Roots on the Rails Roots on the Rails

Upcoming Trips: November in Havana!



Cuba has reopened to visitors and we couldn't possibly be more excited! It's been a long two years of isolation for the Cuban people, and our friends there can't wait to see us again. Ever since our trips in 2019 and early 2020, we've been hearing from those of you who missed those trips that you'd love to go. Bueno, ¡¡Vamos a La Habana!!

If Havana has been on your bucket list, we can provide you with the carefully curated and organized small group trip you've been looking for! Small groups, excellent local guides, and a unique opportunity to immerse yourself in Havana while getting to know Cuban culture.

Our Havana groups  stay in spacious and well-appointed privately-owned apartments (casa particulares)  right in the heart of Old Havana, steps away from dozens of historical sites, restaurants, and shops -- and smack dab in the middle of the daily lives of the local Cubans. We wake up to the calls of the fruit vendors, the chattering of  kids heading off to school, and the bustle of every day life in one of the world's most fascinating cities.  All rooms have air-conditioning, private baths and can be locked individually.

The cost for each trip is $3,800.00 per person, and it includes just about everything outside your plane ticket and the $50-$75 visa -- most meals, museum admissions, tours etc. As of Dec. 1, 2022, three  major US airlines have resumed flights to Havana, so it's an easy hour long flight from Miami, Tampa or Fort Lauderdale. Once you arrive, you'll be picked up at the airport and taken to our casa to meet up with the rest of our group.

We’ve crafted an experience and itinerary that is both affordable and immersive – living in actual Havana neighborhoods, eating and drinking at small, independent restaurants, enjoying private tours of some of Havana’s great artistic and cultural treasures, meeting and socializing with Cuban families, and experiencing this unique place in a way that large group tours can’t possibly replicate.

These trips are slightly different than our typical Roots on the Rails trips in that we don't bring along any “professional” musicians. Instead, we delve into the music and culture of the Cuban people with our local hostess/fixer, Carol Steele who has a rock and roll pedigree as long as your arm, having played percussion with Joan Baez, Peter Gabriel,Tears for Fears and countless others-- here she is on Letterman doing "Higher Love" with Steve Winwood.

Carol - the constant in the photographs above, has been visiting Cuba for the last thirty years, and leading tours there for the last twenty. She is deeply immersed in the Cuban music and arts scene and will be arranging private concerts and visits with local musicians, dancers, and artists while we are there. The running gag on our last trip with Carol was “She knows a guy!”, which is not only true but “knowing a guy” is the way most business gets done in Cuba. Plus, she is an absolute delight to travel with and with her we get to go places and meet people ordinary tourists would never get to see. Check out the rough itinerary below to get a sense of how she’s organized our days together – although be aware that because this is Cuba, plans are always somewhat “flexible”, but with Carol leading the way we are assured of a wonderful set of adventures!

We provide detailed instructions on how to handle getting visas (typically included with your airline tickets), the mandatory Cuban health insurance , currency exchange (not as daunting as it seems) and all of the other details of traveling to Cuba that can seem intimidating, but are actually quite easy.

For the foreseeable future, participation in any of our trips will require proof of full Covid- 19 vaccination – that means providing us with documentation that you have received the full schedule of vaccines and boosters that meet the standards for travel in both your country of origin, and the country you’ll be visiting. We will require all of our guests to comply with any local masking, social distancing, testing, and other safety protocols required by any hotels, transportation, restaurants, and venues that we work with, and where trip organizers deem it necessary to protect the health of all participants. Whenever possible we will give you ample advance notice so that we are all fully prepared, but we also ask that everyone maintain flexibility and concern for the welfare of the group whenever we may need to make adjustments while en route. Such is the world we live in now, and we’re all getting pretty good at mid-course correction!
And what happens if global conditions change or a trip begins to look unwise or unsafe? Well, we’ll do what we’ve been doing for the last 2 years – we pivot. If safety becomes a concern with any of our trips, we will change what we have the power to change, and if that’s not possible, we’ll look to re-schedule or offer refunds. Please see our updated cancellation/refund policy under the "Fine Print" section further down this page.


This is a very fluid overview of some of the experiences and activities we can pack into our week in Havana, and pretty well summarizes the pace and scope of our days there. Being that it is Cuba, you should be prepared for all of this to be very flexible, and for some additional wonderful surprises to be thrown into the mix.

Day One:

Arrive at Jose Marti Airport. You will be met at the airport by car and driver, with a sign with your name on it. Depending on the time of day, there should be time for a little classic car panoramic drive/tour of the city on the way to our casa. (if not, on the way to dinner, if all the flights don’t come in on time, etc.) Guests have time to get settled in, rest, have a welcome cocktail, and then we head to dinner.
Dinner: 8:00 pm @ Paladar Dona Eutemia in Cathedral Square, a short walk from our casa.
Day Two:
Breakfast at the casa.
9:00 am: Lecture at the Casa by Miguel Coyula, architect and City Planner, who gives an amazing lecture with photos of the history of Havana through its architecture. Then we head out on a walking tour of Old Havana to explore and see exactly what he was talking about. It gives a great context and sense of place.
1:00 pm Lunch: El Del Frente - right on bustling O'Reilly Street, for a delicious family-style lunch. All meals are usually a several-hour hour experience.
Late afternoon to further explore Old Havana, and then we head back to the casa, to rest up, and get ready for dinner.
8:00 pm Dinner: Decameron in Vedado -This is one of the pioneers of Private Restaurants in Havana. They have a nice mix of Cuban and European dining.
Evening: Head out for some local music – jazz or new Cuban music, depending on who is playing that night.
Day Three:
Breakfast at the casa.
Morning: a visit to the home of renowned Cuban photographer Roberto Chile. He was Fidel Castro’s personal videographer and photographer for 25 years and has since been experiencing a resurgence of creativity, producing videos for emerging Cuban artists.
1:00 pm Lunch: Habana 61 – a wonderful small restaurant owned by a former employee of a well-known restaurant in Miramar, who likes the size of his restaurant, so that he can keep quality control.The chef is a former chef at La Guarida, where we’ll be eating later in the week. This is Carol’s go-to neighborhood restaurant, that she reports is consistently great. 2:30-4: 00 pm Rest time at the house or independent exploring.
6:00 pm Private performance with CoroVocal Luna.A rare treat.A great womens’ choral mix of classic and contemporary. Won the gold medal at a choir competition in South Africa.
8:00 pm Dinner: Mediterano Habana – a farm-to-table restaurant in Vedado, owned by a Cuban and an Italian.
Day Four:
Breakfast at the casa.
10:00am: Visit the local produce market, and see where locals and local chefs shop.
11:00 am: Private rehearsal of Malpaso, the very best of Cuban Contemporary dance. Watch whatever they are working on at the moment, with time to interact with them, and talk to them about their lives, etc.
1:00pm Lunch - Lamparilla 361 (on our own - cost not included) in Old Havana. One of the newer, tasty, hipster restaurants with a young, fun staff, and a great tapas and cocktail menu.
After lunch: a guided shop crawl through Old Havana with Carol to visit some of her friends that have private businesses here, some of the newer shops, maybe finish up in Plaza Vieja at Café Escorial.
5:00-ish Back to casa – rest and cocktails
8:00 pm Dinner: San Cristobal in Centro Habana – the only restaurant owned by an Afro-Cuban man, and where President Obama and his family ate when they were here in 2016.
Day Five:
Breakfast at the casa
9:00 am Day Trip to Matanzas. We’ll travel all together in a van to get there. This is a very special treat. 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.
This is about an hour and a half journey. During our drive, Carol will give a talk about the place and the people that you’re going to meet, talk about its importance in Afro-Cuban history, the origins of the rumba, why Matanzas, etc. Carol makes sure that we all have a good context of where we’re going, and who we’re going to be with so that you get the most out of this visit. This is often the highlight of most people’s trip.
Anyone who wishes can learn a bit of rumba if they like, non-dancers can just have an awesome time! The music is mind-blowing. Drums and vocals.
8:00 pm Dinner: Atelier in Vedado –This is a wonderful privately-owned restaurant, owned by a woman who is at the forefront of working for the rights of private business owners. Delicious Cuban food served family-style.
Day Six:
Breakfast at the casa.
10:00 am - Guided tour of the Bellas Artes, the fine arts museum. This building only houses the vast Cuban collection, from Colonial to Contemporary. We’ll have our own guide, Glenda, who will take us through on a tour for about an hour or hour and a half. This is also another way to learn a bit more about Cuban history, through its art.
This is another moment that we can walk from the Bellas Artes, to a part of Havana Vieja that we haven’t discovered yet. Lots of community projects and up and coming business, ending up at one of them.
12:30 pm Lunch - 5 Esquinas (5 corners) for pizza on our own
After lunch, we can head over to La Cabaña and Morro Castle. The view of Havana from that side of the bay is absolutely stunning. Also, Carol has a good friend that works in the cigar shop there, so this is a great opportunity to pick up souvenir cigars.
3:30 pm – back to the casa.
5:30 pm – head out for a little jazz “happy hour”, atop one of the Contemporary Section of the Parque Central Hotel, with an amazing view of Centro Havana all the way to Vedado.
7:00 pm Dinner: La Guarida - This is one of the most famous private restaurants that opened in the 1990s, and has expanded to be the fabulous restaurant that it is today. Made famous by the movie, Strawberry and Chocolate. This film was instrumental in opening up the attitude towards gay people in this country. We will talk all about the history of the restaurant when we’re there.
Day Seven:
Breakfast at the casa.
10:00 am: After Breakfast we’ll head out the Christopher Colombus Cemetery, where we’ll meet our private guide that will take us through the main avenue, and talk about the importance of this cemetery and its history.
12:30 pm: Lunch at Fusterlandia – After our visit to the cemetery, we’ll head out to the fishing village of Jaimanitas, where the artist, Jose Fuster, has transformed his entire neighborhood with mosaic art, over the past 22 years. We’ll have time to explore both before and after lunch, which will be a home-cooked meal with whatever the fresh fish of the day is. Jose Fuster is known as the Gaudi or the Picasso of Cuba, and you’ll discover why when we’re there.
After lunch, return to the casa.
8:00 pm Dinner: El Cocinero - This restaurant is one of the best of the new guard of private restaurants. It’s part of a complex, that includes the restaurant, and the award-winning Fabrica de Arte Cubano – which houses three levels of art, music, performance art, painting, spoken word – and is a unique experience! The complex was built on the site of an old cooking-oil factory.
Day Eight:
Breakfast at the casa, then cars to the airport.

PRICE: $3800 per person. All accommodations at the casa are double occupancy. All rooms have individual air conditioners and private baths. If you are a solo traveler, we will pair you up with a similarly-gendered roommate.

$300 deposit to hold your space. Monthly payment schedules are happily accommodated at no extra charge, but must be arranged within 30 days of making your deposit.

To secure your space(s) on this trip, just give Sarah a call at 802-258-1397, or e-mail her at

Credit cards (Visa, MC, Amex, Discover) and checks accepted.  Payment plans at no additional charge are happily accommodated. Payment plan must be agreed upon and set up within 30 days of sign-up. Deposits, whether paid separately or as part of a full payment up front, are non-refundable, though they can be applied to a future trip with us. Liability release signature required.

Cancellation policy: Deposits, whether paid separately or as part of a full payment up front, are non-refundable, though they can be applied to a future trip with us. Outside of deposit and credit card fees, a full refund will be given up until 90 days prior to the start of the trip. 50% refund 60-90 days. No refund less than 60 days prior to the start of the trip. Reservations are fully transferable to another person. Should travel rules to Cuba change, rendering these trips impossible, we will refund all payments to us in their entirety. 

We travel to Cuba under the category of  “Support for the Cuban People.” , one of the allowable categories for  US citizens. We will provide you with the details of how to apply for your visas, fill out any paperwork etc. It's all much easier and less complicated than you might think. We do, as always, recommend that you purchase travel insurance for your flights to and from Havana – see below.


We highly recommend purchasing travel insurance for your trip. By purchasing through this link to Squaremouth  (an aggregator where various insurance company policies can be compared at no additional cost to you), we receive a small commission (about five percent). This helps us keep our trips as affordable as possible. On virtually every trip, we have someone who needs to cancel at the last minute due to injury or illness, family emergency, or any number of unexpected circumstances. Those who had purchased the trip insurance were disappointed to be missing the trip, but very relieved that they were not losing all the funds they had paid us, airline tickets, hotel accommodations, and other expenses. Those who did not purchase the trip insurance were really, really sad to lose a trip and a bunch of money too. We'd hate to see you be one of those people, which is why we stress the importance of trip insurance. Really, truly, we think it is worth it.

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. Given that the world continues to be filled with unknowns, we are proceeding ahead with guarded confidence that we can deliver the products promised (with some reasonable degree of change when necessary) and 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.

Pandemic-specific cancellation policy: In the event that Covid-19 or other concerns cause Roots on the Rails to postpone or cancel a trip, guests will have 30 days to inform us of their choice of one of these three options:
a) Holding their reservation at the price they paid and therefore gaining priority access to claiming a spot on the re-scheduled trip within 30 days of our announcement of the new trip dates.
b) Transferring any payments to another trip, pending availability.
c) If the re-scheduled trip is not viable for a guest, and they wish to request a refund, such requests must be made within 30 days of the announcement of re-scheduled trip dates.
General (non-pandemic-related) cancellation policy: Deposits, whether paid separately or as part of a full payment up front, are non-refundable, though they can be applied to a future trip with us. Outside of deposit and credit card fees, full refund will be given up until 90 days prior to start of trip. 50% refund 60-90 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. Flying Under Radar, LLC 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 Flying Under Radar, LLC acts only as agent. Flying Under Radar, LLC 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. Although all artists are contracted to appear, lineup is potentially subject to change due to illness or force majeure. We reserve the right to cancel any tour prior to departure, in which case payment will be refunded without further obligation on our part. Flying Under Radar, LLC shall not be responsible for any injury to person (whether or not resulting in death) or damage to property.

Flying Under Radar, LLC strongly urges individual passengers to obtain appropriate insurance coverage. 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. Flying Under Radar, LLC reserves the right to cancel or withdraw any person as a member of the tour at any time. Flying Under Radar, LLC and Roots on the Rails management reserve the right to refuse service to anyone whom it considers incompatible with the best interests of its services or its guests.