Oia Sailing trips & boat tours

Our most recommended Oia Sailing trips & boat tours

Santorini: Luxury Small Group Catamaran w/ Meal & Open Bar

1. Santorini: Luxury Small Group Catamaran w/ Meal & Open Bar

Drop anchor on a luxury catamaran tour around the Santorini caldera while enjoying a delicious traditional meal with refreshing drinks from the open bar. Sail in the morning or at sunset on a cruise with a maximum of 20 guests. After being picked up from your hotel, unwind as you’re taken straight to the port. Take advantage of the snorkeling opportunity with a half-hour stop off the coast of Red Beach, plus 1.5 hours to snorkel in the sea caves of White Beach. Bathe in the lagoon’s hot springs and snorkel in clear waters. Taste the flavors of Greece on board a menu of local Santorini delicacies for lunch or dinner, depending on the time of day you choose, with meat and vegetarian options. The menu includes barbecue skewers, dolmadakia (rice-stuffed vine leaves), Greek salad, and other local dishes. Sit back and unwind with a post-meal cocktail and music. Stay refreshed with unlimited drinks on board, including local white wine, Greek beer, and soft drinks. Continue past the two uninhabited volcano islands of Palia Kameni and Nea Kameni and take in other sights such as Aspronisi island and the Akrotiri lighthouse. Later the cruise sails in the caldera below the town of Fira and past the old port. If you chose the late afternoon option, stop below the village of Oia and be wowed by the striking sunset lights adorning the skies with vibrant, pastel colors. This is sure to be an unforgettable highlight to an already unforgettable cruise experience. At the end of your Santorini excursion, relax as your minibus driver conveniently drops you back at your hotel.

Santorini: All-Inclusive Luxury Catamaran Small Group Cruise

2. Santorini: All-Inclusive Luxury Catamaran Small Group Cruise

Explore the clear Mediterranean waters of the Santorini Caldera on a brand new Lagoon 450 catamaran. Make 2 swimming and snorkeling stops, then feast on a barbecue meal.  Once out on the water, the first stop of the tour will be a 30-minute visit to Red Beach, so named for its bright sand. After some relaxed swimming and great snorkeling, get back aboard the sailboat and continue to White Beach, featuring equally striking rock colors and more excellent swimming and snorkeling.  After swimming, the crew members will serve a delicious barbecue meal onboard. From there, take some time to take in the views from the beach before sailing past the beautiful uninhabited islands of Aspronissi and Akrotiri.  The tour's last stop will be at the hot springs for 30 minutes of relaxation, with the chance to go for a soak in the springs. The tour finishes at the port where you'll board a minibus for a transfer.

Santorini: Catamaran Cruise with Meals and Drinks

3. Santorini: Catamaran Cruise with Meals and Drinks

Be driven to the luxury catamaran and take a 5-hour cruise off the coast of Santorini. Hop aboard the catamaran and explore Santorini from the water on this relaxing cruise adventure. Choose from the daytime or evening option, and feast on delicious food as you go. Experience the beauty of the island as you set sail from the southern port of Vlychada. Follow the coast to the red sands of Red Beach. Take a swim in the shallow waters of a private beach.  Venture below the Indian Rocks and marvel at the sea caves and rock formations close to an old Venetian lighthouse. Admire the volcanic landscape as you travel through the middle of the caldera. Visit the hot springs for a healing mud bath before going to a private bay at Palea Kammeni Island. For the sunset option, journey out to open waters after dinner and watch a magnificent sunset in the middle of the Aegean Sea. Then, sail back to port, where a driver will wait to take you back to your hotel.

Santorini: Premium Catamaran Cruise with Fresh BBQ & Drinks

4. Santorini: Premium Catamaran Cruise with Fresh BBQ & Drinks

Climb aboard the 74-foot Ocean Voyager or the 80-foot Tahiti catamaran for a 5-hour cruise around Santorini in the Aegean Sea. Set off on a journey of discovery that will first take you to the hot springs, then the Red Beach, and finally the White Beach. Swim and snorkel and tuck into a delicious meal onboard. Start your adventure with a comfortable hotel pickup and set sail for beautiful Red Beach to swim and snorkel for 30 minutes. Continue to a secluded White Beach, only accessible from the sea, for more swimming and snorkeling in the shadow of the towering white cliffs. Onboard the catamaran, savor a barbecue supper of salads and grilled meat and veggie options. Continue sailing inside the crescent-shaped Caldera, close to the volcano, and enjoy a final dip in the Hot Springs, before sailing back to Oia as the day ends with a spectacular sunset.

Santorini: Private Catamaran Cruise with BBQ Meal and Drinks

5. Santorini: Private Catamaran Cruise with BBQ Meal and Drinks

Explore the shores of Santorini on this cruise from Ammoudi Bay. Admire sights like Indian Rock and the Venetian Lighthouse. Have the option to choose between a sunset tour with dinner or a day tour with lunch. Sip on delectable local wine with your meal. Sail in a comfortable catamaran to the warm therapeutic waters of the volcanic hot springs. Head towards Aspronissi Island and pass by the Indian Rock formation and the 19th-century Venetian Lighthouse. Stop at Mesa Pigadia which is next to the unique White beach. Indulge in a Greek barbecue lunch or dinner and pair your meal with fine regional wines. Dive into the dazzling waters of the famous Red Beach and capture pictures of its reddish sand.

Santorini: 5-Hour Sunset Cruise with Greek Meal and Drinks

6. Santorini: 5-Hour Sunset Cruise with Greek Meal and Drinks

End the day on the romantic island of Santorini with a 5-hour cruise around the coast of the caldera. Set sail across the Aegean Sea and experience the volcanic landscape from a fresh perspective. Swim and wallow in a mud bath, and then sail to the southern part of the island to swim and snorkel off the White Beach. Climb aboard for a meal of chicken chops, Greek salad, pasta salad, bread, and other traditional appetizers. Then, make your way to Red Beach for 30 minutes of free time to swim, snorkel, or laze in the sun. Along the way, avail yourself of the unlimited Greek wine, beer, or soft drinks, and have your camera ready to get a shot of the sunset.

Santorini: Luxurious Catamaran Cruise with Meal & Open Bar

7. Santorini: Luxurious Catamaran Cruise with Meal & Open Bar

A mini bus will take you from your hotel to Ammoudi port, where you will board one of the newest vessels of the fleet. Sail to Santorini's famous hot springs and swim for half an hour. Continue beyond Aspronisi Island, Akrotiri, the Indian rock and the Ancient lighthouse to reach the next stop at the Red Beach, where you can swim and snorkel for another half an hour.  Sail to the White Beach area in a 1.5 hour cruise and enjoy a barbecue feast before another round of swimming, snorkeling or relaxing on board the catamaran. Return to Ammoudi and, if enjoying the sunset tour, experience the sunset from the sea.

Santorini: Catamaran Caldera Cruise with Meal and Drinks

8. Santorini: Catamaran Caldera Cruise with Meal and Drinks

Enjoy the spectacular beauty of the Caldera and the beautiful Santorini sunset, while sailing with a luxury catamaran. Select from the Day Cruise or Sunset Cruise options which both offer a unique chance to admire Santorini’s beauty, sailing through the deep blue waters of the island. Start your Day Cruise journey from the old port of Ammoudi and head to Thirassia Island, a fishermen’s island ideal for swimming and admiring the unique view of Manolas village. Explore the unmanned volcanic beaches or sunbathe on the deck. Feel the energy of the volcano while heading to the hot springs. Sail towards the Black Mountain and the big light house south of the Caldera, as you head to the White Beach and the Red Beach for a swim when anchored, a delicious lunch is served onboard with wine and dessert. The Sunset Cruise begins with a stop at the Red Beach for a refreshing swim and stops at all the same locations as the Day Cruise. On the Sunset Cruise, enjoy dinner with wine and dessert served onboard.

Santorini: Caldera Private Power Catamaran Cruise

9. Santorini: Caldera Private Power Catamaran Cruise

Take a private cruise to discover the beautiful volcanic landscape of Santorini’s caldera. Benefit from the services of an experienced captain, who will personalize the tour to suit your needs. Choose either a 3, 4, or 5-hour cruise to fit with your schedule.  After pickup at your hotel, board a Fountaine Pajot 35 Highland 35 Pilot, a catamaran, ideal for families, couples, or small groups. Explore the Santorini coastline taking in caldera views and passing the islets of St. Nicolas and Agii Eftapedes. Stop at the volcanic hot springs for a 30-minute swim. Continue to Thirasia, a small island formed in recent centuries by volcanic activity. Explore the unique beauty of the underwater world by snorkeling or simply soak up the sun onboard the deck. Enjoy a delicious BBQ meal with the 4 and 5-hour options, or Greek appetizers with the 3-hour cruise. Make the most of an open bar and relax with a drink of wine, beer, ouzo, or soda. On the way back, admire the volcanic coastline before disembarking at Ammoudi Bay, to board a vehicle for the return transfer to your hotel.

Santorini Caldera: Panorama Winter Cruise

10. Santorini Caldera: Panorama Winter Cruise

Enjoy a unique winter sailing experience in the Caldera of Santorini, visiting this sea area’s highlights but also admiring the beauty of the magnificent sunset. This area remains an all-seasons spectacular snapshot, providing incredible views of the sunset. The cruise route starts from the port of Vlychada, passing by the red and white beach. You will take a short stop at Black Mountain, before sailing close to the lighthouse south of the Caldera. Afterwards, you will be directed to the hot springs of the volcano. Your next stop will be in Thirassia, where the lunch will be served. Continuing towards the port of Ammoudi, you will have the opportunity to enjoy the spectacular views of Oia. From here you will begin your return route, stopping to browse inside the Caldera and taking in beautiful views of Fira. Your trip culminates with an amazing sunset shot, before re-entering the port of Vlychada.

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What people are saying about Oia

Overall rating

4.6 / 5

based on 3,615 reviews

Our catamaran tour was everything we'd hoped it would be. With a small group of travelers (9 of us in total) we had plenty of room to mingle if we desired or find a spot to keep to ourselves on the boat. Our boat was in excellent condition, the crew were very kind & attentive, all our wants & needs were met. The lunch was divine & HUGE. We are thrilled that we booked this & highly recommend it to any other Santorini visitors.

Perfect cruise, boat is very nice and decorated with lots of seating options. Drinks really are unlimited and my glass was never empty. Would skip on the snacks part as it was not the nicest, just wait for dinner at a restaurant. Can’t recommend this enough.

Fabulous from start to finish. From the very fun bus journey when collected (especially when they have to free fall backwards to go to the port !) to the beautiful meal and stunning sunset . The crew on board were so friendly .

Very helpful and friendly staff! The boat was comfortable, the views were fantastic, and the food was delicious. Highly recommend this boat experience!

The food was great, the tours was great and the staff was very friendly. I'd highly recommend this tour!