Kai Colson

Tallahassee, FL

Lifestyle Travel Designer

I'm a detail-driven travel specialist crafting seamless, personalized experiences across Florida, the Caribbean, Mexico, and beyond. Whether you're planning a theme park vacation, group retreat, cruise, adult-only escape, or romantic getaway, I tailor every itinerary to fit your travel style, budget, and priorities. Prefer something low-effort? I can also offer curated itineraries with custom add-ons to make planning easy and personal. From organizing multi-room bookings for teams to designing private wine country tours or immersive city breaks, I deliver concierge-level service with a thoughtful, human touch. My goal is simple: to make your travel stress-free, meaningful, and completely aligned with you. Wherever you're headed, I make sure every detail is handled with care. Let’s bring your next unforgettable trip to life—reach out today to get started

My Travel Specialties

Disney Travel Agent Specialist

Your Guide to Magical, stress-Free Disney adventures. As a certified graduate of the College of Disney Knowledge, lifelong Disney enthusiast, and your personal planner for all things magical. I specialize in helping families, couples, friend groups, and solo travelers craft unforgettable Disney experiences...
Read more from my Disney Travel Agent Specialist bio.

Baja California Travel Agent Specialist

Explore Baja Like a Local — with expertly crafted, stress-free travel. Baja California and Baja California Sur are two of my signature specialties. From the wine country charm of Valle de Guadalupe to the luxury resorts of Los Cabos, I curate seamless itineraries that highlight the very best of the...
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Caribbean Travel Agent Specialist

Lets turn your tropical vacation dreams into reality. Explore the vibrant culture and historic charm of Barbados, relax on the pristine white beaches of Aruba, discover the natural beauty and hidden gems of the Virgin Islands, or immerse yourself in the rich traditions and scenic landscapes of the...
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Business Travel & Meetings Specialist

As an experienced travel advisor specializing in business travel, luxury groups, meetings, and incentives, I help corporate teams, associations, and event planners design seamless, stress-free travel experiences across Florida, Hawaii, Canada, the Caribbean, and beyond. From booking room blocks and...
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APA's 2024 Post Conference Florida Aquarium Event

Central Florida Travel Agent Specialist

I'm your Central Florida expert travel planner for the Kissimmee and Orlando areas! Whether you’re dreaming of experiencing the novelty of Orlando's dinner theatre shows and food truck park, or enjoying Kissimmee’s charming attractions and outdoor adventures, I’m here to create a vacation tailored...
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My found family at the most Magical Place on Earth

North Florida Travel Agent Specialist

I'm ready to help you explore the Sunshine State’s most exciting destinations! From the lively college towns of Tallahassee & Gainesville to the vibrant cities of Jacksonville, Panama City, and the stunning beaches of Destin, I specialize in crafting customized vacations packed with fun and adventure....
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Orlando Area Travel Agent Specialist

Did you know Orlando is one of the most visited destinations in the world? Yet most visitors never see more than a few square miles of it. As your Orlando-area travel specialist, I’m here to change that. While I’m well-versed in the magic of Walt Disney World and the thrills of Universal Studios (and...
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Lake Nona Public Art

Quintana Roo & Veracruz Travel Agent Specialist

From the Gulf to the Caribbean, I specialize in the vibrant, culturally rich, and sun-soaked destinations of Veracruz and Mexico’s Quintana Roo region. These coastal gems offer more than just beautiful beaches—they’re full of history, flavor, adventure, and unforgettable hospitality. I craft custom...
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Cuba Travel Agent Specialist

Hola! I will get you ready to enjoy the captivating island of Cuba. From the vibrant streets of Havana to the stunning beaches of Varadero, I specialize in crafting authentic Cuban experiences that bring the island’s rich culture, history, and natural beauty to life. Whether you’re dreaming of exploring...
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Jamaica Travel Agent Specialist

You know you’re seeking the laid-back vibes of Negril’s Seven Mile Beach, the lush beauty of Ocho Rios, or the vibrant culture of Montego Bay, and I’m here to create your dream Jamaican getaway. From booking luxury all-inclusive resorts and private villas to organizing exciting excursions like climbing...
Read more from my Jamaica Travel Agent Specialist bio.

West Coast Florida Travel Agent Specialist

Indulge in the stunning destinations of Florida’s West Coast. From the pristine beaches of Clearwater and Sarasota to the vibrant city life of Tampa and St. Petersburg, I’ll craft the perfect getaway tailored to your wishes. With my extensive knowledge of Florida’s Gulf Coast, I take the stress out...
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My Travel Albums

Tianguis Turistico FAM Baja Mexico 2025
Santo Tomas wine in the vineyard
Disney Dream 2025
Birthday Trip 2024
The Iconic views from Magic Kingdom

My Travel Stories

Disney Dream Cruise 2025

I recently had the pleasure of embarking on my first Disney cruise with my best friend and travel partner, Stef. It was a dream come true, visiting one of my lifetime desired destinations, Mexico, and revisiting the Bahamas. Every day aboard the Disney Dream was truly magical.Upon boarding, we were...Read more.

My Reviews

1 of 1 people found this review helpful
APA Florida Planning Conference 2024
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!
By  APAFL  from  Tallahassee, Florida
Traveled to  Tampa | Florida | USA
I would recommend this agent to my family and friends
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1 of 1 people found this review helpful
Wonderful Las Vegas experience!
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!
By  JCD Builders  from  Tallahassee, FL
Traveled to  Las Vegas | Nevada | USA
I would recommend this agent to my family and friends
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1 of 1 people found this review helpful
Ethiopia trip
Mr Colson was friendly, helpful, attentive and prompt. When he could not solve a problem he escalated it to a higher level with prompt resolution.
By  cj  from  Florida
Traveled to  Ethiopia | Africa
I would recommend this agent to my family and friends
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1 of 1 people found this review helpful
Birthday in Vegas
I'm so grateful to Kai for all his help with my trip. I was honestly a little trepidatious about the idea of a travel agent but after hitting a wall with the planning for my trip I gave it a try and I'm so happy I did. Kai easily saved me over $600 I expected to spend on fancy hotels, dinners, and shows, and I got to experience all of it with a generous chunk shaved off. He's got a return customer in me when I travel next so even if you're not sure I'd recommend giving him a call.
By  Phoenix  from  Tallahassee, Florida
Traveled to  Las Vegas ~ Nevada ~ USA
I would recommend this agent to my family and friends
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1 of 1 people found this review helpful
Stress Free Weekend
Kai is a very hardworking dude that works with you and tries to get you exactly what you want to experience. Even though they're some challenges, he find intuitive ways to combat them and comes up with better ideas. I had a stress free vacation because of Kai.
By  Dancemajor96  from  Tallahassee, Fl
Traveled to  Orlando ~ Florida ~ USA
I would recommend this agent to my family and friends
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Destination Expert:

  • Cuba
  • Jamaica
  • Baja California Norte
  • Veracruz
  • Ensenada
  • Orlando
  • Tallahassee
  • Tampa
  • Walt Disney World
  • Caribbean
  • Barbados
  • Baja California Sur
  • Quintana Roo
  • Castaway Cay
  • Havana
  • Montego Bay
  • Destin
  • Kissimmee
  • St. Petersburg
  • Aruba
  • Hawaii
  • Veradero
  • Negril
  • Tokyo Disneyland
  • Cancun
  • Clearwater
  • Jacksonville
  • Lake Buena Vista
  • Virgin Islands
  • Florida
  • Santiago
  • Ocho Rios
  • Los Cabos
  • Playa Del Carmen
  • Disneyland
  • Gainesville
  • Naples
  • Port Canaveral
  • Dominican Republic
  • Cayo Coco
  • Port Antonio
  • Disneyland Paris
  • La Paz
  • Riviera Maya
  • Panama City Beach
  • St. Pete Beach
  • Universal Orlando
  • Canada

Travel Specialist:

  • All Inclusive
  • Arts & Culture
  • Beach Vacations
  • City Breaks
  • Disney Vacations
  • International Business Travel Specialist
  • Cruises
  • Family Vacations
  • Groups
  • Museums
  • Private Travel
  • Sporting Events
  • Theme Parks
  • Universal Parks & Resort Vacations
  • Animals & Wildlife
  • Culinary & Foodie
  • Hiking & Backpacking
  • Historical Sites
  • Honeymoons
  • Luxury
  • Wine Country Vacations
  • Architecture
  • Luxury Cruises
  • Meetings & Incentives
  • Outdoor Activities & Sports
  • Wellness
  • Adult Only
  • Business Travel
  • Entertainment
  • Escorted Tours
  • Shopping

Top Travel Partners:

  • Celebrity Cruises
  • Disney
  • Disney Cruise Line
  • Marriott Hotels
  • Small Luxury Hotels
  • Disneyland Resorts
  • Viator
  • Enterprise
  • Pleasant Holidays
  • Aulani, A Disney Resort & Spa
  • Royal Caribbean
  • Universal Parks & Resorts Vacations
  • Adventures By Disney
  • Delta Vacations

Certifications/Awards:

  • College of Disney Knowledge 2024

Connect with Me:

Industry Affiliations:

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