Most of the world’s coastline isn’t worth chartering. The waters that are split into a small handful of genuinely great cruising grounds, and they don’t run year-round. Pick the wrong month and you’ve paid premium for a closed program. Here are the grounds we route, paired honestly to season.
1. The British Virgin Islands. December–April.
The BVI is the entry point. Steady trade winds, line-of-sight island hopping, anchorages 90 minutes apart, almost no open-water passages. You can spend a week here without ever losing the next island over the horizon. The whole archipelago is about 60 nautical miles end-to-end, which means the boat is the platform but it doesn’t dominate the day — you’re swimming, eating ashore, and back on the hook by dinner.
The anchorages that earn the routing: The Baths on Virgin Gorda for the granite boulder swim, Anegada for the lobster lunch on the beach and the only coral atoll in the chain, Jost Van Dyke for the Soggy Dollar bar at White Bay if you want the wink at the cruising history, and Norman Island for the protected anchorage at The Bight. Skip Cane Garden Bay unless you want crowds.
Boat to route: sailing catamaran. Sunreef 80 or Lagoon Sixty 7 in the 4-cabin range. The BVI sails itself — you don’t need a motor yacht here.
Window: mid-December to mid-April. Hurricane season runs June through November and is non-negotiable. May and November are shoulder months — viable but the wind softens and the rain risk rises.
2. The Grenadines. December–April.
If the BVI is entry, the Grenadines are the next level. Less developed, longer passages between anchorages, deeper water, and a different cultural register — this is the southern Caribbean, Bequia and Mustique and the Tobago Cays at the center. The water in the Tobago Cays is the postcard — a horseshoe reef with sand flats inside it where turtles come to feed and the visibility is the kind that ruins you for other Caribbean snorkeling.
Mustique is its own thing — a private island with a residents’ association, the Cotton House for shore lunch, and Basil’s Bar on the beach. Bequia is the unspoiled one, still feels like working sailor town, Princess Margaret Beach for the swim. The passage from St. Lucia south to the Grenadines is real water and you’ll feel it — this is not the BVI’s flat sail.
Boat to route: sailing cat or a smaller motor yacht in the 30–40m range. Mid-tier crew, strong chef.
Window: same December–April. Avoid hurricane season.
3. Croatia and the Italian Aeolians. May–September.
This is mid-tier Mediterranean and the most underpriced great cruising ground in the world. The Croatian coast is over 1,200 islands, mostly uninhabited, with anchorages every few miles down the Dalmatian chain — Hvar, Vis, Korčula, Lastovo, the Pakleni archipelago off Hvar town. The water is impossibly clear, the food at the inland konobas is real, and the wind is reliable enough to actually sail.
The Aeolian Islands off northern Sicily are the bridge to Italian water — Stromboli at night with the volcano glowing on the eastern flank, Panarea for the swim, Salina for the food. From the Aeolians you can run up the Amalfi or down to Sicily; both are full programs in their own right.
The honest version: Croatia is the value play and Italy is the cultural anchor. Combine them on a 10-night charter starting from Split or Dubrovnik, run the Dalmatian coast south, cross to the Aeolians, finish on the Amalfi. That’s the trip.
Boat to route: motor yacht in the 35–50m range for the comfort across the open passages. Benetti Oasis 40m or a Heesen 50m. The Med rewards beam at anchor.
Window: mid-May through late September. July and August are peak, expensive, and crowded — late May to mid-June and September are the better months for the same water at lower density.
4. The Greek Cyclades and Dodecanese. June–September.
Peak Mediterranean. The Cyclades — Mykonos, Santorini, Paros, Naxos, Milos, Folegandros — are the iconic chain, and the southern Cyclades (Milos, Folegandros, Sifnos) are the version still worth chartering. Mykonos and Santorini in August are the postcard but they’re also the most crowded waters in the Med. We route through them by passage and anchor in the quieter islands.
The Dodecanese are the second arc — Symi, Patmos, Astypalea, Leros. Closer to the Turkish coast, fewer charter fleets, the architecture is different, the food is closer to Anatolian than Aegean. A 10-night charter that combines the southern Cyclades with the Dodecanese, finishing in Rhodes, is the version of the Greek charter that delivers.
Boat to route: motor yacht 40m+ for the Meltemi crossings. The Aegean wind is real in July and August — a 100+ foot boat handles it; a smaller catamaran will pin you to the harbor on the bad days.
Window: June through September. Avoid mid-July through mid-August if you can — Meltemi peaks, prices peak, crowds peak. Early June and mid-September are the sweet spot.
5. French Polynesia. Year-round. May–October prime.
The Society Islands and the Tuamotus are the headline. Tahiti, Moorea, Bora Bora, Huahine, Taha’a — and then the Tuamotu atolls (Rangiroa, Fakarava) for the drift dives that don’t exist anywhere else on earth. Fakarava’s south pass is one of the great underwater experiences on the planet — a wall of 700 grey reef sharks holding station in the current. You don’t dive it; you drift it.
This is purpose-built charter water. The boats provision out of Papeete or Raiatea. The passages between islands are open ocean but manageable, the anchorages inside the lagoons are calm, and the snorkeling and diving program is the actual point of the trip.
Boat to route: sailing catamaran in the 24m+ range, or a smaller motor yacht with strong dive program. The cats track better in the trades and the shallow draft opens up more anchorages.
Window: May through October is the dry season and the peak. November through April is wetter and the cyclone risk rises. The Tuamotus are diveable year-round but the surface conditions soften in summer.
6. The Seychelles and the Maldives. November–April.
Two different programs in roughly the same band of the Indian Ocean. The Seychelles — the Inner Islands around Mahé, Praslin, La Digue, and the outer Aldabra group for the truly remote charter — is the granite and white-sand version, smaller in scale, with the iconic boulder beaches at Anse Source d’Argent and the Vallée de Mai. Charter fleets operate out of Mahé.
The Maldives is the atoll program — 26 atolls spread across 500 miles of ocean, with thousands of reefs and the kind of overwater visibility that makes the boat redundant. The charter is the way to access the empty atolls (Huvadhoo, Laamu, the southern atolls below the equator) that the resorts can’t reach. Manta and whale shark season runs August–November in Hanifaru Bay if you want to time around that.
Boat to route: sailing cat with a strong dive program. The Indian Ocean charter market is smaller than the Med or Caribbean — the inventory is concentrated and books out early.
Window: November through April. May through October is monsoon and the visibility drops.
7. The Norwegian fjords and Svalbard. June–August.
This is where the trip turns from charter to expedition. The Norwegian fjords — Geirangerfjord, Nærøyfjord, the Lofoten chain — are the entry, accessible to large motor yachts in summer with the long northern days and the steep-walled water that’s unlike any other coast in Europe. The boats stage out of Bergen or Tromsø.
Svalbard is the next step — 78° north, the archipelago between Norway and the pole, polar bears, walrus haul-outs, ice. This is genuine expedition water and requires an ice-class hull, which means the operator universe narrows to EYOS Expeditions and the handful of explorer yachts that work the high latitudes. The window is narrow — July and early August are the only viable months for sea ice access.
Boat to route: for the fjords, any seaworthy 40m+ motor yacht. For Svalbard, an EYOS-managed explorer yacht with ice classification and the right pilot onboard.
Window: June through August for the fjords. July and early August only for Svalbard.
8. The Antarctic Peninsula and South Georgia. November–February.
The expedition tier. This is the trip that ends every other trip — the Drake Passage from Ushuaia to the Peninsula, the iceberg fields of the Weddell Sea, the king penguin colonies of South Georgia, the sheer scale of a continent that’s been protected from tourism by geography alone. The operators here are EYOS Expeditions, Cookson Adventures, and Pelorus — a small group running ice-class yachts and chartered explorer vessels with submersibles, helicopters, and expedition staff onboard.
This is not a charter you build in eight weeks. The lead time is 12–18 months. The window is November through February. The Drake is the Drake — two days of real water in either direction, and the boats either handle it or the operator builds the schedule around it. The reward, once you’re inside the Peninsula and threading through the icebergs in the Lemaire Channel, is the version of the planet that almost nobody sees.
Boat to route: EYOS-managed expedition yacht only. This is not a market for crewed charter — the vessels need to be built for it.
Window: mid-November through February. December and January are the peak.
Honest sequencing.
If this is the first charter, do BVI in February. Learn the rhythm in protected water with the easiest weather window in the world. The second charter is Croatia in early June or French Polynesia in May. The third is Greece in late September or the Grenadines in March. By the fourth charter you know what you want, and that’s when the conversation about Svalbard or the Antarctic Peninsula actually makes sense. Don’t start at the top. The boat teaches you what to want next.
