Where to Sail in the Fall: September, October, November

As summer’s vibrant energy gives way to the golden hues of autumn, a unique and magical window opens for sailors. Sailing in the fall is a secret seasoned sailors have long cherished; a time of comfortable temperatures, reliable winds, and blissfully quiet anchorages. This is the season to experience your favorite destinations in a new light, free from the summer crowds. From the still-warm waters of the Mediterranean to the crisp air of New England, fall sailing offers a diverse range of experiences for every type of sailor.

This guide is your ultimate resource for planning the perfect autumn sailing adventure. We’ll explore why sailing in the fall is such a special experience, from the changing landscapes to the favorable weather conditions. Whether you’re looking for a relaxing bareboat yacht charter or an exciting skippered yacht charter, this section will provide you with the information you need to make the best choice for your fall sailing trips.

Autumn is a magical time, when the leaves start to fall, and life adds its sepia hue to the shortening days. But don’t wave goodbye to summer just yet!

September, October and November are superb times to enjoy prime sailing conditions in the Eastern Mediterranean, Caribbean and further afield. Below is our guide to the best places to sail in the waning months.

From Turkey and Greece to the exotic delights of the Seychelles and Thailand, the late season is the time to go if you want to avoid large summer crowds while enjoying the very best yachting the world has to offer.

September is a fantastic time to sail in the Mediterranean, as the crowds have faded away, and although it is still warm, it’s no longer the stifling heat of mid-summer. The Eastern Med in particular keeps its warmth and winds until the middle of October, and is a glorious place to enjoy an Indian summer. The waters are also at their warmest, and swimming in secluded bays is a real treat.

Turquoise Coast, Turkey - The Turquoise Coast is ideally geographically placed for late season trips. Being the Mediterranean’s most southerly charter outpost means it is blessed with a longer sailing season, staying warmer much later than the rest of the region. In mid-September, it’s not uncommon to find temperatures touching the high 20˚Cs, while the Meltemi has generally lost the worst of its temper by this time. So if you want to sail the Med in warm weather, good winds and zero children, Turkey in September is the place for you

Dodecanese, Greece - Greece’s easternmost island groups benefit from the same climate as the nearby Turquoise Coast, with a distinctly different Greek flavour all their own. Set sail from Kos or Rhodes and weave between a tightly packed sprinkling of islands. September sailing conditions in the eastern Med are practically perfect, with NW winds of 9-14 knots, and 26˚C temperatures.

Pacific Northwest, USA/Canada – The Pacific Northwest is quite unlike any other sailing area in the world – where else can you see snow-capped mountains, whale pods, bald eagles, and brown bears from your charter yacht?! Direct flights from London take around 9.5 hours to Seattle or Vancouver.

October was made for far-flung adventures, from the jungle-fringed, emerald-green Andaman Sea to the swirling sands of Australia's Whitsundays. These are the best sailing areas off the beaten track.

Thailand – For something a little different, you can’t go wrong with Thailand. We sailed out of Phuket and around the Andaman islands in 2018, and they are almost otherworldly. The sea is an eerie emerald, the people couldn’t be warmer, and the sailing area is spectacular, taking you past giant limestone karsts in the middle of the sea. Thai food is another absolute highlight, and the snorkelling is top-notch, too. October is drier than the recently-ended monsoon season, but still with a little occasional rain to help break the humidity. Temperatures average 27˚C, with winds an easy WNW 5/6 knots.

The Seychelles - The Seychelles are simply stunning in October. At this time of year, the remote Indian Ocean islands really show their true colours - there is a little less wind than from June to September, and temperatures are a little warmer (26˚C), but not at full summer yet, so there's a lot less tropical rainfall than you'd find from December to February. The sailing area is astonishing, and moorings are mostly anchorages, with some mooring buoys, particularly near built-up areas like Praslin and Mahe. Navigation is straightforward, with line-of-sight sailing and longer passages possible between islands. The coral reefs and gorgeous scenery create superb snorkelling conditions all around, in impossibly clear waters.

The Whitsundays, Australia - This laid-back sailing area, sheltered by The Great Barrier Reef, is characterised by year-round breezes, with a stable trade wind blowing throughout. Visits in the Autumn give you a great chance to see pods of humpback whales, who arrive in the warm, sheltered waters ready to birth their calves. October is the Whitsundays' driest month, with warm, rather than hot, weather, and average winds of 15knots ESE.

November, well clear of the hurricane season and before the peak Caribbean season, is superb for trips south of the equator. The Leeward islands in particular are worth looking at, while The Seychelles are at the peak of their weather conditions.

St Lucia – Very much sandwiched between the offseason and the high season, November is a superb time to visit St Lucia, as the weather is hot and not too windy. You’ve skirted past the hurricane season, and dodged the crazy holiday times when the Caribbean populations swell drastically. Average temperatures historically range from 26-31˚C.

French Polynesia - A soothing WNW breeze wafts through the remote islands of Raiatea, Bora Bora and beyond in November, leaving you to enjoy this remote paradise in 8-15 knots. November is a prime time for a trip to Raiatea, as it's beginning to heat up, but it hasn't reached the height of summer; the air and water temperatures are both a glorious 29˚C on average.

Antigua - Perfect for late autumn escapes, Antigua is blessed with steady E trade winds at 10knots, in temperatures that reach 30˚C in November. Sheer bliss. Set sail out of Jolly Harbour or the historic English Harbour and see this jewel of the Leeward Islands at her absolute best, complete with exceptional reef and wreck diving conditions.