About On The Fly Vacations

Our Story

How On The Fly Vacations began

Michelle, Founder of On The Fly Vacations

On The Fly Vacations was born from a passion for travel and a recognition of the unique needs and interests of African American travelers. Founder Michelle noticed that many travel experiences weren't designed with Black travelers in mind, often overlooking cultural connections, heritage experiences, and the specific preferences of the African American community.

After years of planning trips for friends and family that incorporated these important elements, Michelle decided to transform her passion into a profession. In 2015, On The Fly Vacations was established with a mission to create travel experiences that resonate with African American travelers—journeys that combine luxury, cultural connection, and authentic experiences.

What began as a small operation focused on Caribbean cruises has grown into a comprehensive travel agency specializing in cruises, Alaska adventures, South African safaris, and luxury travel experiences worldwide. Throughout our growth, we've maintained our commitment to creating journeys that celebrate Black heritage, connect travelers with their roots, and provide exceptional service tailored to our community's needs.

Today, On The Fly Vacations is proud to have helped thousands of African American travelers create meaningful memories through travel experiences that honor their identity while exploring the world's most remarkable destinations.

Our Mission

At On The Fly Vacations, our mission is to create transformative travel experiences that celebrate Black heritage, foster cultural connections, and provide exceptional service for African American travelers.

We believe that travel has the power to broaden perspectives, strengthen identity, and create lasting memories. Through thoughtfully curated itineraries, cultural insights, and personalized service, we aim to make travel more meaningful, accessible, and enjoyable for our community.

Every journey we plan is guided by our commitment to:

Cultural Relevance: Creating experiences that honor and celebrate Black heritage and history
Exceptional Service: Providing personalized attention and support throughout the travel journey
Community Connection: Fostering relationships between travelers and local Black communities
Quality Experiences: Ensuring comfortable accommodations, smooth logistics, and memorable moments
Responsible Travel: Supporting sustainable practices and community-based tourism initiatives

African American travelers enjoying a cultural experience

Meet Our Team

The travel specialists behind your perfect journey

Michelle

Founder & CEO

With over 15 years in the travel industry and a passion for connecting African American travelers with meaningful experiences, Michelle leads our team with vision and expertise. Her specialties include luxury cruises, African heritage journeys, and group travel coordination.

Certified Cruise Counselor Alaska Specialist Africa Travel Expert

James

Cruise & Alaska Specialist

James brings 10 years of cruise industry experience to our team, with particular expertise in Alaska itineraries. His attention to detail ensures that every cruise experience is perfectly tailored to each traveler's preferences and interests.

Master Cruise Counselor Alaska Destination Expert Expedition Cruise Specialist

Tanya

Africa & Cultural Experience Specialist

Born in South Africa and educated in the U.S., Tanya brings a unique perspective to our African travel experiences. Her deep knowledge of African history, culture, and wildlife makes her an invaluable resource for travelers seeking meaningful connections to the continent.

South Africa Specialist Safari Expert Cultural Tourism Professional

Marcus

Luxury Travel & Group Coordinator

With a background in event planning and luxury hospitality, Marcus excels at creating premium travel experiences and coordinating complex group itineraries. His attention to detail and creative approach ensure memorable journeys for our most discerning travelers.

Luxury Travel Specialist Group Travel Expert Virtuoso Advisor

Kimberly

Heritage Travel Specialist

With a background in African American studies and a passion for genealogy, Kimberly specializes in creating heritage journeys that connect travelers with their roots. Her research skills and cultural knowledge add depth and meaning to ancestry-focused travel experiences.

Heritage Travel Consultant Genealogy Research Specialist Cultural Tourism Expert

David

Client Experience Manager

David ensures that every aspect of your travel experience exceeds expectations. From your first inquiry to your return home, he coordinates our team's efforts to provide seamless service, address special requests, and create memorable moments throughout your journey.

Customer Experience Professional Travel Concierge Specialist Hospitality Management

Our Approach to Travel

What makes us different

Personalized Consultation

We begin every client relationship with a detailed consultation to understand your travel dreams, preferences, and needs. This personalized approach allows us to create journeys that truly reflect who you are and what matters to you.

Cultural Connection

We intentionally incorporate experiences that connect African American travelers with their heritage and with Black communities around the world. These meaningful interactions add depth and significance to every journey we plan.

Quality & Comfort

We believe that meaningful travel doesn't have to sacrifice comfort. Our partnerships with premium providers ensure quality accommodations, smooth logistics, and exceptional service throughout your journey.

Community Support

Whenever possible, we partner with Black-owned businesses and community tourism initiatives in the destinations we serve. This approach ensures that tourism benefits local communities while providing authentic experiences for our travelers.

Education & Context

We provide resources, reading materials, and cultural context to enhance your understanding of the destinations you'll visit. This preparation enriches your travel experience and fosters deeper connections with the places and people you encounter.

Ongoing Support

From the moment you begin planning until after you return home, our team provides continuous support and assistance. We're available to address questions, make adjustments, and ensure that every aspect of your journey exceeds expectations.

Our Certifications & Affiliations

Professional credentials that ensure quality service

CLIA Certified

Cruise Lines International Association certification demonstrates our expertise in cruise planning and industry knowledge.

ASTA Member

Our membership in the American Society of Travel Advisors reflects our commitment to professional standards and ethical practices.

Alaska Certified Expert

Our team includes certified Alaska specialists with comprehensive knowledge of the region's experiences and destinations.

South Africa Specialist

Our South Africa certification ensures we provide expert guidance for safari, cultural, and luxury experiences in the region.

IATA Accredited

Our International Air Transport Association accreditation allows us to provide seamless air travel arrangements worldwide.

Black Travel Alliance

We're proud members of the Black Travel Alliance, supporting representation and opportunities in the travel industry.

What Our Clients Say

Experiences from our travelers

"Working with On The Fly Vacations for our Alaska cruise was the best decision we made. Michelle understood exactly what we were looking for and created an experience that exceeded our expectations. From the suite accommodations with glacier views to the private helicopter excursion, every detail was perfect. We've already booked our next adventure with them!"

Robert & Angela Thompson

Alaska Cruise Experience

"Planning our family reunion with 25 people seemed overwhelming until we found On The Fly Vacations. Their group travel expertise made the process seamless, and they created a South African experience that worked for everyone from our 80-year-old grandmother to the teenagers. The cultural connections they arranged made this trip especially meaningful for our family."

The Williams Family

South Africa Family Reunion

"As someone who has traveled extensively, I appreciate the level of service and attention to detail that On The Fly Vacations provides. Their understanding of the unique interests and needs of African American travelers sets them apart. My heritage journey to Ghana was perfectly balanced between historical sites, cultural experiences, and luxury accommodations."

Dr. James Washington

Ghana Heritage Journey