Cuba Travel Agent Specialist

View My Main Profile
Cailel Colson, Travel Agent in Tallahassee, FL

Cailel Colson

Tallahassee, FL Travel Agent
Super Agent

Cailel Colson

Tallahassee, FL · 5 Years of Experience

A full-service Travel Leaders Associate Agency
5.0
(24)
100% Recommended
Along with leaving Kai Colson Travel a five-star review, I'm going to keep using their services. The early wedding season of 2025 began in mid-February. My... Read More >
About
Reviews
My Places

Areas of expertise

Destinations:

Cuba, Havana, Veradero, Santiago, Cayo Coco

Interests:

Arts & Culture, Private Travel, Historical Sites, Architecture, Escorted Tours

About Me

¡Hola! I’m your dedicated Cuba travel specialist, ready to help you explore one of the Caribbean’s most vibrant, soulful, and complex destinations. From the colonial streets of Old Havana to the powdery beaches of Varadero, the lush farms of Viñales Valley, and the Afro-Cuban rhythms echoing through Santiago, I design experiences that immerse you in Cuba’s rich culture, history, and natural beauty. I specialize in personalized, compliant trips that go far beyond cookie-cutter tours, helping travelers engage meaningfully with the people, places, and stories that make Cuba unforgettable. There is plenty worth experiencing like colonial architecture, visiting tobacco farms, enjoying live salsa under the stars, or sipping coffee at a privately owned casa particular. I craft itineraries that celebrate both the country’s magic and its resilience. I partner with local guides to highlight artists, musicians, entrepreneurs, and small business owners to ensure your trip is not only incredible but also responsible and respectful.

What I Offer:

  • Custom itineraries that blend cultural highlights with hidden gems
  • Lodging in authentic casas particulares (guesthouses) or boutique hotels
  • Expert-guided tours of Havana, Trinidad, Viñales, Cienfuegos, and Santiago
  • Cuban music, art, and culinary immersion
  • Private driver arrangements, bilingual guides, and local expert access
  • Optional extensions to beach regions like Cayo Coco or Holguín


Compliant Travel You Can Feel Good About: If you're traveling from the U.S., it's essential that your trip meets OFAC (Office of Foreign Assets Control) regulations, especially under the "Support for the Cuban People" general license category. Don't look at it as just legal red tape because it’s a powerful opportunity to travel with purpose. I design every itinerary to meet the legal standards and double ensure accuracy with assistance from certified guides. That includes ensuring your accommodations, activities, and interactions directly benefit Cuban entrepreneurs and the private sector — not the restricted government-run entities. I will make sure you have proper documentation and travel affidavits, so you're protected and prepared every step of the way. Having a knowledgeable guide who understands the landscape culturally, legally, and logistically can make the difference between a surface-level trip and a truly life-changing one.

Why should you travel to Cuba with MY help? Because I help you:

  • Travel with intention and impact
  • Avoid common pitfalls and non-compliant bookings.
  • Experience authentic Cuba—not just the tourist-facing version
  • Get access to vetted local hosts, guides, and immersive excursions
  • Travel with peace of mind, knowing your trip is meaningful, legal, and enriching


I'm here to design your ideal Cuban adventure whether you're planning a solo cultural deep dive, a romantic escape to Havana, a group trip through the island’s most iconic cities, or simply want to experience the best mojito you've ever had. Let’s plan your journey to Cuba the right way responsibly, legally, and memorably.

REVIEWS

Rating: 5.0
24 reviews
100% Recommended
Your trust is our priority. Every review is submitted by verified travelers after they have booked and completed their trips. Learn more about our review guidelines.
Search reviews:

Showing 24 reviews

March Vows
Reviewed By Elle - Tallahasseee Florida | Traveled to Tallahassee | Florida | USA
Along with leaving Kai Colson Travel a five-star review, I'm going to keep using their services. The early wedding season of 2025 began in mid-February. My client who was getting married in March told me that her friends and family coming from Illinois didn't have a hotel or a way to get around. As the couple's event advisor, I would typically bring up this topic early on, but bear in mind that I had less than four weeks to work my magic on their behalf. I accepted the challenge and contacted Kai Colson. My emails were answered right away, everyone arrived on time, hotel rooms were chosen based on group and block rates, and there was transportation from the airport to the hotels and back.
I would recommend this agent to my family and friends.
3 of 3 people found this review helpful. Was this review helpful to you?YES|NO
Just what I needed!
Reviewed By Secret Popstar - Disney World | Traveled to Orlando | Florida | USA
Perfectly planned trip to Disney with friends! My travel, stay, and reservations were wonderfully coordinated! Kai was easy communicate with and made several suggestions that enhanced the trip overall!
I would recommend this agent to my family and friends.
3 of 3 people found this review helpful. Was this review helpful to you?YES|NO
Celebrity Cruise
Reviewed By Suzie G. - Tallahassee, FL | Traveled to Bimini Islands | Bahamas | Caribbean
Kai was amazing at helping us book our first cruise for May 2025. He guided us along on what to expect and how to get the most out of our trip. Highly recommend!
I would recommend this agent to my family and friends.
3 of 3 people found this review helpful. Was this review helpful to you?YES|NO
APA Florida Planning Conference 2024
Reviewed By APAFL - Tallahassee, Florida | Traveled to Tampa | Florida | USA
APA Florida hosts the Florida Planning Conference every year for planners throughout the state of Florida. This past year our event was in Tampa and had a record-breaking conference of over 1,100 attendees. Kai was our go-to person when communicating with vendors such as Catering, Transportation, A/V and the Tampa Convention Center staff. He also assisted with communications with the 4 hotels that we had under contract for the 3.5-day event. He was ready to take on any challenge and assisted with planning as well as being a boots-on-the-ground participant. He arrived early to the event with the event staff and stayed through tear-down to help us get packed up more quickly. There was nothing that he would not jump in and help with for this event. From this experience, Kai is HIGHLY recommended for any large group planning of events. Thanks for making this event run more smoothly, Kai!
I would recommend this agent to my family and friends.
3 of 3 people found this review helpful. Was this review helpful to you?YES|NO
Wonderful Las Vegas experience!
Reviewed By JCD Builders - Tallahassee, FL | Traveled to Las Vegas | Nevada | USA
Our educational trip to Las Vegas was absolutely amazing! We participated in a student competition with over 30 people in our group, and we loved every single minute of it. The attention to detail was impeccable, and the agent was incredibly patient with all the changes we needed. He took care of our every need, making it a truly wonderful experience working with him. We can't wait to call him again for our next trip!
I would recommend this agent to my family and friends.
3 of 3 people found this review helpful. Was this review helpful to you?YES|NO

My Places

When it comes to travel planning, real-world experience makes a huge difference. Check out the map below to see all the places I have personally visited or booked for my clients. I know these destinations well and can give you reliable guidance.
BESbswy