Oia is famous for its stunning sunsets, whitewashed buildings, and caldera views, but it’s also a fantastic spot to explore by boat. The sailing experiences here let you see Santorini from a completely different perspective, often including swimming in volcano hot springs, snorkeling in clear waters, and enjoying local food onboard. We especially love the Private All-In Catamaran Cruise for its personalized approach and flexible itinerary — perfect if you’re celebrating a special occasion or seeking a truly private experience. Plus, with options like the Luxury Catamaran Cruise with Lunch, you get a taste of the finer things in life, including Greek cuisine and open bar. Whether you want a romantic sunset or a full-day adventure, these tours bring the best of Santorini’s seascape right to your doorstep.
Quick Overview
For those planning their trip, here’s a quick snapshot of what’s available:
- A private all-in catamaran tailored for small groups or couples (details here).
- A luxury group cruise with included lunch, BBQ, and drinks (check it out).
- An intimate private sailing ideal for couples, with a focus on romance and personal touches (more info).
Below, we explore each option in detail, highlighting what makes them unique and helping you decide which fits your style and budget.
1. Santorini: Private All-In Catamaran Cruise, with Food|Drinks
At number one, the Private All-In Catamaran Cruise delivers a personalized experience perfect for small groups or couples. This 5-hour private trip offers the flexibility to craft your own route around Santorini’s caldera, with options to swim in thermal waters, snorkel in crystal-clear seas, or relax on deck while enjoying the view. The crew is known for their friendly, attentive service, and they’ll prepare a fresh Santorini BBQ meal with local flavors, along with wine, beer, soft drinks, and dessert.
What makes this tour stand out is the customizable itinerary. You can choose to visit the Red Beach for a quick swim, enjoy the volcanic hot springs of Nea Kameni, or take scenic photos from the White Beach. The private setting means fewer crowds and more attention to your group’s interests. Reviewers praise the crew’s helpfulness, the delicious food, and the flexibility — one described it as their “best birthday ever.”
Bottom line: This cruise is perfect if you want a tailored, intimate experience with all the comforts and no crowds. It’s ideal for celebrations or just a peaceful day on the water.
2. Santorini: Luxury Catamaran Cruise with Lunch, BBQ & Drinks
The Luxury Catamaran Cruise is the choice for travelers who want a more refined experience with all the comforts of a small-group tour. This 5-hour trip takes you around Santorini and Thirasia island, with swimming stops at hot springs and beaches like Mesa Pigadia. The boat itself is well-appointed, and the crew caters to your every need, from serving a Greek buffet to offering unlimited drinks from the open bar.
One of the tour’s highlights is the combination of sightseeing and relaxation. You’ll sail past the Indian Rocks and the Venetian Lighthouse, with plenty of opportunities to jump into the water or soak in the volcanic springs. The lunch is a traditional Greek buffet, featuring hearty dishes that appeal to all tastes. Guests often comment on the intimate atmosphere and the quality of food, making it a favorite for couples and small groups seeking a luxurious experience.
Value for money is strong, with the added convenience of hotel transfers in most cases. This tour is best suited for those who appreciate comfort, good food, and stunning views in a refined setting.
Bottom line: If you’re after a smooth, elegant day on the water with fantastic scenery and great food, this cruise fits the bill.
3. SANTORINI PRIVATE SAILING CRUISE TOUR
For couples or small groups looking for an intimate, romantic experience, the Private Sailing Cruise Tour offers the chance to sail the caldera with just your partner or close friends. Starting at around $1,355 for up to two people, this tour emphasizes privacy and a personal touch. You’ll be accompanied by a Greek celebrant if you wish to tie the knot or renew vows, which makes it perfect for a special occasion.
What sets this tour apart is the private, exclusive atmosphere. It’s an ideal choice for a romantic getaway or a small celebration, with the boat equipped for an authentic Greek BBQ and a variety of drinks. The crew focuses on creating a memorable moment, whether it’s watching the sunset or just enjoying the calm sea.
Guests appreciate the seclusion and personalized service. While it’s priced higher per group, it’s a fantastic value for an unforgettable, tailor-made experience. The limited size means fewer crowds and more space to relax.
Bottom line: Best for honeymooners or those wanting a private, memorable celebration on the water.
$1,355 per group up to 2
How to Choose
When deciding which sailing experience suits you, consider your budget, interests, and group size. For a fully private, customizable experience with all-in comfort, the Private All-In Catamaran Cruise is hard to beat. If you prefer luxury and a well-organized group setting with included lunch, the Luxury Catamaran Cruise offers exceptional value. For those seeking an intimate romantic experience, the Private Sailing Cruise is ideal, especially if celebrating a special moment.
Think about the time of year — summer months offer the warmest weather, but boat trips can fill up fast, so booking early is wise. Also, consider if you want a full-day adventure or a shorter cruise. Most tours run around 5 hours, making them manageable for a half-day outing.
To sum it up, Oia’s sailing options range from personalized private cruises to luxurious group excursions. For a tailored experience with flexible routes and onboard meals, the Private All-In Catamaran Cruise is a standout. If you’re after a refined, all-inclusive day with excellent service, the Luxury Catamaran is your best bet. And for couples dreaming of a private vow renewal or romantic escape, the Private Sailing Cruise makes for an unforgettable memory.
No matter which you choose, booking early ensures you secure your spot for these popular experiences. So, gather your friends or loved one, and set sail for a memorable day in Santorini’s beautiful waters.