Fira, perched high above Santorini’s volcanic caldera, is as much a gateway to stunning sea views as it is a lively hub of cafes, shops, and sunset watchers. But for those craving a truly memorable way to experience the island’s legendary waters, sailing is the answer. With options ranging from luxurious private charters to lively group excursions, Fira offers a sailing experience for every type of traveler. We especially like the Santorini: Caldera Luxury Catamaran Cruise with Meal & Drinks for its balance of comfort and activity, and the Private Motor Yacht for those seeking exclusivity and speed.
Whether you prefer snorkeling at volcanic hot springs, watching the sunset from a sleek yacht, or enjoying a full-day adventure with local wine and a Greek BBQ, Fira’s sailing experiences cover all bases. The key is choosing one that fits your style, budget, and schedule — so read on to find the perfect match.
Quick Overview
Our list features a variety of sailing options, including luxury private yachts, group catamaran tours, and semi-private day cruises. They range from 3-hour jaunts to full-day excursions, with some offering all-inclusive meals and customizable routes. For an intimate experience, the Luxury Private Cruise with Lunch or Dinner stands out, while families or small groups might prefer the Semi-Private Day & Sunset Cruise. For a quick, thrilling ride, the High-Speed Modern Yacht is hard to beat. Now, let’s explore each in detail.
1. Santorini: Caldera Luxury Catamaran Cruise w/ Meal & Drinks
This 5-hour luxury catamaran cruise is a top choice for those seeking comfort, variety, and stunning scenery. It includes snorkeling at Nea Kameni’s sulfuric waters, swimming off Red and White Beaches, and enjoying a BBQ onboard. The itinerary offers a mix of swimming, sightseeing, and relaxing with music, all while sailing past famous landmarks like the Akrotiri Lighthouse.
What makes this tour special is its flexibility — you can sunbathe, snorkel, or just marvel at the sunset. The onboard meal, paired with drinks, enhances the experience, making it a good value at $147 per person. The reviews highlight the quality of the experience, with a 4.9/5 rating from 233 reviews. Travelers love the mix of activities and the chance to see Santorini from a different perspective.
Bottom line: This cruise is ideal for travelers seeking a relaxed yet activity-filled day with excellent food and plenty of time to soak in the caldera’s beauty.
2. The Fastest All Inclusive Private Motor Yacht in Santorini
If privacy and speed are your priorities, the Private Motor Yacht is a fantastic choice. This 3-5 hour cruise in a brand-new 2023 yacht offers a high-end experience, with stops at the Black Beach, Red Beach, and Thirasia Island. Sailing past the Venetian Lighthouse and Indian Rocks, you get a front-row view of Santorini’s iconic coastline.
What makes this option stand out is the personalized service — the entire experience is tailored to your preferences, including swimming in sulfur-rich hot springs and exploring Thirasia Island. Though it’s more expensive at $536 per person, reviews for this tour are glowing, citing flexibility and attentive crew as highlights. The captain and crew are praised for their friendliness and ability to exceed expectations, making it perfect for couples or small groups wanting ultimate exclusivity.
Bottom line: Best suited for travelers who value privacy, luxury, and a custom itinerary, and don’t mind splurging for a top-tier experience.
3. Caldera Private Cruise with Luxury Fjord 52 Motor Yacht
For those dreaming of a luxury cruise in the caldera, this 5-hour private cruise aboard the Fjord 52 Motor Yacht is hard to beat. It’s an elegant way to see Santorini’s volcanic landscapes with the comfort of onboard amenities. The trip includes stops at Red and White Beaches, snorkeling at Black Mountain, and exploring the volcanic caldera from a truly privileged vantage point.
Guests rave about the exclusivity and style of the experience, which costs $2,258 for up to four people. The tour’s highlights include spectacular photos of the volcanic landscape, snorkeling opportunities, and a chance to relax in style. The vessel’s size and amenities ensure a smooth, luxurious ride. This is best suited for travelers wanting to indulge in elegance and privacy, with plenty of opportunities to swim and enjoy the volcanic scenery.
Bottom line: This tour offers an upscale, intimate experience for small groups or couples who want to combine adventure with luxury.
4. Santorini: Full Day Catamaran Cruise with BBQ & Drinks
Spending a full 11 hours on a catamaran is a fantastic way to explore Santorini’s waters in depth. This full-day cruise from Vlichada Marina includes swimming at Red Beach, White Beach, and Nea Kameni, along with a wine tour at Thirassia Island’s local winery. The itinerary is packed with stops for swimming, snorkeling, and sightseeing, plus a Greek BBQ onboard that’s perfect for hungry travelers.
The highlight is the opportunity to explore lesser-visited spots like Thirassia for 90 minutes, enjoy the sunset, and relax with drinks in hand. It’s suited for travelers who want an immersive day on the water, combining sightseeing with cultural experiences. Priced on request, the value is clear considering its length and inclusiveness. Travelers mention the magnificent sunset as a key feature, making it ideal for those who want to see Santorini in full daylight and twilight.
Bottom line: Perfect for those who want to combine a full day of swimming, sightseeing, and local culture with excellent food and a laid-back vibe.
5. Santorini: High-Speed Cruise on a Sleek, Modern Yacht
For thrill-seekers or those short on time, the 5-hour high-speed cruise offers a fast-paced, exciting ride around Santorini’s caldera. This sleek, modern yacht slices through the water at impressive speeds, giving you plenty of scenic vistas like Red and White Beaches, the volcano, and Thirassia Island, all from a dynamic perspective.
Including snorkeling at Black Mountain and a visit to the hot springs, this cruise balances adrenaline with relaxation. The itinerary emphasizes sightseeing at key volcanic sites, with a focus on efficiency. Travelers appreciate the modern vessel and the ability to see many highlights in a shorter period, making it a great option for active travelers or those on a tight schedule.
Bottom line: A high-energy, fast-paced experience ideal for adventure lovers who want a comprehensive tour in half a day.
6. Santorini: Luxury Private Sailing Cruise Experience
This 5-hour private sailing cruise is perfect for those wanting a bespoke experience. You can choose to sail in the morning with lunch or in the evening with dinner, enjoying the spectacular sunset. The route includes stops at Red and White Beaches, volcanic hot springs, and Thirassia Island, with ample time for swimming and snorkeling.
What sets this tour apart is its flexibility — your private crew will tailor the experience to your preferences, including a three-course meal or dinner and an open bar. The reviews are stellar, praising the personal touch and the quality of the onboard food. It’s best suited for couples, honeymooners, or small groups seeking an intimate, luxurious escape.
Bottom line: If privacy and customization are your priorities, this cruise delivers a truly memorable day on the water with gourmet dining.
7. Santorini: Private Sailing Cruises (Day & Sunset)
Offering day and sunset options, this private sailing cruise is designed for exclusivity. Over five hours, you’ll visit spots like Red and White Beaches, Thirassia Island, and the volcanic hot springs, all while enjoying a relaxed, personalized experience. The tour includes swimming, snorkeling, and a variety of onboard amenities, including food, drinks, and the chance to see Santorini’s famous sunset.
The private nature of this tour makes it ideal for romantic couples or small groups seeking a bespoke experience. Guests praise the attentive crew and the ability to customize the route, with flexible options for meals and stops. Pricing varies, but the focus on privacy and tailor-made experiences makes it a worthwhile investment.
Bottom line: Perfect for those who want a private, customized sailing adventure with exceptional views and flexibility.
8. Santorini: Semi-Private Sailing Cruise Day & Sunset/max 15 p
This semi-private cruise offers a more intimate experience for groups of up to 15 people. Over 5 hours, you’ll explore the highlights like Red and White Beaches, snorkel in volcanic waters, and visit Thirassia Island. The boat provides a relaxed environment, with plenty of space for sunbathing and socializing.
Reviews highlight the friendly crew, the beautiful sunset, and the well-organized itinerary. It’s ideal for travelers who want a small-group vibe without the cost of full privatization. The tour balances sightseeing, swimming, and cultural experiences, making it a good choice for couples or small groups wanting something more personal.
Bottom line: A great option for small groups wanting a semi-private experience with the flexibility of a group tour.
9. Santorini: Catamaran: private cruise with food & drinks
This private 5-hour catamaran cruise is perfect for couples or small groups. Captain and host handle all the details, from anchoring at scenic spots to preparing a Greek buffet onboard. The boat approaches hard-to-reach caldera spots and offers ample swimming and snorkeling opportunities.
Guests mention the personalized service and the delicious onboard meal as key highlights. The tour’s flexibility allows you to select your preferred route, making it ideal for those wanting a tailored experience. At $1,004 for up to two people, it’s a more affordable private option for an intimate day at sea.
Bottom line: A flexible, personalized, and comfortable small-group experience with a focus on good food and scenic exploration.
10. Santorini: Private Catamaran Tour with BBQ & Unlimited Drinks
For ultimate privacy and relaxation, this 5-hour private catamaran includes a BBQ onboard and unlimited drinks. You can choose the route or let the captain customize it, visiting beaches and volcanic sites while enjoying your meal and beverages. Transfers from hotel to marina are included for convenience.
Guests describe the experience as memorable, emphasizing the BBQ, the scenic views, and the peaceful atmosphere. This tour is perfect for small groups or couples celebrating a special occasion, with plenty of time for swimming, snorkeling, and soaking in the sunset.
Bottom line: Best suited for those looking for a private, all-inclusive experience with delicious food, drinks, and personalized service.
How to Choose Your Sailing Experience in Fira
When selecting a sailing tour, consider your budget, time, and what kind of experience you seek. Want a luxurious, private day? The Luxury Private Sailing Cruise is ideal. Looking for an active, fast-paced ride? The High-Speed Cruise checks that box. Traveling with family or a small group and craving intimacy? The Semi-Private Sailing Cruise is a great fit.
Pricing varies widely, from around $147 for the group cruise to over $2,200 for ultra-luxury private yachts. Book early, especially in peak summer months, to secure your preferred date and experience.
Final Thoughts
Santorini’s sailing tours offer a fantastic way to see the island’s volcanic beauty from the water. Whether you’re after a romantic sunset, a full-day adventure, or a private yacht experience, there’s a tour here to fit your style and budget. For most travelers, a group cruise provides excellent value, but if privacy or luxury are your priorities, splurging on a private cruise can make all the difference. Remember to consider your physical comfort, preferred activities, and how much you want to relax vs. explore.
No matter which tour you pick, these experiences will give you a new appreciation for Santorini’s wild volcanic landscapes and shimmering waters. Early booking is recommended; these tours fill up quickly, especially during high season. So, plan ahead and get ready for a memorable day on the Aegean Sea.