Exclusive 2026 travel opportunities crafted with you in mind
Be the first to know about our exclusive 2026 group journeys
We're currently curating a lineup of unforgettable group travel experiences for 2026 — and trust us, you're going to want in. From wine-tasting under South Africa's golden skies and chasing sunsets along the Mediterranean coast... to wellness retreats in lush Bali, soul-soaking mud baths in St. Lucia, and glacier-gazing adventures through the wilds of Alaska — every trip is being designed with YOU in mind.
These are not your average vacations. These are soulful escapes, luxury with ease, and once-in-a-lifetime experiences crafted with care. Each journey is thoughtfully designed to provide African American travelers with meaningful connections, authentic cultural experiences, and the perfect balance of adventure and relaxation.
Want first dibs before everyone else? Join the waitlist to be among the first to receive full trip details, early access, exclusive perks, and VIP booking invitations. Spots are limited — and once they open, they won't last. Let the countdown to your next passport stamp begin...
A preview of our exclusive group journeys
May 2026
Experience the perfect blend of luxury and adventure with wine tastings under South Africa's golden skies, followed by unforgettable safari encounters with the Big Five. This exclusive journey includes premium accommodations, private tastings at Black-owned vineyards, and cultural heritage experiences.
July 2026
Chase sunsets along the Mediterranean coast on this luxury cruise experience featuring exclusive shore excursions, onboard cultural celebrations, and VIP amenities. Visit iconic destinations in Greece, Italy, and Spain while enjoying the comfort of premium cruise accommodations.
September 2026
Rejuvenate your mind, body, and spirit in the lush paradise of Bali. This wellness-focused journey includes luxury villa accommodations, personalized spa treatments, yoga and meditation sessions, cultural immersion experiences, and farm-to-table dining.
November 2026
Indulge in the Caribbean paradise of St. Lucia with this soul-nourishing escape featuring soul-soaking mud baths, luxury accommodations with stunning Piton views, private beach experiences, and authentic cultural connections with local communities.
June 2026
Experience the majestic wilderness of Alaska with glacier-gazing adventures, luxury accommodations, wildlife encounters, and exclusive experiences. This journey combines premium cruise accommodations with unforgettable land excursions for the ultimate Alaska experience.
The On The Fly Vacations difference
Our groups are thoughtfully sized and curated to ensure meaningful connections and personalized attention. Travel with like-minded African American travelers who share your passion for exploration and cultural experiences.
From priority boarding and exclusive access to special welcome gifts and surprise moments, our experiences include VIP touches that elevate your journey and create unforgettable memories.
Each experience includes opportunities to connect with local Black communities, support Black-owned businesses, and explore the African diaspora's influence in destinations around the world.
Select experiences include professional photography services to capture your journey, allowing you to be fully present while ensuring your memories are beautifully preserved.
Enjoy private welcome receptions, farewell celebrations, and special events throughout your journey that foster connection and celebration within your travel group.
Each experience is accompanied by a dedicated On The Fly Vacations host who ensures every detail is perfect and addresses any needs that arise throughout your journey.
Experiences from our travelers
"Our family reunion cruise to Alaska exceeded all expectations. On The Fly Vacations handled every detail perfectly, from our suite accommodations to our private excursions. Having our own group coordinator made everything seamless, and the special touches for our celebration made it truly memorable. We're already planning our next group adventure!"
"Traveling to South Africa with On The Fly Vacations was life-changing. Our group of friends experienced luxury accommodations, exclusive safari drives, and meaningful cultural connections. The wine tour in Stellenbosch was a highlight, especially meeting Black vineyard owners. The attention to detail and understanding of what matters to African American travelers made this trip exceptional."
"Our sorority's Mediterranean cruise was perfectly executed by On The Fly Vacations. From our private shore excursions to our onboard celebrations, every detail reflected our organization's values while providing luxury and cultural connection. Having our own dedicated space for sisterhood activities while still enjoying all the ship had to offer created the perfect balance."
Be the first to know when our 2026 experiences open for booking
Join our exclusive waitlist to receive:
Spots for our exclusive group experiences are limited to ensure personalized attention and optimal group dynamics. Once they're open for booking, they tend to fill quickly. Join the waitlist today to secure your opportunity to be part of these extraordinary journeys.
Common questions about our upcoming experiences
Our 2026 experiences will be released for booking in phases beginning in early 2025. Waitlist members will receive advance notice and early booking opportunities before experiences are opened to the general public. Each experience has a different booking window based on departure date, with most opening approximately 12-18 months prior to departure.
While each experience has its own specific inclusions, our group experiences typically include accommodations, select meals, group activities and excursions, ground transportation, dedicated group host, welcome and farewell events, and special group perks. Detailed inclusions for each experience will be provided when full itineraries are released. Airfare is typically not included but can be arranged through our agency.
Yes! We understand that luxury travel experiences are an investment, and we offer flexible payment plans for all our group experiences. Typically, this involves an initial deposit to secure your spot, followed by scheduled payments leading up to your final payment date. The specific payment schedule depends on the experience and booking date, but we work to create a plan that fits your budget and timeline.
Absolutely! Our group experiences are perfect for solo travelers looking to explore with like-minded individuals. We offer roommate matching services for solo travelers who prefer to share accommodations and avoid single supplements. Our group dynamics and activities are designed to foster connection and community, making solo travelers feel welcome and included.
Each experience has its own cancellation policy based on supplier requirements, which will be clearly communicated at the time of booking. We strongly recommend purchasing travel insurance to protect your investment in case unexpected circumstances require you to cancel. As a courtesy to waitlist members, we offer more flexible cancellation terms during the early booking window.
Our group sizes vary by experience but are thoughtfully limited to ensure quality, personalized attention, and optimal group dynamics. Most of our experiences accommodate between 20-40 travelers, with some specialty experiences limited to smaller groups of 12-16. The specific group size for each experience will be noted in the detailed itinerary.
Join our waitlist today to secure your opportunity to be part of our exclusive 2026 group journeys.