Where to sail each month of 2027: Canaries winter sun, the Med in summer, sea temperatures and half-term picks for UK families.
The best time for a sailing holiday depends on where you sail. Pick the right sea for the month and you will have warm water, reliable breezes and quiet anchorages almost all year round. Get it wrong, and you could be sheltering from the Aegean’s meltemi in August, or watching the rain sweep across the Andaman Sea in September.
This month-by-month guide is written for UK travellers planning the 2027 season. It covers the Mediterranean summer, winter sun in the Canaries and the tropics, and the question every family asks: where can we sail during half term and the school summer holidays?
The quick answer
- May to October: the Mediterranean. Spain’s Balearics, Croatia, Greece and Italy.
- November to April: the Canary Islands, the Caribbean and South-East Asia.
- June to October: the far side of the world, with the Whitsundays, French Polynesia and Tonga in their dry season.
Winter: December, January and February
Winter is not the end of the sailing season. It is when the action moves south and west.
Canary Islands: winter sun close to home
The Canary Islands are the obvious choice for UK sailors who want winter sun without a long-haul flight. Tenerife is around four and a quarter hours from London, with flights from most UK airports. Sea temperatures hold at around 20–21 °C in December and January, and daytime highs reach around 18–19 °C. That is cooler than the Mediterranean in summer, but glorious compared with Britain in January.
Our Canaries week, bookable now from £1,030 per person, sails from Puerto Colón past the cliffs of Los Gigantes to La Gomera. The Atlantic between the islands can be lively, so expect proper sailing on some days. The waters off south-west Tenerife are also among the best places in Europe to see pilot whales and dolphins.
The Caribbean: the classic winter escape
December to May is peak sailing season in the Caribbean, when the steady trade winds blow and the Atlantic hurricane season (officially 1 June to 30 November) is over. Our British Virgin Islands, Grenadines, Antigua and Exumas weeks open in 2027, with pre-registration available now.
South-East Asia
On Thailand’s Andaman coast, the dry season from November to April is the time for limestone karsts and calm bays around Phuket and Phang Nga. It is also one of our best-value long-haul options, from £1,170 per person.
February half term
February half term in England usually falls in mid-February. A week in the Canaries is the easiest family sailing option: a relatively short flight, no jet lag, and a warm sea. Check your local authority’s term dates before booking, as they vary between councils.
Spring: March, April and May
March and April: the long-haul sweet spot
The Caribbean and the Canaries remain excellent. Easter 2027 falls on 28 March, so the Easter school holidays will mostly cover late March and early April. That is perfect timing for a family week in the Canaries or a Caribbean adventure. In Central America, Belize and Panama’s San Blas islands are in their dry season.
May: the Mediterranean wakes up
May is when our Mediterranean season begins. The islands are green, harbours are quiet and the light is beautiful. The sea is still fresh: around 18 °C in Ibiza and Croatia, and 19 °C in the Ionian. Bring a shorty wetsuit if you are not a hardy British swimmer. Daytime highs of 21–24 °C make for very comfortable sailing.
May half term
In most English councils, May half term 2027 is expected to fall in the last week of May or the first days of June. It is one of the most underrated weeks of the year for a family sailing holiday. Prices and crowds are below peak summer, and the Mediterranean is warming up nicely. The Ionian and Mallorca are ideal, thanks to their short passages and sheltered bays. Our Family week slows the pace for younger sailors.
Make the most of May half term with a family week in the Balearics, bookable now.
See Mallorca & MenorcaSummer: June, July and August
June: the best month in the Med?
If you are free to choose, June is hard to beat. You get the longest days of the year, sea temperatures around 21–22 °C, and harbours that are not yet at their August peak. Every Mediterranean destination we sail is in season. It is also the best month for the Cyclades, before the meltemi wind is at its strongest.
July and August: school holidays and peak season
The English school summer holidays usually run from late July to early September. In Scotland they start earlier, around the end of June. This is peak season everywhere in the Mediterranean, with the warmest water and the busiest harbours. It is also when flights from the UK cost the most.
For summer holiday sailing, we recommend:
- Greece: Ionian Islands: lighter winds than the Aegean, with afternoon breezes rather than gales. It is the best summer choice for families and nervous first-timers.
- Croatia: Split & Hvar: reliable sunshine, short hops and great value, from £1,170 per person.
- Ibiza & Formentera: hot, lively and spectacular, ideal for groups of friends, stags and hens.
- Italy: Sardinia & La Maddalena: Caribbean-coloured water between Sardinia and Corsica.
The meltemi is a strong northerly wind that blows across the Aegean between roughly June and September, peaking in July and August. It can reach Force 7–8 at its strongest. That is why our Cyclades weeks run in May, June, September and October. If you want Greece in August, choose the more sheltered Ionian.
The other side of the world
The southern hemisphere’s winter is the dry season in the tropics. June to October is ideal for the Whitsundays, for French Polynesia, and for Tonga, where humpback whales arrive to breed and calve during the southern winter.
Italy in summer
Italy’s sailing areas run from May to October, but each has its own character. The Aeolian Islands off Sicily combine volcanoes, black-sand beaches and the nightly fireworks of Stromboli. Capri and the Amalfi Coast are the glamour option, with Positano’s pastel houses and lemon groves seen from the water. They are among our most in-demand weeks, from £1,290 per person. Sardinia’s La Maddalena archipelago is a national park with some of the clearest water in the Mediterranean. In July and August, all three are busy, so June and September are our favourite times to go.
Croatia through the season
Our Croatian weeks run from May to September. In early summer the islands are fragrant with lavender and pine, the sea is warming up, and harbours such as Hvar and Korčula are lively but not yet packed. The prevailing summer breeze, the maestral, typically builds in the afternoon and dies away in the evening. That makes for relaxed mornings at anchor and good sailing after lunch. By September the water is still warm, around 22 °C near Hvar, and the crowds have thinned.
Autumn: September, October and November
September: the insider’s favourite
Once the schools go back, the Mediterranean exhales. The sea is at its warmest of the year after a whole summer of sunshine: around 25 °C in Ibiza and 24 °C in the Ionian. Prices ease, and anchorages that were packed in August are suddenly peaceful. For couples, groups of friends and anyone without school-age children, September is arguably the best month of all. It is perfect for a Romance week or a Relax week.
October and October half term
October still offers warm water in the southern Mediterranean, around 22 °C in Ibiza and the Ionian, with daytime highs of 20–23 °C. The weather is more changeable, and days are shorter. October half term 2027 is expected to be the week starting 25 October in most English councils. That is late in the Mediterranean season, but our Ionian, Balearic and Italian weeks still run through October, so a half-term sailing week is possible. Pick the Ionian for the most sheltered water. Sunset sailing, food and wine tastings and a quieter island pace make October lovely for grown-ups.
November: the switch to winter destinations
By November the Mediterranean season is over and our winter destinations take over: the Canaries, Thailand, Malaysia and Mexico’s Sea of Cortez.
Month-by-month summary table
| Month | Where to sail | UK school dates (typical, England) |
|---|---|---|
| January | Canaries, Caribbean, Thailand | — |
| February | Canaries, Caribbean, Thailand, Belize | Half term, mid-February |
| March | Canaries, Caribbean, San Blas | Easter holidays begin late March |
| April | Canaries, Caribbean, Thailand | Easter holidays, early April |
| May | Balearics, Croatia, Ionian, Cyclades, Italy | Half term, late May |
| June | All Mediterranean, Whitsundays | Scottish holidays begin late June |
| July | Balearics, Croatia, Ionian, Italy | Summer holidays from late July |
| August | Balearics, Croatia, Ionian, Italy | Summer holidays |
| September | All Mediterranean, Polynesia, Tonga | Schools return early September |
| October | Balearics, Ionian, Cyclades, Italy | Half term, late October |
| November | Canaries, Thailand, Malaysia, Mexico | — |
| December | Canaries, Caribbean, Thailand | Christmas holidays |
The best time to sail for your group
The “best” month also depends on who is coming with you. Here is how we would match month and destination to each type of group.
Families with school-age children
You are tied to school holidays, so choose destinations with sheltered waters and short passages. May half term in the Ionian or Mallorca is our favourite: warm days, few crowds and enough heat for swimming. In the summer holidays, the Ionian and Croatia offer calm mornings and plenty of beaches. At Easter and February half term, the Canaries are the obvious pick. Our Family week keeps sailing legs short and swim stops long.
Couples and honeymooners
Without school dates to worry about, aim for June or September in the Mediterranean, when the sea is warm, the harbours are calmer and the sunsets are glorious. The Amalfi Coast, the Aeolian Islands and Dubrovnik are especially romantic. For a winter honeymoon, look at the Grenadines or French Polynesia in their seasons.
Groups of friends, stags and hens
June to September in Ibiza, Mallorca or Croatia gives you the best mix of hot weather and nightlife. Late September and early October in Ibiza coincide with the island’s famous closing parties. See our Party & Festival week for ideas.
Nature lovers and divers
Timing matters most for wildlife. Humpback whales visit Tonga during the southern winter, and Indonesia’s Komodo is at its best from April to November. Raja Ampat, among the richest reefs on the planet, is in season from October to April. Our Nature & Adventure week builds the route around these moments.
Teams and companies
For team building, May, June and September in the Mediterranean avoid the summer holiday rush and keep prices for flights and hotels down. Short hops between islands leave time for workshops on board in the mornings.
Planning tips for half term and school holidays
- Check your exact term datesHalf-term dates vary between councils and academies. Confirm yours on your local authority website before booking anything.
- Book flights earlyFares from UK airports rise sharply for half-term and summer holiday departures.
- Mind the Saturday changeoverOur weeks run Saturday to Saturday, which fits neatly around a nine-day half-term break.
- Hold your dates with a depositA £175 deposit secures the boat, and free date changes are allowed up to 90 days before.
- Ask for children’s kitRequest children’s lifejackets in the right sizes and any water toys you want when you book.
How season affects price
Our weekly prices are fixed per destination, but the other costs of your trip move with the calendar. Flights from UK airports are at their dearest in the school summer holidays and around half term. Marinas are fullest in July and August, too. If you can travel in June or September, you will usually save on flights and enjoy calmer harbours. Our how it works page explains the €200 (about £175) deposit and the instalment plan. Free date changes are allowed up to 90 days before, which helps if school dates change.
Still deciding where and when? Compare every destination, season and price in one place.
Browse all destinationsFAQs
What is the best month for a sailing holiday in the Mediterranean?
June and September are the sweet spots: warm sea, long days and quieter harbours than July and August.
Where can I sail in winter from the UK?
The Canary Islands (November to April) are closest, with sea temperatures around 19–22 °C. The Caribbean and Thailand are also in season.
Where should we sail during May half term?
The Ionian and Mallorca & Menorca are ideal: sheltered waters, short hops and fewer crowds than the summer holidays.
Is August a good time to sail in Greece?
The Ionian is great in August. The Cyclades can be very windy because of the meltemi, which peaks in July and August, so we sail there in May, June, September and October.
Can I sail during October half term?
Yes. Our Ionian, Balearic and Italian weeks run into October, with sea temperatures of around 22 °C, though the weather is more changeable.
