Wine Tasting Cycling Holidays

Showing 56 out of 339 trips

For all our wine tasting cycling holidays we place huge importance on the pleasure you can gain from sampling local wines. Our routes take you through the finest vineyards and give you pleny of opportunities to sample the local wines - and our reps will collect any purchases you make and take them to your hotel for free.

Click on the appropriate 'View Holiday' button for full holiday details, take a look at our activities section for further information about how our cycling holidays work, or see our memorable meals page for further information about the fine food and wine you can expect on your wine tasting cycling holiday.

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Italy : Puglia

Cycling the Heel of Italy - Alberobello to Lecce

CA$2175


4.7 (44 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Italy

The Wine Trails of Umbria Cycling

CA$2385


5.0 (2 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Italy : The Dolomites

Cycling from the Dolomites to Venice

CA$2500


4.6 (9 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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Albania

E-bike Across Southern Albania

CA$2555


4.9 (7 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

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Portugal : Mainland Portugal

Cycling in the Douro Valley

CA$3220

 
 

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 3
Stretching

Headwater
Navigation App

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France : Champagne

Cycling Champagne in Luxury

CA$3240

NEW FOR 2026

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Self-guided cycling

4 nights,
single centre

Level: 2
Moderate

Navigation App

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Italy : Puglia

Cycling the Heel of Italy - Matera to Lecce

CA$3315


4.7 (14 reviews)

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Self-guided cycling

11 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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France : Atlantic Coast

Cycling along the Atlantic Coast

CA$3410

NEW FOR 2026

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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Bosnia / Croatia

Sarajevo to Dubrovnik by E-Bike

CA$3525

NEW FOR 2026

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

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Portugal : Mainland Portugal

Coimbra to Lisbon Cycling

CA$4095

 
 

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Self-guided cycling

11 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Italy : Veneto

Heart of Veneto Cycling

CA$2235


4.8 (73 reviews)

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Self-guided cycling

7 nights,
single centre

Level: 1
Leisurely

Headwater
Navigation App

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Italy : Veneto

Bolzano, Verona & Venice Ride

CA$2350


4.7 (20 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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Italy : Tuscany

A Taste of Tuscany Cycling

CA$2710


4.9 (29 reviews)

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Self-guided cycling

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

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Portugal : The Algarve

Cycling in The Real Algarve

CA$2860


4.7 (66 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Italy

Cycling through Baroque Sicily

CA$3410


4.5 (23 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Slovenia / Italy

Julian Alps to the Adriatic Cycling

CA$4440


4.8 (128 reviews)

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Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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France : The Dordogne

Dordogne Valleys & Villages Cycling

CA$2425


4.7 (52 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Italy : Puglia

Contrasts of Puglia Cycling

CA$2955


4.6 (126 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Austria / Germany / Switzerland

Lake Constance Cycling

CA$3070


4.7 (95 reviews)

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Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

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Croatia

Coastal Croatia - Porec to Pula Cycling

CA$3110


4.7 (87 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Portugal : Mainland Portugal

Porto Coastal Cycling

CA$3315


4.4 (59 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

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Italy : Piedmont

Gastronomic Barolo Cycling by e-bike

CA$4170


4.8 (89 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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France : Burgundy

Classic Burgundy Cycling

CA$1855


4.0 (1 reviews)

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Self-guided cycling

4 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Printed route
directions

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France : Provence

Tour de France - Provence

CA$2005

 
 

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Self-guided cycling

3 nights,
hotel-to-hotel

Level: 3
Stretching

Navigation App

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France : Champagne

Cycling the Vineyards of Champagne

CA$2045

 
 

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Self-guided cycling

3 nights,
single centre

Level: 2
Moderate

Navigation App

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France : Alsace

Cycling the Wine Route of Alsace

CA$2045


4.8 (10 reviews)

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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Italy : Italian Lakes

Cycling Lake Garda by e-bike

CA$2160


4.6 (5 reviews)

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Self-guided cycling

6 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

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France : Bordeaux

Cycling The Grand Crus of Bordeaux

CA$2195


4.5 (4 reviews)

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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Italy / Slovenia / Croatia

Adriatic Coast - Venice to Porec Ride

CA$2255


4.3 (3 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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France : The Loire

Cycling The Chateaux Of The Loire - Short Break

CA$2290


4.8 (8 reviews)

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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France : The Loire

Cycling The UNESCO Loire Valley

CA$2310


5.0 (4 reviews)

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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France : The Loire

Multi Activity in the Loire

CA$2330


5.0 (2 reviews)

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Multi-activity holiday

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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France : Provence

Provence : between Vineyards and olive groves

CA$2405


4.0 (2 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Navigation App

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France : Champagne

Cycle The Wine Route of Champagne

CA$2615


5.0 (1 reviews)

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Self-guided cycling

5 nights,
twin centre

Level: 2+ & 3

Navigation App

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France : The Loire

Tour de France - Loire

CA$2730

 
 

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 3
Stretching

Navigation App

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France : Burgundy

Cycling the Vineyards From Beaune to Macon

CA$2730


4.8 (6 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

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France : Canal du Midi

Canal du midi Cycling : from Toulouse to Sete

CA$2730


4.7 (6 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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France

Cycling The UNESCO Loire Valley - Deluxe

CA$2765


4.3 (3 reviews)

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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France : Canal du Midi

Tour de France - Canal du Midi

CA$2840


5.0 (1 reviews)

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Self-guided cycling

4 nights,
hotel-to-hotel

Level: 3
Stretching

Navigation App

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Italy : Sardinia

Undiscovered Sardinia Cycling

CA$2840


4.7 (19 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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France : The Loire

Cycling The Chateaux Of The Loire - Upgraded Short

CA$2860


4.8 (4 reviews)

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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Germany : The Moselle

Meandering the Moselle Cycle Path

CA$2860


4.0 (1 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

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France : The Loire

Cycling The Chateaux Of The Loire

CA$2880


4.5 (12 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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Spain : Rioja

Vineyards of La Rioja Cycling

CA$2900


4.5 (8 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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France

Dordogne Activities

CA$2900


4.8 (34 reviews)

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Multi-activity holiday

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Italy : Tuscany

Cycling the hills of San Gimignano by E-bike

CA$3015


4.0 (1 reviews)

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Self-guided cycling

7 nights,
single centre

Level: 2+ & 3

Headwater
Navigation App

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France : Atlantic Coast

Tour de France - Atlantic Coast

CA$3050

 
 

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 2 & 2+

Navigation App

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Portugal : Mainland Portugal

Cycling in Portugal: From the Mountains to the Sea

CA$3315


4.5 (17 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

France : The Loire

Cycling The Chateaux Of The Loire - Upgraded

CA$3620


4.8 (8 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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France : Corsica

Corsica with Ebike

CA$3660


4.7 (3 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

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France

Cycling the Loire in Luxury

CA$3715

NEW FOR 2026

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Self-guided cycling

4 nights,
single centre

Level: 1+
Leisurely plus

Navigation App

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Italy : Italian Lakes

Cycling the Italian Lakes

CA$3735


4.9 (9 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Portugal : Mainland Portugal

Porto to Coimbra Cycling

CA$3790


4.8 (56 reviews)

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Self-guided cycling

9 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Slovenia

Secrets of Slovenia Cycling

CA$3945


4.9 (14 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

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Italy : Puglia

Highlights of Puglia Cycling

CA$4155


4.8 (13 reviews)

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Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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South Africa

Cycling the Cape & Winelands

CA$4920

 
 

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Guided group cycling

11 nights,
hotel-to-hotel

Level: 3
Stretching

Printed route
directions

VIEW TRIP
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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.