Adventures in Italy

81 adventures

A Journey Through Tuscany: Bike, Food, and Wine Tour

Top ChoiceBeginners

4.86

TUSCANY | ITALY

A Journey Through Tuscany: Bike, Food, and Wine Tour

Apr 16 | Jun 18 | Sep 24 | +3 more

From $4,102 | 7 days
Crossing Sicily: A Hiking Adventure Across the Island

Top Choice

SICILY | ITALY

Crossing Sicily: A Hiking Adventure Across the Island

Nov 21 | Nov 21 | Mar 21 | +2 more

From $4,794 $5,327 | 10-11 days
Great Lakes of Italy Walking Holidays: Maggiore, Como & Garda

Top Choice

LOMBARDY | ITALY

Great Lakes of Italy Walking Holidays: Maggiore, Como & Garda

Apr 1 | Sep 30

From $4,529 | 10 days
Val d’Orcia Tour: Week of Hiking in Tuscany

Top Choice

VAL D’ORCIA | TUSCANY

Val d’Orcia Tour: Week of Hiking in Tuscany

Apr 11 | May 9 | Oct 23

From $3,093 | 8 days
Sailing and Rock Climbing in Sardinia

Top ChoiceBeginnersEarly Bird

4.95

Sardinia | Italy

Sailing and Rock Climbing in Sardinia

May 1 | Jun 1 | Sep 1

From $3,156 | 8 days
Hiking Alta Via 1: Guided Tour in the Dolomites

Top ChoiceHuts Confirmed

4.96

Dolomites | Italy

Hiking Alta Via 1: Guided Tour in the Dolomites

Jun 11 | Jul 10 | Jul 18 | +3 more

From $3,085 | 6 days
Secret Summits & Hidden Trails of Tuscany: A Hiking Journey

Top ChoiceLuxury

4.80

TUSCANY | ITALY

Secret Summits & Hidden Trails of Tuscany: A Hiking Journey

May 22 | May 29 | Jun 12 | +3 more

From $2,424 | 8 days
Self-Guided Hiking in Cinque Terre, Italy

Top ChoiceBeginnersSelf-Guided

5.00

CINQUE TERRE | ITALY

Self-Guided Hiking in Cinque Terre, Italy

Available

From $1,310 | 7 days
Amalfi Coast Kayaking: Discover the Italian Riviera

Beginners

5.00

AMALFI COAST | ITALY

Amalfi Coast Kayaking: Discover the Italian Riviera

From $5,895 | 8 days
Sailing and Rock Climbing at Amalfi Coast

Top ChoiceLuxuryBeginners

5.00

Amalfi Coast | Italy

Sailing and Rock Climbing at Amalfi Coast

From $2,951 | 8 days
Active Summer in Italy: Kayaking in the Aeolian Islands

Beginners

5.00

AEOLIAN ISLANDS | ITALY

Active Summer in Italy: Kayaking in the Aeolian Islands

Inquire

From $4,195 | 8 days
Aosta Valley MTB Grand Tour: 40,000 ft Descent in a Week

5.00

Aosta Valley, Italy

Aosta Valley MTB Grand Tour: 40,000 ft Descent in a Week

Jun 8 | Jul 27 | Aug 24 | +1 more

From $3,589 | 7 days
Coast to Coast Basilicata Bike Tour in Italy

5.00

BASILICATA | ITALY

Coast to Coast Basilicata Bike Tour in Italy

From $3,076 | 7 days
Alta Via 1 of the Aosta Valley: The Giants’ Trek

AOSTA VALLEY | ITALY

Alta Via 1 of the Aosta Valley: The Giants’ Trek

Jun 18 | Jul 9

From $3,490 | 8 days
Cycling Holiday in the Dolomites: Five Iconic Passes

BOLZANO | ITALY

Cycling Holiday in the Dolomites: Five Iconic Passes

Jun 20 | Jul 4 | Jul 18 | +1 more

From $5,412 | 5 days
Cycling Holiday in South Tyrol, Italy: Bolzano to Bressanone

5.00

SOUTH TYROL | ITALY

Cycling Holiday in South Tyrol, Italy: Bolzano to Bressanone

Jun 2 | Sep 8

From $5,820 | 7 days
Cycling the Italian Lakes: From Como to Garda

COMO | ITALY

Cycling the Italian Lakes: From Como to Garda

Apr 18 | May 9 | May 30

From $5,412 | 7 days
Self-Guided Bike Tour in Puglia: 9 Days in Southern Italy

Self-Guided

5.00

PUGLIA | ITALY

Self-Guided Bike Tour in Puglia: 9 Days in Southern Italy

Available

From $2,905 | 9 days
E-Biking the Italian Dolomites: Alta Badia to Lago di Braies

Top Choice

5.00

ALTA BADIA | ITALY

E-Biking the Italian Dolomites: Alta Badia to Lago di Braies

Jun 27

From $4,651 | 6 days
Langhe E-MTB Tour: Wine & Trails in Piedmont, Italy

5.00

PIEDMONT | ITALY

Langhe E-MTB Tour: Wine & Trails in Piedmont, Italy

May 30 | Sep 5

From $5,504 | 7 days
Hiking Adventure in Trentino and Lago di Garda: Dolomites to Dolce Vita

5.00

DOLOMITES | ITALY

Hiking Adventure in Trentino and Lago di Garda: Dolomites to Dolce Vita

Jun 20

From $2,222 | 8 days
Italy Cycling Vacation: Coast to Coast in 10 Days

Luxury

5.00

PISA | ITALY

Italy Cycling Vacation: Coast to Coast in 10 Days

May 4 | May 18 | Sep 7 | +1 more

From $5,651 | 10 days
Cycling Holidays in Northern Italy: 3 Lakes, 7 Days

Luxury

5.00

MILAN | ITALY

Cycling Holidays in Northern Italy: 3 Lakes, 7 Days

May 2 | May 9 | Jun 6 | +4 more

From $5,036 | 7 days
Dolomites Cycling Tour: A Luxury Road Bike Adventure in Italy

Top ChoiceLuxury

5.00

DOLOMITES | ITALY

Dolomites Cycling Tour: A Luxury Road Bike Adventure in Italy

Jun 20 | Jul 4 | Jul 18 | +2 more

From $5,082 | 7 days
Dolomites Self-Guided Hiking Tour: Carezza Lake Trails

Self-Guided

5.00

DOLOMITES | ITALY

Dolomites Self-Guided Hiking Tour: Carezza Lake Trails

Available

From $1,350 | 6 days
Loop Around the Dolomites: Self-Guided Cycling Adventure

Top ChoiceSelf-Guided

5.00

DOLOMITES | ITALY

Loop Around the Dolomites: Self-Guided Cycling Adventure

Available

From $1,409 | 8 days
Ski the Dolomites: A Luxury Chalet Holiday in Alta Badia

Top ChoiceLuxury

DOLOMITES | ITALY

Ski the Dolomites: A Luxury Chalet Holiday in Alta Badia

Feb 28 | Mar 8

From $4,785 | 8 days
Self-Guided Dolomites Cycling Holiday: One Hotel, Endless Rides

Top ChoiceBeginnersSelf-Guided

5.00

DOLOMITES | ITALY

Self-Guided Dolomites Cycling Holiday: One Hotel, Endless Rides

Available

From $1,409 | 7 days
Dolomites to Venice Bike Tour: Self-Guided Cycling Adventure

BeginnersSelf-Guided

5.00

DOLOMITES | ITALY

Dolomites to Venice Bike Tour: Self-Guided Cycling Adventure

Available

From $1,182 | 8 days
Hiking & Sailing the Aeolian Islands: 8-Day Italian Adventure

5.00

AEOLIAN ISLANDS | ITALY

Hiking & Sailing the Aeolian Islands: 8-Day Italian Adventure

May 8 | Oct 9

From $2,905 | 8 days
Dolomites Hut-to-Hut Hiking Adventure: The Most Beautiful Rifugios In The Alps

Huts Confirmed

5.00

BOLZANO | ITALY

Dolomites Hut-to-Hut Hiking Adventure: The Most Beautiful Rifugios In The Alps

Jul 11 | Aug 8 | Sep 5

From $3,207 | 8 days
Luxury e-MTB Haute Route: Beginners Ride From Mont Blanc to Verbier

BeginnersLuxury

COURMAYEUR | ITALY

Luxury e-MTB Haute Route: Beginners Ride From Mont Blanc to Verbier

Jun 25 | Jul 25 | Aug 22 | +1 more

From $4,045 | 6 days
Tuscany e-MTB Holiday: Where Singletrack Meets Wine Country

Top Choice

5.00

TUSCANY | ITALY

Tuscany e-MTB Holiday: Where Singletrack Meets Wine Country

May 2 | Jun 9 | Jun 14 | +1 more

From $3,646 | 6 days
Puglia Cycling Holidays: 8 Days From Matera to Otranto

Top ChoiceLuxury

5.00

PUGLIA | ITALY

Puglia Cycling Holidays: 8 Days From Matera to Otranto

May 8 | Jun 5 | Sep 11 | +1 more

From $4,444 | 8 days
Amalfi Coast Walking Tour: 8 Days From Naples to Capri

Beginners

5.00

AMALFI COAST | ITALY

Amalfi Coast Walking Tour: 8 Days From Naples to Capri

May 16 | Jun 13 | Sep 19 | +1 more

From $4,153 | 8 days
Italian Ski Resort Marathon: 7 Days in the Aosta Valley

Beginners

AOSTA VALLEY | ITALY

Italian Ski Resort Marathon: 7 Days in the Aosta Valley

Dec 13 | Dec 27 | Jan 3 | +5 more

From $3,862 | 7 days
Hiking Cinque Terre: 4 or 7 Days Along Italian Riviera

Top Choice

CINQUE TERRE | ITALY

Hiking Cinque Terre: 4 or 7 Days Along Italian Riviera

Oct 21 | Oct 21 | Mar 11 | +5 more

From $1,783 | 4-7 days
Alpe di Siusi & Rosengarten Hiking Tour, Dolomites

Huts ConfirmedEarly Bird

5.00

DOLOMITES | ITALY

Alpe di Siusi & Rosengarten Hiking Tour, Dolomites

Jun 1 | Jul 1 | Aug 1 | +1 more

From $2,855 | 6 days
Alta Via 1: Guided 7-Day Hiking in the Dolomites

Top ChoiceHuts Confirmed

5.00

DOLOMITES | ITALY

Alta Via 1: Guided 7-Day Hiking in the Dolomites

Jun 13 | Jun 27 | Jul 4 | +5 more

From $2,848 | 7 days
Hotel-Based E-Mountain Biking Tour in the Dolomites

Top Choice

5.00

DOLOMITES | ITALY

Hotel-Based E-Mountain Biking Tour in the Dolomites

Jun 14 | Jul 5 | Jul 11

From $4,671 | 7 days
Munich to Venice: Guided Hiking Tour Across the Alps

MUNICH | GERMANY

Munich to Venice: Guided Hiking Tour Across the Alps

Jul 12 | Aug 15

From $6,648 | 14 days
Self-Guided Cinque Terre & Portofino Hiking Tour

Self-Guided

5.00

CINQUE TERRE | ITALY

Self-Guided Cinque Terre & Portofino Hiking Tour

Available

From $2,319 | 8 days
Aeolian Islands Sailing: Bike & Hike in the South of Italy

Top ChoiceBeginners

5.00

AEOLIAN ISLANDS | ITALY

Aeolian Islands Sailing: Bike & Hike in the South of Italy

May 1 | May 8 | May 22 | +9 more

From $2,397 | 8 days
Sail & Bike Tuscany: Explore the Coast and the Islands

Top ChoiceBeginnersEarly Bird

5.00

TUSCANY | ITALY

Sail & Bike Tuscany: Explore the Coast and the Islands

Sep 1 | Oct 1

From $3,151 | 8 days
All-Women Hiking Tour: Cortina d'Ampezzo Hotel Base for the Dolomites' Best Trails

Top ChoiceWomen-Only

4.93

CORTINA D’AMPEZZO | ITALY

All-Women Hiking Tour: Cortina d'Ampezzo Hotel Base for the Dolomites' Best Trails

Jun 27 | Jul 18 | Aug 29

From $4,045 | 7 days
CCC Trail Running Adventure: Run from Courmayeur to Chamonix

Top Choice

5.00

COURMAYEUR | ITALY

CCC Trail Running Adventure: Run from Courmayeur to Chamonix

From $1,830 | 5 days
Bolzano to Cortina d’Ampezzo: Self-Guided Hike in the Dolomites

Self-GuidedHuts confirmed

5.00

DOLOMITES | ITALY

Bolzano to Cortina d’Ampezzo: Self-Guided Hike in the Dolomites

Available

From $1,675 | 10 days
Alta Via Highlights, Lago di Braies, Tre Cime: Self-Guided Hiking in the Dolomites

Self-GuidedHuts Confirmed

5.00

DOLOMITES | ITALY

Alta Via Highlights, Lago di Braies, Tre Cime: Self-Guided Hiking in the Dolomites

Available

From $1,396 | 7 days
Alta Via 1: Self-Guided Hiking Tour

Self-GuidedHuts Confirmed

5.00

DOLOMITES | ITALY

Alta Via 1: Self-Guided Hiking Tour

Available

From $1,607 | 7 days
Alta Via 1 Trail Running Adventure in the Dolomites

Top Choice

CORTINA D’AMPEZZO | ITALY

Alta Via 1 Trail Running Adventure in the Dolomites

Sep 4 | Sep 2

From $4,145 | 8 days
E-Bike & Eat Like a Local: Agriturismo Adventure in Tuscany

Beginners

TUSCANY | ITALY

E-Bike & Eat Like a Local: Agriturismo Adventure in Tuscany

Oct 19 | Nov 2 | Nov 16 | +1 more

From $2,734 | 7 days
Alta Via 1 Guided Tour: Hut-to-Hut Hiking in the Dolomites

Huts confirmed

5.00

DOLOMITES | ITALY

Alta Via 1 Guided Tour: Hut-to-Hut Hiking in the Dolomites

Jul 3 | Aug 28 | Jul 1 | +1 more

From $3,808 | 8 days
Alta Via 1 Tour: Hiking Adventure in the Dolomites

Huts confirmed

DOLOMITES | ITALY

Alta Via 1 Tour: Hiking Adventure in the Dolomites

Jul 10 | Aug 21 | Sep 4

From $4,854 | 10 days
Alta Via 2: Guided Hike in the Dolomites, Italy

Huts Confirmed

5.00

DOLOMITES | ITALY

Alta Via 2: Guided Hike in the Dolomites, Italy

Jul 10 | Sep 11 | Jul 8 | +1 more

From $3,700 | 9 days
Self-Guided Hiking Adventure in Italy: Lake Como and Lake Maggiore

Self-Guided

5.00

LENNO | ITALY

Self-Guided Hiking Adventure in Italy: Lake Como and Lake Maggiore

Available

From $2,461 | 8 days
Self-Guided Hiking Tour of Lake Como in Italy

Self-GuidedBeginners

5.00

LENNO | ITALY

Self-Guided Hiking Tour of Lake Como in Italy

Available

From $957 | 5 days
Tour du Mont Blanc E-Bike Holidays

Top ChoiceLuxury

4.94

AOSTA VALLEY | ITALY

Tour du Mont Blanc E-Bike Holidays

Aug 3 | Aug 17 | Sep 8 | +1 more

From $4,045 | 6 days
Luxury Cycling in Sicily: Food, Wine, and Etna Volcano Biking

Luxury

5.00

SICILY | ITALY

Luxury Cycling in Sicily: Food, Wine, and Etna Volcano Biking

Available

From $4,444 | 7 days
Week-Long Bike Tour from the Alps to Tuscany

Top ChoiceLuxury

5.00

MILAN | ITALY

Week-Long Bike Tour from the Alps to Tuscany

Jun 3 | Jun 8 | Sep 30 | +1 more

From $3,874 | 7 days
Alpe-Adria Trail Running Adventure: 6 or 9 Days in Slovenia and Croatia

Luxury

5.00

JULIAN ALPS | SLOVENIA

Alpe-Adria Trail Running Adventure: 6 or 9 Days in Slovenia and Croatia

May 14 | May 22 | Jun 4 | +4 more

From $3,950 | 6-9 days
Dolomites Trail Running Adventure: 6 or 7 Days in Italy

Top Choice

5.00

VENICE | ITALY

Dolomites Trail Running Adventure: 6 or 7 Days in Italy

Jul 5 | Jul 14 | Aug 14 | +2 more

From $3,850 | 6-7 days
Luxury Sardinia & Corsica Sailing Adventure

LuxuryBeginners

5.00

SARDINIA | ITALY

Luxury Sardinia & Corsica Sailing Adventure

From $4,500 | 8 days
Alta Via 2: Hiking Tour in the Dolomites

Huts confirmed

5.00

DOLOMITES | ITALY

Alta Via 2: Hiking Tour in the Dolomites

Jul 24 | Aug 28

From $4,064 | 9 days
Cortina d'Ampezzo Hiking Tour: Hotel-Based Dolomites Highlights

Top Choice

4.94

DOLOMITES | ITALY

Cortina d'Ampezzo Hiking Tour: Hotel-Based Dolomites Highlights

Jun 13 | Jul 11 | Jul 25 | +6 more

From $4,045 | 7 days
Discover Tuscany by Bike: A Self-Guided Journey

LuxurySelf-Guided

5.00

TUSCANY | ITALY

Discover Tuscany by Bike: A Self-Guided Journey

Available

From $2,096 | 7 days
Self-Guided Hiking: Dolomites & Tre Cime di Lavaredo

Top ChoiceSelf-Guided

4.92

DOLOMITES | ITALY

Self-Guided Hiking: Dolomites & Tre Cime di Lavaredo

Available

From $1,481 | 7 days
Self-Guided Gravel Bike Tour in Tuscany

LuxurySelf-Guided

5.00

TUSCANY | ITALY

Self-Guided Gravel Bike Tour in Tuscany

Available

From $2,039 | 7 days
Hiking Italy’s Val Gardena: Dolomites With a 4-Star Spa Hotel

Top ChoiceLuxury

5.00

VAL GARDENA | ITALY

Hiking Italy’s Val Gardena: Dolomites With a 4-Star Spa Hotel

Jun 13 | Jun 20 | Jun 27 | +2 more

From $3,190 | 7 days
Self-Guided Gravel Bike Journey in Sardinia

Self-Guided

5.00

SARDINIA | ITALY

Self-Guided Gravel Bike Journey in Sardinia

Available

From $1,880 | 7 days
Bike and Food Tour in Sardinia, Italy

Top ChoiceLuxury

4.83

SARDINIA | ITALY

Bike and Food Tour in Sardinia, Italy

Apr 18 | May 2 | May 16 | +7 more

From $4,102 | 7 days
Cross-Country Skiing in Italy: Wonders of Gran Paradiso

5.00

GRAN PARADISO NATIONAL PARK | ITALY

Cross-Country Skiing in Italy: Wonders of Gran Paradiso

Jan 20 | Feb 10 | Feb 24

From $2,086 | 5 days
Rock Climbing in Dolomites' Cortina d’Ampezzo

Cortina D'Ampezzo | Italy

Rock Climbing in Dolomites' Cortina d’Ampezzo

Available

From $581 | 1 day
Hiking the Orecchiella Natural Reserve in Italy

Beginners

5.00

TUSCANY | Italy

Hiking the Orecchiella Natural Reserve in Italy

Available

From $180 | 1 day
Hiking the Pania della Croce in Italy

Beginners

Tuscany | Italy

Hiking the Pania della Croce in Italy

Available

From $195 | 1 day
Via Ferrata in the Dolomites

BeginnersHuts Confirmed

5.00

Dolomites | Italy

Via Ferrata in the Dolomites

Sep 5

From $3,670 | 5 days
Munich to Venice: Self-Guided Hiking Through Germany, Austria, and Italy

Self-Guided

5.00

MUNICH | GERMANY

Munich to Venice: Self-Guided Hiking Through Germany, Austria, and Italy

Inquire

From $4,785 | 15 days
Hiking Adventure on Sardinia’s Rugged East Coast

Beginners

5.00

OLBIA | SARDINIA

Hiking Adventure on Sardinia’s Rugged East Coast

Inquire

From $1,538 | 7 days
Self-Guided Via Francigena Walk: Last 70 Miles to Rome

5.00

VIA FRANCIGENA | ITALY

Self-Guided Via Francigena Walk: Last 70 Miles to Rome

Inquire

From $1,592 | 7 days
Tuscany & Beyond: E-MTB and Sailing Trip

5.00

TUSCANY | ITALY

Tuscany & Beyond: E-MTB and Sailing Trip

Inquire

From $3,625 | 5-7 days
Women’s Wine Walking Tour in Sicily: Private Groups Only

BeginnersWomen-Only

4.89

SICILY | ITALY

Women’s Wine Walking Tour in Sicily: Private Groups Only

Join Waitlist

From $3,092 | 8 days
Ski Touring Adventure in the Remote Valpelline Valley

Valpelline Valley | Italy

Ski Touring Adventure in the Remote Valpelline Valley

Inquire

From $3,480 | 8 days