The Cyclades by Sea in Santorini, Paros & Mykonos

Your journey begins in Santorini, which is accessible through the island’s airport or a five-hour ferry ride from Athens. This is where whitewashed villages perch above the Aegean on the rim of a volcanic caldera, and the island remains one of Greece’s most captivating destinations. Following check-in at Mystique, a Luxury Collection Hotel, your arrival day unfolds at an unhurried pace. Upon arrival, settle into Mystique and spend the afternoon easing into the rhythm of Cycladic life. For ultimate ease, we recommend lunch at Charisma Restaurant on-property, where Mediterranean dishes are shaped by Santorini’s volcanic soil—tomatoes grown in mineral-rich earth, capers from cliffside vines, freshly caught seafood, and olive oil-driven plates that reflect the island’s agricultural heritage.  

As the caldera darkens, the cliffs of Oia set the tone for your Grecian adventure.  

The remainder of your day is intentionally relaxed, with time to unwind by the infinity pool or explore the pathways leading toward Oia by foot. As evening approaches, cocktails are served at Lure Bar, positioned directly above the caldera, where the light shifts across the volcanic basin in deep gold and rose tones. If you prefer to stay on property for a truly laid-backarrival day, dinner unfolds at Mystique’s signature restaurant, Lure, which is rooted in contemporary Greek cuisine. Dishes highlight line-caught fish, local herbs, and Cycladic staples reinterpreted with restraint rather than excess, paired with wines from Santorini’s indigenous Assyrtiko grapes. As the caldera darkens, the cliffs of Oia set the tone for your Grecian adventure.

Today, Santorini reveals its many layers as you explore the cultural traditions and geological forces that have shaped the island. Start the morning with a leisurely walk around Oia, where winding pathways, blue-domed churches, and whitewashed homes seem to tumble toward the sea. Along the way, discover charming cafes like the micro-bakery Phyllon, boutiques like Kisira Concept Store, and spectacular viewpoints before arriving at the 15th-century ruins of Oia Castle. Midday is all about savoring local flavors with lunch at Melitini, a tucked-away taverna in Oia’s backstreets that serves Greek tapas-style plates and is known for its unfussy approach and loyal local following.

Then, take a thirty-minute drive via private car to Fira for a privately guided experience led by an archaeological scholar, offering deeper insight into the civilizations that once flourished across the Cyclades to further enrich your time on the island. During your afternoon tour, head to the Kykladitisses exhibition at the Archaeological Museum of Thera. There, you’ll learn about the women, mythology, artistry, and daily life that shaped ancient Aegean society. End the day with dinner at Niki, a Fira staple with sweeping views of the coast, before taking your private car back to Mystique.  

Spend a restful morning at Mystique, taking in everything the property has to offer. Start with a yoga session in the island’s morning air, before enjoying a slow breakfast. After, get a massage and facial at Elios Spa, rejuvenating your body as you continue your Greek adventure.

Sailing beneath towering caldera cliffs, you’ll pass lava formations, secluded coves, and dramatic volcanic landscapes accessible only by sea

In the afternoon, you have options. For those interested in Santorini’s wine culture, a private tasting can be arranged at one of the island’s historic wineries, where indigenous grape varieties continue to be cultivated using techniques passed down through generations.  If you’re seeking to soak up more sun, board a private catamaran booked by your SmartFlyer travel advisor and experience Santorini from the water. Sailing beneath towering caldera cliffs, you’ll pass lava formations, secluded coves, and dramatic volcanic landscapes accessible only by sea. Have dinner prepared by the private chef aboard your catamaran, or have your vessel drop you off at Armeni Fish Tavern, a waterside restaurant only accessible by sea. The setting is minimal and elemental—wooden tables directly above the water, boats arriving with the daily catch, and a menu built entirely around whatever has been pulled from the Aegean that morning. 

This morning, depart Santorini and continue north through the Cyclades toward Paros on a private boat transfer. For centuries, these waters served as important trade routes connecting island communities throughout the Aegean, and the two-hour journey offers a glimpse into the seafaring traditions that continue shaping life across the region. Upon arrival, transfer to Cosme, a Luxury Collection Hotel, and settle into idyllic accommodations.  The property is situated in Naoussa, a harbor town that has evolved from a humble fishing village into one of Greece’s most sought-after island destinations while retaining much of its original character.

Spend the afternoon at leisure before venturing into Naoussa’s streets. Wander through whitewashed alleyways lined with artisan boutiques, galleries, and cafés before reaching the harbor, where colorful fishing boats still dock alongside waterfront restaurants. As evening falls, return to Cosme, a Luxury Collection Resort, Paros, for dinner at Vrosi, the on-property restaurant that highlights regional Parian recipes, slow-cooked meats, locally sourced fish, and traditional island specialties reinterpreted with a contemporary touch. Set against the shoreline just outside Naoussa, the meal will unfold with the Aegean as a backdrop, embracing the relaxed atmosphere that defines life on Paros.

While Paros is admired for its beaches, today’s journey ventures inland to discover the traditions, architecture, and creative spirit that continue to define the island. Your private guide will first take you to Lefkes, the island’s former capital and one of the Cyclades’ beautiful mountain villages—a thirty-minute drive inland from Naoussa. Built away from the coast to protect residents from pirate raids, Lefkes flourished during the nineteenth century and is still a showcase of marble-paved lanes, neoclassical homes, flowering courtyards, and sweeping views across the countryside. The village also reflects Paros’ longstanding connection to marble, a material once exported throughout the ancient world and used in celebrated sculptures, including the Venus de Milo.

…historic churches, traditional cafés, and local workshops give a glimpse into daily life away from the coastline.

Continue through the villages of Marpissa and Marmara, where historic churches, traditional cafés, and local workshops give a glimpse into daily life away from the coastline. Along the way, enjoy a private visit to a local artist studio and see how the island’s distinctive light, landscapes, and history still inspire contemporary creative work. Following an unhurried lunch at a traditional taverna, return to the coast for an afternoon at leisure. Gather for a glass of local Parian wine at the hotel’s Circe Bar, which offers excellent views of the sunset. For an elevated dinner experience, your SmartFlyer travel advisor can secure you a table at Stilvi Paros, an outdoor restaurant in the heart of Naoussa known for its modern Mediterranean cuisine, atmospheric lighting, and carefully crafted cocktails that make for a full evening.  

Few experiences capture the spirit of the Cyclades quite like a day on the water. This morning, board your private yacht and set out to explore the islands from the perspective that has connected them for centuries. Cruise along Paros’ rugged coastline before continuing toward neighboring Antiparos, a small island known for its laid-back atmosphere and hidden beaches. Along the way, stop to swim in secluded bays where crystalline waters reveal the rocky seabed below. Midday, anchor in a quiet cove for a private chef-prepared lunch served onboard. The menu is set to feature fresh seafood, seasonal produce, and local specialties, offering a relaxed opportunity to experience the flavors of the Aegean surrounded by uninterrupted sea views. The afternoon is yours to sink into the bliss that only a boat day can provide.

Return to Cosme in the early evening to get ready for dinner, and if you’re up for it, head to Naoussa for a final stroll through town. As lanterns illuminate the harbor and locals stand along the waterfront, settle in for dinner overlooking the marina at Barbarossa, which remains one of the most iconic tables on Paros. Known for its waterfront setting right on the harbor and a menu centered on refined Greek seafood dishes served just steps from the marina, it’s the perfect way to end your time on this mesmerizing island.

After breakfast, continue your island-hopping journey to Mykonos. Historically an important stop for merchants and sailors traveling throughout the Aegean, the island has long balanced its maritime heritage with an outward-looking, cosmopolitan spirit. Upon arrival via a private thirty-five-minute boat ride, transfer to Santa Marina, a Luxury Collection Hotel situated on a private peninsula overlooking Ornos Bay, and spend the afternoon settling into your surroundings, enjoying the sea, the resort’s private beach, or a quiet swim in the bay.

…an ideal introduction to the island’s celebrated dining and nightlife culture…

As the sun begins to set, make your way to the iconic Buddha-Bar Beach Mykonos, the island’s original outpost of the internationally acclaimed Buddha-Bar brand and one of its defining waterfront destinations. As part of the Santa Marina property, you will have special access to the best seats in the house. Set directly on the shoreline, the venue pairs panoramic sunset views with resident DJs, signature cocktails, and an Asian-Mediterranean menu featuring dishes such as sushi, sashimi, robata-grilled seafood, wagyu, and vibrant Greek ingredients reimagined through Pacific Rim flavors. As dusk gives way to evening, the music gradually builds, and the atmosphere shifts from a relaxed beach club to one of Mykonos’ signature social scenes, making it an ideal introduction to the island’s celebrated dining and nightlife culture before the short five-minute walk back to your suite at Santa Marina for the night.

After several days of exploration, today offers an opportunity to take a slower pace and delight in the simple pleasures of island life. Begin with an unhurried breakfast overlooking the sea at Elais, Santa Marina’s Mediterranean terrace. Your relaxed breakfast can start as early as eight or as late as eleven o’clock—whatever suits your pace best. Spend the morning at the Oasis Pool, diving into that book you’ve been carrying around for the entire trip. The day unfolds without an agenda, inviting you to swim, read, linger over lunch, or simply appreciate the rhythm of the Aegean. In the afternoon, enjoy a tailored wellness experience at Gingko Spa, drawing inspiration from traditions of rest and renewal that have long been part of Mediterranean culture. As evening arrives, gather for cocktails and dinner overlooking the waterfront. The atmosphere is lively yet laid-back, granting you the chance to enjoy Mykonos at its most effortless.

It’s the kind of party that will make your time on the island memorable long after your tan fades. 

While Mykonos is often associated with its lively beach scene, today’s exploration starts with a richer connection to the island’s history and culture. Begin with a morning of leisure. Choose to enjoy a private boating excursion, a game of tennis, or simply spend time beside the pool taking in the views across Ornos Bay. After lunch overlooking the water, take a guided walk through Mykonos Town, where narrow whitewashed lanes were originally designed to confuse pirates who once tried to breach the island’s shores. You’ll explore some of the 60 churches in town (and nearly 600 on the whole island)—standouts include Agia Kyriaki, with its red-painted domes, and the historic Panagia Paraportiani.

Then, stop in designer boutiques like Luisa and Inasami and local galleries like Lifeline Art Studio and Rarity Gallery tucked among the town’s iconic architecture before continuing to the famous windmills that overlook the harbor. Your tour will conclude in nearby Little Venice, which offers a symbol of the island’s historic ties, with colorful balconies that extend directly over the sea. Gather for a farewell dinner at the iconic Interni Mykonos, just a fifteen-minute drive from Santa Marina. It’s the kind of party that will make your time on the island memorable long after your tan fades. 

Enjoy your final Grecian breakfast overlooking the Aegean. Depending on your onward travel plans, Santa Marina’s complimentary transfer service will escort you to Mykonos Airport for your international departure or to the port for a ferry connection to Athens or another Greek island.  As you leave Mykonos, you’ll depart having experienced three distinct expressions of the Cyclades—from Santorini’s volcanic caldera and Paros’ village traditions to Mykonos’ dynamic coastal culture—each connected by remarkable journeys across the Aegean Sea.