Explore Popular Destinations

Travel to popular destinations in the Caribbean, Central America and North America. Plan your perfect trip or vacation today.

BVI

Island hop your way around the Caribbean with direct flights to the British Virgin Islands, to discover a haven of coastal luxury in locations such as St Barts, Saint Martin and Anguilla.

Aspen

Visit one of the most luxurious mountain towns in the United States.

Vancouver

Experience city life in one of Canada's most vibrant west-coast locations.

Hamptons

Take a break from city life and explore peaceful nature in The Hamptons, known as a summer destination for affluent New York City residents.

Miami

Miami shines with stunning beaches, diverse culture, and vibrant nightlife.

Las Vegas

Las Vegas dazzles with iconic entertainment, fine dining, and vibrant nightlife.

Experiences

Cayman Private Aviation connects you to the most sought-after experiences and events in North America and the Caribbean. Passengers can enjoy seamless, luxurious travel to world-class destinations tailored to your passions and interests.

Sports & Entertainment

F1 Miami Grand Prix
Experience the electric atmosphere of Formula 1 against the vibrant backdrop of Miami. From luxury paddock lounges and waterfront yacht parties to exclusive soirées in South Beach, the city comes alive with speed, style, and spectacle. Feel the adrenaline as the world’s best drivers take on the circuit — where racing meets Riviera glamour and every moment is charged with excitement.

Concerts & Music Festivals
From Coachella’s desert magic to private performances in Miami, Los Angeles, or New York, the world’s most iconic stages await. Experience headline acts, exclusive lounges, and backstage moments that turn live music into a once-in-a-lifetime affair.

Tennis & Golf Championships
Witness the world’s top athletes in action at legendary tournaments like Wimbledon, The Masters, or the US Open. Pair world-class competition with refined leisure — from champagne hospitality to bespoke itineraries designed around each event.

Arts & Culture

Art Basel Miami
Immerse yourself in the energy of the world’s most influential art fair, where creativity meets high society. From private gallery previews to exclusive after-parties along Miami Beach, every moment celebrates innovation and expression. Experience the vibrancy of contemporary art, design, and culture — all against the backdrop of palm-fringed glamour and oceanfront luxury.

New York Fashion Week
Step into the pulse of haute couture and global style. From front-row seats at runway shows to private fittings and rooftop soirées, Fashion Week in New York is where elegance and artistry collide. The city buzzes with designers, models, and tastemakers — and every detail, from your stay to your wardrobe, becomes part of the statement.

Cirque du Soleil Las Vegas
Experience the magic of Cirque du Soleil in the entertainment capital of the world. From the aquatic elegance of O at Bellagio to the electrifying energy of Michael Jackson ONE and the sensual artistry of Zumanity, each production is a masterpiece of movement, light, and sound. Step into a world where imagination has no limits, where every performance captivates the senses and transforms an evening in Las Vegas into something extraordinary.

Gastronomy & Wine

Napa Valley Vineyard Escapes
Immerse yourself in the romance of California’s wine country, where rolling vineyards meet golden sunsets. Indulge in private tastings, chef’s table dining, and vineyard picnics among the vines. Whether it’s a romantic getaway or a weekend with friends, Napa Valley offers an exquisite blend of fine wine, gourmet cuisine, and timeless serenity.

Food Festivals in Miami
Celebrate the vibrant flavors of Miami at world-renowned culinary events like the South Beach Wine & Food Festival. Savor dishes inspired by the city’s many cultural influences — from Latin American to Mediterranean — all served with ocean views and a touch of coastal glamour. Each bite captures the spirit of Miami’s energy, diversity, and unmistakable style.

Aspen Food & Wine Classic
Experience the pinnacle of culinary sophistication in the heart of the Rockies. The Aspen Food & Wine Classic brings together top chefs, sommeliers, and tastemakers for an elevated weekend of gourmet pairings, mountain views, and alpine luxury.

Adventure & Relaxation

Ski Trips to Western Canada
Embrace the thrill of fresh powder and alpine luxury in the Canadian Rockies. Whether it’s carving through Whistler’s pristine slopes, soaking in Banff’s natural hot springs, or heli-skiing the untouched terrain of Revelstoke, every moment blends adventure with elegance. Après-ski in style with mountain-view chalets, private spa treatments, and fireside dining under the stars.

Island-Hopping Adventures
Explore the Caribbean’s most enchanting destinations, each more breathtaking than the last. Dive into the turquoise shallows of Turks & Caicos, swim alongside the famous pigs of the Exumas, or unwind on the secluded beaches of Anguilla. Every island offers its own rhythm — from barefoot luxury to vibrant local culture — creating an unforgettable journey across paradise.

Wellness Retreats of the West
Find balance and renewal in some of North America’s most tranquil settings. From the red rock sanctuaries of Sedona to the mineral-rich hot springs of Colorado, wellness takes on a new dimension in nature’s embrace. Indulge in sunrise yoga overlooking mountain peaks, sound healing beneath open skies, and personalized spa rituals that restore both body and mind.

Luxury Escapes

Private Villas
Gather your closest friends or family for an unforgettable group retreat or celebration in a breathtaking Caribbean villa. Arrive in style with Cayman Private Aviation and unwind in total privacy, surrounded by turquoise waters, panoramic views, and five-star service from the moment you land.

Spa Retreats
Rejuvenate your mind and body at some of the world’s most serene wellness destinations — from the red rock tranquility of Sedona to the coastal calm of Malibu. Let Cayman Private Aviation whisk you away for a restorative escape where luxury meets wellbeing.

Romantic Escapes
Whether it’s a weekend in Harbour Island or a private honeymoon retreat in the Grenadines, Cayman Private Aviation ensures your getaway begins the moment you take off. Enjoy bespoke touches, champagne service, and ultimate privacy in the skies.

Golf & Leisure Escapes
Tee off at championship courses in the Cayman Islands, the Bahamas, or coastal Florida. Whether it’s a golf tournament or a private golf weekend, travel with your clubs and companions in comfort and style.

What Our Clients Say

We want to commend Roger and the team at Cayman Private Aviation on the excellent service they provided us with flying private both to and back from Palm Springs, California this past month!

Not only were they most competitive in pricing, the planes and crew each time were perfect!

We are really impressed with their ability to accommodate us flying private!

We are confirmed repeat customers.

Stephanie & John

Thanks so much to the entire Cayman Private Aviation team for making the charter to Cayman so easy for me and the dogs.

The flights (both the jet and the helicopter) couldn’t have been better. Everything ran exactly as planned without any hitches or stress. From the admin through to the actual flights, customs and pet paperwork on arrival into Cayman. The Cayman Private Aviation team were all extremely flexible, responsive and anticipated all issues which might arise. They even suggested a slightly different routing which I had not thought of but which made my journey much easier!

There was never a moment, from making the initial booking until arrival at final destination, when it did not feel that the CPA team was entirely on top of everything – which is not always the case when chartering. You turned what would normally be a tedious and stressful journey into a pleasurable experience!

I look forward to travelling with you again!

Thanks for everything.

Peter H.

The flight was really smooth and extremely pleasant. Thank you once again for your attention and assistance throughout.

Marie B

Our Aircraft

The Learjet 60 XR offers a range of up to 2,405 nautical miles, connecting Cayman to top destinations across North, South and Central America, and the Caribbean with ease and efficiency.