Check off your bucket-list cycling vacation with our Cross Country bike tours. These tours are point-to-point journeys tackling some of the world's most challenging and scenic terrain.

Experience the ultimate adventure on our fully supported Cross Country bike tours. Traverse the United States, Pyrenees, and Apennine range of Italy on journeys that go beyond typical cycling vacations. When you're done the sense of accomplishment will only be topped by the bragging rights and stories you take home.

View Cross Country Travel Info

Showing 18 Trips

  1. Featured

    Pedal La Bella Toscana: Val d'Orcia to Chianti

    • Classic Guided, Signature Tours
    • 6 Days / 5 Nights
    • Level 3
    • Explorer
    Starting from
    $4,399.00pp
    Featured

    Pedal La Bella Toscana: Val d'Orcia to Chianti

    • Classic Guided, Signature Tours
    • 6 Days / 5 Nights
    • Level 3
    • Explorer
    Starting from
    $4,399.00 pp

  2. Featured

    Ride from the Adriatic coast to the Mediterranean Sea on this bike trip across Italy

    • Cross Country
    • 6 Days / 5 Nights
    • Level 3, Level 4
    • Explorer, Luxury
    Starting from
    $3,999.00pp
    Featured

    Ride from the Adriatic coast to the Mediterranean Sea on this bike trip across Italy

    • Cross Country
    • 6 Days / 5 Nights
    • Level 3, Level 4
    • Explorer, Luxury
    Starting from
    $3,999.00 pp

  3. New Hiking & Walking

    Hike the heart of the Dolomites, from the picturesque Val Gardena to the serene Val Badia

    • Hiking & Walking, Signature Tours
    • 6 Days / 5 Nights
    • Level 3
    • Luxury
    Starting from
    $5,999.00pp
    New Hiking & Walking

    Hike the heart of the Dolomites, from the picturesque Val Gardena to the serene Val Badia

    • Hiking & Walking, Signature Tours
    • 6 Days / 5 Nights
    • Level 3
    • Luxury
    Starting from
    $5,999.00 pp

  4. New Hiking & Walking

    Walk from the rolling hills of Val d'Orcia to the coast of Monte Argentario

    • Hiking & Walking, Signature Tours
    • 6 Days / 5 Nights
    • Level 2, Level 3
    • Luxury
    Starting from
    $4,599.00pp
    New Hiking & Walking

    Walk from the rolling hills of Val d'Orcia to the coast of Monte Argentario

    • Hiking & Walking, Signature Tours
    • 6 Days / 5 Nights
    • Level 2, Level 3
    • Luxury
    Starting from
    $4,599.00 pp

  5. Hiking & Walking

    Venture along the Italian Riviera to discover the colorful coastal villages of Portovenere and the Cinque Terre

    • Hiking & Walking, Signature Tours
    • 6 Days / 5 Nights
    • Level 3, Level 4
    • Luxury
    Starting from
    $5,399.00pp
    Hiking & Walking

    Venture along the Italian Riviera to discover the colorful coastal villages of Portovenere and the Cinque Terre

    • Hiking & Walking, Signature Tours
    • 6 Days / 5 Nights
    • Level 3, Level 4
    • Luxury
    Starting from
    $5,399.00 pp

  6. Featured

    From Lake Bled to Italy along the Goriška Brda Wine Region

    • Classic Guided, Signature Tours
    • 6 Days / 5 Nights
    • Level 3
    • Explorer
    Starting from
    $4,399.00pp
    Featured

    From Lake Bled to Italy along the Goriška Brda Wine Region

    • Classic Guided, Signature Tours
    • 6 Days / 5 Nights
    • Level 3
    • Explorer
    Starting from
    $4,399.00 pp

  7. Featured

    Adventures from the green pastures of the Asiago Plateau to the sheer beauty of the Dolomites

    • Gravel, Signature Tours
    • 5 Days / 4 Nights
    • Level 3, Level 4
    • Explorer, Luxury
    Starting from
    $2,999.00pp
    Featured

    Adventures from the green pastures of the Asiago Plateau to the sheer beauty of the Dolomites

    • Gravel, Signature Tours
    • 5 Days / 4 Nights
    • Level 3, Level 4
    • Explorer, Luxury
    Starting from
    $2,999.00 pp

  8. Venture through Slovenia's Julian Alps and Italy's legendary Monte Zoncolan

    • Classic Guided, Signature Tours
    • 6 Days / 5 Nights
    • Level 4
    • Explorer
    Starting from
    $4,299.00pp

    Venture through Slovenia's Julian Alps and Italy's legendary Monte Zoncolan

    • Classic Guided, Signature Tours
    • 6 Days / 5 Nights
    • Level 4
    • Explorer
    Starting from
    $4,299.00 pp

  9. Conquer the UNESCO-listed Dolomites and stay in charming Alleghe

    • Classic Guided, Discover Tours
    • 5 Days / 4 Nights
    • Level 4
    • Explorer
    Starting from
    $2,399.00pp

    Conquer the UNESCO-listed Dolomites and stay in charming Alleghe

    • Classic Guided, Discover Tours
    • 5 Days / 4 Nights
    • Level 4
    • Explorer
    Starting from
    $2,399.00 pp

  10. Ride the famed white gravel roads of Montalcino, Siena, and the Crete Senesi

    • Gravel, Signature Tours
    • 5 Days / 4 Nights
    • Level 3
    • Explorer, Luxury
    Starting from
    $3,499.00pp

    Ride the famed white gravel roads of Montalcino, Siena, and the Crete Senesi

    • Gravel, Signature Tours
    • 5 Days / 4 Nights
    • Level 3
    • Explorer, Luxury
    Starting from
    $3,499.00 pp