Occupy V: Three Wine Regions to Book Now—Before Harvest Season Ends


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Hi All,

This week we're combining two of our favourite things, wine and walking.

September to November is the sweet spot for vineyard travel. We've picked three regions—Tuscany, Rioja, and Stellenbosch—where you can catch the harvest, hike through stunning countryside, and toast the season with something local in your glass.

1. TUSCANY, ITALY

For September & October

WHY BOOK NOW?

Tuscany shines in early autumn, with grape harvests underway and cooler temperatures for hilltop hikes.

It's a beautiful part Italy, but as harvest season is short, places can fill up quickly.

This organised tour takes in the beautiful hills of Chianti. You can see many of the best wine regions on day trips from Florence.

BOOKING TIPS

Getting There: Vueling currently have excellent-value fares from London Gatwick to Florence starting at £47 per person. From the US, Scandinavian Airlines has round-trip fares from around $450 from Washington Dulles and New York.

Where to Stay: Borgo Santo Pietro is a great-value countryside stay; La Bandita Townhouse in Pienza is perfect for seeing Val d'Orcia. For a luxury escape, Four Seasons Florence is offering credits of up to €200 for dining and spa treatments.

Don't Miss: Hike sections of the Via Francigena and finish with a Brunello tasting in Montalcino.

2. RIOJA, SPAIN

For Late September to October

WHY BOOK NOW?

Late September is harvest season in Rioja—plus it's perfect hiking weather.

From Laguardia, you can hike parts of the GR-38 Wine and Fish Route, a historic trail linking Rioja Alavesa and the Basque coast.

In Haro, considered the wine capital of Rioja, CVNE and Bodegas Muga are classic stops with deep roots in the region's winemaking history.

If you're starting in Madrid, read our guide here.

BOOKING TIPS

Getting There: The closest airports are Bilbao and Madrid. Skyscanner has fares from around $400 return from the US to Madrid. From the UK, Ryanair and easyJet have good value flights to Madrid and Bilbao.

Where to Stay: For a memorable stay, try Hotel Marqués de Riscal designed by Frank Gehry. Palacio de Samaniego is a luxury boutique hotel in a resorted palace.

Don't Miss: The GR-38 Wine Route Trail, an old wine trading path linking towns, caves, and bodegas.

3. STELLENBOSCH, SOUTH AFRICA

For September to November

WHY BOOK NOW?

September–November is South Africa's spring—wildflowers bloom, wine tasting terraces reopen, and trailheads are green and quiet.

Stellenbosch offers some of the country's best vineyard hikes, like the Jonkershoek Panorama Trail, a 17 km loop with sweeping views, fynbos-covered slopes, and optional wine stops nearby.

For more inspiration, start with our guide to Cape Town and our list of the best places to visit in South Africa.

BOOKING TIPS

Getting There: Norwegian Atlantic Airways has direct flights from London Gatwick to Cape Town starting from around £450. From the US, Virgin Atlantic has flights to Cape Town from New York, LA and Miami.

Where to Stay: Delaire Graff Lodges & Spa have luxurious lodges with panoramic vineyard views and find dining. Babylonstoren blends Cape Dutch charm with farm-to-fork dining; Clouds Estate is a scenic boutique stay at the top of Helshoogte Pass.

Don't Miss: The Jonkershoek Nature Reserve hike followed by tastings at nearby Lanzerac
or Tokara.