This unforgettable tour offers a unique perspective of Syracuse—from the sea! You'll cruise along the coastline, admiring the city’s beauty from the comfort of a boat, with the opportunity to explore nearby sea caves. During the summer, you’ll also have a chance to take a refreshing swim directly from the boat. Your journey begins with a panoramic view of the majestic natural harbor—one of the largest in the Mediterranean. You’ll sail past the ancient Italic Forum and catch a glimpse of luxurious yachts moored nearby. Look up to spot part of the striking façade of the Duomo (Cathedral of Syracuse) peeking over the rooftops. As you continue, you’ll pass the enchanting Fountain of Arethusa and the impressive Maniace Castle, which marks the edge of the harbor. Venturing into open sea, you'll be treated to stunning views of Ortigia Island’s colorful façades, elegant churches, and historic city walls—all even more captivating from the water. From there, we’ll head toward the northern coast of Syracuse. While enjoying fresh fruit and sipping cold juice, we’ll approach the caves. Weather permitting, we’ll begin with a 10-minute swim stop in the crystal-clear waters. Next comes the cave exploration: first, the Cappuccini Cave, followed by the Coral Cave, and finally the “Grotta Grande” (Great Cave), also known as the Cave of Stalactites. Inside, you’ll see incredible natural limestone formations that have developed over centuries—details we’ll reveal only once you're on board. (Please note: access to the caves is tide-dependent.) We’ll also pause in front of the famous “Cave of Love”—a heart-shaped grotto perfect for capturing beautiful souvenir photos. To complete the experience, enjoy a delicious onboard meal featuring typical Sicilian delicacies (cold cuts, cheese, and vegetables). 

Please Note: There is a short walk to and from tour boat tour back to your Windstar yacht. We recommend you bring a towel, swimsuit, local currency, sunscreen, and bug spray.

Syracuse evokes images of sunshine, blue skies, a picturesque bay, and ancient ruins of a once-great Greek city that rivaled Athens. It remains one of Sicily’s most captivating destinations. Your tour begins at the Archaeological Park. Here, you'll visit the impressive Greek Theatre, dating back to the 5th century B.C.—one of the largest and best-preserved theatres of the ancient world. Nearby, see the Roman Amphitheatre from the 2nd century A.D., carved directly into the rock. You’ll also explore the intriguing Ear of Dionysius—an artificial grotto shaped like an ear, renowned for its echoing acoustics, said to have been used by the tyrant Dionysius to eavesdrop on prisoners. Continue by coach to Ortigia, the historic heart of Syracuse. From the harbor, enjoy a leisurely walk through the narrow medieval and Baroque streets of the island, lined with elegant palaces, flower-filled balconies, and small squares opening to views of the Ionian Sea. Your first stop is the Arethusa Fountain, steeped in myth and considered the legendary birthplace of the city. From the nearby viewpoint, take in the beautiful Bay of Syracuse. Then, visit the Cathedral—built in the 7th century over the ruins of the ancient Temple of Minerva. Several original columns remain visible, both inside and along the exterior walls. The Baroque façade and the surrounding Piazza Duomo create a striking setting filled with history and charm. The tour concludes with a walk past Piazza Archimede and the remains of the Temple of Apollo before returning to your transportation.

Please Note: We recommend you bring a bottle of water, hat, and local currency.

Enjoy a scenic 1.5 hour drive to the captivating town of Ragusa Ibla, known for its two distinct sections. The first is Ragusa Superiore (the upper town)—a "new" Baroque city rebuilt following a devastating earthquake. Set high on a plateau, this area once housed the landowning nobility. Below lies Ragusa Ibla, the charming lower town, traditionally home to the working class. You’ll explore Ragusa Ibla on foot with your guide for approximately 1.5 hours. Highlights include the magnificent St. George’s Church, with its stunning Baroque façade and belltower, the 19th-century Giardino Ibleo Garden, and the 14th-century Church of St. James the Apostle—rebuilt in the 18th century. You'll also visit the impressive cathedral, constructed between 1706 and 1760. Set on a wide terrace overlooking Piazza San Giovanni, the cathedral is known for its striking, asymmetrical façade and elegant campanile. After your guided walk, enjoy 30 minutes of free time for browsing, shopping, or exploring the Giardino Ibleo at your own pace. You’ll then regroup with your guide for a delicious lunch at a local restaurant. In the afternoon, continue to Modica, nestled along the southern slopes of the Hyblean Mountains. The upper part of this historic town rests on a wedge-shaped plateau, while the lower section wraps around it in a distinctive Y-shape—often described as a city born from stone, with caves once inhabited until recent decades. During your walking tour of Modica’s Baroque quarter, you’ll visit another stunning St. George’s Church. Before heading back to the ship in the late afternoon, enjoy a tasting of traditional chocolate, crafted using an ancient Maya recipe, at a local dolceria.

Your tour begins with a visit to the Arethusa Fountain, the legendary cradle of the city. From the nearby terrace, enjoy panoramic views of the stunning Bay of Syracuse. Continue to the Cathedral, built in the 7th century atop the ruins of the ancient Temple of Minerva. Original temple columns are still visible, both on the north side and within the nave. Strolling through the elegant Piazza Duomo and its surrounding monuments, you’ll make your way to Piazza Archimede and the ruins of the Temple of Apollo. After a short break for free time, the tour continues to the local market, where your guide will introduce you to Sicily’s vibrant produce and regional specialties. The experience concludes with a tasting of typical Sicilian products.

Please Note: We recommend you bring a bottle of water, hat, and local currency.
 

The name Syracuse brings to mind sunny skies, a stunning bay, and the ancient ruins of a city that once rivaled Athens. It's a must-see for history and culture lovers alike. Your tour begins at the Archaeological Park, home to the 5th-century B.C. Greek Theatre, one of the largest and best-preserved of the ancient world. Nearby, explore the Roman Amphitheatre, carved from stone, with original passageways still visible. You'll also visit the Ear of Dionysius, a unique cave known for its incredible acoustics—said to have been used by the tyrant Dionysius to spy on prisoners.  The next stop is Pupillo Winery, located on the historic Targia estate, where fertile soil and tradition meet. Founded in 1909, Pupillo is famous for reviving the native Moscato of Syracuse grape. You’ll tour the vineyards and cellar, then enjoy a tasting of three wines paired with traditional Sicilian bites, served in a charming farmhouse dating back to the time of Frederick II. This tour is the perfect blend of ancient heritage and authentic Sicilian flavor.