Horse Riding Holidays (478) Advanced Horse Riding Holidays (392) Trail Riding (416) Europe (247) Italy (27)
Trail Riding and Advanced Horse Riding Holidays in Italy

Trail Riding and Advanced Horse Riding Holidays in Italy

Find and compare 10+ Trail Riding Horse Riding Holidays for Advanced in Italy
Italy Advanced Trail Riding Reset all

  • Popular Searches

Duration & arrival

optional

Select duration or date

  • Duration

    • 1 day
    • From 2 to 4 days
    • From 5 to 7 days
    • From 1 to 2 weeks
    • More than 2 weeks

  • Select a specific date

Filters

Reset all
Day Experiences
  • Day Activities (0)
Destinations
Reset
Italy (12)
Africa & the Middle East
  • Anywhere in Africa & the Middle East
  • Morocco (35)
  • Turkey (18)
  • South Africa (11)
  • Egypt (6)
  • Jordan (3)
  • Reunion (1)
  • Tanzania (1)
  • Zimbabwe (1)
    • Europe
  • Anywhere in Europe
  • Spain (29)
  • Ireland (17)
  • Bulgaria (16)
  • France (15)
  • Italy (12)
  • Portugal (11)
  • Iceland (10)
  • Poland (9)
  • United Kingdom (8)
  • Sweden (8)
  • Greece (6)
  • Romania (5)
  • Serbia (4)
  • Netherlands (3)
  • Albania (2)
  • Croatia (2)
  • Germany (2)
  • Slovenia (2)
  • Austria (1)
  • Czech Republic (1)
  • Finland (1)
  • Switzerland (1)
    • The Americas & Caribbean
  • Anywhere in The Americas & Caribbean
  • USA (16)
  • Canada (11)
  • Peru (10)
  • Argentina (7)
  • Colombia (6)
  • Costa Rica (6)
  • Uruguay (2)
  • Brazil (1)
  • Mexico (1)
    • Asia & Oceania
  • Anywhere in Asia & Oceania
  • Mongolia (9)
  • China (5)
  • Kyrgyzstan (3)
  • Australia (2)
  • New Zealand (2)
  • Georgia (1)
  • Indonesia (1)
  • Japan (1)
  • Nepal (1)
    • Arrival date
      Show more
      Select a specific date
      Duration
      • 1 day (0)
      • From 2 to 4 days (1)
      • From 5 to 7 days (5)
      • From 1 to 2 weeks (8)
      • More than 2 weeks (0)
      Show more
      Price per trip
      • Below US$ 200 (0)
      • From US$ 200 to US$ 500 (1)
      • From US$ 500 to US$ 1000 (0)
      • From US$ 1000 to US$ 1500 (3)
      • From US$ 1500 to US$ 3000 (7)
      • More than US$ 3000 (1)
      Group / private
      • Group (12)
      Types
      Show more
      Skill Level
      Categories
      Trips Style/ Theme
      Language of Instruction
      • English (12)
      Terrain
      Meals
      • All Meals Included (8)
      • Breakfast (12)
      • Lunch (8)
      • Dinner (8)
      Food Options
      • Standard (Omnivore) (9)
      • Vegetarian (incl. Lacto-Ovo) (4)
      • Custom / Other on Request (3)
      • Vegan (3)
      • Gluten-Free (1)
      Airport Transfer
      • Airport Transfer Available (3)
      Traveller Type
      Package Type
      Special Time of Year

      Showing 12 results

      Trail Riding
      Advanced
      Italy
      Clear all
      Login to save to your favorites
      07 Day Horseback Riding Holiday along The Ancient Medieval Road in Siena, Tuscany, Italy - Photo 1 7 Day Horseback Riding Holiday along The Ancient Medieval Road in Siena, Tuscany, Italy - Photo 2 7 Day Horseback Riding Holiday along The Ancient Medieval Road in Siena, Tuscany, Italy - Photo 3 7 Day Horseback Riding Holiday along The Ancient Medieval Road in Siena, Tuscany, Italy - Photo 4 7 Day Horseback Riding Holiday along The Ancient Medieval Road in Siena, Tuscany, Italy - Photo 5
      Italy
      2 interested
      5 (3)
      7 Day Horseback Riding Holiday along The Ancient Medieval Road in Siena, Tuscany, Italy
      Airport transfer available All meals included Instructed in English
      1 person 7 days • Multiple starting dates
      from
      US$ 2,680
      Login to save to your favorites
      15 Day Long Weekend Horse Riding and Cycling Holiday in Viterbo, Italy - Photo 1 5 Day Long Weekend Horse Riding and Cycling Holiday in Viterbo, Italy - Photo 2 5 Day Long Weekend Horse Riding and Cycling Holiday in Viterbo, Italy - Photo 3 5 Day Long Weekend Horse Riding and Cycling Holiday in Viterbo, Italy - Photo 4 5 Day Long Weekend Horse Riding and Cycling Holiday in Viterbo, Italy - Photo 5
      Italy
      4.9 (12)
      5 Day Long Weekend Horse Riding and Cycling Holiday in Viterbo, Italy
      Airport transfer available Breakfast only Instructed in English
      2 persons 5 days • Multiple starting dates
      from
      US$ 2,841
      Login to save to your favorites
      25 Day Short Break in The Saddle Horse Riding Holiday in Spoleto, Umbria, Italy - Photo 1 5 Day Short Break in The Saddle Horse Riding Holiday in Spoleto, Umbria, Italy - Photo 2 5 Day Short Break in The Saddle Horse Riding Holiday in Spoleto, Umbria, Italy - Photo 3 5 Day Short Break in The Saddle Horse Riding Holiday in Spoleto, Umbria, Italy - Photo 4 5 Day Short Break in The Saddle Horse Riding Holiday in Spoleto, Umbria, Italy - Photo 5
      Italy
      7 interested
      5 (17)
      5 Day Short Break in The Saddle Horse Riding Holiday in Spoleto, Umbria, Italy
      All meals included Instructed in English
      1 person 5 days • Multiple starting dates
      from
      US$ 1,135
      Login to save to your favorites
      37 Day Carpe Diem Horse Riding Holiday in Isernia, Molise, Italy - Photo 1 7 Day Carpe Diem Horse Riding Holiday in Isernia, Molise, Italy - Photo 2 7 Day Carpe Diem Horse Riding Holiday in Isernia, Molise, Italy - Photo 3 7 Day Carpe Diem Horse Riding Holiday in Isernia, Molise, Italy - Photo 4 7 Day Carpe Diem Horse Riding Holiday in Isernia, Molise, Italy - Photo 5
      Italy
      5 (2)
      7 Day Carpe Diem Horse Riding Holiday in Isernia, Molise, Italy
      All meals included Instructed in English
      1 person 7 days • Multiple starting dates
      from
      US$ 1,041
      Login to save to your favorites
      48 Day Show Jumping or Dressage Training with Trail Riding in Spoleto, Province of Perugia, Italy - Photo 1 8 Day Show Jumping or Dressage Training with Trail Riding in Spoleto, Province of Perugia, Italy - Photo 2 8 Day Show Jumping or Dressage Training with Trail Riding in Spoleto, Province of Perugia, Italy - Photo 3 8 Day Show Jumping or Dressage Training with Trail Riding in Spoleto, Province of Perugia, Italy - Photo 4 8 Day Show Jumping or Dressage Training with Trail Riding in Spoleto, Province of Perugia, Italy - Photo 5
      Italy
      2 interested
      5 (17)
      8 Day Show Jumping or Dressage Training with Trail Riding in Spoleto, Province of Perugia, Italy
      All meals included Instructed in English
      1 person 8 days • Multiple starting dates
      from
      US$ 2,248
      Login to save to your favorites
      58 Day Discover Valdrano Horse Riding Holiday in Tuscany, Italy - Photo 1 8 Day Discover Valdrano Horse Riding Holiday in Tuscany, Italy - Photo 2 8 Day Discover Valdrano Horse Riding Holiday in Tuscany, Italy - Photo 3 8 Day Discover Valdrano Horse Riding Holiday in Tuscany, Italy - Photo 4 8 Day Discover Valdrano Horse Riding Holiday in Tuscany, Italy - Photo 5
      Italy
      4 (1)
      8 Day Discover Valdrano Horse Riding Holiday in Tuscany, Italy
      All meals included Instructed in English
      1 person 8 days • Multiple starting dates
      from
      US$ 3,067
      Login to save to your favorites
      65 Day A Taste of Tuscany Horse Riding Holiday in Rendola, Arezzo, Italy - Photo 1 5 Day A Taste of Tuscany Horse Riding Holiday in Rendola, Arezzo, Italy - Photo 2 5 Day A Taste of Tuscany Horse Riding Holiday in Rendola, Arezzo, Italy - Photo 3 5 Day A Taste of Tuscany Horse Riding Holiday in Rendola, Arezzo, Italy - Photo 4 5 Day A Taste of Tuscany Horse Riding Holiday in Rendola, Arezzo, Italy - Photo 5
      Italy
      4 (1)
      5 Day A Taste of Tuscany Horse Riding Holiday in Rendola, Arezzo, Italy
      All meals included Instructed in English
      1 person 5 days • Multiple starting dates
      from
      US$ 1,879
      Login to save to your favorites
      78 Day Exploring Two National Parks on a Trail Riding Holiday in Italy - Photo 1 8 Day Exploring Two National Parks on a Trail Riding Holiday in Italy - Photo 2 8 Day Exploring Two National Parks on a Trail Riding Holiday in Italy - Photo 3 8 Day Exploring Two National Parks on a Trail Riding Holiday in Italy - Photo 4 8 Day Exploring Two National Parks on a Trail Riding Holiday in Italy - Photo 5
      Italy
      5 (2)
      8 Day Exploring Two National Parks on a Trail Riding Holiday in Italy
      All meals included Instructed in English
      1 person 8 days • Starts on: September 19, 2026
      from
      US$ 1,950
      Login to save to your favorites
      88 Day Monte Capraro Horse Riding Trails in Molise, Italy - Photo 1 8 Day Monte Capraro Horse Riding Trails in Molise, Italy - Photo 2 8 Day Monte Capraro Horse Riding Trails in Molise, Italy - Photo 3 8 Day Monte Capraro Horse Riding Trails in Molise, Italy - Photo 4 8 Day Monte Capraro Horse Riding Trails in Molise, Italy - Photo 5
      Italy
      5 (2)
      8 Day Monte Capraro Horse Riding Trails in Molise, Italy
      All meals included Instructed in English
      1 person 8 days • Multiple starting dates
      from
      US$ 1,794
      Login to save to your favorites
      98 Day Brigands Path Enchanting Italian Countryside Riding with Hacks and Full Day, Tuscany - Photo 1 8 Day Brigands Path Enchanting Italian Countryside Riding with Hacks and Full Day, Tuscany - Photo 2 8 Day Brigands Path Enchanting Italian Countryside Riding with Hacks and Full Day, Tuscany - Photo 3 8 Day Brigands Path Enchanting Italian Countryside Riding with Hacks and Full Day, Tuscany - Photo 4 8 Day Brigands Path Enchanting Italian Countryside Riding with Hacks and Full Day, Tuscany - Photo 5
      Italy
      1 interested
      4.9 (12)
      8 Day Brigands Path Enchanting Italian Countryside Riding with Hacks and Full Day, Tuscany
      Breakfast only Instructed in English
      1 person 8 days • Multiple starting dates
      from
      US$ 1,793
      Login to save to your favorites
      108 Day Exciting Horse Riding Holiday in Tuscany, Grosseto, Italy - Photo 1 8 Day Exciting Horse Riding Holiday in Tuscany, Grosseto, Italy - Photo 2 8 Day Exciting Horse Riding Holiday in Tuscany, Grosseto, Italy - Photo 3 8 Day Exciting Horse Riding Holiday in Tuscany, Grosseto, Italy - Photo 4 8 Day Exciting Horse Riding Holiday in Tuscany, Grosseto, Italy - Photo 5
      Italy
      4 interested
      4.3 (64)
      8 Day Exciting Horse Riding Holiday in Tuscany, Grosseto, Italy
      Breakfast only Instructed in English
      1 person 8 days • Available all year
      from
      US$ 1,130
      Login to save to your favorites
      114 Day Amazing Horse Riding Holiday in Tuscany, Montieri, Italy - Photo 1 4 Day Amazing Horse Riding Holiday in Tuscany, Montieri, Italy - Photo 2 4 Day Amazing Horse Riding Holiday in Tuscany, Montieri, Italy - Photo 3 4 Day Amazing Horse Riding Holiday in Tuscany, Montieri, Italy - Photo 4 4 Day Amazing Horse Riding Holiday in Tuscany, Montieri, Italy - Photo 5
      Italy
      22 interested
      4.3 (64)
      4 Day Amazing Horse Riding Holiday in Tuscany, Montieri, Italy
      Breakfast only Instructed in English
      1 person 4 days • Available all year
      from
      US$ 478
      Showing 1 – 12 of 12 results
      Buy a Gift Card


      Gift Card: Great for all Occasions

      A BookHorseRidingHolidays gift card is the perfect present for anyone who loves adventure, nature, and unforgettable riding experiences. From scenic countryside trails to immersive equestrian retreats, let them choose from incredible horse riding holidays around the world.

      The World’s Most Trusted Equestrian Community

      Over 300K horse lovers and travelers like you have chosen us for their unforgettable trips. See what they say about improving their skills and connecting with horses!

      350K+ riding trips and experiences

      enjoyed through us worldwide

      94% of riders

      recommend booking with us

      88,000+ verified reviews

      4.6 star average organizer score

      “Beautiful trails, well cared for horses and lovely people”
      — Stephanie A.
      Flag of United Kingdom United Kingdom
      “A retreat that gave more than I expected”
      — Carole B.
      Flag of United Kingdom United Kingdom
      “An Unforgettable Adventure & Cultural Experience”
      — Stephanie C.
      Flag of United States United States

      Explore

      Hello there.
      Glad to have you back!

       

      Change language & currency

      Language

      Currency

      Australian Dollar AUD Canadian Dollar CAD Euro EUR - € British Pound GBP - £ United States Dollar USD - US$ Brazilian Real BRL - R$ Swiss Franc CHF Chinese Renminbi Yuan CNY Czech Koruna CZK Danish Krone DKK Hong Kong Dollar HKD Indonesian Rupiah IDR - Rp Israeli New Sheqel ILS - ₪ Indian Rupee INR - Rs. Japanese Yen JPY - ¥ South Korean Won KRW Mexican Peso MXN Malaysian Ringgit MYR Norwegian Krone NOK New Zealand Dollar NZD Philippine Peso PHP Polish Złoty PLN Russian Ruble RUB Swedish Krona SEK Singapore Dollar SGD - S$ Thai Baht THB Turkish Lira TRY South Africa, Rand ZAR
      Don't miss out! Join our mailing list to get inspiration, tips & special offers sent directly to your inbox.
      Served by www:8000

      Logging out

      of Tripaneer websites