Fira, perched dramatically above the caldera, is one of the most picturesque spots in Greece. But beyond its stunning cliffside views and vibrant streets, Fira is also a fantastic base for sailing adventures. Whether you’re after a luxurious private yacht experience or a lively day on a catamaran, Santorini’s waters promise unforgettable moments. We particularly love the Luxury Catamaran Sunset Cruise with BBQ for its combination of spectacular sunsets, delicious food, and relaxed vibe. But each of these tours offers a unique way to see the island from the water.
From full-day caldera cruises to speedboat adventures and private charters, Fira provides a variety of options tailored to different preferences and budgets. Whether you want to snorkel in volcanic springs or sip wine as the sun dips behind Oia, there’s a sailing experience for everyone. Below, we’ll walk through the six best tours, helping you decide which one fits your style and travel plans best.
The 6 Best Sailing Experiences in Fira
1. Santorini: Catamaran Caldera Cruise with Meal and Drinks
At number 1 on our list, the Santorini: Catamaran Caldera Cruise with Meal and Drinks offers a classic, well-rounded experience. For around $68 per person, you’ll spend about five hours exploring Santorini’s iconic caldera aboard a comfortable catamaran. This tour stands out because it combines spectacular views, a delicious BBQ meal, and opportunities for snorkeling and sunbathing. The itinerary includes stops at Mesa Pigadia, White Beach, and Red Beach, giving you a close look at the island’s volcanic coastline.
Guests consistently praise the crew’s friendliness and the relaxed atmosphere—”the staff joined us in a dance near the end, which made it really memorable,” one reviewer notes. The small group setting means fewer crowds and more personalized attention. Plus, the hot springs near Palea Kameni add a therapeutic touch to the day.
Bottom line: This cruise is perfect for travelers who want a balanced, fun-filled day with great food, scenic stops, and friendly service—ideal for honeymooners or first-timers wanting the classic Santorini experience.
2. Santorini: Catamaran Cruise with Lunch, Drinks, & Oia Visit
Coming in at number 2, this Catamaran Cruise with Lunch and Oia Visit offers an upgraded experience. For $145, you get five hours of sailing around Santorini, combined with a guided tour of the legendary Oia village. This tour is especially appealing if you want to combine a scenic boat ride with a cultural visit.
Highlights include swimming at Red Beach and Thirasia Island, soaking in the hot springs, and enjoying a delicious onboard meal with drinks from the open bar. The itinerary also includes a photo stop at Palea Kameni and a sunset viewing in Vlichada. The small group size and attentive crew make a big difference in creating a relaxed, intimate experience—”everything was fantastic, especially the crew and the tasty food,” a traveler shares.
Bottom line: This tour suits travelers who want a mix of sailing, sightseeing, and a touch of local culture, perfect for couples or small groups eager to blend adventure with a scenic village exploration.
3. The Fastest All-Inclusive Private Motor Yacht in Santorini
At number 3, the Fastest Private Motor Yacht offers a 3-5 hour custom cruise in top-tier comfort. For around $536 per person, this is a premium experience designed for those seeking privacy and flexibility. You’ll explore Volcano Hot Springs, Red Beach, and Oia, all in style, with a boat that’s as fast as it is luxurious.
This tour is ideal for travelers who prioritize privacy and customization. You can tailor stops, whether you want more snorkeling, relaxing, or taking photos of the caldera from sea level. The guide and crew are praised for their attentive service, ensuring your day is seamless and personalized. Reviews highlight how flexible the experience was—“exceeded expectations,” says one user.
Bottom line: This is perfect for couples celebrating special occasions, small groups seeking luxury, or anyone eager for a private, high-end day on the water.
4. Caldera Private Cruise with Luxury Fjord 52 Motor Yacht
Number 4 features the Caldera Private Cruise with Fjord 52 Motor Yacht. Priced at around $2,258 for up to four people, this is for travelers looking for ultimate exclusivity. The yacht is brand-new (2023) and equipped with luxurious amenities, making it a perfect choice for a special celebration or a once-in-a-lifetime splurge.
The itinerary includes stops at Red and White Beach for photography, snorkeling at Black Mountain, and swimming in sulfur-rich hot springs. You’ll also visit Thirassia Island, with plenty of time to relax in privacy while enjoying personalized service. The cruise’s highlights revolve around luxury, privacy, and extraordinary views.
While costly, reviews emphasize how the “fabulous boat and scenery” made it worth every penny. It’s best suited for travelers who want a private, high-end experience with top-tier comfort.
Bottom line: For those celebrating a honeymoon, anniversary, or simply wanting the best, this tour delivers privacy, luxury, and incredible scenery.
5. Luxury Catamaran Sunset Cruise with BBQ, Fresh Fish & Drinks
Number 5 offers a luxury sunset experience that combines sailing, dining, and stunning views. The Sunset Catamaran Cruise lasts about 4-6 hours and costs $176 per person. It’s ideal for travelers who want to enjoy the most iconic moment in Santorini—its sunset—while relaxing on a Lagoon vessel.
The itinerary includes stops at Thirassia Island, Volcano, and southern beaches for swimming and snorkeling, all topped with a BBQ meal served onboard. The trip’s highlight is the Oia sunset, which is truly breathtaking. The vessel’s design allows for plenty of sunbathing and listening to music as the sky turns orange. Reviewers mention the “fantastic view and delicious food,” noting it’s perfect for a romantic evening.
Bottom line: Best suited for couples or small groups seeking a luxurious, scenic sunset with good food and a relaxed vibe.
6. Santorini: High-Speed Cruise on a Sleek, Modern Yacht
Rounding out our list, the High-Speed Cruise offers a 5-hour adrenaline-pumping ride. For those wanting to see everything fast and in style, this tour features speedboat thrills combined with scenic stops. You’ll visit Red and White Beaches, snorkel in clear waters at Black Mountain, and marvel at the caldera from sea level.
The boat’s impressive speed and modern amenities make it stand out. The itinerary includes multiple stops at volcanic sites and Thirassia Island, with an emphasis on adventure. The reviews are glowing—“felt like a VIP all day,” says one traveler—highlighting the boat’s power and comfort.
Bottom line: This experience is perfect for those who love a bit of thrill and want a fast-paced, high-energy day exploring Santorini’s most famous sites.
How to Choose the Right Sailing Experience in Fira
Picking the best tour depends on your budget, interests, and travel style. If you want a relaxed, all-inclusive day with great food, the Catamaran Caldera Cruise is a solid choice. Looking for a luxury private outing? The Fjord 52 Motor Yacht offers the highest level of comfort and exclusivity. For those eager to capture stunning sunsets, the Sunset Cruise delivers breathtaking views with a delicious meal.
Budget travelers or those wanting a more energetic ride might prefer the High-Speed Yacht for its speed and excitement. Meanwhile, couples celebrating special occasions will find the private yacht options perfect for personalized service.
When booking, consider the best times—spring and early fall often have calmer seas, but summer is the most popular. Booking early ensures you get your preferred date, especially for the more exclusive private options.
Final Thoughts
Fira offers a wide range of sailing experiences, from lively group cruises to ultra-luxurious private charters. For a balanced day with scenic stops and good food, the Catamaran Caldera Cruise is a great pick. If exclusivity and privacy top your list, the private motor yacht or Fjord 52 cruise provide unmatched luxury.
No matter your choice, booking early is wise—these tours fill up quickly, especially in peak season. With so many options, you’re sure to find a sailing experience that makes your visit to Santorini truly memorable.