Top Cyclades Islands Cruises & Sailing - page 2

Explore the Aegean island of Milos on this sailing excursion. Enjoy a small group experience with up to 12 passengers that includes visits to Cape Vani, Kalogries Beach, and Agios Dimitrios bay. Check out the caves of Kleftiko and Sykia by dinghy, go swimming and snorkeling, and relax by the sea. Enjoy complimentary lunch, snacks, drinks, access to snorkeling equipment, and GoPro photos.

Our semi-private Mykonos sunset cruise offers the perfect blend of luxury, relaxation, and breathtaking scenery. Sail along the island’s famous southern coast, passing iconic beaches like Psarou and Super Paradise, while enjoying refreshing swims in crystal-clear waters. Onboard, indulge in a freshly prepared Greek ΒΒQ meal, featuring delicacies, salad, and authentic local flavors, paired with refreshing drinks. As the sun begins to set, experience the magic of the Aegean sky transforming into shades of gold, pink, and purple, creating a truly unforgettable moment. With a premium catamaran, expert crew, and intimate atmosphere, this is more than just a boat tour, it’s a once-in-a-lifetime Mykonos sunset experience. Book now and let the Aegean’s beauty take your breath away!

Skip crowded beaches and experience the Cyclades from the water on a traditional Greek kaiki (fishing boat) cruise around Antiparos and Despotiko. Swim and snorkel in clear blue coves, explore hidden sea caves, and relax on deck as you sail along the rugged coastline. A freshly grilled BBQ lunch with seasonal fruit and drinks is served on board, so you can settle in and enjoy an easygoing day at sea.

Visit Santorini on your own terms with a private guide by booking this fully customizable experience. You'll get the chance to visit beaches, villages, and scenic viewpoints in a private, air-conditioned vehicle. Your guide will help you create an itinerary that's best suited to your interests, or you can design one of your own.

Many of Milos’ beautiful beaches and snorkel spots are inaccessible by land. This half-day cruise is the answer. Zipping between beauty spots by speedboat means more time for snorkeling and exploration than if going solo or via bigger-boat excursions. Explore the Kleftiko and Sykia caves; take guided snorkels, snap photos, and swim at remote spots that many tourists miss. Refreshments, snorkel equipment, and drone and underwater photos are included.

Set sail on an adventure that combines history and relaxation. Cruise from Mykonos to Rhenia, admiring the sea views along the way, then explore the ancient ruins of the Archaeological Site of Delos on a guided tour. Take the opportunity to swim or snorkel in Rhenia’s turquoise waters. Everything you need is included: a freshly prepared Greek lunch, beverages, snorkeling gear, and floatation devices.

Santorini is one of the most popular Greek islands and you’ll discover why when you explore it during this private day tour. Whether you’re arriving via cruise port, airport, or are staying the night in town, receive round-trip transportation for this exciting tour that covers everything from the Red Beach and Santo Winery to the medieval village of Pyrgos and hillside town of Oia.

Designed for cruise passengers, this tour lets you explore Santorini without wasting time in long lines. Instead of waiting in the heat for the cable car, step onto our boat from your cruise ship’s tender and enjoy a scenic ride across the Aegean Sea with stunning views of the Caldera. Upon arrival, an air-conditioned bus will take you on a journey across the island. Your first stop is Finikia, where you can admire the blue-domed church and enjoy the peaceful surroundings. Next, visit Oia, Santorini’s most famous village, known for its whitewashed houses, boutique shops, and breathtaking caldera views. You’ll also visit Perivolos Black Beach, where you can relax by the water or enjoy a drink on the beach. At the end of your tour, skip the cable car lines once again as our boat takes you back to your cruise ship’s tender for a smooth and stress-free return.

A semi-private cruise, this trip takes you on a comfortable voyage around Paros and Antiparos, allowing you to avoid large crowds while still giving you the opportunity to meet new friends. Hop aboard your luxurious catamaran and set sail. Indulge in a delectable lunch featuring authentic Greek delights as you take in the scenery. Discover both Paros and its sister island, Antiparos, on this round-trip sailing adventure.

Semi-Private Cruise in Milos aboard the Raptor • Morning & Sunset Options • Explore Kleftiko, Sarakiniko & more on a luxury open-yacht • Open bar and meals included – Join a Small-Group Cruise in Milos aboard a luxury open-yacht with three curated route options across Milos, Kimolos, and Poliegos. Our cruises cover more coastline than you'll find on a typical day out. Our captain selects the best route for the day and confirms your meeting point 48 hours before departure. – Stops may be adjusted on the day based on conditions to ensure the best experience. Reserve your spot!

Discover Santorini’s most picturesque landscapes in a comfortable, air-conditioned minivan when you book this private sightseeing tour. Delve into Santorini's history, from cave houses to caldera cliffs, and explore highlights like Firostefani, the iconic village of Oia, and the Monastery of Prophet Elijah. Discover the local culture and traditions at Megalochori village and unwind at the vibrant Red and Perivolos beaches.

The strict itineraries of many tours mean you can end up missing sights you want to visit. On this private, flexible-duration tour, your local driver-guide will whisk you around Santorini with hotel and cruise ship pickup, taking care of navigation while you soak up the scenery. Visit famous landmarks, hidden gems, or enjoy the island like a local—this tour is completely customizable.

Discover the wonders of Delos on a half-day tour from Mykonos, where ancient history comes alive. With an expert guide, uncover the fascinating stories behind the temples, sanctuaries, and artifacts, and explore hidden highlights that you might otherwise miss. This immersive experience ensures you leave with a deep appreciation of the island’s classical treasures.

See the sights of Santorini without the hassle of self-driving when you take part in this group tour. Get around in a comfortable air-conditioned vehicle as you travel around the island’s highlights, including beaches, picturesque towns, and lookout points for lovely views of the Aegean Sea. Get an overview of Santorini's highlights even if you're short on time on this efficient tour.

Indulge in the ultimate day of fun in the sun on this full-day sailing trip to ancient Delos island, a UNESCO World Heritage Site. You also stop in scenic Rhenia Island for a refreshing swim and snorkeling session in sparkling, sun-dappled waters. A freshly prepared BBQ lunch is included, and you can upgrade to include door-to-door hotel transfers.

Avoid the challenge of piecing together scattered rural highlights on your own and experience authentic Naxos in a single, streamlined half-day tour. With hotel pickup included, travel effortlessly between cultural stops— wandering villages Chalki and Filoti and sampling locally produced olive oil and spirits, honey, and marmalades. It’s an easy way to connect history, craftsmanship, and village life without the logistics.

A small island with little by way of public transport, Mykonos takes time to get around. Skip the stress and see the essential sights even if you only have a short time in port on this guided half-day shore excursion with pickup from the terminal. Visit beautiful Kalafatis Beach, enjoy a walking tour of Mykonos Town, photograph the Mykonos Windmills (Kato Milli), admire Little Venice, see the 15th-century Church of Panagia Paraportiani, and more. Accompanied by a local guide, see hidden gems that many travelers miss, and gain insight you won't find in a guidebook.

This private, flexible sightseeing tour covers Santorini’s most spectacular sights with a guide. Travel in a comfortable vehicle between the locations of your choice and at your own pace. Choose to explore iconic villages such as postcard-perfect Oia, volcanic beaches and scenery, panoramic viewpoints, and more. This tour is well-suited to couples, families, friends, and multi-generational groups.

Upgrade your vacation photos in Santorini by booking a private professional photoshoot—and the iconic flying dress. Your photographer knows the best spots on the island for great views not swarming with tourists, and your dress rental (and private changing area) is included in the session, so you don’t have to worry about planning the look.

Enjoy a half-day cruise and discover the most beautiful places in Milos sailing on the West and South side of the island, exploring the caves of the famous old pirate bay of Kleftiko and discovering a part of the South side.

Santorini is no place to self-drive. Enjoy the sights without the stress on this to-the-point half-day tour, direct from your Santorini hotel. See cliff-top Oia and Megalochori villages, medieval Pyrgos, and sandy beaches, all without having to do any of the driving yourself.

Visit top sights along Santorini’s rocky coastline as well as two neighboring islands during this full-day sailing excursion. Enjoy a guided tour of the Santorini volcano, take a soak in the sulfur-rich hot springs of Palea Kameni, swim near the island of Thirassia, and watch the sunset just under the stunning village of Oia over dinner and wine.

Take a cruise out to the caldera of Santorini aboard a catamaran and spend some time checking out the island's colorful beaches with this tour. You'll have time to swim at Red Beach and soak in the hot springs at the caldera of Santorini, with time left over for swimming and an included lunch or dinner at Mesa Pigadia Beach.

Santorini’s most striking beaches and volcanic sites are best reached by boat—but planning separate trips to each spot can be time-consuming. This sailing cruise connects the island’s highlights in one relaxed day on the water. Visit dramatic shores such as Red Beach and White Beach, swim near the volcanic hot springs around Nea Kameni, and stop by Thirassia. Between swims, enjoy a traditional Greek meal served onboard as you cruise the Aegean.