A circular sailing holiday from Lefkada through the heart of the southern Ionian Islands, with short daily passages, sheltered anchorages and traditional Greek waterfront villages.
The route departs from Lefkada Marina, a well-equipped sailing base connected to the mainland by a retractable bridge, and follows a circular circuit south and east through the central Ionian archipelago before returning north along the protected eastern coastline of the island. The entire route stays within a compact area of the southern Ionian, with inter-island distances short enough to leave most of each day free for swimming, eating and exploring ashore.
Summer navigation here is governed primarily by the Maistros, a reliable northwesterly thermal wind that builds through the late morning and peaks in the afternoon before easing toward evening. The wind is consistent enough to give every day a natural sailing window, predictable enough to plan departures around, and moderate enough that it rarely creates conditions that would compromise comfort for guests sailing for the first time. The abundance of sheltered anchorages on the eastern, lee sides of the islands adds a further layer of protection throughout the week.
The islands along the route carry distinct identities despite their proximity. Meganisi is green and quiet, with olive groves and pine forest descending to a handful of clear bays. Ithaca has a deeply indented coastline of narrow fjord-like harbors and wooded ridges, with a pace of life largely untouched by mass tourism. Kefalonia offers its widest and most varied landscape, particularly along the northern coast, with limestone cliffs, turquoise water and the village of Fiskardo, the only settlement in Kefalonia to survive the 1953 earthquake intact.
Kastos, one of the smallest inhabited islands in the archipelago, rounds out the circuit with a harbor-side village of whitewashed houses and fishing boats, no motor vehicles and a quiet rhythm that has remained largely unchanged for decades. The return leg north along the eastern coast of Lefkada passes through some of the calmest and most scenic water of the entire week, including the sheltered inlet of Desimi Bay and the waters around Skorpios, the private island that once belonged to Aristotle Onassis.
Days follow a natural pattern shaped by the wind, a morning departure from the previous night's anchorage, a swim stop at sea or in a cove along the way, arrival at the day's destination in the early afternoon, and an evening ashore in a waterfront village or on deck in a quiet bay, depending on the stop and the mood of the group.
Itinerary
Day1
Boarding in Lefkada and Evening Sail to Meganisi
Boarding takes place at Lefkada Marina in the afternoon, with time to settle into the cabins and a welcome briefing covering the plan for the week and the practical aspects of life onboard. The first passage heads south through the Lefkada Canal, a narrow sheltered waterway running between the island and the mainland that provides a calm introduction to Ionian sailing. Meganisi appears at the southern end of the channel, its hillsides covered in olive groves and pine forest descending to quiet bays with clear water. The evening is spent at Spartochori or Vathi, two traditional villages above sheltered anchorages where waterfront tavernas serve grilled fish and local wine directly above the mooring.
Day2
Meganisi to Ithaca
After breakfast at anchor, the boat sails south toward Ithaca, crossing open Ionian water with the wind typically filling in from the northwest through the morning and producing comfortable sailing conditions for the crossing. Small islets and rocky outcrops mark the route south, with clear water that invites a mid-passage swimming stop in calm conditions. The approach to Ithaca reveals a deeply indented coastline of narrow inlets and high wooded ridges descending steeply to the sea. Arrival is planned at Kioni on the northeastern coast, a village of pastel-colored houses around a protected harbor, or at Vathi, the island's main town at the head of a long fjord-like bay. Ithaca is one of the least altered islands in the Ionian, with a working agricultural economy and an evening atmosphere of genuine local life along the waterfront.
Day3
Ithaca to Fiskardo
A morning sail follows the eastern shoreline of Ithaca, tracing a coastline of forested slopes, occasional fishing huts and coves with clear pebble beaches, before the boat crosses the short channel west toward Kefalonia. The approach to Fiskardo on the northern tip of the island is one of the most anticipated arrivals of the week. Fiskardo is the only settlement in Kefalonia that survived the catastrophic 1953 earthquake completely intact, preserving a cluster of Venetian-era architecture along its harbor front that gives the village a visual consistency unlike anywhere else in the Ionian. The horseshoe-shaped harbor is lined with restored stone houses painted in ochre, terracotta and pale yellow, with restaurants and cafés occupying the ground floors directly above the water. The afternoon is free to explore the harbor, walk the coastal paths or swim in the surrounding bays, with the evening spent in the village.
Day4
Northern Kefalonia and Hidden Bays
A slower day dedicated to the northern coastline of Kefalonia, with shorter navigations and more time at anchor in bays accessible only by boat. The coastline north and east of Fiskardo breaks into a series of sheltered inlets and clear-water anchorages, including Foki Bay and the area around Afales, where the water takes on a particular shade of turquoise over the shallow limestone seabed. Swimming, snorkeling and paddleboarding occupy the warmer hours of the afternoon while the boat lies at anchor in near-complete quiet, with dinner either on deck or ashore in a simple village restaurant.
Day5
Kefalonia to Kastos
Departure from Kefalonia heads northeast toward Kastos, a small island that appears on fewer sailing itineraries than its character deserves. The passage combines open sea sections where the Maistros gives the boat real momentum with calmer stretches in the lee of intermediate islands, allowing swimming stops in clear water along the way. Kastos village sits directly on the harbor, a single row of simple whitewashed houses with a small church, a handful of fishing boats and a couple of tavernas serving whatever was caught that morning. There are no motor vehicles on the island, and the overall atmosphere is that of a community that has maintained a quiet equilibrium between welcoming visitors and retaining its own pace. The night is spent at anchor in the harbor.
Day6
Kastos to the Eastern Coast of Lefkada
The return leg heads northward along the sheltered waters between Lefkada and the mainland, a stretch that includes some of the calmest and most scenic anchorages of the entire week. Desimi Bay, a sheltered inlet fringed by pine trees with a small seasonal taverna at its head, is a natural stop for lunch. The area around Skorpios, the private island once owned by Aristotle Onassis, lies just offshore, with calm, clear water for a final afternoon swim. The pace of this last full day is deliberately unhurried, with time to appreciate the green hills and mirror-flat water of the Lefkada channel in the late afternoon light before the boat settles for the evening.
Day7
Return to Lefkada Marina and Disembarkation
After breakfast, the final short navigation heads back through the Lefkada channel toward the marina. Depending on timing and conditions, a last swim stop is possible before the approach to the berth. Arrival is planned for the morning, with the final night spent on board. Disembarkation takes place the following morning after breakfast.
Important Note
This itinerary may vary depending on weather conditions, currents and marine activity. Dive sites and schedule are adjusted daily by the team to ensure safety and the best possible underwater experience.
The cockpit arch keeps the mainsheet completely out of the way, turning the outdoor seating area into a genuinely clear social space for the whole group.
Two long cockpit benches seat the crew comfortably around a fold-out table, with twin helm positions set wide enough to leave a clear central passage to the transom, which drops down to form a practical swim platform at water level.
Below deck, the owner's cabin forward is accessed through double doors, giving it a level of privacy and spaciousness that works better than most single-door solutions at this size. The saloon is notably bright for a thirty-eight foot boat, with overhead hatches and multiple opening ports keeping the air moving, and a galley arranged in an L-shape to free up seating space around the main table. The chart table folds away when not in use, adding further room below.
The charter layout typically offers three double cabins, well suited to a group of four to six guests, with the level of bathroom comfort varying depending on whether the boat has one or two heads.
The exact year and configuration of the boat assigned will be confirmed before departure, with comfort and layout kept consistent across similar vessels in the fleet.
What to pack for a sailing holiday?
Pack smart for your yacht charter: choose a soft bag instead of a hard suitcase, bring lightweight layers, reef-safe sunscreen, and non-slip shoes for onboard use. A couple of swimsuits and motion sickness remedies can also make a big difference. Each boat has limited storage, so pack light, but wisely! Need help building the perfect list? Read our full guide: What to pack in a suitcase for a yacht charter
What’s a Typical Day Like on a Yacht Charter?
Start your day with a swim in a quiet bay, sail to hidden beaches or seaside villages, and enjoy a slow lunch on deck. Afternoons mean snorkeling, sunbathing, or exploring ashore. As the sun sets, your boat anchors in a scenic cove or near a harbor, ready for a relaxed dinner and a night under the stars. Curious about the full experience? Discover more in our guide: What’s a typical day like on a sailing holiday?
Who Handles Cooking and Cleaning on a Yacht Charter?
On skipper-only charters, guests usually share cooking and cleaning duties, think salads, pasta, and good teamwork. If there's a hostess, light meals and tidying are included, but it's still a casual, collaborative vibe. On fully crewed yachts, you’ll enjoy full service with a chef and crew managing everything. Want to know what’s included in your setup? Read the full guide: Who takes care of cooking and cleaning on a sailing charter?
What Happens in Case of Bad Weather During a Sailing Holiday?
Summer sailing holidays rarely face major weather issues, but when the sea gets rough, skippers adjust the route for your safety. Expect protected bays, marina stops, or a change in plan. These moments often lead to unexpected gems: local towns to explore, time to relax on board, or cozy dinners ashore. Curious about how crews handle these changes? Read the full FAQ: What to do in case of adverse weather conditions or changes to the itinerary
