Best time to sail: a month-by-month charter calendar

Free tool · sources checked 26 Oct 2026

When should you charter a sailboat or catamaran? Pick a month to see where the sailing is good, or pick a destination to see its year. Ratings cover wind, weather, hurricane or monsoon season, crowds and price season for all 11 of our charter destinations, and each one links to its source. Months marked ? (20 in total) are ones our sources don't cover directly, so check them with your charter company.

Best: in season, with the conditions sources rate highest.
Good: in season, with a trade-off such as peak prices, crowds or strong wind.
Shoulder: workable and often cheaper, with more weather risk or a low season.
Avoid: peak hurricane or monsoon risk, or outside the charter season.
? = uncertain: no source covers this month directly.

The sailing calendar at a glance

Charter rating by destination and month. ★ best, ✓ good, ◐ shoulder, ✕ avoid, ? uncertain.
Destination	Jan	Feb	Mar	Apr	May	Jun	Jul	Aug	Sep	Oct	Nov	Dec
BVI	Best	Best	Best	Best	Good	Shoulder	Shoulder, uncertain	Avoid, uncertain	Avoid	Avoid	Shoulder	Best
USVI	Best	Best	Best	Best	Shoulder, uncertain	Shoulder, uncertain	Shoulder, uncertain	Avoid	Avoid	Avoid	Shoulder, uncertain	Best
Caribbean	Best	Best	Best	Best	Shoulder	Shoulder	Shoulder, uncertain	Avoid, uncertain	Avoid	Avoid	Shoulder	Best
Bahamas	Best	Best	Best	Best	Best	Shoulder, uncertain	Shoulder, uncertain	Avoid	Avoid	Avoid	Shoulder, uncertain	Best
Turks & Caicos	Good	Good	Best	Best	Best	Shoulder	Shoulder	Avoid	Avoid	Avoid	Shoulder	Good
Croatia	Avoid	Avoid	Avoid	Shoulder, uncertain	Good	Best	Good	Good	Best	Shoulder, uncertain	Avoid	Avoid
Greece	Avoid	Avoid	Avoid	Shoulder, uncertain	Best	Best	Good	Good	Best	Shoulder, uncertain	Avoid	Avoid
Italy & Sardinia	Avoid	Avoid	Avoid	Avoid	Best	Best	Good	Good	Best	Shoulder, uncertain	Avoid	Avoid
Mallorca	Avoid	Avoid	Avoid	Shoulder, uncertain	Best	Best	Good	Good	Best	Shoulder, uncertain	Avoid	Avoid
Amalfi Coast	Avoid	Avoid	Avoid	Shoulder, uncertain	Good	Best	Good	Good	Best	Shoulder, uncertain	Avoid	Avoid
Thailand	Best	Best	Good	Good	Avoid	Avoid	Avoid	Avoid	Avoid	Avoid	Best	Best

On a phone, swipe the calendar sideways. Hover over or tap a destination for the reasons, or use the pickers above.

Month by month, destination by destination

Best time to sail British Virgin Islands

Hurricane season runs June 1 to November 30; Sulu says the real risk peaks from late August to early October. Read the BVI charter guide: prices, licence and bases →

January ★ Best High season: dry, with steady 15–20 kn easterly trade winds (sometimes 25). Highest prices of the year. ^[Sulu]^{[WI Yachts]}
February ★ Best High season: dry, with steady 15–20 kn easterly trade winds (sometimes 25). Highest prices of the year. ^[Sulu]^{[WI Yachts]}
March ★ Best High season: dry, with steady 15–20 kn easterly trade winds (sometimes 25). Highest prices of the year. ^[Sulu]^{[WI Yachts]}
April ★ Best High season: dry, with steady 15–20 kn easterly trade winds (sometimes 25). Highest prices of the year. ^[Sulu]^{[WI Yachts]}
May ✓ Good Still good weather and low rain, with prices 15–25% below high season. Sulu calls it some of the best value of the year. ^[Sulu]
June ◐ Shoulder Low season and the start of hurricane season. Sulu says early June is often fine. Get the right insurance. ^[Sulu]^{[NOAA National Hurricane Center]}
July ◐ Shoulder · uncertain Low season inside hurricane season. NOAA: the first Atlantic hurricane typically forms in early to mid August, so July is before the peak. ^[Sulu]^{[NOAA National Hurricane Center]}
August ✕ Avoid · uncertain Peak hurricane risk starts in late August. Most Atlantic activity falls between mid-August and mid-October. ^[Sulu]^{[NOAA National Hurricane Center]}
September ✕ Avoid Peak hurricane risk (NOAA: the season peaks around September 10). Many companies cut fleets or close bases from September to mid-November. ^[Sulu]^{[NOAA National Hurricane Center]}
October ✕ Avoid Peak hurricane risk (NOAA: the season peaks around September 10). Many companies cut fleets or close bases from September to mid-November. ^[Sulu]^{[NOAA National Hurricane Center]}
November ◐ Shoulder Hurricane season ends November 30, and Sulu says late November is often fine. Some bases reopen only from mid-November. WI Yachts counts November in its best season. ^[Sulu]^{[WI Yachts]}
December ★ Best Start of high season. Christmas weeks are the busiest and dearest. ^[Sulu]^{[WI Yachts]}

Best time to sail US Virgin Islands (St. Thomas)

Ratings use WI Yachts' USVI season dates plus NOAA hurricane climatology. We haven't found a USVI source covering each month in more detail, so treat the in-between months as a guide. Read the USVI charter guide: prices, licence and bases →

January ★ Best Best season per WI Yachts: steady trade winds, dry weather and pleasant temperatures. It's also high season. ^{[WI Yachts]}
February ★ Best Best season per WI Yachts: steady trade winds, dry weather and pleasant temperatures. It's also high season. ^{[WI Yachts]}
March ★ Best Best season per WI Yachts: steady trade winds, dry weather and pleasant temperatures. It's also high season. ^{[WI Yachts]}
April ★ Best Best season per WI Yachts: steady trade winds, dry weather and pleasant temperatures. It's also high season. ^{[WI Yachts]}
May ◐ Shoulder · uncertain Low season per WI Yachts, before hurricane season starts on June 1. ^{[WI Yachts]}^{[NOAA National Hurricane Center]}
June ◐ Shoulder · uncertain Low season, inside the Atlantic hurricane season (June 1 to November 30), before its usual peak. ^{[WI Yachts]}^{[NOAA National Hurricane Center]}
July ◐ Shoulder · uncertain Low season, inside the Atlantic hurricane season (June 1 to November 30), before its usual peak. ^{[WI Yachts]}^{[NOAA National Hurricane Center]}
August ✕ Avoid Most Atlantic hurricane activity falls between mid-August and mid-October, peaking around September 10. ^{[NOAA National Hurricane Center]}
September ✕ Avoid Most Atlantic hurricane activity falls between mid-August and mid-October, peaking around September 10. ^{[NOAA National Hurricane Center]}
October ✕ Avoid Most Atlantic hurricane activity falls between mid-August and mid-October, peaking around September 10. ^{[NOAA National Hurricane Center]}
November ◐ Shoulder · uncertain WI Yachts lists November as both high and low season. Hurricane season runs to November 30. ^{[WI Yachts]}^{[NOAA National Hurricane Center]}
December ★ Best Best season per WI Yachts: steady trade winds, dry weather and pleasant temperatures. It's also high season. ^{[WI Yachts]}

Best time to sail Caribbean (St. Martin & the Grenadines)

This guide covers St. Martin and the Grenadines together. The St. Martin season dates come from WI Yachts and the Grenadines dates from SVG Yachting. Neither source rates August or September for the Grenadines. Read the Caribbean charter guide: prices, licence and bases →

January ★ Best Grenadines high season with steady 15–20 kn trade winds. Christmas, New Year and February half-term are peak weeks, often 20–30% above high season. St. Martin's best season is December to April. ^{[SVG Yachting]}^{[WI Yachts]}
February ★ Best Grenadines high season with steady 15–20 kn trade winds. Christmas, New Year and February half-term are peak weeks, often 20–30% above high season. St. Martin's best season is December to April. ^{[SVG Yachting]}^{[WI Yachts]}
March ★ Best Grenadines high season with steady 15–20 kn trade winds. Christmas, New Year and February half-term are peak weeks, often 20–30% above high season. St. Martin's best season is December to April. ^{[SVG Yachting]}^{[WI Yachts]}
April ★ Best Grenadines high season with steady 15–20 kn trade winds. Christmas, New Year and February half-term are peak weeks, often 20–30% above high season. St. Martin's best season is December to April. ^{[SVG Yachting]}^{[WI Yachts]}
May ◐ Shoulder Shoulder season: usually 15–25% below high season, with lighter winds and quieter anchorages. Hurricane season starts June 1. ^{[SVG Yachting]}^{[NOAA National Hurricane Center]}
June ◐ Shoulder Shoulder season: usually 15–25% below high season, with lighter winds and quieter anchorages. Hurricane season starts June 1. ^{[SVG Yachting]}^{[NOAA National Hurricane Center]}
July ◐ Shoulder · uncertain SVG Yachting counts early July as shoulder season. Later in July you're further into hurricane season. ^{[SVG Yachting]}^{[NOAA National Hurricane Center]}
August ✕ Avoid · uncertain Neither source rates August. It's in hurricane season, and NOAA says activity ramps up from mid-August. ^{[NOAA National Hurricane Center]}
September ✕ Avoid St. Martin's low season (September to November per WI Yachts) and the peak of Atlantic hurricane activity. We have no Grenadines-specific rating for these months. ^{[WI Yachts]}^{[NOAA National Hurricane Center]}
October ✕ Avoid St. Martin's low season (September to November per WI Yachts) and the peak of Atlantic hurricane activity. We have no Grenadines-specific rating for these months. ^{[WI Yachts]}^{[NOAA National Hurricane Center]}
November ◐ Shoulder Shoulder season in the Grenadines (15–25% below high season) and still St. Martin's low season. Hurricane season ends November 30. ^{[SVG Yachting]}^{[WI Yachts]}^{[NOAA National Hurricane Center]}
December ★ Best St. Martin's best season starts. Christmas and New Year are the dearest weeks of the year in the Grenadines. ^{[WI Yachts]}^{[SVG Yachting]}

Best time to sail Bahamas (Exumas)

Exumas season dates come from WI Yachts. The hurricane timing is NOAA's Atlantic basin climatology, not specific to the Bahamas. Read the Bahamas charter guide: prices, licence and bases →

January ★ Best Best season (December to May): constant trade winds and dry tropical weather. Peak demand runs December to April, so book 6–12 months ahead. ^{[WI Yachts]}
February ★ Best Best season (December to May): constant trade winds and dry tropical weather. Peak demand runs December to April, so book 6–12 months ahead. ^{[WI Yachts]}
March ★ Best Best season (December to May): constant trade winds and dry tropical weather. Peak demand runs December to April, so book 6–12 months ahead. ^{[WI Yachts]}
April ★ Best Best season (December to May): constant trade winds and dry tropical weather. Peak demand runs December to April, so book 6–12 months ahead. ^{[WI Yachts]}
May ★ Best Still inside WI Yachts' December–May best season, after the December–April peak in demand. ^{[WI Yachts]}
June ◐ Shoulder · uncertain Low season, inside the Atlantic hurricane season (from June 1) but before its usual peak. ^{[WI Yachts]}^{[NOAA National Hurricane Center]}
July ◐ Shoulder · uncertain Low season, inside the Atlantic hurricane season (from June 1) but before its usual peak. ^{[WI Yachts]}^{[NOAA National Hurricane Center]}
August ✕ Avoid Low season and the peak of Atlantic hurricane activity (mid-August to mid-October). ^{[WI Yachts]}^{[NOAA National Hurricane Center]}
September ✕ Avoid Low season and the peak of Atlantic hurricane activity (mid-August to mid-October). ^{[WI Yachts]}^{[NOAA National Hurricane Center]}
October ✕ Avoid Low season and the peak of Atlantic hurricane activity (mid-August to mid-October). ^{[WI Yachts]}^{[NOAA National Hurricane Center]}
November ◐ Shoulder · uncertain Low season. Hurricane season runs to November 30. ^{[WI Yachts]}^{[NOAA National Hurricane Center]}
December ★ Best Best season (December to May): constant trade winds and dry tropical weather. Peak demand runs December to April, so book 6–12 months ahead. ^{[WI Yachts]}

Best time to sail Turks & Caicos

Core season runs December to May. June to November brings hurricane season, peaking August to October. Read the Turks & Caicos charter guide: prices, licence and bases →

January ✓ Good Core season, but the Christmas Winds can blow 20–25 kn for days. Humpback whales pass from January to April. ^{[SailScanner]}
February ✓ Good Core season, but the Christmas Winds can blow 20–25 kn for days. Humpback whales pass from January to April. ^{[SailScanner]}
March ★ Best Core season: steady easterly trades and 26–28°C, after the strongest Christmas Winds. Whale season runs to April. ^{[SailScanner]}
April ★ Best Core season: steady easterly trades and 26–28°C, after the strongest Christmas Winds. Whale season runs to April. ^{[SailScanner]}
May ★ Best Last month of the December–May core season. ^{[SailScanner]}
June ◐ Shoulder Hotter, with lighter winds, more squalls and hurricane season. The hurricane peak is August to October. ^{[SailScanner]}
July ◐ Shoulder Hotter, with lighter winds, more squalls and hurricane season. The hurricane peak is August to October. ^{[SailScanner]}
August ✕ Avoid Peak of the hurricane season. ^{[SailScanner]}^{[NOAA National Hurricane Center]}
September ✕ Avoid Peak of the hurricane season. ^{[SailScanner]}^{[NOAA National Hurricane Center]}
October ✕ Avoid Peak of the hurricane season. ^{[SailScanner]}^{[NOAA National Hurricane Center]}
November ◐ Shoulder Hotter, with lighter winds, more squalls and hurricane season. The hurricane peak is August to October. ^{[SailScanner]}
December ✓ Good Start of core season. The "Christmas Winds" can blow a steady 20–25 kn for days at a time from December to February. ^{[SailScanner]}

Best time to sail Croatia

The Maestral sea breeze is reliable most afternoons from late spring through September. Read the Croatia charter guide: prices, licence and bases →

January ✕ Avoid Low season, outside the May–September charter season. We haven't sourced winter sailing conditions. ^{[WI Yachts]}
February ✕ Avoid Low season, outside the May–September charter season. We haven't sourced winter sailing conditions. ^{[WI Yachts]}
March ✕ Avoid Low season, outside the May–September charter season. We haven't sourced winter sailing conditions. ^{[WI Yachts]}
April ◐ Shoulder · uncertain Still low season per WI Yachts, just before the May–September best season. ^{[WI Yachts]}
May ✓ Good Start of the best season, at shoulder prices 20–40% below peak. ^{[Up & Sail]}^{[WI Yachts]}
June ★ Best Best season (May to September) at shoulder prices: excellent conditions at 20–40% below peak. The Maestral is reliable most afternoons. ^{[Up & Sail]}^{[WI Yachts]}
July ✓ Good High season: top prices, and Saturday turnovers in Split are extremely busy. Book early, as Croatia sells out faster than most of the Med. ^{[Up & Sail]}^{[WI Yachts]}
August ✓ Good High season: top prices, and Saturday turnovers in Split are extremely busy. Book early, as Croatia sells out faster than most of the Med. ^{[Up & Sail]}^{[WI Yachts]}
September ★ Best Best season (May to September) at shoulder prices: excellent conditions at 20–40% below peak. The Maestral is reliable most afternoons. ^{[Up & Sail]}^{[WI Yachts]}
October ◐ Shoulder · uncertain Low season per WI Yachts (October to April). Neither source rates October's weather specifically. ^{[WI Yachts]}
November ✕ Avoid Low season, outside the May–September charter season. We haven't sourced winter sailing conditions. ^{[WI Yachts]}
December ✕ Avoid Low season, outside the May–September charter season. We haven't sourced winter sailing conditions. ^{[WI Yachts]}

Best time to sail Greece

In the Cyclades the Meltemi picks up strongly in July and August. The Ionian is calmer. Read the Greece charter guide: prices, licence and bases →

January ✕ Avoid Low season (November to March). We haven't sourced winter sailing conditions. ^{[WI Yachts]}
February ✕ Avoid Low season (November to March). We haven't sourced winter sailing conditions. ^{[WI Yachts]}
March ✕ Avoid Low season (November to March). We haven't sourced winter sailing conditions. ^{[WI Yachts]}
April ◐ Shoulder · uncertain Between WI Yachts' best season (May to September) and low season (November to March). No source rates this month directly. ^{[WI Yachts]}
May ★ Best Best season (May to September) at shoulder rates: fantastic conditions at 20–40% below peak. ^{[Up & Sail]}^{[WI Yachts]}
June ★ Best Best season (May to September) at shoulder rates: fantastic conditions at 20–40% below peak. ^{[Up & Sail]}^{[WI Yachts]}
July ✓ Good High season with peak prices, especially from Athens to the Cyclades. The Meltemi blows strongly in the Cyclades, so pick the calmer Ionian if you want an easy week. ^{[Up & Sail]}^{[WI Yachts]}
August ✓ Good High season with peak prices, especially from Athens to the Cyclades. The Meltemi blows strongly in the Cyclades, so pick the calmer Ionian if you want an easy week. ^{[Up & Sail]}^{[WI Yachts]}
September ★ Best Best season (May to September) at shoulder rates: fantastic conditions at 20–40% below peak. ^{[Up & Sail]}^{[WI Yachts]}
October ◐ Shoulder · uncertain Between WI Yachts' best season (May to September) and low season (November to March). No source rates this month directly. ^{[WI Yachts]}
November ✕ Avoid Low season (November to March). We haven't sourced winter sailing conditions. ^{[WI Yachts]}
December ✕ Avoid Low season (November to March). We haven't sourced winter sailing conditions. ^{[WI Yachts]}

Best time to sail Italy (Sardinia)

The Mistral can bring sudden strong gusts. Read the Italy & Sardinia charter guide: prices, licence and bases →

January ✕ Avoid Low season (November to April), outside the best season. We haven't sourced off-season sailing conditions. ^{[WI Yachts]}
February ✕ Avoid Low season (November to April), outside the best season. We haven't sourced off-season sailing conditions. ^{[WI Yachts]}
March ✕ Avoid Low season (November to April), outside the best season. We haven't sourced off-season sailing conditions. ^{[WI Yachts]}
April ✕ Avoid Low season (November to April), outside the best season. We haven't sourced off-season sailing conditions. ^{[WI Yachts]}
May ★ Best Best season (May to September): the Mistral gives good sailing winds, and the weather is dry and warm. Prices are below the July–August peak. ^{[WI Yachts]}
June ★ Best Best season (May to September): the Mistral gives good sailing winds, and the weather is dry and warm. Prices are below the July–August peak. ^{[WI Yachts]}
July ✓ Good High season: peak prices and crowded marinas. Book 6–12 months ahead. ^{[WI Yachts]}^[Yachtic]
August ✓ Good High season: peak prices and crowded marinas. Book 6–12 months ahead. ^{[WI Yachts]}^[Yachtic]
September ★ Best Best season, and prices drop about 15–25% from the summer peak. ^{[WI Yachts]}^[Yachtic]
October ◐ Shoulder · uncertain Between the best season (to September) and low season (from November). No source rates October directly. ^{[WI Yachts]}
November ✕ Avoid Low season (November to April), outside the best season. We haven't sourced off-season sailing conditions. ^{[WI Yachts]}
December ✕ Avoid Low season (November to April), outside the best season. We haven't sourced off-season sailing conditions. ^{[WI Yachts]}

Best time to sail Mallorca (Balearics)

The afternoon embat sea breeze builds to about 16 kn from April to October. Northerly Tramuntana gusts can top 25 kn. Read the Mallorca charter guide: prices, licence and bases →

January ✕ Avoid Outside the May–October bareboat season. We haven't sourced winter conditions. ^{[ECC Yacht]}
February ✕ Avoid Outside the May–October bareboat season. We haven't sourced winter conditions. ^{[ECC Yacht]}
March ✕ Avoid Outside the May–October bareboat season. We haven't sourced winter conditions. ^{[ECC Yacht]}
April ◐ Shoulder · uncertain The embat starts in April, but ECC Yacht's bareboat season starts in May. ^[SeekSail]^{[ECC Yacht]}
May ★ Best Best months per SeekSail, inside the May–October charter season. The embat sea breeze gives reliable afternoon sailing. ^[SeekSail]^{[ECC Yacht]}
June ★ Best Best months per SeekSail, inside the May–October charter season. The embat sea breeze gives reliable afternoon sailing. ^[SeekSail]^{[ECC Yacht]}
July ✓ Good Peak summer: hot and crowded, but still in season with the afternoon embat. ^[SeekSail]^{[ECC Yacht]}
August ✓ Good Peak summer: hot and crowded, but still in season with the afternoon embat. ^[SeekSail]^{[ECC Yacht]}
September ★ Best Best months per SeekSail, inside the May–October charter season. The embat sea breeze gives reliable afternoon sailing. ^[SeekSail]^{[ECC Yacht]}
October ◐ Shoulder · uncertain Last month of the May–October season, and the embat still blows. SeekSail doesn't list October among the best months. ^{[ECC Yacht]}^[SeekSail]
November ✕ Avoid Outside the May–October bareboat season. We haven't sourced winter conditions. ^{[ECC Yacht]}
December ✕ Avoid Outside the May–October bareboat season. We haven't sourced winter conditions. ^{[ECC Yacht]}

Best time to sail Amalfi Coast & Bay of Naples

Summer winds are mostly gentle north-westerlies of about 8–12 kn. Read the Amalfi Coast charter guide: prices, licence and bases →

January ✕ Avoid Low season (November to March). We haven't sourced winter conditions. ^{[WI Yachts]}
February ✕ Avoid Low season (November to March). We haven't sourced winter conditions. ^{[WI Yachts]}
March ✕ Avoid Low season (November to March). We haven't sourced winter conditions. ^{[WI Yachts]}
April ◐ Shoulder · uncertain Outside both the May–October season and the November–March low season. No source rates April. ^{[Ship O´Hoi]}^{[WI Yachts]}
May ✓ Good Inside WI Yachts' May–September best season, before the June–August high season. ^{[WI Yachts]}^{[Ship O´Hoi]}
June ★ Best The sweet spots of the May–October season: summer weather without the July–August crowds. ^{[Ship O´Hoi]}^{[WI Yachts]}
July ✓ Good Busiest months, with the most boats and the fullest harbours. Book 6–12 months ahead for June to August. ^{[Ship O´Hoi]}^{[WI Yachts]}
August ✓ Good Busiest months, with the most boats and the fullest harbours. Book 6–12 months ahead for June to August. ^{[Ship O´Hoi]}^{[WI Yachts]}
September ★ Best The sweet spots of the May–October season: summer weather without the July–August crowds. ^{[Ship O´Hoi]}^{[WI Yachts]}
October ◐ Shoulder · uncertain Ship O'Hoi includes October in the season, but WI Yachts' best season ends in September. No source rates October's weather. ^{[Ship O´Hoi]}^{[WI Yachts]}
November ✕ Avoid Low season (November to March). We haven't sourced winter conditions. ^{[WI Yachts]}
December ✕ Avoid Low season (November to March). We haven't sourced winter conditions. ^{[WI Yachts]}

Best time to sail Thailand (Phuket)

This is the Andaman coast (Phuket). Tropical cyclones are rare there, so the real deciding factor is the monsoon. The Gulf of Thailand (Koh Samui) has a different season. Read the Thailand charter guide: prices, licence and bases →

January ★ Best Northeast monsoon: dry, with the most settled conditions and 8–18 kn NE–E winds. Christmas, New Year and Chinese New Year are the busiest weeks. ^{[SailScanner]}^{[WI Yachts]}
February ★ Best Northeast monsoon: dry, with the most settled conditions and 8–18 kn NE–E winds. Christmas, New Year and Chinese New Year are the busiest weeks. ^{[SailScanner]}^{[WI Yachts]}
March ✓ Good Still dry season, but hotter, with lighter winds. Afternoon sea breezes of 10–15 kn are still good for relaxed sailing. ^{[SailScanner]}^{[WI Yachts]}
April ✓ Good Still dry season, but hotter, with lighter winds. Afternoon sea breezes of 10–15 kn are still good for relaxed sailing. ^{[SailScanner]}^{[WI Yachts]}
May ✕ Avoid Southwest monsoon: more rain, squalls, 12–25 kn SW–W winds and swell that make the west-coast anchorages uncomfortable or untenable. Sheltered Phang Nga Bay is still sailable. The Similan park closes from mid-May to mid-October. ^{[SailScanner]}^{[WI Yachts]}
June ✕ Avoid Southwest monsoon: more rain, squalls, 12–25 kn SW–W winds and swell that make the west-coast anchorages uncomfortable or untenable. Sheltered Phang Nga Bay is still sailable. The Similan park closes from mid-May to mid-October. ^{[SailScanner]}^{[WI Yachts]}
July ✕ Avoid Southwest monsoon: more rain, squalls, 12–25 kn SW–W winds and swell that make the west-coast anchorages uncomfortable or untenable. Sheltered Phang Nga Bay is still sailable. The Similan park closes from mid-May to mid-October. ^{[SailScanner]}^{[WI Yachts]}
August ✕ Avoid Southwest monsoon: more rain, squalls, 12–25 kn SW–W winds and swell that make the west-coast anchorages uncomfortable or untenable. Sheltered Phang Nga Bay is still sailable. The Similan park closes from mid-May to mid-October. ^{[SailScanner]}^{[WI Yachts]}
September ✕ Avoid Southwest monsoon: more rain, squalls, 12–25 kn SW–W winds and swell that make the west-coast anchorages uncomfortable or untenable. Sheltered Phang Nga Bay is still sailable. The Similan park closes from mid-May to mid-October. ^{[SailScanner]}^{[WI Yachts]}
October ✕ Avoid Southwest monsoon: more rain, squalls, 12–25 kn SW–W winds and swell that make the west-coast anchorages uncomfortable or untenable. Sheltered Phang Nga Bay is still sailable. The Similan park closes from mid-May to mid-October. ^{[SailScanner]}^{[WI Yachts]}
November ★ Best Dry season starts. WI Yachts puts November in its best season, and the Similan park usually opens from mid-October. ^{[WI Yachts]}^{[SailScanner]}
December ★ Best Northeast monsoon: dry, with the most settled conditions and 8–18 kn NE–E winds. Christmas, New Year and Chinese New Year are the busiest weeks. ^{[SailScanner]}^{[WI Yachts]}

Caribbean hurricane season: what it means for a charter

The Atlantic hurricane season officially runs from June 1 to November 30. NOAA says it peaks around September 10, with most activity between mid-August and mid-October.^{[NOAA National Hurricane Center]} For the BVI, Sulu says the real risk is from late August to early October, early June and late November are often fine, and many companies cut fleets or close bases from September to mid-November.^[Sulu] That's why the BVI, USVI, St. Martin, the Exumas and Turks & Caicos are marked "avoid" for August to October. If you do book in hurricane season, read the cancellation terms and get insurance that covers named storms.

Best time to sail the Mediterranean: Croatia, Greece and Italy

In Croatia, Greece, Sardinia, Mallorca and the Amalfi Coast the charter season runs roughly May to September or October. July and August are the peak: the highest prices and the busiest marinas, plus a strong Meltemi in the Greek Cyclades.^{[Up & Sail]} May, June and September give you excellent sailing at 20–40% below peak rates in both Croatia and Greece.^{[Up & Sail]}^{[Up & Sail]} Winter months are marked "avoid" because they're outside the season our sources describe. That doesn't mean you can't sail then; we just haven't sourced the conditions.

How we rate each month

Every rating is based on the published season dates and conditions in the sources below. We don't add our own guesses. Where a source doesn't cover a month, we say so and mark it ?.
Hurricane timing comes from NOAA's Atlantic basin climatology, which covers the whole basin, not individual islands.
"Best" weighs the weather and wind first, then crowds and price. A cheap shoulder month can beat a crowded peak month.
Weather varies from year to year. Always check the forecast and your operator's terms before you book.

Ready to look at prices? See This Week's Charter Deals or compare all destinations.

Sources

Sulu, British Virgin Islands Sailing Guide: The BVI Week (14 Apr 2026; re-checked 26 Oct 2026)
WI Yachts, Yacht charter British Virgin Islands: best time to charter (checked 26 Oct 2026)
NOAA National Hurricane Center, Tropical Cyclone Climatology (checked 26 Oct 2026)
WI Yachts, Yacht charter US Virgin Islands: best time to charter (checked 26 Oct 2026)
SVG Yachting, How much does a yacht charter in the Grenadines cost? (2026–27 season) (re-checked 26 Oct 2026)
WI Yachts, Yacht charter Saint Martin: best time to charter (checked 26 Oct 2026)
WI Yachts, Exumas Yacht Charters (re-checked 26 Oct 2026)
SailScanner, Sailing in Turks & Caicos (checked 26 Oct 2026)
WI Yachts, Yacht charter Croatia: best time to charter (checked 26 Oct 2026)
Up & Sail, How much does it cost to charter a yacht in Croatia in 2026? (2026; re-checked 26 Oct 2026)
WI Yachts, Yacht charter Greece: best time to charter (checked 26 Oct 2026)
Up & Sail, Yacht Charter Cost in Greece & Athens 2026: Complete Price Guide (2026; re-checked 26 Oct 2026)
WI Yachts, Sardinia Yacht Charters (re-checked 26 Oct 2026)
Yachtic, Yacht Charter Italy and Sardinia 2026 (last updated Feb 2026)
ECC Yacht, Bareboat charter in Mallorca (checked 26 Oct 2026)
SeekSail, Sailing Mallorca: destination guide (checked 26 Oct 2026)
WI Yachts, Yacht charter in Salerno (checked 26 Oct 2026)
Ship O´Hoi, Sailing the Amalfi Coast and Capri: a 7-day itinerary (checked 26 Oct 2026)
SailScanner, Sailing Thailand's Andaman Sea: Phuket & the Similans (checked 26 Oct 2026)
WI Yachts, Phuket Yacht Charters (re-checked 26 Oct 2026)