This fly-drive holiday is perfect for food and wine lovers, curious explorers and anyone looking to experience a lesser-known corner of Europe at a relaxed pace.
You'll discover two countries in one journey, starting in the elegant border towns of Gorizia and Nova Gorica before heading into Slovenia’s vineyard-covered Vipava Valley. With your own hire car, you can explore at your leisure while following a thoughtfully planned route that balances sightseeing, local experiences and time to simply enjoy your surroundings.
Walk between Italy and Slovenia in a single afternoon, sample regional wines aboard the Vipava Valley Wine Train and cycle through rolling vineyards on a guided e-bike excursion. Along the way, you'll uncover medieval villages, meet local winemakers and enjoy the rich culinary traditions that define this fascinating border region.
Staying in carefully selected boutique accommodation and a stylish forest glamping retreat, you'll experience the landscapes, flavours and culture that make the Vipava Valley one of Slovenia’s most rewarding destinations.

Fly from London Stansted to Trieste and collect your hire car on arrival. A short drive brings you to Gorizia, an elegant border town where Italian, Slovenian and Austro-Hungarian influences meet. Spend the remainder of the day exploring the historic centre, with its attractive piazzas, cafés and atmospheric streets.
Overnight in Gorizia.

Today, you're free to explore Gorizia and neighbouring Nova Gorica at your own pace. Once separated by an international border, the two towns now form a unique cross-border destination and were jointly awarded European Capital of Culture 2025. Wander between the two countries, visit local museums and enjoy the region's renowned food and wine scene. (B)
Overnight in Gorizia.

Leave Italy behind and drive into Slovenia's picturesque Vipava Valley. Surrounded by vineyards, orchards and limestone hills, the valley is one of Slovenia's most important wine-producing regions. En route, stop to explore charming villages and enjoy spectacular views across the countryside before arriving at your accommodation in Planina. (B)

Enjoy a day at leisure to discover the Vipava Valley independently. Visit family-run wineries, explore medieval villages such as Vipavski Križ, or simply relax and enjoy the peaceful rural surroundings. (B)

Today experience one of the region's most unique attractions – the Vipava Valley Wine Train. Travel aboard a vintage train through rolling vineyards and picturesque countryside while local winemakers introduce their wines and share stories of the valley's rich wine-making heritage. Along the way, enjoy tastings of regional wines and local specialities, as well as stops to explore the surrounding area. (B)

Transfer to Theodosius Forest Village, a stylish glamping retreat nestled amongst pine woodland overlooking the valley. The remainder of the day is free to relax and enjoy the peaceful setting, perhaps unwinding in your private hot tub while taking in views across the surrounding countryside. (B)

Discover the Vipava Valley on two wheels during a guided Bike & Wine excursion. Using e-bikes, cycle along quiet country roads and vineyard trails, stopping to learn about local wine production and the region's culinary traditions. The leisurely route combines beautiful scenery, local culture and wine tasting, providing an immersive introduction to the valley and its winemaking heritage. (B)

Drive back to Trieste Airport, return your hire car and fly back to the UK.
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Price Notes
A municipal tax of approximately €2.50 per person per night applies in Gorizia and is typically payable locally. On this holiday to Italy it would be €5 per person in total for the 2-night stay, which is approximately £4.33 per person or £8.65 per couple. Exchange rates and local taxes may change before you pay at the hotel.
A municipal tax of approximately €2.00 per person per night applies in Slovenia and is typically payable locally. On this holiday to Slovenia it would be €10 per person in total for the 5-night stay, which is approximately £8.93 per person or £17.86 per couple. Exchange rates and local taxes may change before you pay at the hotel.