Sailing from Fira offers travelers practical and memorable ways to experience Santorini’s stunning caldera. Most tours last 4-5 hours and depart from the old port, accessible by cable car or donkey path. Three standout options deserve special mention: The Panorama Winter Cruise works well for off-season visitors, offering heated cabins and clear winter views. The Sunset Fishing Trip combines local culture with dinner – you’ll help catch (and later eat) the fresh fish. For pure luxury, the Catamaran Caldera Cruise hits all the marks with its gourmet meal service and premium wines. Every cruise includes essential amenities: hotel pickup, snorkel gear, and knowledgeable local guides who know these waters well. Check out our favorite sailing tours below.
Key Points
- Private sailing cruises in Fira offer diverse options like Panorama Winter Cruise and Catamaran Caldera Cruise, with customizable experiences and luxury offerings.
- Catamaran cruises in Fira provide all-inclusive experiences with stops at natural wonders, such as Nea Kameni hot springs, and offer opportunities for swimming and snorkeling.
- Scenic cruises around Fira showcase iconic landscapes, including Akrotiri Lighthouse and Santorini’s hilltop villages, and feature stunning sunset views from locations like Oia and Vlychada.
- Culinary experiences on sailing excursions in Fira include gourmet meals with fresh seafood and meat, complemented by unlimited local Santorinian wines.
- Sailing experiences in Fira offer accessible amenities, such as round-trip hotel transfers, snorkeling gear, and wheelchair accessibility, providing great value for money.
From Fira: 3 Islands Sailboat Cruise With Hot Springs Swim
If you’re seeking a unique sailing adventure in Fira, the “From Fira: 3 Islands Sailboat Cruise With Hot Springs Swim” is a must-try experience.
This 5-hour tour takes you on a captivating journey across the Aegean Sea, visiting three picturesque islands. You’ll have the opportunity to swim in the renowned Santorini Caldera and enjoy the natural hot springs.
The cruise is highly rated, with 4.7 out of 94 reviews, and is priced at Kč 3,524 per person.
With pickup available and an optional audio guide, this sailing excursion provides a memorable way to explore Santorini’s stunning coastline and natural wonders.
Read our full review: From Fira: 3 Islands Sailboat Cruise With Hot Springs Swim Review
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Santorini: Luxury Full Day Private Sailing Cruise
For a truly unforgettable sailing experience in Fira, the “Santorini: Luxury Full Day Private Sailing Cruise” is an exceptional choice.
Lasting 5-6 hours, this private tour allows you to explore the stunning Santorini coastline at your own pace. Aboard a luxurious catamaran, you’ll enjoy a delectable meal, an open bar, and the opportunity to swim, snorkel, and soak in the breathtaking views of the caldera.
With pickup available, this cruise offers a personalized and exclusive way to experience the beauty of Santorini from the sea. At $115.62 per person, this luxury sailing adventure is an unparalleled way to make the most of your time in Fira.
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Luxury Yacht Cruises in Santorini Island
Indulge in the ultimate sailing experience on Santorini’s stunning waters with the island’s luxury yacht cruises.
Explore the enchanting Caldera and its iconic whitewashed villages from the comfort of a lavish catamaran. Enjoy a 5-6 hour excursion with gourmet meals, an open bar, and ample opportunities to swim, snorkel, and soak up the breathtaking views.
For a more personalized adventure, opt for a tailor-made private tour with a local guide. Capture the picturesque landscape during a photo shoot with a professional photographer.
Whether you’re seeking a romantic sunset sail or an unforgettable day on the water, Santorini’s luxury yacht cruises offer an unparalleled way to experience the island’s natural beauty.
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Santorini: Private Sailing Cruises (Day & Sunset)
Elevate your Santorini experience with a private sailing cruise, where you’ll learn about the island’s breathtaking landscapes and crystal-clear waters.
Choose from a range of options, including the Santorini Caldera: Panorama Winter Cruise, Santorini Sunset Fishing Trip, and Santorini: Catamaran Caldera Cruise, all with high ratings and excellent reviews.
For a luxurious experience, consider the Santorini: Luxury Catamaran Day Trip or the Santorini Gold Catamaran Cruise.
Customize your sailing adventure with private tours, buggy or quad bike rentals, and even a photo shoot with a professional photographer.
Whether you opt for a daytime or sunset cruise, you’re sure to create lasting memories on the Aegean Sea.
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Santorini: Catamaran Caldera Cruise With Meal and Drinks
Experience the captivating Santorini Caldera aboard a luxurious catamaran. This 5-hour cruise offers a delightful combination of sightseeing, swimming, and dining.
Explore the volcano, beaches, and iconic landmarks while enjoying free-flowing drinks and a traditional Greek meal. The catamaran features a spacious deck for sunbathing and a cozy dining area.
Amenities include snorkeling gear, Wi-Fi, and an open bar. With a starting price of $63.06 per person and free cancellation, this cruise provides excellent value.
Rated 4.7/5 by past guests, it’s a must-do activity in Fira, praised for its relaxed atmosphere, delicious food, and breathtaking scenery.
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Santorini: Catamaran Cruise With Greek BBQ and Drinks
Set out on a captivating catamaran cruise off the stunning Santorini coastline and savor a delectable Greek BBQ alongside free-flowing drinks.
This 5-hour experience offers panoramic views of the iconic caldera and a chance to swim in the crystal-clear waters. With a pickup option available, you’ll board the comfortable catamaran and enjoy a relaxing sail, stopping for a refreshing swim.
Indulge in a traditional Greek BBQ featuring an array of mouthwatering dishes, complemented by unlimited local wine and beer.
As the sun sets, soak in the breathtaking vistas of Oia’s famous cliffside villages. This highly rated tour is perfect for those seeking a luxurious and unforgettable day on the water in Santorini.
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Santorini: Semi-Private Sailing Cruise up to 15pax
Sail along the captivating Santorini coastline on a semi-private cruise limited to 15 passengers.
Enjoy the stunning views of the caldera, volcanic islands, and the famous Oia village as you cruise along the crystal-clear waters.
The 5-hour tour includes swimming, snorkeling, and a traditional Greek lunch with drinks.
With a rating of 4.7 from 196 reviews and priced at €119.28 per person, this shore excursion is a popular choice for those seeking a personalized sailing experience in Fira.
Upgrade your tour with a visit to a local winery for wine tastings, or opt for a sunset cruise to witness the breathtaking Santorini sunset.
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Santorini:Private Catamaran Tour With BBQ & Unlimited Drinks
For those seeking a luxurious and intimate sailing experience in Santorini, the Private Catamaran Tour With BBQ & Unlimited Drinks is an exquisite choice.
This 5-hour private tour whisks you away on a catamaran to picturesque spots, allowing you to swim and snorkel at two unique beaches.
Indulge in a delectable BBQ meal prepared onboard, accompanied by unlimited wine, beer, and soft drinks.
Enjoy the flexibility of choosing between a morning or sunset cruise, with the sunset option offering a stunning view of Oia village.
With round-trip hotel transfers, modern amenities, and an attentive crew, this tour promises an unforgettable Santorini sailing adventure.
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Santorini: Sailing Catamaran Yacht Cruise With Food & Drinks
Seeking an alternative to the luxurious private catamaran tour? Consider the Santorini: Sailing Catamaran Yacht Cruise with Food & Drinks.
Priced at €110 per person, this 5-hour excursion offers a range of highlights, from safety briefings at Vlychada Marina to swimming stops at Mesa Pigadia Beach and the Hot Springs.
You’ll enjoy a Greek BBQ meal and an open bar with local wine and beers. While the crew’s friendliness and meal quality receive praise, reviews note mixed feedback on the captain’s demeanor.
This tour may not suit those with visual impairments, motion sickness, or mobility issues.
With free cancellation up to 24 hours in advance, it’s worth considering for a memorable Santorini sailing experience.
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Sailing Into Sunset: With La Maia: Elegance & History at Sea
If you’re seeking a sailing experience that blends elegance and history, the Santorini: Sailing Into Sunset with La Maia tour may be the perfect choice.
This 5-hour catamaran cruise takes you on a journey through the stunning Santorini caldera, offering breathtaking views of the island’s iconic cliffs and the Aegean Sea.
You’ll enjoy a delicious meal and open bar, as well as the opportunity to swim and snorkel in the crystal-clear waters.
With pickup available and an optional audio guide, this small-group tour provides a luxurious and informative way to experience the beauty of Santorini from the sea.
Priced at Kč 1,510 per person, it’s a great value for the experience.
Read our full review: Sailing Into Sunset: With La Maia: Elegance & History at Sea Review
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Santorini: Motor Yacht Day Cruise With 5-Course Lunch
On the Santorini: Motor Yacht Day Cruise With 5-Course Lunch, you’ll embark on a 5-hour journey that showcases the island’s breathtaking landscapes and culinary delights.
Departing from Vlihada at 10:00 am, you’ll cruise past stunning red and white beaches, the Indian Head Mountain, and the Akrotiri Lighthouse, taking in panoramic views of the Caldera and Santorini’s hilltop villages.
Swim stops at the volcano and Mesa Pigadia provide opportunities to cool off, before indulging in a homemade 5-course lunch.
With all-inclusive amenities, from transportation to unlimited drinks, this experience offers an exceptional way to explore Santorini’s natural beauty and savor its flavors.
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Santorini Oia: Private Sailing Cruise With Meal & Drinks
While exploring the breathtaking island of Santorini, indulge in a private sailing cruise that showcases the stunning Oia sunset and the region’s captivating natural wonders.
Priced from $788.30 per group (up to 4 participants), this 5-10 hour experience includes a BBQ meal, unlimited drinks, and round-trip hotel transfers.
Enjoy the salty waters of volcanic islets, relax and sunbathe on the yacht, and witness Santorini’s iconic landscapes from the sea.
With the ability to modify the itinerary to suit your preferences, this private cruise earns a 5/5 rating for its exceptional service, delectable cuisine, and breathtaking scenery.
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Santorini: Private Sailing Cruise With Meal & Swim Stops
Enjoy Santorini’s captivating seascapes with a privately chartered sailing cruise that showcases the island’s natural wonders.
This 5-hour excursion aboard a luxury yacht offers stunning views of the volcanic caldera, thermal springs, and hidden coves. Savor a delicious 3-course meal with an open bar as you glide along the Aegean breeze.
Swim in the island’s famous volcanic bays, then relax and admire the sunset on an evening cruise. With complimentary transportation, snorkeling gear, and wheelchair accessibility, this private sailing experience is a must-do for your Santorini adventure.
Priced at $1,156.17 for up to 4 guests, it’s an unforgettable way to explore this stunning Greek island.
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Santorini: Cruise Catamaran With BBQ & Drinks Day or Sunset
Santorini: Cruise Catamaran With BBQ & Drinks Day or Sunset
Priced from €95 per person, this 5-hour cruise takes you sailing along Santorini’s stunning coastline.
Explore Nea Kameni hot springs, swim and snorkel at Red and White beaches, and capture scenic views of Akrotíri, Aspronisi, and Oia’s famous sunset.
The all-inclusive package covers round-trip transfers, Greek BBQ with unlimited Santorinian wine, snorkeling gear, and amenities like WiFi and towels.
Though not wheelchair-accessible, this cruise offers fantastic value with its range of activities and complimentary services.
Past guests rave about the friendly staff and overall experience.
Considering booking this memorable sailing adventure during your time in Fira.
Read our full review: Santorini: Cruise Catamaran With BBQ & Drinks Day or Sunset Review
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Private Sailing & Wine Tasting on a Sailboat With Sommelier
Sailing through the turquoise waters of Santorini while savoring the finest local wines is a captivating experience you won’t want to miss.
This private sailing tour offers an exclusive opportunity to taste 8 different Santorini wines, including the renowned Assyrtiko, Nykteri, and Vinsanto. Accompanied by a certified wine guide, you’ll enjoy a Greek menu prepared fresh onboard as you witness the breathtaking Santorini sunset.
The itinerary includes sailing past iconic beaches, entering the caldera, and swimming in the warm waters of the hot springs.
With personalized attention, private transportation, and complimentary amenities, this is a truly exceptional way to experience the beauty and flavors of Santorini.
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Santorini Catamaran Cruise With Swimming, Meal and Open Bar
For those seeking a more leisurely and inclusive Santorini sailing experience, the Santorini Catamaran Cruise with Swimming, Meal, and Open Bar offers an enticing option. Priced from $115.62 per person, this 5-hour excursion departs from the Old marina of Vlychada and includes stops at picturesque beaches, the Akrotiri Lighthouse, and the Santorini Volcano.
Passengers can enjoy swimming, snorkeling, and a delicious onboard meal featuring seafood, meat, and vegetarian options, complemented by an open bar. Roundtrip hotel transfers and equipment are provided, ensuring a hassle-free adventure.
With an impressive 4.9/5 rating from 24 reviews, this cruise promises an unforgettable way to experience Santorini’s stunning coastline and natural beauty.
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Santorini: All-Inclusive Private Luxury Catamaran Cruise
A luxurious private catamaran cruise offers an unparalleled way to experience the breathtaking sights of Santorini’s caldera. Priced from $1,471.50 for up to 4 participants, this 5-hour excursion aboard a Lagoon 42 catamaran includes pickup, an open bar, freshly prepared meals, and snorkeling gear.
Enjoy scenic views of the volcanic landscapes, swim in hot springs, and explore the island’s pristine beaches. With a live English-speaking guide, customizable itinerary, and free cancellation up to 24 hours in advance, this all-inclusive cruise provides a truly memorable and stress-free sailing experience in Santorini.
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Santorini: Catamaran Cruise With Lunch, Drinks, & Oia Visit
Explore Santorini’s stunning vistas and quaint villages aboard a comfortable catamaran cruise.
This 5-hour excursion offers an all-inclusive experience, with prices starting from $157.66 per person.
You’ll visit picturesque destinations like Ammoudi Bay, Thirassia Island, and the Santorini Caldera, while enjoying a delicious seafood, meat, or vegetarian meal, along with an open bar.
Snorkeling gear and safety equipment are provided, and you’ll have the chance to relax on the boat or take a dip in the crystal-clear waters.
With a maximum of 18 passengers, you can expect attentive service from the experienced crew, who’ll provide live commentary throughout the journey.
Don’t miss the chance to catch the stunning sunset at Vlychada.
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Santorini Oia: Caldera Catamaran Cruise With Meal & Drinks
Set out on a luxurious Santorini day cruise aboard a state-of-the-art catamaran, offering a captivating journey through the island’s iconic caldera.
Depart from one of 12 convenient locations and enjoy a morning of sunbathing, snorkeling, and a delicious BBQ meal. Savor fresh fish, chicken, or vegetable skewers as you take in the stunning views of Thirassia Island, Nea Kameni islet, and Ammoudi Bay.
With complimentary drinks, towels, and snorkeling equipment, this 4-hour cruise promises an unforgettable experience. Rated 4.7/5 by past travelers, the attentive crew and exceptional value make this the perfect way to explore Santorini’s captivating coastal beauty.
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Santorini: Private Yacht Cruise With Open Bar and Meal
Why not experience the beauty of Santorini from the comfort of a private yacht?
The Santorini: Private Yacht Cruise With Open Bar and Meal offers a 5-6 hour excursion with pickup available, an open bar, and a delicious meal. Rated 4.7 out of 5 stars, this private cruise allows you to explore the stunning Caldera at your own pace.
Sail along the volcanic cliffs, stop for a swim, and enjoy the breathtaking sunset over the Aegean Sea. At Kč 2,769 per person, this luxury experience is the perfect way to make the most of your Santorini visit.
Whether you’re seeking a romantic getaway or a memorable group outing, this private yacht cruise is sure to impress.
Read our full review: Santorini: Private Yacht Cruise With Open Bar and Meal Review
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The Sum Up
Fira, Santorini offers a variety of sailing experiences, from private luxury cruises to group tours. You can explore the stunning caldera, swim in natural hot springs, and enjoy meals and drinks on board. Whether you prefer a catamaran, yacht, or sailboat, there’s an option to suit your needs and budget. The best way to experience the breathtaking beauty of Santorini is from the sea.