Sicily Itineraries: Day Charters and Multi-Day Routes

Sicily’s charter cruising ground centres on the Aeolian Islands, a volcanic archipelago of seven islands spread across a 140-kilometre arc off the north-east coast. Individual passages between islands are short (Lipari to Vulcano is 5 nautical miles, Lipari to Panarea 12 nautical miles), making the Aeolians ideal for multi-day exploration. The itineraries below are designed to be combined: a guest looking at the 3-day and 4-day routes can stitch them together into a full 7-day Sicilian charter without repeating a single island. Every itinerary is fully customisable – your Boatcrowd charter specialist and onboard captain will tailor stops, pacing and activities to your group’s interests and the conditions on the day.

Day Charter Routes

Vulcano and Lipari Day Charter

Depart from Milazzo or Portorosa marina by 9 a.m. and cruise to Vulcano (25 nautical miles, roughly 1.5 hours). Anchor at Porto di Ponente and hike to the Gran Cratere summit (391 metres, roughly 45 minutes) for panoramic views across the entire Aeolian chain. Descend to the Laghetto di Fanghi – a natural pool of warm volcanic mud near the harbour, reputed for its therapeutic properties. A rinse in the sea washes off the sulphur and leaves your skin feeling silky. Cruise 5 nautical miles north to Lipari for lunch ashore at one of the harbour’s trattorias, then cruise to Lipari’s north coast and the otherworldly white landscape of the pumice quarries at Spiaggia Bianca and Acquacalda, where white volcanic rock meets impossibly blue water. Snorkel over pumice formations before returning to Sicily in the late afternoon.

Panarea and Stromboli Day Charter

Cruise from Milazzo or Lipari to Panarea (30–40 nautical miles from Milazzo, roughly 2 hours). Anchor off Cala Junco, a prehistoric bay backed by a Bronze Age village, and swim in crystal water. Snorkel over the underwater fumaroles near the harbour – volcanic gas bubbling from the seabed in warm streams. Take the tender ashore for a stroll through car-free lanes and lunch at a terrace restaurant. In the late afternoon, cruise 12 nautical miles north to Stromboli. Position the yacht off the Sciara del Fuoco as darkness falls and watch incandescent lava erupt every 15–20 minutes against the night sky. Return to base under the stars – or, for an overnight, anchor in Stromboli’s harbour and return the following morning.

Taormina and Isola Bella Day Charter

Cruise from Milazzo or Portorosa south along Sicily’s east coast to Taormina (roughly 30 nautical miles, 1.5–2 hours). Anchor off Isola Bella, a tiny nature-reserve island connected to the mainland by a thin sand strip, with excellent snorkelling in clear water. Take the tender ashore and ride the cable car (or taxi the winding road) up to Taormina town. Visit the ancient Greek Theatre (3rd century BC, with its jaw-dropping views of Etna and the Ionian Sea), browse the boutiques on Corso Umberto, and stop for granita and cannoli at a piazza café. Lunch at one of the terrace restaurants with Etna views before returning to the yacht for an afternoon swim at Isola Bella and the cruise back north.

3-Day Sicily Yacht Charter Itinerary: Lipari, Panarea and Stromboli

Day 1: Milazzo to Vulcano and Lipari

Board your yacht at Portorosa marina or Milazzo harbour by mid-morning. After a welcome briefing and a champagne toast on the flybridge, cruise north to Vulcano (25 nautical miles, roughly 1.5 hours). Anchor at Porto di Ponente for a morning hike to the Gran Cratere summit – the views across all seven Aeolian islands from the rim of an active volcanic crater are worth every step. Descend and (optionally) soak in the therapeutic mud baths near the harbour. After lunch on the aft deck, cruise 5 nautical miles north to Lipari. Dock at Lipari’s harbour and explore the town: the Norman cathedral, the archaeological museum (one of the best in the Mediterranean), and the charming lanes of the old quarter. In the late afternoon, cruise to Lipari’s pumice coast at Spiaggia Bianca for a swim in surreal white-on-blue water. Dinner ashore at one of Lipari’s waterfront restaurants – fresh grilled swordfish, caponata, a carafe of Malvasia.

Day 2: Salina and Panarea

Depart early and cruise 12 nautical miles north-west to Salina, the greenest of the Aeolians. Anchor off Pollara – the volcanic-crater bay where Il Postino was filmed, with dramatic cliffs falling into deep blue water. Swim and snorkel in the clear water (look for sea bream and octopus), then continue to Santa Marina Salina for a mid-morning espresso and a bag of Salina’s famous capers from a harbourside shop. Cruise 15 nautical miles east to Panarea, arriving for lunch. Anchor off Cala Junco for a swim and a snorkel over underwater fumaroles, then take the tender ashore. Panarea’s car-free lanes, whitewashed houses and terrace restaurants are the most atmospheric in the Aeolians. Dinner on a cliff-edge terrace: swordfish carpaccio, caper and tomato salad, a bottle of Malvasia, and the distant glow of Stromboli on the northern horizon.

Day 3: Stromboli and Return

Rise early and cruise 12 nautical miles north to Stromboli. Anchor at the main harbour of San Vincenzo and spend the morning exploring the island: the black-sand beach of Ficogrande, the car-free village, the tiny church. After lunch on the aft deck, cruise slowly around Stromboli’s west coast to the Sciara del Fuoco. If you stayed overnight at Panarea, you can time your arrival for dusk and watch the eruptions from the flybridge as darkness falls – incandescent lava arcing against the night sky every 15–20 minutes, reflected in the black water below. This is the climactic moment of any Aeolian charter. Depart Stromboli and cruise back to Milazzo (50 nautical miles, 2.5–3 hours) overnight or at first light, arriving bronzed, volcanically enlightened and thoroughly spoilt. Guests looking for a longer voyage can combine this 3-day route with the 4-day itinerary for a comprehensive 7-day Aeolian charter without repeating a single island.

4-Day Sicily Yacht Charter Itinerary: Taormina, Syracuse and the Egadi Islands

Day 1: Milazzo to Taormina

Board your yacht at Portorosa marina or Milazzo harbour by mid-morning. Cruise south along Sicily’s east coast to Taormina (roughly 30 nautical miles, 1.5–2 hours), with Mount Etna dominating the port-side view – its 3,403-metre summit often trailing a plume of volcanic smoke. Anchor off Isola Bella for a swim and snorkel in this nature-reserve bay. Take the tender ashore and ride the cable car to Taormina town. Visit the ancient Greek Theatre (3rd century BC) and walk Corso Umberto – the main street lined with 15th-century palazzi, boutiques, and terrace cafés. If Season 2 of The White Lotus piqued your interest, the Four Seasons San Domenico Palace is the former Dominican monastery where it was filmed. Dinner at one of Taormina’s clifftop restaurants, with Etna glowing gently above and the Ionian Sea shimmering below.

Day 2: Syracuse (Siracusa)

Cruise south from Taormina to Syracuse (roughly 45 nautical miles, 2.5–3 hours). Moor in Ortigia’s harbour – the island quarter of Syracuse, a UNESCO World Heritage Site and one of the most beautiful old towns in the Mediterranean. Walk the Baroque streets of Ortigia: the Piazza del Duomo (where the cathedral incorporates the columns of a 5th-century BC Temple of Athena), the Fountain of Arethusa (a natural freshwater spring on the harbourfront, steeped in Greek mythology), and the labyrinth of narrow lanes lined with honey-coloured limestone. Visit the Archaeological Park on the mainland: the Greek theatre (5th century BC, one of the largest in the ancient world), the Roman amphitheatre, and the Ear of Dionysius (a limestone cave with remarkable acoustics). Dinner ashore at one of Ortigia’s harbourside restaurants – pasta con le sarde (sardine pasta with fennel, pine nuts and raisins), fresh raw red prawns from Mazara del Vallo, and a glass of chilled Grillo.

Day 3: South Coast to Egadi Islands

This is the transition day. Depart Syracuse in the morning and cruise west along Sicily’s southern coast (roughly 160 nautical miles to Trapani, broken into manageable segments or an overnight passage). Alternatively, if your charter is repositioning west, stop en route at Agrigento – Sicily’s south coast town with the extraordinary Valley of the Temples, a UNESCO site preserving some of the finest Doric temples outside Athens (the Temple of Concordia, built around 430 BC, is one of the best-preserved Greek temples in the world). Continue west to the Egadi Islands off Trapani. Anchor off Favignana, the largest Egadi island (16 km from Trapani). The star attraction is Cala Rossa – a former tuna quarry whose turquoise water, enclosed by white limestone cliffs, is one of Sicily’s most stunning swimming spots. Dinner on the aft deck as the sun sets over the open western Mediterranean.

Day 4: Levanzo, Marettimo and Disembarkation

Morning cruise to Levanzo (6 km from Favignana – the shortest marine route in Italy). This tiny island hides the Grotta del Genovese, a prehistoric cave with Palaeolithic paintings and Neolithic engravings dating back 10,000 years (accessible by boat and a short hike; pre-booking required). Snorkel in the crystalline water around Levanzo’s rocky coastline. For the adventurous, continue 30 km west to Marettimo – the most remote Egadi island, virtually uninhabited, with hiking trails, sea caves and some of the clearest diving water in the Mediterranean. Your chef prepares a farewell gourmet lunch on the aft deck – fresh tuna (Favignana’s historic speciality), Sicilian caponata, cannoli for dessert – as you cruise back to Trapani for disembarkation. Guests looking for a longer voyage can combine this 4-day route with the 3-day Aeolian itinerary for a comprehensive 7-day Sicilian charter covering two island groups, a volcano, two UNESCO sites, and the breadth of Sicily’s extraordinary coastline.

5-Day Sicily Yacht Charter Itinerary: The Complete Aeolian Circuit

Day 1: Milazzo to Vulcano and Lipari

Board at Portorosa or Milazzo. Cruise to Vulcano (25 nm, 1.5 hours). Crater hike, mud baths, then 5 nm to Lipari for harbour exploration, pumice-coast swimming at Spiaggia Bianca, and waterfront dinner.

Day 2: Filicudi and Alicudi

Cruise west to Filicudi (25 nm from Lipari), the wilder side of the Aeolians. Dive or snorkel at Grotta dei Gamberi, swim at Capo Graziano’s underwater archaeological site (Bronze Age shipwreck debris), and hike to the abandoned village of Zucco Grande for panoramic views. If conditions allow, continue 10 nm west to Alicudi – the most remote Aeolian island, with no cars, no roads (only donkey paths and steps), and a population of roughly 100. Anchor and snorkel in water so clear the volcanic rock formations on the seabed look close enough to touch. Return to Filicudi for dinner and an overnight anchor.

Day 3: Salina

Cruise east to Salina (20 nm from Filicudi). Full day exploring the greenest Aeolian island: the Il Postino bay at Pollara, caper harvesting (June–July) on the volcanic slopes, a Malvasia wine tasting at one of the island’s historic wineries, and a sunset swim at Punta Perciato – a natural rock arch on the western coast. Dinner ashore at Santa Marina Salina.

Day 4: Panarea and Stromboli

Cruise to Panarea (15 nm from Salina). Morning at Cala Junco, fumarole snorkelling, lunch ashore at a terrace restaurant. Late afternoon cruise to Stromboli (12 nm). Position off the Sciara del Fuoco at dusk for the volcanic eruption show – the climactic moment of the Aeolian circuit.

Day 5: Stromboli and Return

Morning exploring Stromboli’s village and black-sand beaches. Farewell lunch on the aft deck as you cruise back to Milazzo (50 nm, 2.5–3 hours), passing the entire Aeolian chain on the horizon. This 5-day itinerary covers all seven Aeolian Islands – a comprehensive volcanic circuit that few charter guests complete, and one that rewards every extra day. Combine with the 3-day Taormina and Syracuse route for an 8-day grand Sicilian voyage.