Taormina offers some of Sicily’s most stunning coastline, with dramatic cliffs, sparkling waters, and charming bays that make sailing not just a way to see the sights but a highlight of your trip. Its proximity to well-loved spots like Isola Bella and Villagonia Bay means you can explore these beautiful areas from the water, avoiding the busy streets and the heat. We especially like the Half Day Sailing Tour Taormina Bay for its intimate feel and the chance to swim in crystal waters. For a more relaxed, sunset experience, the Aperitif on a sailboat in Taormina offers a lovely way to unwind with Sicilian snacks and a glass of wine. And if dolphins are on your wish list, the Giardini Naxos: Dolphin Catamaran Sunset Tour with Aperetif combines dolphin spotting with scenic cruising and regional flavors. Each tour offers a different way to enjoy the coast, whether you want active swimming, sunset relaxation, or dolphin watching.
Quick Overview
Our list features three top sailing experiences in Taormina, each with its own distinctive appeal:
- Half Day Sailing Tour Taormina Bay — A small-group cruise along the coast with swimming, snorkeling, and cultural insights. Learn more here.
- Giardini Naxos: Dolphin Catamaran Sunset Tour with Aperetif — A larger boat adventure searching for dolphins, with scenic stops and regional tastings. See details here.
- Aperitif on a sailboat in Taormina — A shorter, elegant cruise ending with a sunset aperitif over Villagonia Bay. Check availability here.
1. Half Day Sailing Tour Taormina Bay
At number one, the Half Day Sailing Tour Taormina Bay is a great choice for travelers wanting a relaxed yet active experience. Priced at around $52, it lasts about 4 to 5 hours and is perfect for those who want to explore Sicily’s coastline without feeling rushed. The tour features a small group of only nine people, which means more space on board and a more personalized experience. Your skipper shares sailing basics, along with stories about Sicilian culture, making it both fun and informative.
The itinerary includes cruising past popular spots like the bays of Spisone and Mazzarò, visiting the famous Blue Grotto, and stopping at Isola Bella. The real highlight is the chance to drop anchor, swim, and snorkel in the clear waters of the Mediterranean — snorkeling gear is provided, so no need to bring your own. Reviewers rave about Lulu, the captain, noting her expertise and friendly attitude. Many say it’s a perfect way to see the coast without the crowds, with water that’s ideal for swimming.
Bottom line: For a balanced mix of sightseeing, swimming, and local insights, this tour offers excellent value and a memorable, small-group atmosphere.
2. Giardini Naxos: Dolphin Catamaran Sunset Tour with Aperetif
Number two on our list is the Dolphin Catamaran Sunset Tour, which lasts about 2.5 to 3 hours. The larger boat makes it comfortable, with plenty of space for relaxation and socializing. This tour departs from Porto di Giardini Naxos, giving you a chance to see Sicily’s east coast from a different perspective. The main draw is the search for dolphins, which many travelers find magical — and the itinerary also includes a visit to Isola Bella, one of Sicily’s most photographed spots.
What makes this trip stand out is the combination of scenic cruising, dolphin watching (a real thrill), and regional tastings. You’ll stop at scenic points for photos, enjoy regional cheeses and snacks, and watch the sunset over the coast with a glass of regional wine or Aperol spritz in hand. Reviewers appreciate the friendly crew and the opportunity to see dolphins in their natural habitat. Many note that the large boat and open spaces make for a comfortable trip, especially if you prefer a more leisurely experience.
Bottom line: This tour is ideal if dolphin spotting is a priority and you want a relaxed, scenic cruise with plenty of space and regional flavors.
3. Aperitif on a sailboat in Taormina
Third on our list is the Aperitif on a sailboat in Taormina, a delightful 2-hour cruise priced at around $68. It’s perfect for those seeking a short, stylish escape. This cruise takes you along Villagonia Bay, often regarded as one of Sicily’s most charming areas, and culminates with a sunset view that’s hard to beat.
What sets this experience apart is the opportunity to enjoy an authentic Sicilian aperitif — think regional cheeses, cured meats, and local wines — while sailing in calm waters. You can also take a refreshing dip in the crystal-clear waters of Villagonia Bay, which many guests find invigorating after a day of sightseeing. The review from a very satisfied guest highlights the professionalism of Letizia and the quality of the aperitif, emphasizing this trip’s relaxed, intimate vibe.
Bottom line: Best suited for travelers wanting a quick yet elegant way to enjoy a sunset with regional bites, this cruise offers a refined taste of Sicily’s coastline.
$67.97 per person
How to Choose
When deciding between these sailing options, think about your priorities: Are you looking for a relaxed swim and cultural stories? The Half Day Sailing Tour delivers that. Want a dolphin search combined with scenic stops and regional snacks? The Dolphin Catamaran Sunset is your best bet. Or is a short, stylish sunset with an elegant aperitif more your style? The Aperitif on a sailboat offers a refined, intimate experience perfect for a quick escape.
Consider your budget, time constraints, and what experiences excite you most. Booking early is recommended, especially during peak season, to secure your preferred date.
Final thoughts
Whether you choose a small-group coastal cruise, a dolphin-watching adventure, or a sunset aperitif, Taormina’s waters provide unforgettable views and moments. For those wanting active exploration with opportunities to snorkel, the Half Day Sailing Tour offers great value. If dolphin sightings top your list, the Dolphin Catamaran Sunset Tour is hard to beat. And for a romantic, short experience, the Aperitif on a sailboat will not disappoint.
No matter your choice, these sailing tours in Taormina promise a memorable way to enjoy Sicily’s coast from the water. Be sure to book in advance, especially during the busy summer months, to secure your spot on these fantastic excursions.