Wine Tasting Holidays

Showing 118 out of 340 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...

READ MORE

France : Provence

Provence Walking in Van Gogh's Footsteps

NZ$1670

NEW FOR 2026

VIEW TRIP

Self-guided walking

4 nights,
single centre

Level: 1+ & 2

Headwater
Navigation App

Spain : Asturias

Majestic Mountains of the Picos de Europa

NZ$2180


4.7 (11 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2 & 3

Navigation App

Spain : The Canary Islands

Contrasts of Lanzarote

NZ$2245


5.0 (4 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

Italy : Puglia

Cycling the Heel of Italy - Alberobello to Lecce

NZ$2290


4.7 (44 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Austria : The Tyrol

Walking the Kitzbuhel Alps Trail

NZ$2375

NEW FOR 2026

VIEW TRIP

Self-guided walking

6 nights,
hotel-to-hotel

Level: 3
Stretching

Printed route
directions

Italy : Umbria

Undiscovered Villages of Umbria Walk

NZ$2375


4.7 (16 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Portugal : Madeira

Walking the Waterways and villages of Madeira

NZ$2510


4.2 (6 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

Italy

The Wine Trails of Umbria Cycling

NZ$2530


5.0 (2 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Italy : The Dolomites

Cycling from the Dolomites to Venice

NZ$2660


4.6 (9 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

Spain : The Canary Islands

Contrasts of La Gomera

NZ$2705


4.2 (5 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Albania

E-bike Across Southern Albania

NZ$2730


4.9 (7 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

Spain : The Canary Islands

Walking on Gran Canaria

NZ$2750


5.0 (7 reviews)

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

Portugal : Mainland Portugal

Cycling in the Douro Valley

NZ$3500

 
 

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 3
Stretching

Headwater
Navigation App

France : Champagne

Cycling Champagne in Luxury

NZ$3520

NEW FOR 2026

VIEW TRIP

Self-guided cycling

4 nights,
single centre

Level: 2
Moderate

Navigation App

Italy : Puglia

Cycling the Heel of Italy - Matera to Lecce

NZ$3610


4.7 (14 reviews)

VIEW TRIP

Self-guided cycling

11 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

France : Atlantic Coast

Cycling along the Atlantic Coast

NZ$3720

NEW FOR 2026

VIEW TRIP

Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

Bosnia / Croatia

Sarajevo to Dubrovnik by E-Bike

NZ$3850

NEW FOR 2026

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

Portugal : Mainland Portugal

Coimbra to Lisbon Cycling

NZ$4510

 
 

VIEW TRIP

Self-guided cycling

11 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

France : The Loire

Chateaux Of The Loire Walk

NZ$3125


4.4 (7 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Navigation App

France : Corsica

North Corsican Wonders Between Coast and Mountains

NZ$2950


4.0 (3 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

Italy : The Bay of Naples

Paths of the Amalfi Coast

NZ$1980


4.6 (28 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

Italy : Veneto

Heart of Veneto Cycling

NZ$2355


4.8 (73 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
single centre

Level: 1
Leisurely

Headwater
Navigation App

Italy : Veneto

Bolzano, Verona & Venice Ride

NZ$2485


4.7 (20 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

Italy : Veneto

Walking in the Venetian Hills

NZ$2530


4.7 (91 reviews)

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

Italy : Tuscany

A Taste of Tuscany Walking

NZ$2795


4.9 (31 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

Italy : The Dolomites

Walks in The Italian Dolomites

NZ$2815


4.9 (136 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

Italy : Tuscany

A Taste of Tuscany Cycling

NZ$2905


4.9 (29 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

NZ$3080


4.7 (66 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Italy : The Dolomites

Walking the Dolomites of Alta Badia

NZ$3235


4.8 (28 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

Portugal : Madeira

Marvels of Madeira Walk

NZ$3235


4.7 (129 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Italy

Cycling through Baroque Sicily

NZ$3585


4.5 (23 reviews)

VIEW TRIP

Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Slovenia / Italy

Julian Alps to the Adriatic Cycling

NZ$4905


4.8 (128 reviews)

VIEW TRIP

Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

France : The Dordogne

Dordogne Valleys & Villages Cycling

NZ$2575


4.7 (52 reviews)

VIEW TRIP

Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Portugal : The Algarve

Walk the Algarve's Wild West

NZ$2575


4.8 (90 reviews)

VIEW TRIP

Self-guided walking

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

France : The Dordogne

Dordogne River Walk

NZ$2750


4.7 (32 reviews)

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Italy : Puglia

Contrasts of Puglia Cycling

NZ$3190


4.6 (126 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

Austria / Germany / Switzerland

Lake Constance Cycling

NZ$3320


4.7 (95 reviews)

VIEW TRIP

Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

Croatia

Coastal Croatia - Porec to Pula Cycling

NZ$3365


4.7 (87 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

Portugal : Mainland Portugal

Porto Coastal Cycling

NZ$3610


4.4 (59 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

Italy : Piedmont

Gastronomic Barolo Cycling by e-bike

NZ$4600


4.8 (89 reviews)

VIEW TRIP

Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Italy : Piedmont

Gastronomic Barolo Walk

NZ$4600


4.9 (97 reviews)

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Portugal : Mainland Portugal

Walking the Green Coast of Minho

NZ$1430


4.0 (1 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

Cyprus

Walking the Akamas Peninsula

NZ$1740


4.5 (12 reviews)

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 1 & 2

Headwater
Navigation App

Portugal : Mainland Portugal

Walking the Mountains, Valleys & Coast of Minho

NZ$1740


5.0 (3 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

France : Alsace

Villages & Vineyards of Alsace- Short Break

NZ$1760


5.0 (2 reviews)

VIEW TRIP

Self-guided walking

4 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Italy : Veneto

Walking in the Prosecco Hills

NZ$1805

NEW FOR 2026

VIEW TRIP

Self-guided walking

5 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

France : Burgundy

Classic Burgundy Cycling

NZ$1915


4.0 (1 reviews)

VIEW TRIP

Self-guided cycling

4 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Printed route
directions

Italy : Tuscany

Treasures of Tuscany Walk: San Gimignano to Volterra

NZ$1915

 
 

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 2+
Moderate plus

Headwater
Navigation App

Cyprus

Contrasts of Cyprus Walking

NZ$1960


4.6 (10 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+ to 2+

Headwater
Navigation App

France : The Loire

Chateaux Of The Loire Walk - Short Break

NZ$1980

 
 

VIEW TRIP

Self-guided walking

4 nights,
hotel-to-hotel

Level: 1
Leisurely

Navigation App

France : Burgundy

Tour de France - Burgundy

NZ$2045

 
 

VIEW TRIP

Self-guided cycling

3 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Navigation App

France : Provence

Tour de France - Provence

NZ$2090

 
 

VIEW TRIP

Self-guided cycling

3 nights,
hotel-to-hotel

Level: 3
Stretching

Navigation App

Greece

Walking on Kythnos Island

NZ$2110


5.0 (2 reviews)

VIEW TRIP

Self-guided walking

6 nights,
twin centre

Level: 2+
Moderate plus

Headwater
Navigation App

France : Champagne

Cycling the Vineyards of Champagne

NZ$2135

 
 

VIEW TRIP

Self-guided cycling

3 nights,
single centre

Level: 2
Moderate

Navigation App

France : Alsace

Cycling the Wine Route of Alsace

NZ$2135


4.8 (10 reviews)

VIEW TRIP

Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

Germany : Bavaria

Walking in the Altmuhltal Nature Park

NZ$2135


4.0 (1 reviews)

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

Portugal : Madeira

Walk the Garden Island of Madeira

NZ$2155


4.8 (4 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

Italy : Sardinia

Walking Sardinia's Green Coast

NZ$2220


5.0 (1 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Italy : Italian Lakes

Cycling Lake Garda by e-bike

NZ$2265


4.6 (5 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

France : Champagne

Walking The Vineyards of Champagne - Deluxe

NZ$2265


4.0 (1 reviews)

VIEW TRIP

Self-guided walking

4 nights,
single centre

Level: 1+
Leisurely plus

Printed route
directions

Austria : The Danube

Walking the Wachau Heritage Trail

NZ$2265


5.0 (2 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

France : Bordeaux

Cycling The Grand Crus of Bordeaux

NZ$2310


4.5 (4 reviews)

VIEW TRIP

Self-guided cycling

5 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

Italy / Slovenia / Croatia

Adriatic Coast - Venice to Porec Ride

NZ$2375


4.3 (3 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

Greece

Walking on Kythnos Island - Premium

NZ$2375


4.6 (7 reviews)

VIEW TRIP

Self-guided walking

6 nights,
twin centre

Level: 2+
Moderate plus

Headwater
Navigation App

France : The Loire

Cycling The Chateaux Of The Loire - Short Break

NZ$2420


4.8 (8 reviews)

VIEW TRIP

Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

Italy / Slovenia / Croatia

Walking the Highlights of Istria: Italy, Slovenia & Croatia

NZ$2420


5.0 (2 reviews)

VIEW TRIP

Self-guided walking

6 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

France : The Loire

Cycling The UNESCO Loire Valley

NZ$2440


5.0 (4 reviews)

VIEW TRIP

Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

France : The Loire

Multi Activity in the Loire

NZ$2465


5.0 (2 reviews)

VIEW TRIP

Multi-activity holiday

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

Italy : Puglia

Journey through Puglia to Matera

NZ$2485


4.8 (15 reviews)

VIEW TRIP

Cultural tour

7 nights,
hotel-to-hotel

7 meals
included

Headwater
Navigation App

France : Provence

Provence : between Vineyards and olive groves

NZ$2550


4.0 (2 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Navigation App

Spain : Balearic Islands

Walking Mallorca trails and traditional Fincas

NZ$2595

 
 

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

Italy : Umbria

Walking on the Francigena Way

NZ$2620


4.6 (11 reviews)

VIEW TRIP

Self-guided walking

9 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

France : Burgundy

Walking in Burgundy's Vineyards - Short Break

NZ$2640

 
 

VIEW TRIP

Self-guided walking

4 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

France : Champagne

Cycle The Wine Route of Champagne

NZ$2795


5.0 (1 reviews)

VIEW TRIP

Self-guided cycling

5 nights,
twin centre

Level: 2+ & 3

Navigation App

Italy : Tuscany

Wine & Walk in Chianti

NZ$2795


4.0 (2 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Portugal : Mainland Portugal

Tour the Treasures of Portugal

NZ$2815


4.8 (5 reviews)

VIEW TRIP

Cultural tour

7 nights,
twin centre

7 meals
included

France : The Loire

Tour de France - Loire

NZ$2925

 
 

VIEW TRIP

Self-guided cycling

5 nights,
hotel-to-hotel

Level: 3
Stretching

Navigation App

France : Burgundy

Cycling the Vineyards From Beaune to Macon

NZ$2925


4.8 (6 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

France : Canal du Midi

Canal du midi Cycling : from Toulouse to Sete

NZ$2925


4.7 (6 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

France : The Dordogne

Canoeing on the Dordogne

NZ$2950


4.9 (61 reviews)

VIEW TRIP

8 nights,
hotel-to-hotel

Printed route
directions



France

Cycling The UNESCO Loire Valley - Deluxe

NZ$2970


4.3 (3 reviews)

VIEW TRIP

Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

France : Burgundy

Walking in Burgundy's Vineyards

NZ$2970


4.8 (8 reviews)

VIEW TRIP

Self-guided walking

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

Spain : Andalucia

Three Cities of Andalucia

NZ$2990


4.8 (6 reviews)

VIEW TRIP

Cultural tour

7 nights,
hotel-to-hotel

7 meals
included

Croatia

Hike, Bike & Paddle Croatia

NZ$3035


4.0 (1 reviews)

VIEW TRIP

Multi-activity holiday

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

France : Alsace

Villages & Vineyards of Alsace

NZ$3035


4.4 (7 reviews)

VIEW TRIP

Self-guided walking

6 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

France : The Loire

Canoeing on the Loire

NZ$3060


4.0 (1 reviews)

VIEW TRIP

5 nights,
hotel-to-hotel

Navigation App



France : Canal du Midi

Tour de France - Canal du Midi

NZ$3060


5.0 (1 reviews)

VIEW TRIP

Self-guided cycling

4 nights,
hotel-to-hotel

Level: 3
Stretching

Navigation App

Italy : Sardinia

Undiscovered Sardinia Cycling

NZ$3060


4.7 (19 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

France : The Loire

Cycling The Chateaux Of The Loire - Upgraded Short

NZ$3080


4.8 (4 reviews)

VIEW TRIP

Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

Germany : The Moselle

Meandering the Moselle Cycle Path

NZ$3080


4.0 (1 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

France : The Loire

Cycling The Chateaux Of The Loire

NZ$3100


4.5 (12 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

Spain : Rioja

Vineyards of La Rioja Cycling

NZ$3125


4.5 (8 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

France

Dordogne Activities

NZ$3125


4.8 (34 reviews)

VIEW TRIP

Multi-activity holiday

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Italy : Veneto

Northern Italy: Venice, Verona and Bologna

NZ$3125

NEW FOR 2026

VIEW TRIP

Cultural tour

7 nights,
hotel-to-hotel

7 meals
included

Headwater
Navigation App

Greece : Crete

Walking the Wonders of Crete

NZ$3170


3.7 (3 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

Italy : Sicily

Sicily: Vino & Volcanoes

NZ$3190


5.0 (2 reviews)

VIEW TRIP

Cultural tour

7 nights,
hotel-to-hotel

8 meals
included

Headwater
Navigation App

Italy : Tuscany

Cycling the hills of San Gimignano by E-bike

NZ$3255


4.0 (1 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
single centre

Level: 2+ & 3

Headwater
Navigation App

France : Atlantic Coast

Tour de France - Atlantic Coast

NZ$3300

 
 

VIEW TRIP

Self-guided cycling

5 nights,
hotel-to-hotel

Level: 2 & 2+

Navigation App

Portugal : Mainland Portugal

Walk the Highlights of Northern Portugal

NZ$3475


4.5 (6 reviews)

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

Portugal : Mainland Portugal

Cycling in Portugal: From the Mountains to the Sea

NZ$3610


4.5 (17 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

France : The Loire

Cycling The Chateaux Of The Loire - Upgraded

NZ$3960


4.8 (8 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

France : Corsica

Corsica with Ebike

NZ$4005


4.7 (3 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

France

Cycling the Loire in Luxury

NZ$4070

NEW FOR 2026

VIEW TRIP

Self-guided cycling

4 nights,
single centre

Level: 1+
Leisurely plus

Navigation App

Italy : Italian Lakes

Cycling the Italian Lakes

NZ$4090


4.9 (9 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Portugal : Mainland Portugal

Porto to Coimbra Cycling

NZ$4160


4.8 (56 reviews)

VIEW TRIP

Self-guided cycling

9 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

Slovenia

Secrets of Slovenia Cycling

NZ$4335


4.9 (14 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

Italy : The Bay of Naples

Highlights of the Amalfi Coast

NZ$4380

NEW FOR 2026

VIEW TRIP

Cultural tour

7 nights,
hotel-to-hotel

7 meals
included

Headwater
Navigation App

Denmark / Sweden

Nordic Cities by Rail

NZ$4400


5.0 (1 reviews)

VIEW TRIP

Cultural tour

9 nights,
hotel-to-hotel

9 meals
included

Italy : Puglia

Highlights of Puglia Cycling

NZ$4575


4.8 (13 reviews)

VIEW TRIP

Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

Portugal

Island Hopping in the Azores

NZ$4575


4.6 (5 reviews)

VIEW TRIP

Self-guided walking

14 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

South Africa

South Africa’s Coast, Wine and Safari

NZ$8910

NEW FOR 2026

VIEW TRIP

Cultural tour

12 nights,
hotel-to-hotel

21 meals
included

New Zealand

Wonders of New Zealand’s Long White Cloud

NZ$12340

NEW FOR 2026

VIEW TRIP

Cultural tour

18 nights,
hotel-to-hotel

20 meals
included

Italy : The Bay of Naples

Walking the Amalfi Coast

NZ$2815


4.7 (12 reviews)

VIEW TRIP

Guided group walking

7 nights,
single centre

Level: 2
Moderate

Printed route
directions

Italy : Veneto

Walk The Prosecco Hills & Hidden Venice

NZ$3430


4.8 (5 reviews)

VIEW TRIP

Guided group walking

7 nights,
single centre

Level: 2
Moderate

Printed route
directions

Italy : Puglia

Walking in Puglia & Matera

NZ$3520


4.3 (12 reviews)

VIEW TRIP

Guided group walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

Italy : The Dolomites

Snowshoeing in the Dolomites - Premium Adventure

NZ$3695

 
 

VIEW TRIP

Winter snow holiday

7 nights,
single centre

Printed route
directions

Operated by
Exodus Travels

Italy : The Dolomites

Classic Dolomites - Premium

NZ$4530


5.0 (1 reviews)

VIEW TRIP

Guided group walking

7 nights,
single centre

Level: 3
Stretching

Printed route
directions

South Africa

Cycling the Cape & Winelands

NZ$5700

 
 

VIEW TRIP

Guided group cycling

11 nights,
hotel-to-hotel

Level: 3
Stretching

Printed route
directions

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
  • Albania
  • Andorra
  • Austria
  • Belgium
  • Bermuda
  • Bosnia
  • Canada
  • Cape Verde
  • China
  • Costa Rica
  • Croatia
  • Cyprus
  • Czechia
  • Denmark
  • Ecuador
  • Egypt
  • Estonia
  • Faroe Islands
  • Finland
  • Germany
  • Greece
  • Holland
  • Iceland
  • India
  • Ireland
  • Japan
  • Malta + Gozo
  • Montenegro
  • Morocco
  • New Zealand
  • Norway
  • Peru
  • Romania
  • Slovakia
  • Slovenia
  • South Africa
  • Sri Lanka
  • Sweden
  • Switzerland
  • USA
  • Vietnam
  • New Zealand

Departure month
All

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

Activity level
All


  • Leisurely

  • Moderate

  • Demanding

  • Challenging

Accommodation type
All


  • Single centre

  • Twin centre  

  • Hotel-to-hotel

Best for
Wine lovers

  • Singles
  • Couples
  • Families
  • Food lovers
  • Wine lovers
  • Nature lovers
  • Bird watchers
  • Historic sites
  • Vegetarians
  • Swimming opportunities
  • Electric bikes
  • Tandem bikes
  • Headwater Navigation App
  • Dog friendly
  • Positive impact
  • In luxury
  • Coastal routes
  • Island exploring
  • Lakes and rivers
  • High peaks
  • Parador hotels
  • Multi-country trips
  • 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.