A seven-day charter is a constraint and a gift. The constraint is that you cannot sail far — 100-150 nautical miles is a comfortable week's distance, allowing for anchoring time, swimming, provisioning, and at least one day of doing nothing at all. The gift is that this limitation forces a kind of intimacy with a coastline: you come to know six or seven harbours well, rather than twenty superficially. These routes have been selected not for ambition but for satisfaction — the week that leaves the crew planning the next one before the sails are furled.
Split to Dubrovnik, Croatia (one-way)
Distance: 120 NM | Best months: May-June, September | Skill level: Intermediate
The Dalmatian coast's greatest hits in a single week. Depart Split's ACI marina, sail south through the Splitska Vrata channel to Brac, cross to Hvar town for the first night. Day two: Vis, the most remote of the inhabited islands, with Komiza's fishing harbour and the extraordinary Blue Cave on Bisevo. Day three: Korcula, Marco Polo's reputed birthplace, with its herringbone medieval streets. Day four: the quiet island of Mljet, whose national park contains saltwater lakes and a twelfth-century Benedictine monastery. Days five and six: work south through the Elaphiti islands — Sipan, Lopud, Kolocep — before the final approach into Dubrovnik.
The one-way format eliminates the return slog and means every day moves through new water. The passage from Vis to Korcula is the longest (approximately 20 NM) and the most exposed; the rest is sheltered island-hopping with daily distances of 10-15 NM.
The Ionian triangle: Lefkada, Ithaca, Kefalonia
Distance: 80 NM | Best months: May-October | Skill level: Beginner
The classic first-charter route, and popular for good reason. Depart Lefkada's marina, sail south to Meganisi's Vathi — a miniature harbour of startling beauty — for the first night. Day two: Ithaca's Kioni, stone houses around a tiny port. Day three: south to Vathi, Ithaca's capital and the reputed home of Odysseus. Day four: across the strait to Fiskardo on Kefalonia, the island's prettiest harbour and its best restaurant town. Day five: north along Kefalonia's coast, anchoring in Agia Efimia or doubling back to explore Ithaca's western coves. Days six and seven: sail north through the Lefkada Canal or along its eastern shore, arriving back at base with time for a final swim.
Wind is gentle throughout — 8-15 knots from the northwest in summer. No passage exceeds 15 NM. The holding in most anchorages is good sand or mud. This route is forgiving without being dull.
BVI circuit: Tortola to Tortola
Distance: 70 NM | Best months: December-April | Skill level: Beginner
The BVI's compact geography allows a full circuit in a week without hurrying. Day one: south from Tortola to Norman Island's The Bight, the classic first-night anchorage. Day two: Peter Island for swimming, then Cooper Island for the night. Day three: across to Virgin Gorda; dinghy to The Baths in the morning when the day-trip boats have not yet arrived. Day four: north to Anegada — the BVI's flat coral atoll, accessible only in settled weather and worth the passage for the lobster and the emptiness. Day five: west to Jost Van Dyke's White Bay for the beach-bar experience. Day six: Cane Garden Bay on Tortola's north shore. Day seven: return to base.
The passages are short (the longest, to Anegada, is 15 NM) and the trades provide consistent 15-knot reaching. The route can be sailed clockwise or anticlockwise depending on wind direction.
The Cyclades: Lavrion to Lavrion (round trip)
Distance: 120 NM | Best months: May-June, September-October | Skill level: Advanced
This route is for sailors who want to be tested. Depart Lavrion (on the Attic coast, an hour from Athens airport), sail southeast to Kea — the nearest Cycladic island and a gentle introduction. Day two: south to Kythnos, with its hot springs and quiet anchorages. Day three: Serifos, whose hilltop chora is one of the most dramatic in the Cyclades. Day four: Sifnos, the gastronomic island. Day five: if the meltemi permits, push south to Milos — the geological wonder of the chain, with Kleftiko's sea caves accessible only by boat. Days six and seven: return north via Kythnos or Kea, timing the passages to avoid the worst of the afternoon wind.
The meltemi dominates. In shoulder season (May-June, September-October), it blows 15-20 knots and the sailing is superb. In July-August, 25-35 knots is common and the return beat from Milos to Lavrion can take all day. This route requires flexibility and the willingness to abandon the plan if the wind insists.
The Grenadines: St Vincent to Grenada (one-way)
Distance: 90 NM | Best months: December-April | Skill level: Intermediate-Advanced
Widely considered the finest week's sailing in the Caribbean. Depart St Vincent, sail south to Bequia — the first Grenadine island and the most characterful, with Admiralty Bay's anchorage surrounded by boatyards and rum bars. Day two: Mustique, private and pristine. Day three: the Tobago Cays — four uninhabited islets inside a horseshoe reef, with the kind of turquoise water that makes you question your camera settings. Day four: linger in the Cays or sail to Mayreau. Day five: Carriacou, the northernmost of Grenada's dependencies, with a boatbuilding tradition and an end-of-the-world feel. Day six: south to Grenada's capital, St George's — one of the Caribbean's most attractive harbour towns. Day seven: return the boat.
The passages are 10-20 NM with consistent 15-25 knot trades. The windward sides of the islands generate swell; the leeward sides offer calm anchorages. Navigation requires care around reefs, particularly in the Tobago Cays.
The Amalfi Coast and Aeolians: Naples to Milazzo (one-way)
Distance: 130 NM | Best months: June-September | Skill level: Intermediate
An Italian odyssey that combines the Amalfi Coast's vertical drama with the Aeolians' volcanic strangeness. Depart Naples (or Castellammare di Stabia), round the Sorrento peninsula to Capri — anchor in Marina Piccola or take a berth in the harbour. Day two: the Amalfi Coast — Positano from the water is one of the Mediterranean's great sights. Anchor off Amalfi town. Day three: cross the Tyrrhenian Sea to the Aeolian island of Lipari (45 NM, the longest passage of the week — depart early). Day four: Vulcano's mud baths and fumaroles. Day five: Stromboli — anchor off the western shore and watch the eruptions at night. Day six: Salina, the greenest of the Aeolians, with caper farms and Malvasia wine. Day seven: south to Milazzo on Sicily's north coast.
This route requires experience with open-water passages and Mediterranean-style stern-to mooring in crowded harbours. The reward is a week of extraordinary variety — geological, cultural, and culinary.
Thailand: Phuket to Langkawi (one-way)
Distance: 100 NM | Best months: November-April | Skill level: Beginner-Intermediate
A gentle downwind run through the Andaman Sea's limestone islands. Depart Phuket's Yacht Haven marina, sail to Phang Nga Bay's sea stacks and hongs (collapsed cave lagoons accessible by dinghy). Day two: south to Koh Yao Noi, a Muslim fishing island that tourism has touched lightly. Day three: Koh Lanta, with long beaches and a languid pace. Day four: Koh Rok, a national park island with coral reefs a few metres from the anchor. Day five: Koh Lipe, the southernmost Thai island, near the Malaysian border. Days six and seven: cross into Malaysian waters to Langkawi, clearing customs on arrival.
Winds are light (8-15 knots) and the sea state is calm in season. The one-way format eliminates backtracking and the border crossing adds novelty. Provisioning is excellent and cheap in Thailand; less so in Langkawi.
