AUTUMN ADVENTURES

As the summer crowds fade and landscapes turn golden, autumn is the perfect time to explore. Whether you're chasing autumnal colours, cosy escapes, or late-season sun, we've handpicked the best destinations to visit in September and October.

Below, we've put together a helpful list of our top picks for Autumn.

 

United Kingdom : Devon

The English Riviera & Dart Valley Walk

CA$1455


5.0 (1 reviews)

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Self-guided walking

4 nights,
twin centre

Level: 2
Moderate

Printed route
directions

VIEW TRIP

Slovenia

Lake Bled and Lake Bohinj Walk

CA$1685


4.6 (31 reviews)

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Self-guided walking

7 nights,
single centre

Level: 1+
Leisurely plus

Printed route
directions

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Italy : The Bay of Naples

The Islands of Amalfi Walk

CA$2310


4.6 (14 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

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United Kingdom : Scotland

Walking the Rob Roy Way

CA$2445

 
 

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Navigation App

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United Kingdom : Scotland

Walking the West Highland Way

CA$2480


4.3 (4 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Navigation App

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France : Brittany

St. Malo to Mont-Saint-Michel Cycling

CA$2670

 
 

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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Portugal : The Algarve

Walking Rota Vicentina North Fishermen's Trail

CA$2840


4.5 (2 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : Italian Lakes

Walking at Lakes Orta and Maggiore

CA$3050

NEW FOR 2025

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 1+ & 2

Headwater
Navigation App

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Portugal : Mainland Portugal

Cycling in the Douro Valley

CA$3090

 
 

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 3
Stretching

Headwater
Navigation App

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Switzerland : The Bernese Oberland

Cycling the Swiss Lakes - Vevey to Lucerne

CA$3490

NEW FOR 2025

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Navigation App

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France : Atlantic Coast

Cycling along the Atlantic Coast

CA$3695

NEW FOR 2025

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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Portugal : Mainland Portugal

Coimbra to Lisbon Cycling

CA$3980

NEW FOR 2025

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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 Norway's Fjords: Hardangerfjord from Bergen

CA$5180

NEW FOR 2025

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 2 & 3

Printed route
directions

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Canada : Sunshine Coast

Walk & Paddle Canada's Sunshine Coast

CA$5350

NEW FOR 2025

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Multi-activity holiday

8 nights,
hotel-to-hotel

Level: 1+ to 3

Headwater
Navigation App

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Norway

Cycling the Norwegian Archipelago South of Bergen

CA$5825

NEW FOR 2025

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 2 & 3

Printed route
directions

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Norway

Walking Norway's Fjords: Hardangerfjord from Bergen

CA$6395

NEW FOR 2025

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2 & 3

Printed route
directions

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Italy : Sicily

Walking the Highlights of Western Sicily

CA$2350

NEW FOR 2025

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Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

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France : The Loire

Chateaux Of The Loire Walk

CA$2785


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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Italy : Veneto

Walking in the Venetian Hills

CA$2270


4.7 (90 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Italy : Sicily

Secrets of Sicily Cycling

CA$2595


4.6 (24 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Italy : Veneto

Venetian Villas and Vineyards Cycling

CA$2710


4.7 (57 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

Switzerland : The Bernese Oberland

Walking the Bernese Highlights West

CA$2900


4.5 (2 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 4
Challenging

Navigation App

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Switzerland : The Bernese Oberland

Walking the Bernese Highlights East

CA$3145


5.0 (3 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 3
Stretching

Navigation App

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Switzerland : Valais

Walking in Val D'Anniviers

CA$3335


4.5 (2 reviews)

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Self-guided walking

7 nights,
single centre

Level: 1 to 3

Headwater
Navigation App

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Slovenia

Julian Alps to the Adriatic Cycling

CA$4440


4.8 (126 reviews)

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Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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United Kingdom : Northumberland

Walking the Best of Hadrian's Wall

CA$1530


4.8 (29 reviews)

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Self-guided walking

5 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

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United Kingdom : Cornwall

Walking the Lizard Peninsula

CA$1855


4.3 (3 reviews)

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Self-guided walking

5 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

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United Kingdom : Lake District

Literary Walking in the Lake District

CA$2080


4.8 (36 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

United Kingdom : Cornwall

Walking Cornwall's North coast Padstow to Perranporth

CA$2140

 
 

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Self-guided walking

5 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

VIEW TRIP

Ireland

Walking the Kerry Way and Killarney N.P.

CA$2365


4.9 (7 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

VIEW TRIP

Switzerland : The Bernese Oberland

Classic Swiss Alps Walk

CA$2350


4.8 (151 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : Puglia

Contrasts of Puglia Cycling

CA$2995


4.6 (125 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

United Kingdom : Norfolk

Contrasts of Norfolk Cycling

CA$3145


5.0 (1 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Portugal : Mainland Portugal

Porto Coastal Cycling

CA$3145


4.4 (59 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

Spain : Galicia

Walking the Camino de Santiago

CA$3715


4.6 (43 reviews)

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Self-guided pilgrimage

10 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : Piedmont

Gastronomic Barolo Cycling by e-bike

CA$4075


4.8 (89 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Portugal : Mainland Portugal

Walking the Green Coast of Minho

CA$1320


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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Spain : Catalonia

Catalan Classic Walk - Short Break

CA$1645


4.7 (7 reviews)

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Self-guided walking

4 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Portugal : Mainland Portugal

Walking the Mountains, Valleys & Coast of Minho

CA$1645


5.0 (3 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Italy : Tuscany

Treasures of Tuscany Walk: San Gimignano to Volterra

CA$1760

NEW FOR 2025

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Self-guided walking

7 nights,
twin centre

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

United Kingdom : Northern Ireland

Walking the Antrim Way

CA$1780

 
 

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Self-guided walking

4 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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United Kingdom : Dorset

Jewels of the Jurassic Coast Walk

CA$1815


4.3 (3 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Portugal : Madeira

Walk the Garden Island of Madeira

CA$1815


4.8 (4 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Ireland

Walking the Kerry Way and Killarney N.P. - Short Break

CA$1875


4.0 (2 reviews)

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Self-guided walking

4 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

VIEW TRIP

Romania : Transylvania

Transylvanian Castles Walk

CA$1875


4.9 (19 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Spain : Catalonia

Contrasts of Catalunya Cycling - Short Break

CA$1910


4.8 (8 reviews)

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Self-guided cycling

4 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

United Kingdom : Devon

Contrasts of Devon Walking

CA$1950


4.5 (4 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : Puglia

Undiscovered Puglia Walk - Discovering the South-East Coast

CA$1985


4.8 (13 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Slovakia

Walking the Tatra Mountains in Slovakia

CA$2025

NEW FOR 2025

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Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : Italian Lakes

Cycling Lake Garda with e-bike

CA$2160


4.6 (5 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Czechia

Walking through Bohemia

CA$2195


4.9 (7 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

United Kingdom : Devon

Walking South Devon's Coastal Path

CA$2195


5.0 (1 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

France : The Loire

Multi Activity in the Loire

CA$2215


5.0 (2 reviews)

VIEW TRIP

Multi-activity holiday

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

VIEW TRIP

France : The Loire

Cycling The UNESCO Loire Valley

CA$2235


5.0 (4 reviews)

VIEW TRIP

Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

VIEW TRIP

Italy : Sardinia

Walking Sardinia's Green Coast

CA$2255

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Switzerland : The Bernese Oberland

Walking in Kandersteg - Short Break

CA$1950


4.9 (12 reviews)

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Self-guided walking

5 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Andorra

Walk across Andorra

CA$2270


4.7 (7 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 4
Challenging

Headwater
Navigation App

VIEW TRIP

United Kingdom : Wales

Highlights of the Gower Peninsula Walk

CA$2310


5.0 (2 reviews)

VIEW TRIP

Self-guided walking

5 nights,
twin centre

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

United Kingdom : Cornwall

Walking the Western Tip of Cornwall

CA$2385


4.9 (18 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Printed route
directions

VIEW TRIP

United Kingdom : Wales

Walk the Welsh Highland Railway

CA$2385


3.7 (3 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Switzerland : Davos

Walk the Crossroads of Five Passes

CA$2385


4.9 (8 reviews)

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Self-guided walking

7 nights,
single centre

Level: 1 to 3

Headwater
Navigation App

VIEW TRIP

France : Normandy

D-Day Beaches Of Normandy Cycling

CA$2480


4.6 (7 reviews)

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Printed route
directions

VIEW TRIP

Portugal : Mainland Portugal

Tour the Treasures of Portugal

CA$2480


4.8 (5 reviews)

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Self-guided cultural tour

7 nights,
twin centre



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France : Normandy

Normandy Walk from Deauville to Bayeux

CA$2520


4.8 (5 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

VIEW TRIP

France : Mont Blanc

Mont Blanc Walks - Short Break Premium

CA$2615

 
 

VIEW TRIP

Self-guided walking

4 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Ireland

Walking and Cycling the Wild Atlantic Way

CA$2635

 
 

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Multi-activity holiday

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

VIEW TRIP

France : Burgundy

Walking in Burgundy's Vineyards

CA$2635


4.8 (8 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

United Kingdom : Norfolk

Highlights of Norfolk Cycling

CA$2650


4.4 (11 reviews)

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

France : The Dordogne

Canoeing on the Dordogne

CA$2670


4.9 (56 reviews)

VIEW TRIP

8 nights,
hotel-to-hotel

Printed route
directions



VIEW TRIP

France : Canal du Midi

Canal du midi Cycling : from Toulouse to Sete

CA$2710


4.8 (5 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

VIEW TRIP

France : The Loire

Canoeing on the Loire

CA$2730


4.0 (1 reviews)

VIEW TRIP

5 nights,
hotel-to-hotel

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

VIEW TRIP

Montenegro

Highlights of Southern Montenegro Walk

CA$2730


5.0 (1 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

France : The Loire

Cycling The Chateaux Of The Loire - Upgraded Short

CA$2745


4.8 (4 reviews)

VIEW TRIP

Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

VIEW TRIP

United Kingdom : Wales

Walking Offa's Dyke Path (South)

CA$2765

 
 

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Portugal : Mainland Portugal

Walk the Highlights of Northern Portugal

CA$2805


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

Portugal : The Algarve

Cycling the Algarve's Rota Vicentina

CA$2975


4.9 (9 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Italy : Tuscany

Cycling the hills of San Gimignano by E-bike

CA$2975

NEW FOR 2025

VIEW TRIP

Self-guided cycling

7 nights,
single centre

Level: 2+ & 3

Headwater
Navigation App

VIEW TRIP

Portugal : Mainland Portugal

Portugal Coastal Way to Santiago

CA$2995


5.0 (11 reviews)

VIEW TRIP

Self-guided pilgrimage

14 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

VIEW TRIP

Croatia

Hike, Bike & Paddle Croatia

CA$3015

NEW FOR 2025

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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

CA$3110


4.5 (17 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Norway

Walking in Balestrand

CA$3315


4.6 (5 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1 to 3

Headwater
Navigation App

VIEW TRIP

United Kingdom : Wales

Walking Offa's Dyke Path (North)

CA$3355

 
 

VIEW TRIP

Self-guided walking

9 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

France : Normandy

Paris to the Sea Along the Seine River

CA$3430

NEW FOR 2025

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Printed route
directions

VIEW TRIP

United Kingdom : The Cotswolds

Best of the Cotswolds Cycling

CA$3470


4.0 (1 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Portugal : Mainland Portugal

Porto to Coimbra Cycling

CA$3680


4.8 (56 reviews)

VIEW TRIP

Self-guided cycling

9 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Denmark

Nordic Cities by Rail

CA$3680

NEW FOR 2025

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Self-guided cultural tour

9 nights,
hotel-to-hotel



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Slovenia

Secrets of Slovenia Cycling

CA$3715


4.9 (14 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

France : Mont Blanc

Walking Tour du Mont Blanc - Premium

CA$3755


4.8 (5 reviews)

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 3
Stretching

Headwater
Navigation App

VIEW TRIP

Iceland

Walking Iceland's Diamond Circle

CA$4570

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1 to 3

Headwater
Navigation App

VIEW TRIP

Canada : Sunshine Coast

Walking Canada's Sunshine Coast

CA$5160


4.7 (3 reviews)

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 1 to 3

Headwater
Navigation App

VIEW TRIP

USA : Maine

Cycling Maine's Coast & National Park

CA$6280

 
 

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Japan

Walk the Nakasendo Trail

CA$6660

 
 

VIEW TRIP

Self-guided walking

10 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Printed route
directions

VIEW TRIP

Faroe Islands

Walking the Faroe Islands - With Private Guide

CA$7210

NEW FOR 2025

VIEW TRIP

Private guided walking

7 nights,
single centre

Level: 2+
Moderate plus

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.

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