Top Cyclades Islands Cruises & Sailing - page 3

There's so much to see in Santorini, but getting into the heart of the island can prove tricky. Save precious vacation time with this shore excursion, skipping long cable car lines with pickup directly from the port. Relax onboard a private, air-conditioned minibus as you head out to explore island highlights such as the villages of Oia and Fira, Perivolos Beach, and more. Timed to suit your ship's schedule, you're back onboard in plenty of time for depature, having thoroughly immersed yourself in Santorini's most charming spots.

Reaching Mykonos’ hidden coves and neighboring islands can be tricky by land. This catamaran cruise lets you explore the Aegean from the water, with stops to swim and snorkel around Rhenia and historic Delos, or along the southern beaches of Mykonos. In between swims, relax on deck and enjoy a freshly prepared Greek meal served on board, with beer and wine included.

Planning the perfect boat day around Milos can mean comparing tours, packing supplies, and worrying about what’s included. This all-inclusive catamaran cruise simplifies it. Sail in comfort to standout spots such as Kleftiko and the turquoise waters of Galazia Nera, with meals, drinks, and snorkeling gear provided on board. With everything arranged in advance—and even photos captured for you—you can fully relax and enjoy the coastline instead of managing logistics.

Explore Santorini's iconic blue domes, stunning caldera views, traditional villages, and volcanic beaches on a fully customized private tour. Choose 3-8 hours with your expert local driver/guide who helps craft the perfect itinerary based on your interests. Enjoy hassle-free hotel pickup and drop-off as you visit Oia's famous sunset, charming Pyrgos village, unique red and black sand beaches, historic sites, or renowned wineries—your choice.

If you’re seeking a luxurious way to see Santorini, look no further than this exclusive catamaran cruise—an extra-special way to explore one of Greece’s most picturesque islands. On a luxury sailing yacht, arguably the best mode of transport to explore Santorini, you’ll cruise to the Red Beach and stop at top swim and snorkel spots. Plus, unlimited alcoholic and soft drinks, hotel pickup and drop-off, and a Greek BBQ meal are included.

Leave the crowds on Mykonos behind and catch the wind with this sailing cruise to two nearby Aegean islands. Set sail from Tourlos Bay to the UNESCO-listed island of Delos to explore the ancient Greek ruins at your own pace. Then head to the island of Rhenia, with a stop to swim and snorkel in the crystalline waters. Relax over lunch on board, served with wine, beer, and soft drinks.

Discover a side of Santorini that few other visitors get to experience—and make exploring beyond the mainland easy—on this half-day tour. Look forward to visiting Santorini's unique volcanic landscapes, and head to two islets accessible only by boat. Sail to Nea Kameni to hike up to the crater of the active volcano (entry tickets own expense), and to Palea Kameni, where you can soak in natural hot springs.

Get views of Santorini from aboard a catamaran during this boat excursion. Sip unlimited beer, wine, and soft drinks while taking in glimpses of the island's beaches and volcanic landscape. Make stops at the White Beach, soak in some local hot springs, go snorkeling, and watch the sun dip below the horizon in Oia. Barbecue meal and hotel pickup and drop-off included.

Enjoy a seamless one-way transfer within Santorini with this private service. Enjoy a stress-free journey from start to finish with pickup from Santorini Airport (JTR), the ferry, or your hotel. Relax and take in the beauty of Santorini, knowing every detail of your transfer is carefully arranged.

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 a new perspective on the beaches, bays, and islands around Santorini—and enjoy a more personal sightseeing experience—on this small-group, half-day catamaran cruise. Jump offboard to swim and snorkel at the Red and White Beaches; take a dip in the volcanic hot springs; and tuck into a delicious BBQ lunch on-board. Pick between morning and afternoon departure times hotel pickup and drop-off is also included for your convenience.

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.

Step aboard Galatea, a traditional wooden gulet, and enjoy a full-day cruise to Blue Lagoon, Antiparos, and Despotiko. With a maximum of 25 guests, you'll experience a relaxed atmosphere away from the crowds while sailing through the crystal-clear waters of the Aegean Sea. Swim and snorkel in stunning turquoise bays, including the famous Blue Lagoon. At Despotiko, depending on sea conditions, you'll stop at the Temple of Apollo channel, the White Cliffs, or Livadia Beach. Enjoy freshly prepared sandwiches, a traditional Greek lunch made with local ingredients, and complimentary soft drinks, wine, beer, and ouzo. If weather or sea conditions prevent us from stopping at South Antiparos or Despotiko, we'll visit the beautiful bays of Agios Myronas and Agios Nikolaos instead, ensuring a safe and unforgettable experience.

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.

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.

Step aboard Agia Kali, a beautifully restored kaiki, for an intimate semi-private cruise of just 12–14 guests. Glide across turquoise waters to hidden coves and pristine beaches, swim and snorkel in ever-changing shades of blue, and savor a gourmet onboard lunch celebrating authentic Greek flavors. With attentive English-speaking crew, personalized routes, and the Cyclades’ natural beauty at every turn, this voyage blends sea, sun, and the heartfelt spirit of island life. This tour is exclusively designed and operated by Anemomylos Travel. When you book this experience, you are booking directly with the original creators and official provider — not a reseller. Our in-house team manages every detail, ensuring seamless coordination, direct communication, and consistently high service standards before and during your experience.

Experience the authentic side of Mykonos far from the crowds with this wine tasting at a traditional family farm. Enjoy convenient transportation directly to the estate near the village of Ano Mera, where a sommelier will lead you through a tasting of four island wines paired with local products. Learn about the history of Mykonian wine production while you sip the island’s distinct blends in the scenic countryside.

Combine a visit to Santorini's caldera and hot springs with a trip out to the island of Thirasia with this cruise. You'll start at Nea Kameni, a volcanic island, where you'll have time to walk around the island and swim in its hot springs. You'll the cruise on to Thirasia, where you'll have enough time to have lunch and explore before sailing back to Santorini.

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.

Spend an afternoon wine tasting with this small-group, chauffeured tour to three of Santorini's best wineries. Visit Arvanitis Traditional Canava, Artemis Karamolegos, and Estate Argyros in Episkopi Gonias, to sample delicious local wines without having to worry about driving back to your hotel afterwards. Wrap your tour up with the chance to watch the sun set over the sea.

Set sail aboard one of the most luxurious vessels in Santorini, the one-of-a-kind Ipanema 58 catamaran. On this tour, feel like a member of the jet-set as you cruise inside the caldera for a soak in volcanic hot springs, swim and snorkel at the island’s Red and White Beaches, and watch a famous Santorini sunset from the water (if later time selected). Relax on spacious deck lounges and be pampered by an attentive crew, who serve up a delicious Greek barbecue lunch.

Make the most of your time ashore with a sightseeing tour of Santorini’s most iconic villages and landscapes. Visit Firostefani, Finikia, Oia, and Megalochori before unwinding at the black sands of Perivolos Beach. With round-trip transfers from the cruise port and free time for photos, shopping, and swimming, this excursion balances guided sightseeing with independent exploration.

Simplify your time in Santorini and avoid the hassle of self-driving by taking a private, customizable day tour. Your guide is a local so can show and tell you things that you might otherwise miss. Visit the lighthouse, the monastery, the castle, lookout points, and many other beautiful spots. Learn more about Santorini while having fun.

Even if you only have a short time on Santorini, make the most of it on this private, fully customizable half-day tour with your personal driver-guide. Set your own pace to explore the sights that interest you most, from small villages to panoramic viewpoints, and avoid the hassle of planning logistics.