Discover our charming hotels and authentic places to stay

If discovering hidden restaurants whose food and wine epitomise the local cuisine or sampling wine that reflects the climate and terroir of a destination is what you’re looking for on a holiday abroad, then our selection of wine tasting holidays is sure to impress. Whether you’re looking to have an intimate wine-tasting experience, hear the fascinating history surrounding some of Europe’s best century-old vineyards or venture out for an impromptu wine-tasting evening of your own, rest assured that all of this is possible on a Headwater holiday.

Why not cycle through the heart of the famous Rioja wine region, where you’ll ride with a backdrop of the Sierra de la Demanda mountains? With time to explore around the medieval walled town of La Guardia, your route passes ancient monasteries while cycling through a section of the Camino de Santiago. On our Vineyards of La Rioja Cycling trip, you’ll also get to sample the award-winning wines of the region with visits to wineries in Haro, the Wine Museum of the Vivancos vineyard in Briones and El Ciego’s renowned Marques de Riscal vineyard.

On our Taste of Tuscany Walking holiday, you can enjoy delicious local produce and wine tastings in the charming town of Chianciano Vecchia, a cookery course in Chianciano Terme and have time to explore Montepulciano’s warmly lit enotecas (wine bars). We’d recommend spending an evening tasting the Nobile di Montepulciano while watching the sunset over avenues of sunflowers in the Val d’Orcia. And if that wasn’t relaxing enough, you can also unwind in the Hotel Posta Marcucci’s sulphur-rich healing waters in the Roman town of Bagno Vignoni.

When it comes to wine tasting regions, the Dordogne Valley’s temperate climate, limestone soil and sloping hillsides all contribute to the exquisite flavours and aromas of Dordogne’s finest wines. So, why not have an unforgettable tasting experience in Domaine du Mas des Merveilles? Named after the prehistoric Merveilles cave in Rocamadour, the vineyard cultivates outstanding Viognier and Chardonnay that you can try for yourself with a cheeseboard while you’re exploring the picture-perfect clifftop village of Rocamadour on our Dordogne River Walk. On this trip, you’ll also stop in the small, historic town of Souillac, where there are a number of quaint wine shops that you can pick up a bottle for the perfect memento of your trip in the Dordogne region.

Take a look at our complete Wine Tasting Holidays below for some much-needed inspiration for your next holiday.

 

Italy : Tuscany

A Taste of Tuscany Cycling

£1219


4.9 (27 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

Portugal : The Algarve

Cycling in The Real Algarve

£1279


4.7 (61 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

France : The Loire

Cycling The Chateaux Of The Loire

£1269


4.5 (10 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

Spain : Rioja

Vineyards of La Rioja Cycling

£1279


4.6 (7 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

France : The Dordogne

Dordogne Activities

£1289


4.8 (31 reviews)

VIEW TRIP

Multi-activity holiday

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Tap here to filter results

Filter and sort

Holiday type
All

  • Self-guided walking
  • Self-guided cycling
  • Ski holidays
  • Canoeing
  • Multi activity
  • Pilgrimage
  • Private guided walking
  • Cultural tour
  • Guided group walking
  • Guided group cycling

Destination
All

  • Italy
  • Spain
  • France
  • Portugal
  • UK
  • Andorra
  • Austria
  • Belgium
  • Bermuda
  • Bosnia
  • Canada
  • Cape Verde
  • China
  • Croatia
  • Czechia
  • Denmark
  • Finland
  • Germany
  • Gozo
  • Holland
  • Ireland
  • Malta
  • Montenegro
  • Norway
  • Romania
  • Slovenia
  • Sweden
  • Switzerland
  • USA

Departure month
All

  • Jan
  • Feb
  • Mar
  • Apr
  • May
  • Jun
  • Jul
  • Aug
  • Sep
  • Oct
  • Nov
  • Dec

Activty level
All


  • Leisurely

  • Moderate

  • Demanding

  • Challenging

Accommodation type
All


  • Single centre

  • Twin centre  

  • Hotel-to-hotel

Best for
All

  • Singles
  • Couples
  • Families
  • Food lovers
  • Wine lovers
  • Nature lovers
  • Bird watchers
  • Historic sites
  • Vegetarians
  • Swimming opportunities
  • Electric bikes
  • Tandem bikes
  • GPS navigation
  • Coastal routes
  • Island exploring
  • Lakes and rivers
  • High peaks
  • Unique accommodation
  • New holidays
  • Bestsellers

Sorted by


  • Price

  • Duration

  • Level

Update filters

 

Where appropriate, we grade our holidays based on distance, terrain, elevation gain, remoteness, etc and categorise them into 4 relative groups. This is ultimately subjective and may vary slightly day to day; for more advice, please see the specific trip page or call one of our friendly team.

Back to top