Where to Travel This Autumn | The Best Places to Visit in October

October is the golden month of travel - crisp air, beautiful landscapes, and fewer crowds. Whether you’re chasing the last light of summer or craving a cosy retreat, these are the places we're flying to this autumn, in collaboration with Heavens Portfolio.

Tuscany, Italy

Temperature: 22°C high; 11°C low

Flight time from London: Approx. 2 hours

As summer fades and Tuscany’s rolling hills turn rich shades of gold, amber and crimson, autumn casts a cinematic spell. This is truffle and wine season, a time when the countryside comes alive with local festivals and long, lazy lunches under golden skies.

Find Autumn’s Magic at Castelfalfi

Nestled among golden vineyards and romantic vineyards, Castelfalfi captures Tuscany at its most beautiful. This five-star hotel seamlessly blends the storied charm of its medieval roots with contemporary luxury.

By day, explore ancient olive groves or take an e-bike through winding hilltop roads. By evening, sip estate-grown wine under a canopy of stars. For culinary travellers, October also marks the start of truffle season, best enjoyed with handmade pasta and a glass of Chianti in hand.

Paris, France

Temperature: 17°C high; 10°C low

Flight time from London: 1 hour

There’s no bad time for Paris, but October might be the most poetic. As the city glows under auburn trees, spend your days gallery-hopping, vintage treasure-hunting, or simply watching the world go by from a café terrace near the Seine.

Uncover Timeless Parisian Charm at Villa Junot

Tucked away in the hills of Montmartre, Villa Junot is a private Art Deco townhouse with surrealist flair. Originally built in the 1920s for French operatic composer André Mauprey, today it’s a sanctuary of quiet luxury, offering modern comforts such as a cinema room, a fitness & yoga studio, a vitality pool, a steam room and a sauna. Complete with a garden and panoramic rooftop views across the city, Villa Junot combines the comforts of a five-star stay with the freedom of having a place all to yourself.

 Images courtesy of Mr Tripper

Kenya

Temperature: 25°C high; 14°C low

Flight time from London: Approx. 9 hours

Kenya in October offers mild, pleasant weather and a more peaceful pace, perfect for those seeking a quieter, more authentic safari experience. Though it marks the transition into the "short rains" season with occasional, brief showers, wildlife viewing remains excellent, with the added bonus of fewer crowds.

Find the Ultimate Safari Playground at Ol Jogi

This 58,000-acre private conservancy in Laikipia is as exclusive as it gets, no other guests, just you and the wildlife. Inside the estate’s main house, nestled among tropical greenery, you'll find a grand living room with a fireplace, a games room, a TV room, a library and a bar, each space dressed in bold, maximalist décor. Scattered across the grounds are charming cottages, while an enormous pool complex with flowing water streams houses a spa and fitness centre.

 Images courtesy of Silverless

From conservation-focused encounters with endangered species to sundowners in the bush, every experience at Ol Jogi is one to remember.

 Images courtesy of Durston Saylor & Johnnie Cross

Athens, Greece

Temperature: 27°C high; 16°C low

Flight time from London: Approx. 3 hours 40 minutes

Athens in October offers the best of both worlds. It's still warm enough to swim in the sea, but you can also relish the city's downtown delights and archaeological sites without the heat and crowds.

Take in the Jaw-Dropping Views of the Acropolis at The Dolli

A neoclassical gem in the heart of Athens, The Dolli blends historic grandeur with modern boutique charm. With just 46 thoughtfully designed rooms, pied-à-terres, and private apartments, it offers an intimate retreat with incredible panoramic views of the Acropolis. From rooftop breakfasts to sunset swims in the infinity pool, every detail invites you to slow down and savour the city’s timeless beauty.

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Interested in learning more? Get in touch at charter@365aviation.com for more information or to begin planning your private jet charter today.