Luxury Holidays to Santorini & Mykonos
Two Icons. One Extraordinary Escape.
Santorini and Mykonos are the crown jewels of the Aegean — two islands, each with its own rhythm, beauty, and brand of luxury. Together, they create a holiday that blends relaxation, celebration, and soul-stirring views.
From Santorini’s volcanic cliffs and whitewashed elegance to Mykonos’s vibrant beach clubs and bohemian spirit, these Cycladic islands offer a dreamlike setting for a luxury getaway. Whether you're watching the sunset from your infinity pool in Oia or dancing barefoot at a private Mykonos beach villa, every moment is crafted with style. Awake & Wander designs bespoke Greek island holidays that combine the romance of Santorini with the electric charm of Mykonos—tailored for couples, friends, and style-savvy travellers looking to experience the best of both.
A Small Selection of our Latest Offers to Santorini & Mykonos
These latest offers have been generated through our online booking system which is powered by our sister company , Jamie Wake Travel, and using our handpicked suppliers.
Prefer a more personal touch? We're always here to tailor your journey—simply get in touch and let us create the perfect luxury holiday to Santorini & Mykonos for you.
Effortless Arrivals to Your Aegean Escape from the UK
Direct flights from the UK to Santorini (JTR) and Mykonos (JMK) operate frequently from London and regional airports, with flight times around 4 hours. Many travellers choose to begin in one and transfer to the other via luxury ferry or private speedboat, which Awake & Wander can coordinate seamlessly. Helicopter transfers are also available for those wishing to travel in elevated style. We handle everything—from airport fast-track and VIP lounge access to island-hopping itineraries that maximise your time and comfort.
When to Travel: Chasing Sunsets and Cycladic Summer
The best time to visit Santorini and Mykonos is from May to October, with the peak summer months (June to September) offering the full Greek island experience—sun-drenched days, warm evenings, and a lively atmosphere. May and October are ideal for a more peaceful escape, with pleasant temperatures, fewer crowds, and excellent light for photography. Whether you're after the buzz of Mykonos nightlife or the serenity of Santorini’s caldera views, Awake & Wander will time your trip to suit your pace and style.
The Top 4 Unforgettable Experiences and Things to Do in Santorini & Mykonos
These islands promise more than pretty views—they offer experiences that inspire, indulge and surprise. Here are four luxurious highlights to elevate your Aegean escape.
1
Watch the Sunset from a Caldera-View Suite in Santorini
Santorini’s famed sunsets live up to the hype—especially when viewed from your own private infinity pool in Oia or Imerovigli. Stay in a luxury cave suite carved into the cliffside, complete with champagne service, spa treatments, and total seclusion. As the sky turns gold and the lights twinkle across the caldera, you’ll understand why Santorini remains one of the world’s most romantic destinations. Awake & Wander secures the finest boutique stays for an unforgettable retreat.
2
Sail the Aegean and Explore Hidden Gems on a Private Catamaran
Charter a private catamaran to explore hidden beaches, volcanic hot springs, and iconic coastlines from the sea. In Santorini, sail past the red and white beaches and into the caldera itself. In Mykonos, cruise to the uninhabited islands of Delos and Rhenia for swimming, snorkelling and lunch in a secluded bay. Your crew handles every detail—gourmet meals, open bar, sun-loungers and music—making it a carefree day of sun, sea, and Aegean luxury.
3
Experience Mykonos Nightlife with a VIP Twist
Mykonos is known for its vibrant nightlife, but with Awake & Wander, it’s experienced in absolute comfort and style. Begin with cocktails at Scorpios or Nammos, dine at a table overlooking the sea, and end your night with VIP access to a private beach party or elite club, complete with bottle service and discreet transfers. Prefer a quieter vibe? We’ll curate a more relaxed evening of fine dining, hidden bars, and golden-hour views over Little Venice.
4
Explore Ancient Delos with a Private Archaeologist
Step away from the glamour and into the birthplace of Apollo with a private guided tour of Delos, one of the most important archaeological sites in Greece. Located just off Mykonos, this sacred island reveals ruins of temples, mosaics, and amphitheatres dating back thousands of years. Your personal guide will tailor the experience to your interests, offering context and storytelling that transforms stones into legends. It’s a fascinating cultural interlude during your beach-chic escape.
Why Santorini & Mykonos Are the Perfect Luxury Pairing
Santorini and Mykonos are yin and yang—serenity and energy, romance and revelry, tradition and trend. Together, they offer a luxury escape with range and rhythm: from spa days and sailing to sunset dining and cultural discovery. You can wake to peace and end your day in celebration—or vice versa.
For honeymooners, these islands offer picture-perfect romance. For friends and couples, they provide stylish backdrops and indulgent experiences. And for seasoned travellers, they deliver all the charm of the Greek islands with an elevated edge. With Awake & Wander, your time in Santorini and Mykonos is not just beautiful—it’s seamless, bespoke, and completely unforgettable.
