Just a 40-minute train journey from Lisbon, Cascais is the weekend getaway of choice for well-heeled locals. The sailing is also impressive – as you’d expect from a destination that’s hosted the America’s Cup – with the rugged Portuguese coastline punctuated by beaches and historic forts. The streets of this 19th-century Riviera town are packed with excellent seafood-centric restaurants such as Maré, run by renowned local chef José Avillez, while the revamped food market is another drawcard.

Zanzibar is far more than a post-safari stopover. The Spice Island offers all the elements of a memorable sailing holiday: pristine beaches, crystalline waters and reliable winds between June and October and then mid-December until March. A three-day trip could find you anchoring for sunset drinks at the palm-fringed paradise of Nungwi Beach, exploring medieval ruins on Tumbatu Island or snorkelling the hidden oasis of Mnemba Island, which is encircled by coral reefs.

Norway, as English author Douglas Adams wrote, is a country with “lovely crinkly edges”. In nautical terms, that translates to a magnificent western coastline dotted with thousands of tiny islands. Sailing allows you to explore the many hard-to-reach fjords that cut inland, disembarking for the occasional ramble among blueberry bushes and wildflowers. If time allows, venture north to the Lofoten Islands, a mountainous archipelago in Nordland county that’s also one of the best places to see the Northern Lights.

This stretch of Queensland’s central coast is home to 74 idyllic islands. While the luxurious resorts on Hamilton and Hayman islands and Whitehaven Beach’s world-famous curve of dazzlingly white sand are reason enough to visit, a sailing holiday enables you to choose your own barefoot adventure. Snorkel among parrot fish on the reef at Hook Island or hike to the scenic Hill Inlet Lookout on Whitsunday Island or spot turtles in Tongue Bay.

If you want to combine an urban escape with an unforgettable day’s sailing then head to San Francisco Bay – venue of the 2013 America’s Cup. Start east of Alcatraz and glide around Belvedere Point before stopping at the Sausalito waterfront for lunch at Fish (the Dungeness crab tossed with butter and chives on a toasted roll is a crowd-pleaser). Hug the shoreline on the way back until you move past Horseshoe Cove and you’ll be rewarded with unobstructed views of the Golden Gate Bridge from the water.

In the late 1930s, two Portuguese merchants approached IWC with a special request: a timepiece that offered the precision of a marine chronometer. IWC responded with a model defined by its impressive dimensions and highly legible dial, inspired by nautical deck watches. Today, that crisp and functional design language continues to resonate in the modern Portugieser family. To find out more about the IWC Portugieser collection, visit a Kennedy boutique in Melbourne, Perth or online.

Volcanic mountains and moss-green landscapes meet the turquoise sea in the South Pacific archipelago of French Polynesia, which comprises more than 100 islands and numerous atolls. A sailing boat is the ideal mode of exploration, although a skippered vessel is advised to help you navigate the bountiful reefs. The larger islands of Tahiti and Moʻorea are well-suited bases for families, while couples might prefer the overwater bungalows of Bora Bora or the intimate anchorages of Raʻiāte and Tahaʻa.

Writers have always taken inspiration from the Ionian islands and sailing is the perfect way to follow in their literary wake: consider making your first port of call Captain Corelli’s Kefalonia, Odysseus’s home of Ithaca or Gerald Durrell’s Corfu. Larger islands such as Zakynthos (Zante) are livelier and geared for families, while under-the-radar gems including Paxos offer more secluded charm. Wherever you visit, the food will impress. Must-tries include skordostoumbi (a garlic-infused eggplant and tomato dish) and loukoumades (deep-fried doughnuts soaked in honey and sesame).

The traditional drink of sailors is rum. The signature beverage of Antigua is rum punch. But that’s not the only reason why this Caribbean island continues to lure nautical visitors. The island is  peppered with 365 sun-soaked beaches and sailing is the best way to tick off as many as possible. You’ll also want to visit Nelson’s Dockyard, a UNESCO World Heritage-listed maritime hub that buzzes with restaurants serving steaming bowls of king crab, goat curry and jerk chicken.

Known as one of the sunniest regions in New Zealand, the Bay of Islands – on the north-east coast of the North Island – hosts the country’s biggest sailing regatta. Make sure you bring a fishing rod on board your charter to try your hand at luring the bountiful stocks of snapper, trevally and kingfish. All that  marine life lures in an abundance of local fauna, ranging from penguins to whales. The area is also rich in heritage, with Rangihoua Bay being New Zealand’s first integrated township of Māori and European settlers.

Inspired by marine chronometers, IWC Schaffhausen’s Portugieser Automatic 42 combines the sportiness of a chronograph with the elegance of a classic dress watch. Perched on a glossy alligator-leather strap, the 42.4-millimetre stainless-steel case holds a silver-plated dial with contrasting gold-plated hands and appliques. Two subdials – representing seconds and the timepiece’s seven-day power reserve  – offer visual balance, while a date window nestles unobtrusively at the base. To find out more about the IWC Portugieser collection, visit a Kennedy boutique in Melbourne, Perth or online.

These Idyllic Islands Are Just One Flight From Mainland Australia