Syros Tours in May 2027
Planning for a trip to Syros during May? We offer 10+ tour packages to Syros departing in May 2027 that have 30+ customer reviews. Operated by our hand-picked, qualified travel experts, you will experience the best of Syros on your May holiday.
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Select from 10+ tours
Ever wondered what it’s like to wake up to the turquoise waters of the Cyclades? The "Sailing Greece - Santorini to Santorini" tour is designed for experienced travelers seeking a blend of moderate activity and pure relaxation. Over 10 days, you’ll cruise aboard a state-of-the-art 57 ft yacht, navigating the legendary islands of Ios, Mykonos, and Syros. Each day brings opportunities for hiking, snorkeling, and unwinding on sun-drenched decks.
Savor fresh seafood in taverna-lined harbors, explore ancient archaeological sites, and sample local ouzo for a true taste of Greece. This tour package stands out for its intimate island-hopping by luxury yacht, offering a unique perspective on the region’s beauty, culture, and cuisine.
10 days
Set sail through the sparkling Northern Cyclades with the "Sailing Greece - Mykonos to Athens" tour. Designed for experienced travelers, this eight-day moderate-activity journey whisks you from vibrant Mykonos to historic Athens via Syros and other enchanting islands. Enjoy the thrill of sailing on a top-tier 57 ft yacht, with plenty of time for hiking, snorkeling, or relaxing under the Grecian sun.
Guided by expert skippers, you’ll navigate deserted bays, explore archaeological wonders, and indulge in local seafood. This tour package’s standout feature is the balance of hands-on sailing experiences and cultural immersion, creating an unforgettable voyage across the Aegean.
8 days
Cruise through Greece’s dazzling Cyclades with the "Sailing Greece - Mykonos to Mykonos" tour package, a 10-day sailing adventure designed for experienced travelers seeking both relaxation and discovery. Set sail from Mykonos, exploring lesser-known gems like Syros and Ios alongside iconic Santorini. Whether you’re lounging on sun-kissed beaches, wandering age-old ruins, or sampling craft brews at a local microbrewery, every day is shaped by the whims of the wind and the expertise of your skipper aboard a modern 57 ft yacht. Witness the legendary windmills of Mykonos and bask in the awe-inspiring caldera views as you glide into Santorini. This sailing tour provides the perfect balance of leisure, exploration, and cultural highlights, all with the comfort of included accommodation, transport, meals, and a small group setting. The standout feature? The freedom to explore the Cyclades’ best spots at your own pace, guided by local insight and the ever-changing Aegean breeze.
10 days
Dreaming of island-hopping the Cyclades? The "Sailing Greece - Athens to Mykonos" tour is an eight-day moderate-activity adventure for experienced travelers seeking a mix of relaxation and discovery. Board a modern 57 ft yacht in Athens, sailing through Syros before arriving in glamorous Mykonos.
Unwind on deck in the Mediterranean sun, explore ancient ruins, or dive into local seafood at waterfront tavernas. With an experienced skipper steering you through hidden bays and famous sites alike, this tour package shines with its blend of hands-on sailing and authentic Greek charm.
8 days
If the call of the Greek isles is irresistible, the Sail Greece: Mykonos to Santorini adventure delivers eight days of sailing, sunbathing, and exploring. This trip charts a course through Cyclades, Syros, Amorgos, Naxos, Ios, and beyond, offering travelers the chance to swim in turquoise waters, relax on golden beaches, and delve into the myth-laden villages along the way.
Moderate activity keeps the pace upbeat but not overwhelming. Savor the flavors of local cuisine, bask in spectacular sunsets, and enjoy the hospitality of the Greek islands before falling asleep to the gentle rocking of your yacht.
The unique selling point of this tour is its seamless blend of relaxation, cultural exploration, and the ever-changing scenery of a true sailing adventure. For those who want to experience the best of the Cyclades by sea, this tour package is a dream come true.
8 days
From the Parthenon’s timeless columns to the sun-kissed beaches of Santorini, the "Best of Greece" tour lets you experience the full spectrum of Greek wonders in 15 easy-paced days. This cruise and land adventure winds from Athens’ historic marvels to the mythic sites of Delphi and Meteora, and onwards to the olive groves and idyllic beaches of the Cyclades. Along the way, discover the passionate Greek zest for life—expressed through food, music, and warm hospitality. The unique selling point is a comprehensive itinerary that blends both mainland and island highlights, ensuring travelers sample the full flavor of Greece’s ancient legacies and vibrant modern culture.
15 days
Sun-kissed islands, ancient ruins, and crystalline waters—could there be a better way to explore Greece? The "Athens to Santorini" tour lets you discover the magic of the Cyclades over 8 leisurely days, beginning in the vibrant capital and culminating on the cliffs of Santorini. Glide across the Aegean Sea by local ferry, stopping at Syros, Delos, and other storied destinations.
This easy-paced tour package is perfect for those looking to immerse themselves in Greek culture and scenery without the rush. Uncover hidden archaeological sites, unwind on remote beaches, and soak in the relaxed island lifestyle. With comfortable hotel stays, included transport, and meals, you’ll enjoy a seamless journey through iconic and lesser-known gems alike.
A highlight of this trip is the balanced blend of sightseeing and free time, allowing you to savor every moment—whether that’s exploring ancient temples or watching a Santorini sunset. Ideal for travelers of all ages, especially those seeking a gentle yet enriching adventure, this tour stands out for its authentic island-hopping experience and stunning variety of landscapes.
8 days
If you dream of unraveling ancient legends while basking on sun-drenched shores, the "Highlights of Turkey & the Greek Islands" tour is your perfect getaway. Over 15 days, travel from Istanbul to Santorini, weaving through Turkey’s storied ruins and Greece’s idyllic islands. Visit Ephesus and the sacred island of Delos, blend bustling city life with tranquil beaches, and indulge in culinary delights that will spark friendly debates over which country serves the best fare.
This easy-paced city sightseeing tour seamlessly balances guided excursions with free time to explore, relax, or dive into local culture at your own rhythm. Marvel at romantic towns, vibrant markets, and world-class historical sites, all while cruising between destinations that have captured imaginations for millennia.
The unique selling point? A carefully curated blend of culture, history, and beachfront relaxation—plus the chance to compare, firsthand, the charms of two legendary Mediterranean cultures in a single, unforgettable tour package.
15 days
Picture yourself cruising the cerulean waters of the Cyclades—this Greece Sailing Adventure offers a ten-day island-hopping tour from Santorini, weaving through Amorgos, Ios, Mykonos, and other gems of the Aegean Sea. Travelers can expect a blend of relaxed yachting, regular swims in turquoise bays, and insider access to ancient towns and lively beachside hotspots.
Guided by a knowledgeable local, you’ll enjoy the freedom to explore secluded coves, indulge in fresh seafood, and sip local wines as sunsets paint the horizon. The trip’s moderate activity level keeps the pace lively—perfect for those seeking a balance of exploration and relaxation, with opportunities for snorkeling, walking tours, and cultural immersion.
What sets this sailing tour apart is its seamless blend of adventure and local flavor, ensuring every day reveals a new facet of Greek island life. If you’re after a trip that combines iconic destinations with the spontaneity and comfort of life at sea, this package is your ticket to an unforgettable Mediterranean escape.
10 days
Travel from the Adriatic to the Aegean on the Dubrovnik to Santorini tour, a 22-day adventure through the Mediterranean’s most captivating towns, beaches, and islands. Begin with a tour of Dubrovnik’s enchanting old city, then follow the Dalmatian coast to Montenegro and onward through Albania and Macedonia’s hidden gems. In Greece, relax in provincial Syros and revel in the sun-soaked delights of Mykonos and Santorini.
The tour’s easy activity level makes it accessible to a wide range of travelers, while the itinerary delivers a perfect mix of history, scenic beauty, and culinary discovery. Enjoy legendary landscapes, taste local cuisine, and experience the welcoming spirit of each destination.
The unique selling point is its comprehensive sweep through the Mediterranean’s best, blending iconic sites with lesser-known treasures for a trip package that captures the region’s essence.
22 days
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