Skiathos Town is a lively hub of charming streets, colorful tavernas, and a waterfront that buzzes with activity. But what makes it truly special for tours is its proximity to stunning islands, crystal-clear waters, and authentic Greek culture. Whether you’re eager to sail through the Aegean, explore off-the-beaten-path beaches, or learn about local traditions, Skiathos offers a variety of experiences that can turn your trip into a memorable adventure. We especially love the Full-Day Sailing Cruise for its combination of delicious food and dolphin sightings, or the Historic Walk that reveals the soul of this lively island’s past.
If you’re short on time, the Guided Audio Walk with Papadiamantis Stories provides a quick but richly atmospheric introduction to Skiathos’ heritage, while the Evening of Wine and Scenic Views offers a relaxed way to enjoy local flavors with panoramic vistas. For those who want to mix sightseeing with active fun, sea kayaking along the coast or exploring hidden beaches offers an authentic way to connect with nature. Whatever your style, Skiathos Town has a tour tailored to your interests.
1. Skiathos: Full-Day Sailing Cruise with Lunch
At number 1 on our list, the Full-Day Sailing Cruise with Lunch offers a standout experience, rated 4.9/5 by over 200 travelers. This 7-hour trip takes you on a large sailing yacht, with options for private or shared arrangements, making it perfect for couples, families, or groups. The itinerary includes visits to Skopelos, Tsougria, and Dasia, with ample time for swimming, snorkeling, and relaxing on deck.
What sets this tour apart is the focus on authentic Mediterranean cuisine prepared on board, with a variety of traditional recipes and fresh seafood that make the meal a highlight. The chance to see dolphins and sea life adds a special touch, while the visit to Kastani beach, famous from Mamma Mia, is a fun photo opportunity. The crew’s friendly approach and the quality of the yacht mean you’ll feel pampered as you soak up both the sun and the stunning scenery. With high reviews praising the value and atmosphere, this cruise is ideal for those wanting a full day of sailing adventure with excellent food, views, and the chance to spot marine life.
Bottom line: This tour offers a perfect blend of sailing, swimming, and good food — a fantastic choice for lovers of the sea and scenic islands.
2. Skiathos: Guided Sea Kayaking Tour with Swim Stop
Rated 4.9/5 by 19 reviews, the Guided Sea Kayaking Tour is a compact 2-hour adventure. It’s perfect if you want to explore Skiathos’ coastline actively but without committing a whole day. The tour kicks off from Skiathos Supway, where guides lead you along the south coast, revealing secluded beaches and quiet coves often hidden from larger boats.
What makes this trip stand out is the opportunity to swim and snorkel in remote beaches where crowds are scarce. The guides are praised for their friendliness and local knowledge—Nikos, in particular, brings a personal touch and takes photos of your group. The tour includes safety briefings and equipment, making it accessible for beginners. Reviewers highlight the views and the chance to visit Diamanti beach, a lesser-known spot with pristine waters, as a highlight. Paddleboarding is also available at the end if you’re feeling energetic.
Bottom line: If you’re after a short, active, and scenic experience that immerses you in Skiathos’ untouched beauty, this kayak tour hits the mark.
3. Daytrip with Diamanti Sailing Skiathos, lunch included
Spanning 8 to 8.5 hours, the Diamanti Sailing Daytrip offers a full day of classic sailing, swimming, and snorkeling. The boat—a spacious Beneteau Cyclades 50.5—takes you around Skiathos and Skopelos islands, with 4 to 5 stops for water activities. The emphasis on comfort and leisure makes it perfect for travelers who want to relax while enjoying the scenery.
This tour shines with its exploration of Dasia’s blue sea cave and the opportunity to snorkel in crystal-clear waters. The onboard snacks and drinks keep you refreshed, and a delicious lunch on Skopelos (excluding drinks) adds a cultural flavor. Reviewers often mention how well-organized and comfortable this trip is, with plenty of time to unwind and soak up the sun. It’s especially suited for those seeking a leisurely day on the water, with options to snorkel or paddleboard.
Bottom line: If you’re looking for a well-rounded sailing experience that combines comfort, good food, and water activities, this trip won’t disappoint.
4. Evening of Wine and Scenic Views in Skiathos
Rated 5/5 based on 8 reviews, the Evening of Wine and Scenic Views is a cozy 3-hour experience that’s perfect for relaxing after a day of exploring. You’ll taste six different wines—mainly whites, with a rose and a red—paired with finger foods, all while enjoying panoramic views of Skiathos Town and the Aegean Sea.
The host’s hospitality and knowledge about local grape varieties elevate the experience, making it both educational and enjoyable. Reviewers love the intimate group setting and the chance to learn about Greek winemaking secrets. The venue’s scenery, combined with generous tastings and delicious bites, makes this a well-priced, memorable evening. It’s ideal for wine lovers or anyone seeking a mellow, scenic way to end the day.
Bottom line: This tour offers a relaxed, informative experience perfect for couples or small groups who enjoy good wine and spectacular views.
5. Skiathos: All-Inclusive Sailing Cruise with Lunch
At number 5, the All-Inclusive Sailing Cruise offers a 7-hour journey with all food and drinks included. This cruise covers Skiathos, Skopelos, and nearby islands, with stops for swimming, snorkeling, and paddleboarding. The emphasis on all-inclusive amenities makes it ideal for travelers who want a stress-free day on the water.
The tour features multiple scenic stops, including hidden spots best enjoyed away from crowded beaches. The crew supplies snacks, a full lunch, fruits, and refreshments throughout the day, ensuring you stay fueled. The boat’s comfort and the variety of water activities appeal particularly to families and groups seeking a comprehensive experience. Reviewers mention the crew’s friendliness and the quality of the onboard food as highlights.
Bottom line: For a full day of sailing with everything included, this cruise offers excellent value and a seamless way to explore the islands.
6. From Skiathos: Cruise to Lalaria, Kastro, and Tsougris
With a 3.7/5 rating from 17 reviews, the Cruise to Lalaria, Kastro, and Tsougris gives you a taste of the dramatic coastlines and historic sites. For around $50, this 7-hour trip focuses on swimming at Lalaria Beach, famous for its white pebbles and cliffs, and exploring the Kastro village, the old capital of Skiathos.
It’s a good option for travelers wanting a combination of beach time, history, and scenic cruising. The tour also takes you to Tsougris Island, a small paradise with clear waters. While reviews note some variability in experiences, most appreciate the chance to see top sights without a long commitment. This trip is best suited for those on a budget or with limited time who want a snapshot of Skiathos’ coast.
Bottom line: An affordable, scenic trip with a focus on beaches and historical sites, ideal if you want a quick overview with swimming and sightseeing.
$49.69 per person
7. Exploring Skiathos Town: A Historic Walk
Rated 4.4/5, the Historic Walk takes about 2 hours to uncover the local charm. You’ll visit Papadiamantis House, the Skiathitian House museum, and enjoy a taste of local liqueur. The walk explores churches, neighborhoods, and landmarks that tell the story of Skiathos’ past.
The guide’s knowledge makes this an engaging way to get acquainted with the town’s character. It’s perfect for history enthusiasts or travelers wanting an easy, cultural introduction. Reviewers appreciate the relaxed pace and the chance to see a quieter side of Skiathos Town, away from the busy waterfront.
Bottom line: A short, insightful walk that’s great for those interested in the island’s heritage and local life.
$42.91 per person
8. Skiathos: Guided Audio Walk with Papadiamantis Stories
This 1-hour, self-guided Audio Walk offers a unique way to experience Skiathos through stories and soundscapes. Using headphones, you’ll listen to narratives, music, and excerpts from Papadiamantis’ works, enjoying the town’s history and culture.
It’s an inexpensive, flexible option ideal for those who want to explore at their own pace or fit a cultural experience into a busy day. The inclusion of the first recording of the bouzouki from 1917 adds a special touch for music lovers. Reviewers mention how engaging this walk is, especially for fans of Greek literature and storytelling.
Bottom line: If you prefer a personalized, cultural journey with some audio guide magic, this experience offers a rich taste of Skiathos’ soul.
$18 per person
How to Choose the Right Tour
When deciding which tour fits best, consider your budget, time availability, and interests. For a full day of sailing with excellent food, the Full-Day Sailing Cruise is a top pick for water lovers. If you want a quick, active exploration, the Sea Kayaking Tour is perfect. Those looking for culture might prefer the Historic Walk, while wine enthusiasts will find the Evening of Wine just right.
Budget-conscious travelers should note the Cruise to Lalaria, Kastro, and Tsougris offers a good value, while the all-inclusive sailing trip provides a seamless experience with food, drinks, and activities included.
Booking early is wise, especially in high season, as popular tours like the sailing cruises tend to fill quickly. Check availability ahead of time and match your choice to your preferred pace and interests.
Final Thoughts
Skiathos Town offers a variety of tours that suit different tastes and schedules. For a full-day adventure, the Sailing Cruise with Lunch delivers excellent value and memorable views. If you prefer something shorter and more active, the Sea Kayaking Tour is a great way to explore the coastline intimately. History buffs and cultural explorers will find the Historic Walk and Audio Tour enriching, while wine lovers can unwind with scenic vistas and delicious tastings.
No matter which you choose, these experiences will deepen your connection to Skiathos and create lasting memories. Be sure to book ahead, especially if visiting during the busy summer months, and enjoy discovering this beautiful island’s many facets.