The sporting calendar just wouldn't be the same without Cowes Week (01983 295744; aamcowesweek.co.uk): this year from 2-9 August. It's been a summer highlight since 1826 when just seven yachts first raced off the Isle of Wight. Now it's the world's largest regatta, with around 40 races a day and up to 1,000 boats scudding across the waves. If you want to get out on the water, you can book a one-hour trip on a spectator boat (£12.50) or for an adrenalin fix, take a RIB ride (£35).
At other times of the year, Red Funnel (0844 844 2687; redfunnel.co.uk) includes a one-hour dinghy taster session as part of a three-night package with Wightwater Adventure Watersports for £172 per person based on two sharing B&B accommodation and return vehicle crossings. Or go the whole hog with a Tall Ships (02392 832055; tallships.org) sail training voyage, featuring day sails, European and UK coastal adventures and RYA practical courses on board the fleet of six vessels. The Channel Cruise from 8-14 September on the Stavros S Niarchos, a 200ft Brig, is a six-night voyage out of Greenwich for the finale of the Tall Ships Regatta, finishing in Southampton from £449 per person.
In the Swiss Alps, the famous Maloja wind on Lake Silvaplana makes the area ideal for sailing. Indeed, the Nira Alpina hotel (00 41 81 838 69 69; niraalpina.com) has just introduced a new three-night sailing package including two two-hour sailing lessons, beach barbecue, massage and dinner at Stars restaurant from £630 per person B&B.
Stretch your legs
On Explore's (0844 499 0901; explore.co.uk) new eight-day Greek Cruise and Island Walking holiday, you live on a traditional sailing boat finding turquoise bays, snorkelling in rocky coves and trekking through olive groves and hillside villages to ancient sites: from £799 per person, including return flights, six nights' boat and one-night hotel accommodation B&B with some meals and transport.
Or cycle and sail around the Turkish coast from Kalkan to the ancient city of Olympos, scrabbling around rock-hewn tombs and swimming in azure bays with Freedom Treks (01273 224066; freedomtreks.co.uk), sleeping on a three-masted wooden sailing boat from £1,047 per person including seven nights' half-board and activities, but excluding flights.
Go for gold
Learn to sail where the British Olympic medallist, Ben Ainslie honed his skills. In Falmouth, Mylor Yacht Harbour and its RYA-accredited sailing school creates bespoke sailing holidays from £540 per person (01326 372121; mylorharbourside.com) for a family of four during August including one week's luxury self-catering accommodation overlooking the water and a five-day Royal Yachting Association (RYA) sailing course with Mylor Sailing School.
A whale of a time
Take part in whale and dolphin research while sailing around Italy's Ligurian Sea (01273 823700; responsibletravel.com). You'll be part of the crew: sailing the yacht, gathering data and analysing sightings to determine the effect of human activity. No research or sailing experience necessary. The six-day trip costs from €799 (£632) full board, excluding flights.
There's also a good chance of spotting whales and dolphins off the remote Knoydart peninsula in the Highlands. Wilderness Scotland (01479 420020, wildernessscotland.com) has a trip on a beautifully converted 70-year-old Gaff cutter. Sailing up the west coast you can explore some of the less trampled areas on foot with a walking guide. From £1,195 per person including six nights' full board on the yacht, a skipper and walking guide.
The world's your oyster
If you've money to burn, charter the latest addition to the Y.CO fleet (00 377 93 50 12 12; y.co), aptly named Tiara, a 54-metre sailing yacht, swanning around the Med this summer (and the Caribbean during the winter). The front deck can be embellished with a Bedouin tent for chilled out coastal cruising, there's an open-air cinema, a Jacuzzi and a DJ console on deck for starlit partying. Below deck it's Art Deco in style: rich mahogany, leather and lacquer. It sleeps up to 12 from – make sure you're sitting down – £145,000 per week, including staff.
Rubicon 3 (020 3086 7245; rubicon3.co.uk) is a new company offering off-the-beaten-track sailing adventures around Europe from one week to six months. No experience is required but you need to do a couple of days' training before joining one of the expeditions, such as the one-week Norwegian Fjords, Bergen-to-Stavangar leg from 19-25 September. The price of £980 includes berth accommodation on board the 60ft race yacht Hummingbird and all on-board meals plus tuition from instructors, foul-weather gear and all safety equipment.