Taormina is one of Sicily’s best destinations for seaside adventures, thanks to its stunning coastline, clear waters, and dramatic sea cliffs. While many travelers come for the ancient ruins and charming streets, the water offers just as many memorable experiences. Among the top options are small-group sailing trips that let you escape the crowds, explore hidden coves, and enjoy authentic Sicilian moments on the water. Our favorites include a peaceful half-day cruise along the coast, a lively sunset dolphin tour on a spacious catamaran, and a luxurious private yacht experience. These tours highlight the region’s natural beauty and offer a chance to relax with local drinks and snacks.
Several types of tours made our list, from group excursions ideal for social travelers (see the half-day sailing tour) to luxury private yacht adventures (check out this private yacht tour). There are also energetic boat parties, scenic fishing trips, and romantic sunset sails with aperitifs. Whether you want to snorkel in Blue Grotto, hunt for dolphins, or simply relax with a glass of local wine, there’s a sailing experience in Taormina for you. Now, let’s look at each one in detail.
1. Half Day Sailing Tour Taormina Bay
At number 1, this half-day sailing tour offers a relaxed way to explore Taormina’s coastline without the hassle of crowds. Starting from Taormina, the small group (just nine passengers) sets sail along the coast, passing spots like the Blue Grotto, Isola Bella, and the bays of Spisone and Mazzarò. The itinerary includes stops for swimming and snorkeling in waters known for their clarity—snorkeling equipment is provided, making it accessible even for beginners.
What makes this trip stand out is the personal touch from the skipper, who shares insights into Sicilian culture and local history. The boat provides a comfortable setting to relax, with drinks and snacks served onboard. Guests consistently praise the captain Lulu for her friendly demeanor and knowledge, with reviews noting how spectacular the coast looks from the water and how enjoyable the small-group atmosphere is.
This tour is perfect if you want a short but memorable escape from the busy streets of Taormina, with enough time to swim and take photos. The value for money is excellent, offering a 4 to 5-hour experience at just $52.
Bottom Line: A great choice for those wanting a manageable, scenic cruise with personal attention, ideal for families or couples seeking a half-day getaway.
2. Giardini Naxos: Dolphin Catamaran Sunset Tour with Aperetif
Number 2 on our list is the dolphin search combined with a sunset cruise aboard a large, comfortable catamaran. Starting from Porto di Giardini Naxos, this tour takes you on a 2.5 to 3-hour journey that’s perfect for the evening. The boat is the largest in the area for dolphin tours, giving you plenty of space to spread out and enjoy the scenery.
The itinerary includes cruising past Isola Bella for memorable photo stops, tasting regional cheeses and drinks during a scenic stop, and then heading towards Taormina for dolphin watching at sunset, which is the highlight. The chance of spotting playful dolphins makes this trip special, and the large vessel enhances comfort and stability. Reviews mention the crew’s friendliness and the authentic regional food, adding to the relaxed atmosphere.
This tour balances nature watching with social fun, making it ideal for travelers interested in marine life, beautiful sunsets, and a lively boat vibe. It’s a fantastic value, considering the scenic views and the memorable dolphin encounter.
Bottom Line: Perfect for a fun, relaxed evening with chances to see dolphins, sample local food, and enjoy stunning sunset views—especially good for families or couples.
3. Giardini Naxos and Taormina sailing tour
Number 3 offers a comprehensive 4-hour sailing adventure starting from Giardini Naxos. This tour is all about discovering both the Sicilian coast and its charming coves, including Isola Bella and the Blue Grotto. You’ll have time to swim in crystal waters and explore these famous sights with the guidance of your crew.
What elevates this trip is the combination of scenic sailing and culture—you’ll enjoy a relaxing aperitif of local Sicilian products and wines onboard. The boat’s itinerary emphasizes water activities, scenic stops, and a chance to listen to interesting stories about the region. With only 7 reviews and a high 4.9/5 rating, it’s a boutique experience that appeals to travelers seeking intimacy and authentic moments.
It’s ideal if you want to combine sightseeing with leisurely swimming and tasting regional treats. The three-hour journey offers good value for its focus on both scenery and cultural experience.
Bottom Line: A well-rounded choice for travelers who want to explore Sicily’s coast, relax with local flavors, and enjoy a peaceful sail in a small-group setting.
4. Taormina: Sailing boat tour with aperitif included
Number 4 features a 4-hour sailing adventure departing from Giardini Naxos that highlights the eastern Sicilian coast. The trip includes visits to Mazzarò Bay and Isola Bella, plus a scenic sail along the coast. One of the key highlights is the onboard aperitif, featuring high-quality local products as you drift past iconic spots like Blue Grotto.
This trip is especially appealing for its expert crew and the opportunity to snorkel in beautiful waters. The itinerary balances water activities with relaxing moments, making it well-suited for those who want a taste of everything—sailing, swimming, and local cuisine. The reviews reflect satisfaction with the onboard experience and the quality of the aperitif, though some may wish for a slightly longer trip.
Good for travelers who prefer a more relaxed pace with good food and scenic views. The 4-hour duration makes it a manageable option for most budgets and schedules.
Bottom Line: A solid choice for those wanting a mix of sailing, snorkeling, and Sicilian flavors in a comfortable setting.
5. Taormina: Unforgettable yacht private tour experience
Number 5 is the luxury private yacht experience that offers a completely personalized excursion. With durations from 2 to 8 hours, you decide how much time you want on the water, from a quick 3-hour trip to a full-day adventure. Departing from Giardini Naxos, this recently updated yacht includes a captain and hostess dedicated solely to your group, ensuring an intimate and exclusive experience.
What sets this apart is the luxury of the vessel, equipped with a bathroom and plenty of space to relax or sunbathe. The itinerary can include visiting Isola Bella, Capo Taormina, and Mazzarò, with flexible stops based on your interests. Ideal for celebrating special occasions or just indulging in an opulent escape. Reviewers appreciate the professional service and the panoramic views.
This tour is perfect if you’re after a private, high-end experience and want total control over your day at sea. It’s a higher-cost option but offers unmatched exclusivity and comfort.
Bottom Line: The best pick for travelers seeking a luxurious, customizable day on the water with privacy, comfort, and personalized service.
6. Aperitif on a sailboat in Taormina
Number 6 is a short 2-hour sail that combines scenic sailing with the pleasure of an authentic Sicilian aperitif. Launching from Sicily’s east coast, this tour takes you to Villagonia Bay, where you can enjoy a sunset cruise and a refreshing dip in the clear waters.
The highlight is the delicious local aperitif, which includes regional treats, and the opportunity to swim in the calm bay. The reviews mention the professionalism of the crew and the quality of the food, making it a popular choice for romantic evenings or a quick way to savor Sicily’s coastal beauty.
It’s ideal if you’re short on time but want to experience a beautiful sunset from the water with a drink in hand. The tour’s intimate size and relaxed pace make it suitable for couples and small groups.
Bottom Line: Perfect for a romantic or quick scenic escape that includes a taste of Sicilian hospitality during the sunset.
7. TAORMINA: BOAT PARTY IN TAORMINA ON A CATAMARAN
Number 7 offers a lively boat party on a catamaran, turning your sailing experience into a fun-filled celebration. With energetic music, refreshing aperitifs, and a lively atmosphere, this is the only party boat in Taormina on our list. The focus is on having a good time, with no detailed itinerary but plenty of dancing and socializing.
While the reviews are not specified, this tour is clearly geared toward those who want a high-energy, party-focused experience**. It’s suitable for travelers looking to combine a day on the water with a lively night of music and drinks.
This option is best for young travelers, groups of friends, or anyone who wants to combine sailing with a party vibe. It’s a different flavor from the more relaxed tours and offers a memorable night out.
Bottom Line: The go-to for travelers wanting a lively, energetic experience and a different way to enjoy sailing in Taormina.
8. TAORMINA: CATAMARAN FISHING TRIP WITH ROY FISHING
Finally, number 8 is a fishing trip aboard the Venus Catamaran, led by Roy Fishing with over 30 years of experience. Starting from Giardini Naxos, this 4-hour trip is suitable for those interested in trying their hand at sea fishing in the waters near Taormina and Naxos Bay.
This tour offers a hands-on experience for fishing enthusiasts, with all equipment provided, including a complimentary Roy Fishing hat. The boat’s stable platform makes for good fishing conditions, and the itinerary is focused on northern Sicily’s waters. Although reviews aren’t available, the emphasis on professional technique and gear suggests a serious, rewarding experience.
Ideal for those who want to combine sailing with a fishing adventure, this trip is perfect for anglers of all levels. It’s a quieter, more involved activity, making it different from your typical sightseeing cruise.
Bottom Line: Excellent for fishing buffs or those eager to try their luck in Sicily’s waters, with a knowledgeable crew and all necessary gear included.
How to Choose the Best Sailing Experience in Taormina
When selecting your perfect sailing outing, consider your budget, interests, and how long you want to spend on the water. For a quick, scenic escape with swimming and snorkeling, the Half Day Sailing Tour Taormina Bay offers great value. If you’re after luxury and privacy, the private yacht tour provides an exclusive, tailored experience. For those wanting fun and social activity, the boat party delivers lively entertainment, while nature lovers will appreciate the Dolphin Catamaran Sunset Tour.
Budget-wise, the Aperitif on a sailboat provides a shorter but charming experience, perfect for a romantic evening. If fishing appeals, the Catamaran Fishing Trip offers a unique adrenaline rush.
Booking early is advisable, especially in peak season, to secure your preferred date and enjoy Sicily’s spectacular waters without last-minute surprises.
In summary, Taormina’s sailing options cover everything from quiet, scenic cruises to lively parties and private luxury. Whether you’re seeking a family-friendly swim, a romantic sunset, or an adventure with dolphins or fish, these tours can turn a day on the coast into a highlight of your trip. For a memorable experience, pick the one that best fits your interests, and don’t forget to reserve in advance.
