these tours and/or passage. By accepting the ticket the passenger also agrees to its terms and conditions. By forwarding of deposit, the passenger certifies that he/she does not have any mental, physical or other condition or disability that would create a hazard for him/herself or other passengers. Roots, Rails and Rambles reserves the right to cancel or withdraw any person as a member of the tour at any time. Roots, Rails and Rambles management reserves the right to refuse service to anyone whom it considers incompatible with the best interests of its services or its guests.