Cruises
Cruise with Confidence
At On The Fly Vacations, we specialize in creating exceptional cruise experiences tailored your preferences and interests. Whether you're dreaming of glaciers in Alaska, pristine beaches in the Caribbean, cultural treasures in the Mediterranean, or exotic adventures in Asia, our cruise specialists will help you find the perfect voyage.
We understand that cruising offers a unique blend of convenience, luxury, and exploration that appeals to many travelers. With our expertise and industry relationships, we ensure that your cruise experience includes not just the best accommodations and itineraries, but also culturally relevant experiences, group opportunities, and personalized service that enhances your journey.
From selecting the right cruise line and ship to arranging private shore excursions and onboard celebrations, we handle every detail of your cruise vacation with care and attention. Our goal is to create seamless, memorable experiences that allow you to relax, explore, and connect with destinations in meaningful ways.
Why Cruise with On The Fly Vacations
Certified Cruise Specialists
Our team includes certified cruise counselors with extensive training and firsthand experience on major cruise lines and ships. We know the nuances of different cruise experiences and can match you with the perfect option for your preferences.
Exclusive Amenities
Through our industry relationships and affiliations, we offer exclusive amenities that enhance your cruise experience, from onboard credits and specialty dining to cabin upgrades and private shore excursions not available to the general public.
Group Cruise Expertise
Planning a family reunion, organization trip, or friend getaway? Our group cruise specialists handle all the complex details, from group dining arrangements to private excursions and onboard celebrations that make your group experience special.
Cultural Connections
We enhance your cruise experience with culturally relevant shore excursions, onboard gatherings, and opportunities to connect with local communities and heritage sites in ports of call around the world.
Comprehensive Support
From your first inquiry through your return home, we provide personalized support and assistance. We're available to answer questions, address concerns, and handle any unexpected situations that may arise during your cruise.
Value & Transparency
We ensure you receive the best value for your cruise investment with clear pricing, explanation of inclusions, and flexible payment options. We monitor for price drops and promotions even after booking to secure you the best deal.
Featured Cruise Destinations
Alaska Cruises
Experience the majestic beauty of Alaska's glaciers, wildlife, and pristine wilderness from the comfort of a luxury cruise ship. Our Alaska cruise packages include exclusive shore excursions, cultural experiences, and opportunities to witness the state's natural wonders up close.
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Glacier viewing experiences
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Wildlife encounters
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Cultural heritage connections
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Luxury accommodations
Caribbean Cruises
Sail through the crystal-clear waters of the Caribbean, visiting islands rich in African diaspora heritage and natural beauty. Our Caribbean cruise experiences include opportunities to connect with local cultures, explore historical sites related to the African diaspora, and enjoy pristine beaches and tropical adventures.
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Island heritage experiences
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African diaspora connections
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Beach and water activities
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Luxury ship amenities
Mediterranean Cruises
Discover the rich history, stunning architecture, and diverse cultures of the Mediterranean region. Our Mediterranean cruise experiences include Black heritage tours in European ports, culinary experiences, and visits to iconic landmarks, all while enjoying the comfort and luxury of premium cruise accommodations.
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Black heritage in Europe tours
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Historical and cultural sites
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Culinary experiences
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Luxury cruise amenities
Africa Cruises
Connect with other travelers through cruise experiences that explore the African continent's coastlines and nearby islands. From South Africa to Morocco, from Madagascar to the Seychelles, our Africa cruise experiences provide meaningful connections to the continent's diverse cultures, wildlife, and landscapes.
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Heritage connection experiences
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Wildlife viewing opportunities
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Cultural immersion
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Luxury accommodations
Cruise Lines We Recommend
Partners in creating exceptional experiences
We work with a carefully selected portfolio of cruise lines that offer exceptional service, diverse itineraries, and experiences that resonate with wanderlust travelers. Our recommendations are based on firsthand experience, client feedback, and each cruise line's commitment to inclusivity and cultural sensitivity.
Premium Ocean Cruises
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Celebrity Cruises
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Princess Cruises
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Holland America Line
These cruise lines offer an excellent balance of quality, value, and diverse experiences. With multiple dining venues, entertainment options, and comfortable accommodations, they provide a well-rounded cruise experience suitable for first-time cruisers and experienced travelers alike.
Luxury Cruise Experiences
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Seabourn
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Silversea
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Regent Seven Seas
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Oceania Cruises
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Viking Ocean Cruises
For travelers seeking the ultimate in personalized service, gourmet dining, and elegant accommodations, these luxury cruise lines deliver exceptional experiences. With higher staff-to-guest ratios, all-inclusive pricing, and sophisticated ambiance, they offer a premium cruise experience.
Expedition & Adventure Cruises
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Lindblad Expeditions
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Hurtigruten
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UnCruise Adventures
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Ponant
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Atlas Ocean Voyages
For those seeking deeper exploration and adventure, these expedition cruise lines offer immersive experiences in remote destinations. With expert guides, educational programs, and vessels designed to access unique locations, they provide unforgettable adventures combined with comfortable accommodations.
River Cruise Experiences
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AmaWaterways
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Viking River Cruises
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Uniworld
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Avalon Waterways
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Tauck River Cruises
River cruises offer intimate, culturally immersive experiences along the world's most iconic waterways. With smaller ships, personalized service, and itineraries that explore historic cities and charming villages, river cruises provide a different perspective on destinations from Europe to Asia to Africa.
Cruise Tips & Insights
Expert advice for the best cruise experience
When to Book
For the best selection and pricing, book your cruise 9-12 months in advance, especially for popular itineraries like Alaska (which sells quickly) and holiday sailings. However, if you have flexibility, last-minute bookings (60-90 days before sailing) can sometimes offer excellent values.
Choosing Accommodations
Consider a balcony cabin for scenic destinations like Alaska or the Mediterranean, where private outdoor space enhances your experience. For Caribbean cruises, the decision depends on how much time you'll spend in your cabin versus public areas of the ship.
Shore Excursions
While cruise lines offer shore excursions, our privately arranged experiences often provide more authentic cultural connections, smaller groups, and better value. Book these early, as the most desirable experiences fill quickly, especially in popular ports.
Dining Strategies
Most cruise lines now offer flexible dining options, but we recommend making reservations for specialty restaurants early in your cruise. For group travelers, we can arrange private dining experiences that keep your group together while accommodating individual preferences.
Packing Essentials
Pack for both onboard activities and shore excursions, considering the climate and cultural norms of your destinations. Don't forget formal attire if your cruise includes elegant evenings, and remember that most ships offer laundry services for longer voyages.
Staying Connected
While most ships offer Wi-Fi, service can be expensive and sometimes unreliable. Consider purchasing internet packages in advance for better rates, or use your time at sea to disconnect and your time in port to connect using local services.
Let’s Work Together
Get in touch so we can start working together.
