An autumn escape in southern Portugal's wild, little-populated Alentejo region makes a lot of sense, with temperatures of around 23ºC making for breezy explorations of the area's famously golden landscapes and historic towns - minus the crowds. Bookend your days with sun-drenched, multi-course breakfasts and farm-to-fork dinners featuring the best of the Alentejo's rich natural larder and make time for at least one wine tasting - innovative regional winemakers are producing some fantastic reds, whites and rosés. Wind your way through the medieval streets of Unesco-listed Évora, dropping in and out of its many independent boutiques (the gorgeous cork pieces at O Cesto Artesanato will solve any gift-buying headaches), and stroll along the rugged cliffs of Costa Vicentina. In these parts, October is olive harvest season. At the 200-year-old agricultural estate-turned-design-led retreat São Lourenço do Barrocal, guests are invited to pick and stomp the bounty of the estate's 600,000sq m grove, before dining on an olive oil-drenched menu at one of its two restaurants.

We love Greece's largest and southernmost island at any time of the year, but when the high tourist season winds down, mid-October, balmy temperatures and gentle breezes create the ideal conditions for strolling between Minoan archaeological wonders (without the tour groups to contend with) and hiking the island's wildflower-carpeted interior. Base yourself at the island's beguiling third city, Rethymno, whose bustling old town is filled nightly with young creatives sitting outside at wobbly-legged tables grazing on meze plates and drinking raki late into the night. Try Avli, for the likes of goat with honey, rabbit stew, and handmade stuffed ravioli, alongside a line-up of excellent wines produced at its own winery. When dawn breaks, many hikers head for Samaria, but we suggest making a beeline for the Kourtaliotis gorge, 22km south of town, instead. Dip into rugged caves and cool hot feet in the crystalline waters of the Kourtaliotis, keeping eyes peeled for the buzzards and Bonelli's eagles that call this natural springs-studded ravine home. Having a getaway with the gang, or going with a multi-gen family group? Bed down at The Manor, a fully renovated, three-bedroom, two-bathroom 16th-century Venetian residence.

Moroccan summers are sun-scorched, so visiting as the warmer months wind down ensures you'll be able to adventure beyond your air-conditioned riad. In land-locked Fez, temperatures hover at a pleasant 25ºC from the end of September onwards. Base yourself at the 15-room boutique riad Palais Amani, located in the northern end of the city's medina, for easy navigation of the market's twisting alleyways. This city has a crafting heritage, and it's showcased in the brass etching studios and woodcarving workshops located around the market. Take yourself on an artisan hunt with stops at Fez Tannery, to spot a centuries-old trade in action, and Art Naji ceramic factory, to see the manufacturing process behind the country's colourful tiles. At ADER-Fès, a craft centre housed in four fondouks that once sheltered the nomadic merchants of the Silk Road as they peddled their wares in the city, practitioners of traditional Fassi handicrafts have been given space and support to hone their skills in embroidery, woodcarving and pottery. Seeking a souvenir of your adventures around Fez? Anajam Home curates wares from around Morocco, including hand-blown glass carriages, geometric rugs and hand-woven baskets.

Think New Jersey, and horse-drawn carriages and old-world Victorian homes probably don't spring to mind, but the nostalgic waterfront of pretty-as-a-picture Cape May offers just that. Founded in 1611, this grande dame town is America's oldest seaside resort and designated a National Historic Landmark to boot. It's been welcoming vacationers for more than 200 years, but don't think that means it's stuck in the past. Just as Asbury Park has revamped itself of late, so, too, has Cape May had a recent identity reinvention. Soak up the last of the summer sun with a sandy-toed, 3km walk along the seafront, taking snaps of the "painted ladies" that overlook the shoreline, before diving into Cape May's other offerings. Top of our list? Exploring the wine. The town is home to a half-dozen vineyards - try Jessie Creek or Hawk Haven - and a just-as-impressive selection of breweries. In late summer, the beer garden at Cape May Brewing Co's tasting room is the place to be. End the evening with a Cape May classic of a beer and a bucket of peel-and-eat shrimp at the much-loved Rusty Nail (205 Beach Ave). For a nostalgic throwback, book a room at one of the many guesthouses tucked inside the elegant, old mansions - The Mason Cottage is cookie-cutter cute.

Located between Sicily and the North African coast, the honey-hued island of Malta benefits from elongated southern Med summers, getting an average eight hours of sunshine a day in September. Temperatures top out at a comfortable 20ºC - warm enough to wear your Birkenstocks. Come autumn, beach days aren't as much a priority (although Malta's meandering coastline offers up inviting waters aplenty, should you fancy) but the balmy weather offers a chance to explore Europe's smallest capital in its entirety. The coastal city is small enough that you can walk it, bastion wall to bastion wall, taking in the citadel's architectural embellishments. You'll recognise the fairy-tale forts from their silver screen cameos in Game of Thrones. Food, or rather the socialisation that surrounds a meal, is the lifeblood of this city and, come evening, the limestone streets are packed with diners and drinkers spilling out from shabby-chic bars that hum with live music. For a lunch that explores the island cookbook, try Is-Suq tal-Belt, a historic food hall that was recently renovated to appeal to contemporary tastes. At dusk, head to Strait Street to mingle with the easy-living Maltese professionals who frequent the innovative bars and restaurants constantly opening along its length. The nostalgic Tico Tico is a favourite. The pint-sized SU29, tucked away on one of the most historic streets of the Unesco-listed city, offers an intimate stay close by.