Why settle for one dreamy island when you can experience several? After all, the opportunity of a lifetime should be ceased in the lifetime of the opportunity. For affluent travelers with an appetite for comfort, culture, and spontaneity, island hopping is the best way to explore the world, bar none.
With the help of a well-curated plan and the right travel partners, you can skip the crowds and move from one paradise to another, embracing one stunning shoreline at a time.
Affluent travelers beach and island guide
Why island hopping is the ultimate flex
Trends come and go, but life-changing and perspective-altering memories are forever. Island hopping just so happens to fall into that category. It is more than a travel trend; it gives you the freedom to explore, indulge, and relax, completely on your own terms. Fancy starting your day in a chic villa in Mykonos and ending it with sunset drinks in Corsica? That’s not a pipedream. It’s a reality and entirely possible.
While the islands may be close, their experiences offer something new: a private cove here, a Michelin-starred lunch there, and maybe even a spontaneous beachside massage. It’s uncertainty without the anxiety. Expectation with all the excitement. Island hopping is fast-paced and fun without stress. The key is an itinerary that’s tailored to your preferences with just a hint of enough adventure to broaden your horizons.
Dream Routes affluent travelers will never forget
Enough waffle and curtain raising. Here are four luxe island-hopping routes that deliver big on beauty, cuisine, and unforgettable moments. Each delights the senses in its own way.
Related: Car rental on Santorini Island
Mediterranean marvels
If you own a smartphone with any social media app, you’ve been exposed to the grandiose beauty of Greece’s whitewashed villages. But how about extending your travels with an island-hopping excursion? You could feel the sand between your toes in Mykonos before exploring Santorini’s glittering coastline, iconic views, and volcanic landscapes, or adventure across to Corsica for its rugged allure with a few sun-soaked yacht days in between. Each island has its own charm.
Sharing the view with other tourists in Fira, Santorini
Tropical time in Southeast Asia
A hop, skip, and jump across the Philippines, Indonesia, and Thailand will give you your golden ticket to the perfect tan on some of the world’s most beautiful beaches.
In the Philippines, explore the crystal-clear lagoons of Palawan and the stunning white-sand beaches of Boracay. Thailand offers a bustling social scene, with Phuket’s nightlife and the serene islands of Koh Samui. A fan favorite among digital nomads, Indonesia’s Bali has a host of surf-friendly shores, the pristine Gili Islands, and the legendary Komodo National Park. It’s safe to say your Southeast Asia postcard will be the envy of all your friends.
Caribbean calling
The Caribbean offers a string of gems to rescue you from the monotony of daily US life with virtually no hassle. You’ll be spoilt for choice with 100 inhabited islands and countless transport options, including cruise ships, yachts, ferries, and private speedboats.
Island hop to St. Barts, a popular celebrity destination or consider Anguilla. It’s a tranquil haven with quiet coves and peaceful beaches to explore. Other popular destinations include the British and US Virgin Islands and Aruba and Puerto Rico. The Caribbean offers laid-back living with a premium touch from beaches to bars and restaurants.
Malta, your best-kept secret
Malta has indescribably beautiful views. It also has two small neighbors that often fly under the radar—Gozo and Comino.
If subtlety and relative solitude pique your interest, you’ll want to remember what follows. A trip to Gozo can take a mere 20 minutes by ferry. There, you can take in panoramic views from Victoria, and, for the more courageous, go snorkeling and wildlife watching in Dwejra on the west coast. A further 20 minutes from Gozo, you’ll arrive at Comino. Two words: Blue lagoon. Think glistening blue waters and silky-fine sands.
Affluent travelers guide
Private jet = pure freedom
Part of the magic of island hopping is the ease with which you can move from one island to the next. It’s not supposed to be hard work. It’s simply not the time to play the waiting game on your time away from the daily grind. That’s where a carefully selected private jet charter comes in. Skip the ferry queues, avoid the connection chaos, and fly direct—on your schedule and guilt-free.
Working with an experienced broker means you can land closer to your destinations, travel with just your crew, and enjoy total privacy from takeoff to touchdown. It’s smooth, fast, and fully tailored, which is exactly how island hopping should feel.
What to book, eat, and do at each stop
Half the fun of this experience is deciding what to do. Here’s a little cheat sheet to keep close and on your radar:
- Stay smart: Go for private villas, boutique resorts, or ultra-luxe eco retreats with standout service.
- Dine like royalty: From fresh-caught seafood on the beach to world-class chefs preparing a meal just for you—each island brings something delicious.
- Live in the moment: Book a private yacht for a day, take a guided cultural tour, or unwind with a custom spa treatment. You’re on island time now.
Quick tips for a breezy trip
Just a few things to keep in mind so everything runs smoothly:
- Pack well, pack light: Think breezy resort wear, your favorite sandals, and skincare that’s kind to the ocean.
- Use a concierge: Let someone else handle the details. You have one job—stay in vacation mode.
- Travel smart: Shoulder seasons (right before or after peak months) offer great weather and a more relaxed vibe. You’ll also avoid any suffocating crowds.
Affluent travelers cheers
A parting thought
If you’ve made it this far, you likely have itchy fingers and feel all but ready to click your way to your first or next island-hopping getaway. Remember, it’s a chance to turn your vacation into a personal highlight reel. Each destination brings a new view, a new flavor, and a fresh reason to celebrate.
And when you have the flexibility of a private jet charter and the comfort of custom planning, the whole journey feels effortless. Wherever you go, go in style—and make every island your own.
Adventure on!
