Trip planner

Where to sail, when to go

Pick a country to overlay your school and public holidays, toggle what matters for the trip, and see which destinations actually fit your window.

British Virgin Islands (VG)

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Used for school + public holiday overlays.

Filters

Sailing level

Best fits for the selected week

  • British Virgin Islands

    100

    VG · Tortola

    Line-of-sight Caribbean classic — easiest tropical first charter.

    Wind 13 kn
    24 °C
    3.7 mm/day
    12.0 h sun/day

    Atlantic hurricane season

    More info

Destinations by week

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JanFebMarAprMayJunJulAugSepOctNovDec
Sail score
British Virgin Islands
VG · Tortola

How sailing seasons work

Charter weeks are shaped by three factors: prevailing wind, sea temperature, and demand. The Mediterranean's summer window — roughly May through October — brings reliable thermal winds like the meltemi in the Aegean and the mistral in the Gulf of Lion, but charter prices peak alongside the school holidays in July and August. The Caribbean trade-wind season runs late November through May with steady easterlies and dependable sun. Northern European waters open briefly between May and September. The calendar pairs climate norms with school and public holidays so you can spot the weeks where wind, weather, and price line up.

Sailing seasons by region

Peak weeks below are the hottest week of the year — a useful proxy for high season, peak crowds, and peak charter prices. Shoulder weeks fall just outside the peak window, when conditions are still good for sailing but bookings are noticeably cheaper.

Balearics

2 destinations

Peak around week 31 (July 27)

Cyclades

1 destination

Peak around week 31 (July 27)

Attica

1 destination

Peak around week 31 (July 27)

Campania

1 destination

Peak around week 31 (July 27)

PACA

1 destination

Peak around week 32 (August 3)

  • French Riviera

Corse

1 destination

Peak around week 31 (July 27)

Dodecanese

1 destination

Peak around week 31 (July 27)

Queensland

1 destination

Peak around week 6 (February 2)

  • Whitsundays

Thessaly

1 destination

Peak around week 32 (August 3)

Mahe

1 destination

Peak around week 17 (April 20)

Saint John

1 destination

Peak around week 35 (August 24)

  • Antigua

Faro

1 destination

Peak around week 32 (August 3)

  • Algarve

South England

1 destination

Peak around week 30 (July 20)

  • The Solent

Exuma

1 destination

Peak around week 33 (August 10)

  • Bahamas — Exumas

Saint-Martin

1 destination

Peak around week 35 (August 24)

  • Saint Martin

Catalonia

1 destination

Peak around week 31 (July 27)

Male

1 destination

Peak around week 21 (May 18)

  • Maldives

Florida

1 destination

Peak around week 33 (August 10)

  • Florida Keys

Fort-de-France

1 destination

Peak around week 35 (August 24)

  • Martinique

Basse-Terre

1 destination

Peak around week 35 (August 24)

  • Guadeloupe

Maryland

1 destination

Peak around week 31 (July 27)

  • Chesapeake Bay

Society Islands

1 destination

Peak around week 14 (March 30)

  • Society Islands (Tahiti)

Kotor

1 destination

Peak around week 31 (July 27)

  • Bay of Kotor

Bretagne

1 destination

Peak around week 32 (August 3)

  • Brittany

East Nusa Tenggara

1 destination

Peak around week 46 (November 9)

  • Komodo & Flores

Madeira

1 destination

Peak around week 35 (August 24)

  • Madeira

Kedah

1 destination

Peak around week 22 (May 25)

  • Langkawi

Northland

1 destination

Peak around week 7 (February 9)

  • Bay of Islands (NZ)

Stockholm

1 destination

Peak around week 31 (July 27)

  • Stockholm Archipelago

Washington

1 destination

Peak around week 32 (August 3)

  • Pacific Northwest — Puget Sound

South Denmark

1 destination

Peak around week 31 (July 27)

  • Funen Archipelago

Noord-Holland

1 destination

Peak around week 32 (August 3)

  • IJsselmeer

Acores

1 destination

Peak around week 34 (August 17)

  • Azores

California

1 destination

Peak around week 32 (August 3)

  • San Francisco Bay

Maine

1 destination

Peak around week 29 (July 13)

  • Maine Coast

Scotland

1 destination

Peak around week 32 (August 3)

  • Scottish West Coast

Yasawa

1 destination

Peak around week 7 (February 9)

  • Fiji — Yasawa & Mamanuca

Nordland

1 destination

Peak around week 31 (July 27)

  • Lofoten

Mecklenburg-Vorpommern

1 destination

Peak around week 31 (July 27)

  • Rugen & German Baltic

Vavau

1 destination

Peak around week 7 (February 9)

  • Tonga — Vavau

Munster

1 destination

Peak around week 34 (August 17)

  • West Cork

Jardines de la Reina

1 destination

Peak around week 33 (August 10)

  • Cuba — Jardines de la Reina

West Papua

1 destination

Peak around week 46 (November 9)

  • Raja Ampat

Aland

1 destination

Peak around week 31 (July 27)

  • Aland Islands

Newfoundland

1 destination

Peak around week 32 (August 3)

  • Newfoundland

Year-round sailing destinations

These destinations stay warm enough to sail (≥18 °C average) and dry enough to enjoy (≤15 mm/day mean precipitation) for at least 30 weeks of the year — a flexible window for off-peak charters and one-way deliveries.

Frequently asked questions

When is the best time to sail in the Mediterranean?
The classic Mediterranean charter window runs from May to October. June and September strike the best balance: warm water, steady wind, and prices noticeably lower than the July–August peak. Croatia and Greece sail comfortably into mid-October, while Italy and southern France start cooling earlier.
When is the Caribbean charter season?
The Caribbean trade-wind season runs from December through April, with reliable 15–20 knot easterlies and dependable sun. Hurricane season (June through November) shuts most charter fleets in the northern islands, though the southern Caribbean — Grenada, Trinidad, the ABCs — stays open year-round.
How do school holidays affect charter prices?
Charter prices rise sharply during school holidays in the major source markets — Germany, France, the UK, Italy, the Netherlands. If your travel dates are flexible, sailing the week before or after a school break can cut the boat price by 20–40% with no meaningful change in the weather.
What makes a good sailing week?
Steady wind in the 10–18 knot range, sea temperatures above 22 °C if you want to swim, low rainfall, and ideally a shoulder week outside school holidays. The week-by-week sail score above weighs these factors and lets you bias the ranking toward what matters most for your trip.