Fira isn’t just the bustling heart of Santorini; it’s also the perfect starting point for some of the most memorable sailing experiences in Greece. With its panoramic views, dramatic cliffs, and proximity to volcanic hot springs, Fira offers a natural playground for sea lovers. We especially love the Catamaran Caldera Cruise with Meal and Drinks because it combines scenic beauty with a well-organized itinerary and friendly crew. Plus, you get to snorkel in clear waters and soak in the volcanic hot springs, making it a well-rounded choice for travelers wanting both relaxation and adventure. For a more luxurious experience, the Luxury Catamaran Cruise with Meal & Drinks offers a premium morning cruise with a gourmet BBQ onboard. If you’re after a private, high-end option, the Private Motor Yacht takes you around in style, with customizable routes and ultimate comfort.
In this guide, we’ll walk you through 11 of the best sailing experiences in Fira, detailing what makes each unique and helping you decide which one fits your style and budget. Whether you’re after a laid-back day of swimming and sunbathing or a sunset cruise with fine dining, there’s something here to match your mood.
1. Santorini: Catamaran Caldera Cruise with Meal and Drinks
At number 1, this 5-hour catamaran cruise offers a classic Santorini experience. It’s highly rated at 4.6/5 from over 1,100 reviews, which speaks to its popularity and quality. The trip features a delicious BBQ meal, unlimited drinks, and stops at iconic spots like White Beach, Red Beach, and Mesa Pigadia. You’ll sail close to the volcano and swim in the hot springs — an essential part of any Santorini trip. The crew is known for being attentive, and the relaxed vibe allows plenty of time for photos and sunbathing. The cruise also includes hotel transfers, making logistics hassle-free.
Unique highlights include passing the imposing caldera, exploring volcanic beaches, and ending the day with a lively staff dance session aboard. It’s perfect for first-timers wanting a comprehensive yet laid-back day on the water. The reviews rave about the friendly staff, plentiful food, and the opportunity to capture fantastic photos. The value—around $68 per person—makes it an accessible choice for most travelers.
Bottom line: This cruise balances scenery, comfort, and local flavor, making it an excellent all-round option for most visitors.
2. Santorini: Day Luxury Catamaran Cruise with Meal & Drinks
For those seeking a more upscale experience, the Luxury Catamaran Cruise is a perfect pick. At just 4 hours and rated 4.7 out of 5 from 62 reviews, it offers a refined atmosphere with a focus on comfort. The cruise features snorkeling at Thirassia Island and the volcano, along with a sumptuous BBQ meal including fresh fish and handmade skewers.
This tour emphasizes relaxation, with ample time to sunbathe and enjoy music while taking in the picturesque surroundings. The itinerary includes multiple stops for swimming and sightseeing, all from the comfort of a sleek yacht. The higher price—about $135 per person—reflects its premium quality, but many travelers say the crew’s attention to detail and the food’s freshness justify the cost.
It’s ideally suited for couples or travelers who want a stylish, less crowded experience without sacrificing the scenic highlights. The main drawback might be its shorter duration for those wanting a full day at sea.
Bottom line: An elegant, well-organized cruise for those who prefer comfort and quality over quantity.
3. Santorini Catamaran Cruise with Swimming, Meal and Open Bar
At number 3, this 5-hour small-group tour offers intimate sailing with an emphasis on personalized service. It’s rated an impressive 4.9 from 28 reviews, which shows how much travelers appreciate its attention to detail. You’ll cruise around the caldera, enjoying views of the Akrotiri Lighthouse and Vlychada Marina. The highlight is swimming and snorkeling at Red Beach and Thirasia island, with a delicious onboard meal and open bar.
What makes this trip special is its smaller size, allowing for a more relaxed atmosphere and more interaction with the crew. The boat’s route is carefully selected to maximize swimming opportunities and scenery. The reviews note the “approachable and friendly” staff and the quality of the food, which is prepared onboard. Cost at $124 per person offers good value, especially for the intimacy and personalized experience.
Ideal for travelers wanting a more exclusive feel, this cruise balances adventure with comfort, making it great for couples or small groups.
Bottom line: If you prefer fewer people and a chance to customize your experience, this small-group cruise is hard to beat.
4. Santorini: Catamaran Cruise with Lunch, Drinks, & Oia Visit
Number 4 on our list is the 5-hour cruise that combines sailing with a visit to Oia, rated 4.9/5 from 14 reviews. It’s perfect if you want to combine sailing with exploring the iconic village of Oia, famous for its sunsets. The tour includes stops at Red Beach, Thirasia, and the volcanic hot springs, with the option to snorkel and swim. Onboard, enjoy a delicious meal and drinks, all while cruising in a cozy, well-organized group.
What sets this tour apart is its focus on both the water and the land. You get time for a guided tour of Oia, plus the boat experience, making it ideal for travelers who want a taste of island life and scenic sailing in one trip. The reviews praise the “delicious onboard meal” and the “amazing route,” especially noting the opportunity to swim in the hot springs.
At $145 per person, it’s a slightly higher-end option that appeals to those wanting to combine sightseeing on land and sea. The main consideration is the longer duration, which might be less suitable for tight schedules.
Bottom line: A great choice for travelers wanting a mix of sailing and cultural exploration.
5. The Fastest All Inclusive Private Motor Yacht in Santorini
Number 5 is the private yacht experience, rated 5/5 from 6 reviews. At around $536 per person, it’s a significant investment, but you’re paying for exclusivity. The brand-new 2023 yacht allows you to customize your route, with stops at Red Beach, Oia, Thirasia, and the volcano. The yacht’s luxury amenities ensure a comfortable, private experience.
This tour is perfect for special occasions or travelers who want a tailored day on the water. The crew is described as flexible and attentive, making sure your trip aligns with your interests. The highlight is the privacy — you won’t share the boat with strangers — and the ability to visit specific spots at your own pace.
The main drawback is the price, but for those wanting a once-in-a-lifetime experience, this is unbeatable. It’s suited for couples celebrating special moments or small groups seeking privacy.
Bottom line: For a truly personalized, high-end experience, this private yacht tops the list.
6. Santorini: Cruise Catamaran with BBQ & Drinks Day or Sunset
Number 6 offers a 5-hour cruise that’s versatile for daytime or sunset, rated 4.6/5 from 9 reviews. It’s known for sailing past volcanoes, Akrotiri, and Indian Rock, with stops at Red and White Beaches for swimming and snorkeling, plus a sunset view below Oia.
What makes this trip stand out is its adaptable schedule and the onboard BBQ, making it great for those who want good food and spectacular views. The itinerary includes several scenic stops, with plenty of time for photos and relaxation. Many reviews appreciate the friendly staff and the beautiful sunset at Oia.
Costing about $107 per person, it’s a solid mid-range option offering a good balance of scenery, food, and comfort, especially for sunset lovers.
Bottom line: A reliable choice for those who want to combine sailing with sunset romance and good food.
7. Caldera Private Cruise with Luxury Fjord 52 Motor Yacht
Number 7 is the ultimate in luxury, with the Fjord 52 Motor Yacht offering an exclusive private cruise. It’s rated 4.7, and at around $2,258 per group, it’s targeted toward those seeking high-end comfort and privacy. The cruise takes you to the Red and White Beaches, the Black Mountain waters, and Thirassia, with snorkeling spots included.
This tour is ideal for small groups or families wanting an elegant day with personalized service. The onboard amenities and the chance to explore the caldera in style are major selling points. Reviews highlight the attention to detail and flexibility of the crew, making it a once-in-a-lifetime experience.
Bottom line: If budget isn’t a concern and you want an exclusive, luxurious adventure, this private yacht is unmatched.
$2,258 per group up to 4
8. Luxury Catamaran Sunset Cruise with BBQ, Fresh Fish & Drinks
The Sunset Cruise (rated 4.9/5 from reviews) combines luxury with the romance of a Greek sunset. It lasts about 4-6 hours and features snorkeling, swimming, and a BBQ meal onboard. You’ll glide past volcanic islets and enjoy the sunset over Oia, with plenty of time to relax and take photos.
The highlight is the spectacular sunset at Oia, one of the most photogenic moments in Santorini. The onboard fresh fish BBQ and drinks elevate this experience, making it ideal for couples or anyone celebrating a special occasion. The approximately $176 per person price reflects its premium nature.
This cruise is best for sunset lovers who also enjoy fine food and a touch of luxury. The only limitation might be its schedule, as it’s primarily a sunset experience.
Bottom line: Perfect for romantic evenings and those who want a scenic, gourmet experience.
$176 per person
9. Santorini: Full Day Catamaran Cruise with BBQ & Drinks
Number 9 is the most comprehensive, with an 11-hour cruise rated 4.9/5. It covers swimming at Red and White Beaches, exploring Thirassia, and even includes a wine tour at a local winery (for an extra fee). The trip offers plenty of time for swimming, snorkeling, and sightseeing, with a Greek BBQ onboard.
Travelers who want the most out of their day in Santorini will appreciate the extensive itinerary and the opportunity to visit multiple beaches and islands. The long duration makes it suitable for those with a full day to spare. The reviews mention the excellent food, friendly crew, and beautiful sites.
Pricing isn’t specified, but the value lies in the duration and variety of experiences. It’s suited for travelers wanting a deep-dive into the caldera and surrounding islands.
Bottom line: For those eager to explore extensively over a full day, this cruise is a top choice.
10. Santorini: High-Speed Cruise on a Sleek, Modern Yacht
Number 10 features a 5-hour high-speed cruise rated 5/5, perfect for thrill-seekers. The modern speedboat whisks you around the caldera with stops at Red and White Beaches, the volcano, and Thirassia. It offers snorkeling, swimming, and geothermal hot springs, all in a more exhilarating format.
This cruise appeals to travelers craving speed, efficiency, and a stylish vessel. It’s ideal for those with limited time but who want a dynamic experience. The reviews praise the powerful boat, friendly crew, and the spectacular scenery.
Priced similarly to other mid-range options, it’s a good choice for active travelers who want to see as much as possible in a shorter period.
Bottom line: A lively, fast-paced tour for adventure lovers and speed enthusiasts.
11. Santorini: Private Catamaran Tour with BBQ & Unlimited Drinks
Finally, the private experience offers personalized service for up to 4 people at around $1,412. It includes a BBQ meal, unlimited drinks, and the flexibility to choose your route or follow a suggested one. The hotel transfers included make it especially convenient.
Ideal for couples celebrating a special occasion or small groups wanting exclusivity, this tour combines privacy with gourmet dining and scenic cruising. The reviews note the attention to detail and the delight of having a tailor-made day.
While it’s pricey, the customization and privacy make it worthwhile for those seeking a high-end, private adventure.
Bottom line: The best choice for small groups or couples wanting an exclusive, bespoke day on the water.
$1,412 per group up to 4
How to Choose Your Perfect Sailing Experience
Picking the right sailing trip depends on your budget, time available, and what kind of experience you’re after. If you want a full day of variety with multiple beaches and optional wine tours, the Full Day Catamaran Cruise is a solid bet. For a romantic sunset, the Luxury Sunset Cruise offers unbeatable views and fine food. If privacy and personalized service are your top priorities, the Private Yacht options deliver the ultimate luxury.
Consider your level of adventure—some tours, like the high-speed cruise, suit thrill-seekers, while others focus on relaxation and scenic beauty. Booking early, especially for popular tours, guarantees better availability and options.
Final Thoughts
Santorini’s sailing options in Fira are as diverse as the island’s landscapes. Whether you choose a relaxed catamaran with a delicious BBQ, a luxury private yacht, or a speedy high-speed boat, each offers a different slice of the island’s stunning seascape. For travelers seeking a balanced experience, the Caldera Calypso Cruise or the Luxury Catamaran Cruise are excellent picks. For those wanting to splurge on privacy or special occasions, the private yacht tours provide unmatched exclusivity.
Whatever your choice, booking early is wise—these tours fill up fast in peak season. Prepare your camera, your swimsuit, and your appetite for a day of unforgettable views and authentic Greek hospitality in Santorini’s waters.