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.