Roots on the Rails Roots on the Rails

Upcoming Trips: Adventures in Havana!

We’ve been exploring the idea of some small group trips to Cuba for a while now, wanting to investigate this fascinating city while it is still in its tourism infancy/adolescence. We've had a few cancellations on our upcoming 2020 trips to Cuba so if Havana has been on your bucket list, we can provide you with the carefully curated and organized 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.

Here's what we have available:

January 8 - 15, 2020: ESCAPE TO HAVANA!


This group will be staying in a lovely, ground floor casa with an open-aired courtyard, and beautiful common spaces in the residential district of Vedado. All rooms have air-conditioning, private baths, and individual locks. Its an easy ten-minute cab ride into Old Havana and within walking distance of the fabled Malecon Havanas seawall where locals hang out, sip rum, and watch the sunset each night.

March 21 - 28, 2020: A WEEK IN HAVANA VIEJA! 
SOLD OUT! A/O 10/8/19

We'll stay in a spacious and airy apartment right in the heart of Old Havana, steps away from dozens of historical sites, restaurants, shops with our own balcony overlooking lively Calle Oreilly. All rooms have air-conditioning, private baths and can be locked individually.

Scroll further down for the daily itinerary.  

The cost for each trip is $3,500.00 per person, and it includes just about everything outside your plane ticket and the $50-75 visa -- most meals, museum admissions, tours etc. Many major US airlines fly to Havana, and once you arrive, youll be picked up at the airport and taken to our casa to meet up with the rest of our group.

To find out more, or to book your reservation, call or e-mail Sarah at : 802-258-1397 or

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 will be slightly different than our typical Roots on the Rails trips in that we won’t be bringing along any “professional” musicians. Instead, we’re going to 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 (taken during Charlie’s March, 2019 recon trip), 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!

The cost for each is $3,500.00 per person, and it includes just about everything outside your plane ticket and the $50-75 visa – most meals, museum admissions, tours, etc. Most major US airlines fly to Havana, and 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 provide detailed instructions on how to handle getting visas (typically included with your airline tickets), the mandatory Cuban health insurance (purchased for a few bucks at the Havana airport), 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.

All of our Havana trips will be following roughly the same itinerary, and depending on availability, we will be staying at either an Old Havana casa or one in a residential district with easy access to all the major sites of interest.

Again, the standard Cuba disclaimers – all things may not happen exactly on the days or at the times that we are currently outlining, but this gives a good sense of the possibilities that are available to us, and the types of experiences Carol is able to arrange. This is, essentially, the itinerary of Charlie’s 2019 exploratory trip with Carol and will doubtless change at least slightly. As we get closer in, we’ll have this tightened up quite a bit. Calendar dates may cause some re-jiggering of the itinerary, but Carol has a deep well of places and people from which to draw.

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 @ El Aljibe This is the only government-run restaurant that we, and basically anyone else, go to. Its known for its chicken in citrus sauce, and the most delicious black beans. 

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 to Old Havana in our classic cars to explore and see exactly what he was talking about. It gives a great context and sense of place.

1:00 pm Lunch: Al Carbon - a chef-owned restaurant, 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 Hotel Nacional to enjoy a coffee on the patio, remembering the days gone by when the Hotel was run by the Mafia.

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 Cocktails at the house with 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 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 Coffee 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.


$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.

Assuming costs stay relatively even in Cuba,  we anticipate that the current trip price will remain $3500.00 USD for the foreseeable future. This price is per person for seven nights accommodation at the private casa in Havana (solo travelers will be paired with a same-gendered roommate), most meals (see itinerary), airport transfers, tours, and activities.

Sound Intriguing? Get on our Early Bird Notice list by emailing Sarah at with "HAVANA? YOU BET!" in the subject line or call 866-484-3669 (toll-free in the US & Canada).

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 US travel policy to Cuba change, rendering these trips impossible, we will refund all payments to us in their entirety. 

The changes in travel policy recently announced by the Trump administration do not affect our category of travel, “Support for the Cuban People.” Our contacts in Cuba report that tourism is continuing as usual. In the past, when travel restrictions have been announced, existing reservations have been “grandfathered” in, so we are monitoring the situation closely, but proceeding ahead. 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.


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.