Kristen Jelley – Cuba Tour Guide

Kristen Jelley is a Cuba Travel Expert with over 20 plus years of experience in the travel industry. She is a certified travel agent, and specializes in Cuba Tours. Kristen was born in Los Angeles, California and has lived in various locations including Colorado, Texas and Virginia.  Her love for travel is what prompted her into the travel industry, where she is dedicated to helping people plan a vacation of a lifetime. She believes in helping her clients, whether a group, family, couple, or individual, create a customized vacation package that suites their particular interests and tastes. This includes arranging their accommodations, extra amenities, special services, dining options, and planned excursions.

As a Certified Cuba Specialist and travel agent, Kristen is very familiar with all the accommodations, amenities and services offered by Cultural Island Travel.  Kristen can help her clients plan vacations in any of the popular Cuban locations. As a specialist, she can also help clients make arrangements for special services like celebrations, transportation, and candlelight dinners. She can also make pre-arrangement for special activities, including local tours, water or land sports, adventure tours, scuba diving, or a hike  to a waterfall in Trinidad. Kristen can assist anyone and any size group traveling to Cuba.

Kristen helps each customer create a travel experience that will be remembered for a lifetime.  Kristen listens and helps customers with their dream trip to Cuba with our itineraries.  She always finds that best match for their specific interests and likes in order to plan a vacation that they will truly enjoy. She assists her clients by making any necessary arrangements, and plans complete packages for each customer.


What Our Customers Say About Cultural Island Travel

Michael DiMauro

June 2017

Hi Kristen,
I am still mentally not home yet. Very difficult to come right back to work after a 24 year old dream is realized. I have been to 15 countries for pleasure, business and cultural exploration, but Cuba has far surpassed them all. Our guide(s) were excellent. Our drivers were excellent. I have new friends and brothers for life. We met so many people there from the States on their own without a guide. How short sighted of them! Every turn of the corner is rich with history and it would be so foolish to walk those streets without guidance. Two women flew in from Chicago and were just hanging out by the pool all day. Imagine!  You can go in a pool anywhere in the world and they wasted the day away in Havana. Nuts. We met two young guys at the Hemingway House whose guide only met with them in the morning to give them advice and then sent them out on their own! They were shocked to learn that Ari was with us all day from morning to night. Your service is flawless and I especially appreciate arranging the cars for us to use instead of a tour bus. I know this was an issue in the beginning. By no fault of Ari, we did not get to see a working cigar factory because it was closed when we could have gone. I did visit the Partagas factory one afternoon, however. My only recourse is to plan another trip, which I am already working on by the way. Our visit to the Montesino farm allowed me to grasp the hands of both Marcelo and Eulogio Montesino, men who have actually had a significant impact on the Cuban cigar industry, and on my life personally. This experience was so surreal. It’s like loving Ford cars and being able to shake hands with Henry Ford. Mario and his family were awesome. He could not be more kind. We were so happy to see his good work in the community and we happily bought art, made donations and left well fed and feeling like family. Our visit to the Cuban art museum with Laura will be unforgettable. Cuba’s history is a story truly told through its artists. I felt like I was experiencing every decade and Laura could not be a better guide in there.
Restaurants were comparable to NYC quality restaurants. Whoever had the homemade pasta at the Italian restaurant will surely agree that it ranks as one of the best out there. (my mouth is watering now)
I can go on and on, so in sum, I will just say thank you for being so professional, accommodating, fun, and for helping me realize my dream of visiting Cuba during this particularly good window of opportunity that was opened up on October 16, 2016. Not sure what President Trump has in mind, but for the next trip, would like your thoughts on end of April, 2018 with 2 or 3 nights in Trinidad and 3 nights in Havana at the Nacional.

With much love to my travel partners for putting up with me…

Michael DiMauro

June 2017

Linda Mercaldo

June 2017

Hello Kristen,

I had a wonderful time in Beautiful Cuba and look forward to returning soon.

Our first tour guide Santiago was a delight. We all loved him!

Ebony was wonderful and helpful. We were taken to so many great places showing the real Cuba.

We had the pleasure of meeting her husband Ari. He was very attentive to all of us. They are a wonderful couple. I learned a lot of history and culture from them.

The excursions were well planned and very interesting.

Our bus driver Ruben was fantastic. He was always on time and took extra special care of us all. He was both gracious and had a wonderful personality.

It was wonderful to have our own private bus which was always keep cold for us in the humid weather. Ruben would go back to the bus to ready it for us! He was an excellent careful driver. We all marveled at his ability to get that bus down those narrow streets.

The food was excellent and plentiful. The  restaurants we selected were wonderful and gave the flavor of Cuba.

The architecture of Cuba is amazing.

The hotel was the best ever! The accommodations were luxurious, We loved the lobby and our rooms were elegant.

The breakfast at the hotel was sumptuous!

I thoroughly enjoyed this trip. My only drawback was that it only lasted 5 days. I wish it would have been 2 weeks.

Looking forward to returning to Cuba,

Sincerely, Linda Mercaldo

June 2017

Karen Fasciana

June 2017

Hello Kristen!

I’ve been meaning to email to let you know what a great experience we had in Cuba!  Our tour guide, Irma, was top notch – very professional and knowledgeable during our entire tour.  The whole team that supported our tour from our drivers, walking tour, museum tour, etc. were all very helpful, courteous, and a pleasure to be with.  We were very pleased with our accommodations at the hotel, almost everything we wanted to see and do was within walking distance in the evenings.  The Cuban people are so friendly and we never felt unsafe, the food was excellent, and I really enjoyed the live music everywhere!

Most enjoyable was the walking tour, we got to see and learn so much about old town.  The tobacco farm tour is a lot of driving and even though we really enjoyed the community project (the lunch there was amazing) we didn’t get to see the valley due to the rain and wet conditions.

Thank you, Kristen, for your prompt reply to all my questions on the front end.  Traveling to an unfamiliar country, especially somewhere like Cuba, made me a little apprehensive but you and CIT were great to work with and made everything so easy.  The experience is one I’ll never forget and I hope to be able to return to Cuba in the not so distant future.

Karen Fasciana

June 2017

Rob Sparandera Jr.

May 2017

Dear Kristen,

I had always been fascinated by Cuba and the tales of Che Guevara as a youth. Now seeing it I come away with the idea of Cuba being like a 1957 time capsule shaped by bureaucracy and selective outside influence and now starting to open itself to capitalism, It’s fascinating. I loved our guide Ari, he was informative and ever so helpful. He made the journey so much better then it would’ve been without him. The drivers were excellent especially Andy who I sat next to 90% of the time. Laura, the museum tour guide,was fantastic and very well spoken and informative. The highlight of my trip was meeting Mario Pelegrín Pozo and seeing all the good he does in his community, I felt the most at home there. Mario is such a great person and I’m so glad to have bonded with him.

Thank you for your time and courtesy, Rob Sparandera Jr.

May 2017


March 14, 2017
Hi Kristen,
Thank you for your note; we’ve actually been meaning to email you to tell you what a fantastic trip we had. Everyone we met from Cultural Island were amazing and made us feel so welcome.

All of the guides we met were great. Santiago and Ari were both terrific hosts; they were so open and easy to talk to and we truly enjoyed spending time with them. It was nice to get to know Havana through their personal stories. Patricia and Camilla were both extremely knowledgeable and it was great to meet them and have an opportunity to learn from their expertise.

The Hotel was nice and clean and we enjoyed being on the Malecon. We really enjoyed the next night at La Zorra y El Cuervo jazz club and would definitely go back.

Overall the entire weekend was a great experience and we would definitely recommend going to Cuba with Cultural Island Tours!

Thank you to you and Donna for all of your help in putting the trip together. If you have any questions, we’re happy to provide additional feedback.

Have a great day.

Thank you,


Sue & Warren (Woody) Woodmansee

March 13, 2017
Dear Kristen,
We had such a wonderful time in Cuba! We loved the guides!! All of them. The first day we had Laura who was just magical. We so hit it off. She was incredibly knowledgeable as well as just basically fun. We had her to ourselves the first day which we loved. She took us to a great mediterrain restrauant with wonderful food. We were going to museums, the Nationale hotel, the catacombs under the hotel until 5pm then off for a convertible ride in a 56 Chevy and then to the Hotel Capri. The hotel was great with wonderful gigantic breakfasts.

We loved the San Cristobol and the La Guardia. The atmosphere was lovely as well as great food. The second day our main guide was Irma. She was very warm & friendly & knowledgeable. Camilla, the art museum guide, was so good ; she really brought the Cuban art, religion, & politics together in a way that was extremely meaningful. The second , third , & fourth days we were in a group of 9 people. They were all very likable & made the experience doubly fun. Patricia & her fiancé were the guides on the walking tour of old town.

The fiance was helpful in keeping up the rear & keeping Woody from wandering too far away. Woody restores old cars so was in heaven looking at all the old vehicles & talking to the drivers. Kristen, you and Donna were very helpful and organized. I would love to go back to Cuba and take a longer trip. Four days was too short. I will include some of our pictures but I am not very savy with Facebook & not sure how to tag Cultural Island Travel but will try. Thanks again for a great trip. I have already recommended you to several people.


March 13th, 2017
Hi Kristen,
We had a great trip.
I thought our guide Irma was excellent. She was prompt and happy to be flexible with our requests.
The Iberostar in Havana by Central Park was nice! The tour around old Havana was interesting.
Overall, interesting experience and I’m glad we went.

Patty Walker

March 13th, 2017
What a wonderful experience we had in Cuba! The guides were so amazing and well informed. The people in Cuba were very welcoming. I was most impressed with the art and music. Such a talented people.
Overall the Cultural Island Travel experience was planned well. Lunches were amazing!! Enjoyed tremendously.

The apartment was in walking distance to many good restaurants for dinner and just a short taxi ride to the plazas of Havana where more wonderful restaurants and experiences awaited.

As mentioned earlier, all of the tour guides were fantastic and knowledgeable. Loved each!! The hike was nice but we had hoped to get a little more strenuous hike, as we requested. Ernesto told us we did the hike in record time. He was so good!

All in all, I would recommend travelers use your services as a company to help plan and orchestrate a trip.
Thank you so much for your help in making this a great journey!


March 13th, 2017
Had a WONDERFUL time.
I intend on doing write ups all over the internet! Especially tripadvisor. Before the trip I could not find much out about you guys and it worried me a little, but I was blown away.
The hotel was good and in a great location. I was happy I could get money changed there and wifi which was great. Breakfast was very busy and that was one thing that I did not like so much. Too many people in one place and one time. The breakfast its self was nice and really great choice. On Monday morning they had no tea left – which was upsetting to this english girl – but I always carry some with me!

All the guides, without exception were fantastic. I loved everything I did. I especially loved the art gallery and really wished we had spent at least another hour there. It was the highlight for me, and the guide showing us around Camille I think was very enthusiastic which rubbed off on us all!

Kristen you were very attentive and always on time with information. i felt like you really were on top of everything and gave a great impression of the company. They are lucky to have you!

So not much to say other than thank you for a trip with memories that will last a lifetime.

Gayle Townsend – Dandridge, Tennessee

March 13th, 2017
Sorry that I’m responding late to your e-mail, but I did want to let you know that I thought you and Donna did an excellent job for us before our Cuba trip February 17. You kept us informed, answered our questions promptly, and guided me through sending the necessary forms, which I really appreciated. We were met at the airport and taken immediately to a really nice restaurant , then on to meet Irma, our guide for the week, who could not have been more attentive, friendly, and helpful. The first hotel was great, the one at the beach resort was really nice although my husband and I were sick during those two days, but there was a doctor on site who prescribed medicine that really helped us. The last hotel, The Seville, was musty and dusty, and I got the feeling no one had stayed in our room before us for a really long time. We were not comfortable there but survived okay. We found Cuba to be interesting , and the people were very friendly. It was unlike anywhere else we had ever been so I’m glad we went. The tobacco farm trip was okay, a little far and not much there, the Hemingway house was interesting, and the walking tour in Havana was good. The guide for that was very knowledgeable. The community project visit was interesting and humbling. The concert at someone’s home was surprising, and the musicians were very good.. The food at the last restaurant was amazing, family style with lots of courses. I’m glad we visited the market on the last day and picked up some souvenirs. Both our taxi drivers were very nice, and the one who spoke English was helpful in answering our questions. We never felt unsafe during the trip. Overall, it was a good trip and made a lasting impression. I returned home with a grateful heart. Thank you for all you did to make it special.

Cyndy Shepherd

January 2017


Our trip to Cuba was AMAZING!  Mainly so because of our tour guide SANTIAGO!  He was absolutely the BEST!  His English was understandable, his knowledge of Cuba and Cubans was impressive, his concern for us, his tourists/passengers, was admirable.  He was always thinking of us and our well being during all excursions and activities.  He went beyond the call of duty to please us.  I wanted to take him home with me!

Our flight to Havana was delayed for 4 hours, so we were late arriving there.  We missed our scheduled activities for the afternoon, but we did arrive in time . . . and we were met at the airport by a wonderful young lady who escorted us to the Hotel Capri helped us check in, exchange money, and escort us to the paladar La Guarida where we had a reservation for dinner . . . to enjoy our first ride in a classic car, first sights at Cuba and its delightful cuisine.  It was a nice ending to a long day!

I must say that 3 or 4 days is not enough time to see everything in Havana!  We wished we had more time in Havana!  I loved hearing about Cuba’s history, its people and even the revolution.  It was a sight to witness the lives of the people frozen in time with the classic cars.

Santiago was determined.   It took him an hour from home to get to our hotel.  So he came earlier and gave us the highlight of our trip . . . the hour tour in a classic convertible!  We were thrilled!  The tour of the National Hotel was given to us after the day tour was over.  We even were treated to the BEST Mojito in the world!  He was just the most thoughtful sincere tour guide I have ever met!  He is a smart young man.  He can think on his feet and reschedule a dozen activities at one time.

Although our stay in Havana was too short, our drive to Varadero in a classic car was most enjoyable.  We got to see the sights on the road which we wouldn’t have seen, a huge rum factory, electric plant, and beautiful beach drive.  We stopped at a rest stop for a quick lunch and impressive Pina Colada.  Our arrival at the beach resort was an eye opener!  We thought we were in paradise!  What a contrast to the city!  

The Royalton Hicacos was quite a layout!  I did not know that it was all-inclusive!  We had exchanged money in Havana to have plenty for meals and drinks at the resort.  It was our first experience at an all-inclusive.  It felt weird getting up from the table not paying for the meal or drinks!  I would recommend letting the customer know it is an all-inclusive, so not to worry with having enough cash on hand.  Again, maybe you did tell me and I erred yet again in assuming that the meals were not included in the purchased package.  I would highly recommend this resort.  I must add that I had a birthday celebration like no other!  The BEST yet!  All day and night!  There was a huge BBQ festival at noon, a bubbles pool party at 4:00 pm, a European New Year Toast at 6:00 pm, New Year’s Eve Gala in the evening with huge buffet, music, entertainment, party favors and countdown to midnight!  Oh, and our butler surprised me with champagne, birthday cake, flowers, special note, and hot bath with bubbles and flower petals waiting for me when I came back to my room from the beach!  What a day!  I just may have to go there every year!!!!!!

The information of most frequently asked questions was very helpful, especially the tipping guidelines.  Both hotels we stayed had hair dryer, soaps, shampoos, lotions, toilet paper, and an umbrella in the rooms.  We were very pleased with both hotels.  A+.  Staff and service were excellent.  Everyone was most helpful and very pleasant.  They all wanted to help in any way to make our stay comfortable.  The food was fabulous everywhere we ate.  We did not taste any bad food or drink anywhere in Cuba.  The breakfast buffet at the Hotel Capri was extensive and plentiful.  The paladares recommendations in Havana were excellent.  We ate at La Guardia and La Terraza.  We had to cancel at Rio Mar due to lateness of tour, but Santiago called in our cancelation for us.  The lunches at San Cristobal (once we got our food) and Ivan Chef Justo were very good too.  The foods at the Royalton Hicacos was overwhelmingly impressive.  Our butler canceled our dinner reservation at Salsa Suarez in Varadero because of the New Year’s Eve Gala he was able to get a dinner reservation for us.  And it was WOW!  In all my years of galas and buffets, I’ve never seen such a sight of foods!

We enjoyed the walking guided tours of Havana.  We saw a lot of architecture of different eras of Cuba’s past.  The reinvention of churches to concert halls impressed me that they the structures were not torn down, but used for another purpose.  We saw the people, lots of people, going about their day.  For the most part, happy and content people.

We stopped at a leather store which made purses owned and operated by a family.  We stopped at a cigar and rum store to purchase Cuban cigars.  We would have loved to tour a cigar factory to watch them roll the cigars.  I guess that will be another trip!   

We enjoyed our concerts and art museums/galleries you planned for us.  They were quite impressive. We were entertained, as well as, informed about Cubans’ influence in the art world.  Santiago and all of our guides, including the ones at the museums, were quite knowledgeable.

The home and neighborhood of artist Jose Fuster was most impressive.  We thoroughly enjoyed seeing Fusterlandia.

Many of the public bathrooms at the tourist stops had toilet paper available for a small tip.  We were fortunate that we didn’t have to use any of our own, and that the toilet facilities were quite modern.   We left behind a lot of toilet paper when we left.

A highlight, of course, was Hemingway’s home.  Santiago gave us an excellent tour, as always.

Again, I can’t say enough about Santiago.  He made our trip for us.  He is an excellent tour guide.  We all could see that he truly loves his job as a tour guide, and that he loves Cuba.  What better person could there have been for us as a tour guide?  None.  Santiago was the BEST!   

Overall, our trip to Cuba was AMAZING!  Thanks to your help and knowledge.  Thank you very much!  I am indebted to you both for making our trip such a  WONDERFUL TRIP TO REMEMBER FOREVER!


Cyndy Shepherd

January 2017

Peggy Balliet

January 2017

Dear Kristen,

Our trip could not have been more perfect. We were happy with all our choices. We were also able to do everything on our itinerary. The hotels were good, better than we expected. The best part of the trip was our guide, Irma Gonzalez. She was outstanding. Our whole family fell in love with her. It was painful to leave her. She was a jewel.

I just wish we had been able to stay longer.

Thanks again for everything,  Peggy Balliet, January 2017

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