Creating unforgettable journeys for families, friends, and organizations
The joy of shared experiences
There's something magical about experiencing the world's wonders with the people who matter most to you. At On The Fly Vacations, we specialize in creating group travel experiences that bring people together while exploring amazing destinations.
Whether you're planning a family reunion, a friends getaway, a church group outing, or an organization trip, our expertise in coordinating group travel ensures that everyone enjoys a seamless, memorable experience. We understand the unique dynamics and needs of African American group travelers and create itineraries that resonate with your interests, preferences, and heritage.
From the majestic landscapes of Alaska to the cultural richness of South Africa, from luxury cruises to customized land tours, we handle all the complex details of group travel so you can focus on creating lasting memories together.
Perfect for every type of group
Bring generations together for meaningful connections in beautiful destinations. Our family reunion packages include activities for all ages, group dining arrangements, and special celebration options to honor your family's heritage and create new traditions.
Combine spiritual growth with exploration on a church group journey. We create travel experiences that align with your faith community's values while providing opportunities for fellowship, worship, and service in destinations around the world.
Turn "someday we should travel together" into reality with our friend group packages. Whether it's a milestone birthday celebration, an annual getaway tradition, or just because, we'll create the perfect balance of group activities and individual flexibility.
Combine professional development with exceptional travel experiences. From sororities and fraternities to professional associations and alumni groups, we create journeys that strengthen bonds while exploring new destinations.
Perfect settings for your group experience
Experience the majesty of Alaska's glaciers, wildlife, and pristine wilderness together. Our group cruise packages include private excursions, group dining arrangements, and onboard celebration options.
Explore Alaska Groups
Connect with your roots on a group journey through South Africa. From safari adventures to cultural heritage experiences, these trips create powerful shared memories.
Discover South Africa Groups
Enjoy tropical paradise with your group on a Caribbean cruise experience. Perfect for family reunions, milestone celebrations, and organization retreats.
View Caribbean Options
Explore Europe's rich history, architecture, and cuisine as a group. Our European packages include Black heritage sites and experiences throughout the continent.
Explore European OptionsWhy traveling together makes sense
Group travel often means special rates on accommodations, transportation, and activities. The more people in your group, the more you can potentially save.
Gain access to private tours, special events, and unique experiences that aren't available to individual travelers.
Distribute the work of planning among group members, with our expert guidance to ensure everything runs smoothly.
Create lasting bonds through shared experiences, challenges, and discoveries that bring your group closer together.
Create memories that can be reminisced about for years to come, with photos and stories that preserve your journey together.
How we create your perfect group experience
We begin with a detailed consultation to understand your group's size, interests, budget, and travel goals. This helps us create a customized experience that meets everyone's needs.
Based on your input, we develop a comprehensive travel proposal with destination options, accommodation choices, activities, and pricing tiers to suit your group's preferences.
We handle all the logistics of collecting traveler information, managing payments, and coordinating special requests to make the planning process stress-free for group leaders.
As your departure approaches, we provide detailed itineraries, packing lists, and travel tips. We can also arrange pre-trip virtual meetings to answer questions and build excitement.
During your journey, we provide 24/7 support to address any concerns or special requests that arise, ensuring a smooth and enjoyable experience for everyone.
After your return, we gather feedback to ensure your experience met expectations and begin planning for your group's next adventure.
Hear from our group leaders
"Planning a family reunion for 35 people seemed overwhelming until we found On The Fly Vacations. Michelle coordinated everything from our Alaska cruise cabins to our group excursions and even arranged a special family celebration dinner. Everyone from our 80-year-old grandmother to the teenagers had an amazing time!"
"Our sorority chapter wanted a meaningful travel experience that combined luxury, cultural connection, and sisterhood. Our South African journey exceeded all expectations. The private safari vehicles, township tour, and winelands experience were perfectly tailored for our group of 22 sisters. We're already planning our next trip!"
"Coordinating a church group cruise for 40 people with different budgets and expectations seemed impossible. On The Fly Vacations made it seamless, offering payment plans, handling all the details, and even arranging a private worship service onboard. The Caribbean cruise was the perfect blend of fellowship, relaxation, and spiritual growth."
Common questions about group travel
Group rates typically begin with as few as 10 travelers, though the specific number varies by destination, cruise line, and season. Larger groups of 16 or more often qualify for additional benefits such as complimentary spots for group leaders, private excursions, and exclusive onboard or resort amenities.
For optimal availability and pricing, we recommend planning group trips 12-18 months in advance, especially for popular destinations and cruise sailings. This timeline allows for securing group space, coordinating payments from multiple travelers, and planning special events or excursions. However, we can also accommodate groups with shorter planning windows when necessary.
Yes! We offer individual payment options for group members, allowing each traveler to manage their own reservations and payments while still being part of the group booking. This removes the burden from the group leader of collecting payments and provides flexibility for each traveler's budget and preferences.
Absolutely. We coordinate with cruise lines, resorts, and tour operators to accommodate all dietary requirements including vegetarian, vegan, gluten-free, kosher, and allergy-specific needs. For group meals and events, we ensure that everyone's dietary preferences are respected and accommodated.
Our group bookings are flexible, allowing travelers within the same group to select different accommodation categories, flight options, and even add pre/post extensions while still participating in all group activities and benefits. This ensures everyone can travel according to their budget and preferences.
Yes, we offer customized payment plans for groups, allowing members to make deposits and payments over time leading up to the final payment date. This makes group travel more accessible and helps with budgeting for larger trips.
Let us create a customized group travel experience that brings your family, friends, or organization together for an unforgettable journey.