Wine Tasting Holidays

Showing 113 out of 315 trips

For the wine enthusiast, our holidays provide the opportunity to tour some of the great wine regions of the world, from the vineyards of the Alsace region in France to stunning San Gimignano, the mediaeval 'Manhattan of Tuscany', where the landscape is dominated by vines! Our selection of active cycling and walking holidays below are all guaranteed to provide you with the chance to get the corks out and sample some outstanding wines...

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Spain : The Canary Islands

Contrasts of Lanzarote

AU$1885


5.0 (4 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

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Italy : Puglia

Cycling the Heel of Italy - Alberobello to Lecce

AU$2130


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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Austria : The Tyrol

Walking the Kitzbuhel Alps Trail

AU$2215

NEW FOR 2026

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 3
Stretching

Printed route
directions

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Portugal : Madeira

Walking the Waterways and villages of Madeira

AU$2215


4.2 (6 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

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Spain : Asturias

Majestic Mountains of the Picos de Europa

AU$2215


4.7 (11 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2 & 3

Navigation App

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Spain : The Canary Islands

Contrasts of La Gomera

AU$2235


4.2 (5 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Italy : Puglia

Journey through Puglia to Matera

AU$2315


4.8 (15 reviews)

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Cultural tour

7 nights,
hotel-to-hotel

Headwater
Navigation App

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Spain : The Canary Islands

Walking on Gran Canaria

AU$2315


5.0 (7 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

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Italy : Umbria

Undiscovered Villages of Umbria Walk

AU$2315


4.7 (16 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Albania

E-bike Across Southern Albania

AU$2440


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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Italy : The Dolomites

Cycling from the Dolomites to Venice

AU$2480


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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Italy : Umbria

The Wine Trails of Umbria Cycling

AU$2685


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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Portugal : Mainland Portugal

Cycling in the Douro Valley

AU$3260

 
 

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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

AU$3280

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

AU$3360


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

AU$3465

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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Portugal : Mainland Portugal

Coimbra to Lisbon Cycling

AU$4205

 
 

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Self-guided cycling

11 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Norway

Cycling in the Lofoten Islands

AU$7585


4.8 (4 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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France

Chateaux Of The Loire Walk

AU$2910


4.4 (7 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Navigation App

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France : Corsica

North Corsican Wonders Between Coast and Mountains

AU$2480


4.0 (3 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2 & 2+

Printed route
directions

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Italy : The Bay of Naples

Paths of the Amalfi Coast

AU$1700


4.6 (28 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

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Italy : Veneto

Heart of Veneto Cycling

AU$2195


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

AU$2315


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 : Veneto

Walking in the Venetian Hills

AU$2360


4.7 (91 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Italy : Tuscany

A Taste of Tuscany Walking

AU$2605


4.9 (31 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

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Italy : Tuscany

A Taste of Tuscany Cycling

AU$2705


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

AU$2870


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 : The Dolomites

Walks in The Italian Dolomites

AU$3015


4.9 (136 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

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Portugal : Madeira

Marvels of Madeira Walk

AU$3055


4.7 (126 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Italy : The Dolomites

Walking the Dolomites of Alta Badia

AU$3405


4.8 (28 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

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Italy : Sicily

Cycling through Baroque Sicily

AU$3465


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

Julian Alps to the Adriatic Cycling

AU$4570


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

AU$2400


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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Portugal : The Algarve

Walk the Algarve's Wild West

AU$2400


4.8 (90 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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France : The Dordogne

Dordogne River Walk

AU$2565


4.7 (32 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Italy : Puglia

Contrasts of Puglia Cycling

AU$2975


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 : Lake Constance

Lake Constance Cycling

AU$3095


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

AU$3240


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

AU$3360


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 Walk

AU$3895


4.9 (97 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Italy : Piedmont

Gastronomic Barolo Cycling by e-bike

AU$4490


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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Portugal : Mainland Portugal

Walking the Green Coast of Minho

AU$1210


4.0 (1 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Printed route
directions

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Cyprus

Walking the Akamas Peninsula

AU$1560


4.5 (11 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 1 & 2

Headwater
Navigation App

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Italy : Veneto

Walking in the Prosecco Hills

AU$1600

NEW FOR 2026

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Self-guided walking

5 nights,
hotel-to-hotel

Level: 1+ & 2

Navigation App

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Portugal : Mainland Portugal

Walking the Mountains, Valleys & Coast of Minho

AU$1620


5.0 (3 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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France : Alsace

Villages & Vineyards of Alsace- Short Break

AU$1640


5.0 (2 reviews)

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Self-guided walking

4 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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France : The Loire

Chateaux Of The Loire Walk - Short Break

AU$1660

 
 

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Self-guided walking

4 nights,
hotel-to-hotel

Level: 1
Leisurely

Navigation App

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Portugal : Madeira

Walk the Garden Island of Madeira

AU$1765


4.8 (4 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

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Cyprus

Contrasts of Cyprus Walking

AU$1765


4.6 (8 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+ to 2+

Headwater
Navigation App

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Greece

Walking on Kythnos Island

AU$1785


5.0 (2 reviews)

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Self-guided walking

6 nights,
twin centre

Level: 2+
Moderate plus

Headwater
Navigation App

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Italy : Tuscany

Treasures of Tuscany Walk: San Gimignano to Volterra

AU$1785

 
 

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Self-guided walking

7 nights,
twin centre

Level: 2+
Moderate plus

Headwater
Navigation App

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France : Champagne

Cycling the Vineyards of Champagne

AU$1805

 
 

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Self-guided cycling

3 nights,
single centre

Level: 2
Moderate

Navigation App

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Germany : Bavaria

Walking in the Altmuhltal Nature Park

AU$1805


4.0 (1 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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France : Burgundy

Classic Burgundy Cycling

AU$1845


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 : Burgundy

Tour de France - Burgundy

AU$1905

 
 

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Self-guided cycling

3 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Navigation App

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France : Provence

Tour de France - Provence

AU$1950

 
 

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Self-guided cycling

3 nights,
hotel-to-hotel

Level: 3
Stretching

Navigation App

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France : Alsace

Cycling the Wine Route of Alsace

AU$1990


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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France : Champagne

Walking The Vineyards of Champagne - Deluxe

AU$2110


4.0 (1 reviews)

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Self-guided walking

4 nights,
single centre

Level: 1+
Leisurely plus

Printed route
directions

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Austria : The Danube

Walking the Wachau Heritage Trail

AU$2110


5.0 (2 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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France : Bordeaux

Cycling The Grand Crus of Bordeaux

AU$2155


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 : Istria

Walking the Highlights of Istria: Italy, Slovenia & Croatia

AU$2175


5.0 (2 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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Greece

Walking on Kythnos Island - Premium

AU$2215


4.6 (7 reviews)

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Self-guided walking

6 nights,
twin centre

Level: 2+
Moderate plus

Headwater
Navigation App

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France : Burgundy

Walking in Burgundy's Vineyards - Short Break

AU$2235

 
 

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Self-guided walking

4 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Italy : Sardinia

Walking Sardinia's Green Coast

AU$2235


5.0 (1 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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France : The Loire

Cycling The Chateaux Of The Loire - Short Break

AU$2255


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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Italy : Veneto

Adriatic Coast - Venice to Porec Ride

AU$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 UNESCO Loire Valley

AU$2275


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

AU$2295


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 : Champagne

Cycle The Wine Route of Champagne

AU$2360


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 : Provence

Provence : between Vineyards and olive groves

AU$2380


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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Spain : Balearic Islands

Walking Mallorca trails and traditional Fincas

AU$2420

 
 

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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Italy : Italian Lakes

Cycling Lake Garda by e-bike

AU$2480


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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Italy : Umbria

Walking on the Francigena Way

AU$2565


4.6 (11 reviews)

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Self-guided pilgrimage

9 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

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Portugal : Mainland Portugal

Tour the Treasures of Portugal

AU$2625


4.8 (5 reviews)

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Cultural tour

7 nights,
twin centre



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Italy : Trentino

Wine & Walk in Chianti

AU$2625


4.0 (2 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

VIEW TRIP

France : The Loire

Tour de France - Loire

AU$2725

 
 

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 3
Stretching

Navigation App

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France : Canal du Midi

Canal du midi Cycling : from Toulouse to Sete

AU$2725


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 : The Dordogne

Canoeing on the Dordogne

AU$2745


4.9 (61 reviews)

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8 nights,
hotel-to-hotel

Printed route
directions



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France

Cycling The UNESCO Loire Valley - Deluxe

AU$2770


4.3 (3 reviews)

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

VIEW TRIP

France : Burgundy

Walking in Burgundy's Vineyards

AU$2770


4.8 (8 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Spain : Andalucia

Three Cities of Andalucia

AU$2790


4.8 (6 reviews)

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Cultural tour

7 nights,
hotel-to-hotel



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France : Burgundy

Cycling the Vineyards From Beaune to Macon

AU$2810


4.8 (6 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

VIEW TRIP

France : Alsace

Villages & Vineyards of Alsace

AU$2830


4.4 (7 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

France : The Loire

Canoeing on the Loire

AU$2850


4.0 (1 reviews)

VIEW TRIP

5 nights,
hotel-to-hotel

Navigation App



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France : Canal du Midi

Tour de France - Canal du Midi

AU$2850


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

AU$2850


4.7 (19 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

VIEW TRIP

France : The Loire

Cycling The Chateaux Of The Loire - Upgraded Short

AU$2870


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

AU$2870


4.0 (1 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

VIEW TRIP

France : The Loire

Cycling The Chateaux Of The Loire

AU$2890


4.5 (12 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

VIEW TRIP

Spain : Rioja

Vineyards of La Rioja Cycling

AU$2910


4.5 (8 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

France

Dordogne Activities

AU$2910


4.8 (34 reviews)

VIEW TRIP

Multi-activity holiday

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Portugal : Mainland Portugal

Walk the Highlights of Northern Portugal

AU$2930


4.5 (6 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Greece : Crete

Walking the Wonders of Crete

AU$2950


3.7 (3 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Italy : Sicily

Sicily: Vino & Volcanoes

AU$2975


5.0 (2 reviews)

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Cultural tour

7 nights,
hotel-to-hotel

Headwater
Navigation App

VIEW TRIP

Italy : Tuscany

Cycling the hills of San Gimignano by E-bike

AU$3035


4.0 (1 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
single centre

Level: 2+ & 3

Headwater
Navigation App

VIEW TRIP

France : Atlantic Coast

Tour de France - Atlantic Coast

AU$3075

 
 

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 2 & 2+

Navigation App

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Croatia

Hike, Bike & Paddle Croatia

AU$3135


4.0 (1 reviews)

VIEW TRIP

Multi-activity holiday

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Portugal : Mainland Portugal

Cycling in Portugal: From the Mountains to the Sea

AU$3260


4.5 (17 reviews)

VIEW TRIP

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

AU$3690


4.8 (8 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

VIEW TRIP

France : Corsica

Corsica with Ebike

AU$3730


4.7 (3 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

VIEW TRIP

Italy : Italian Lakes

Cycling the Italian Lakes

AU$3815


4.9 (9 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Portugal : Mainland Portugal

Porto to Coimbra Cycling

AU$3875


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

France : The Loire

Cycling the Loire in Luxury

AU$4020

NEW FOR 2026

VIEW TRIP

Self-guided cycling

4 nights,
single centre

Level: 1+
Leisurely plus

Navigation App

VIEW TRIP

Slovenia

Secrets of Slovenia Cycling

AU$4040


4.9 (14 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Denmark

Nordic Cities by Rail

AU$4100


5.0 (1 reviews)

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Cultural tour

9 nights,
hotel-to-hotel



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Italy : Puglia

Highlights of Puglia Cycling

AU$4265


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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Portugal

Island Hopping in the Azores

AU$4265


4.6 (5 reviews)

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Self-guided walking

14 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Italy : The Bay of Naples

Walking the Amalfi Coast

AU$2975


4.7 (11 reviews)

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Guided group walking

7 nights,
single centre

Level: 2
Moderate

Printed route
directions

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Italy : Puglia

Walking in Puglia & Matera

AU$3280


4.3 (12 reviews)

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Guided group walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

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Italy : Veneto

Walk The Prosecco Hills & Hidden Venice

AU$3855


4.8 (5 reviews)

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Guided group walking

7 nights,
single centre

Level: 2
Moderate

Printed route
directions

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Italy : The Dolomites

Snowshoeing in the Dolomites - Premium Adventure

AU$4100

 
 

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Winter snow holiday

7 nights,
single centre

Printed route
directions

Operated by
Exodus Travels

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Italy : The Dolomites

Classic Dolomites - Premium

AU$4675


5.0 (1 reviews)

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Guided group walking

7 nights,
single centre

Level: 3
Stretching

Printed route
directions

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South Africa

Cycling the Cape & Winelands

AU$5595

 
 

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Guided group cycling

11 nights,
hotel-to-hotel

Level: 3
Stretching

Printed route
directions

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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.