Holy rosary academy

Tuscany & Cinque Terre

Join Holy Rosary Academy of Anchorage, Alaska for an incredible pilgrimage that boasts some of Italy’s most iconic beauty from its colorful coastline to the rolling green hills of Tuscany, and from the Renaissance city of Florence to the hilly town of Siena.  St. Catherine of Siena’s relics and many other holy destinations await us along the way. A wonderful combination of adventure, beauty, and fellowship await you on the trip!


  • The feast day of St. Fina in her native Tuscan town of San Gimignano
  • Hiking on the Via Francigena, the path from Canterbury, England to Rome
  • The city of Florence and all of its artistic and spiritual treasures



Days 1-2 Arrive in Florence I Brief orientation I Visit the Uffizi Museum I See the statue of Dante Alighieri in the Piazza of Santa Croce I  Explore the cathedral and see the famous baptistery doors by Ghiberti I Admire the Ponte Vecchio, the colorful “old bridge” I Discover the relics of the saints buried in Florence 

Cinque Terre

Days 2-5 Transfer to the five colorful fishing villages on the coast known as the Cinque Terre I Enjoy the coastal hiking paths between the towns or take the train I Bike the old railway trail from Levanto to Bonassola weaving in and out of coastal tunnels with amazing views of the sea to the church of Santa Maria della Punta I Take a dip in the sea if you are up for it! 

    The Via Francigena

    Days 5-6 Start your journey to Siena on foot along the Via Francigena I Hike from the Sanctuary of Pancole, where it is believed Our Lady appeared to a mute shepherdess in 1668, to San Gimignano, one of the most beautiful towns in Tuscany I Discover the life of St. Fina and celebrate her feast day in the town before hiking from Strove to the town of Monteriggioni, mentioned by Dante in his Divine Comedy


    Days 6-8 Spend a full day in the lovely (and hilly) town of Siena I Pray at the relics of St. Catherine of Siena and visit her house I Explore the stunning cathedral of Siena with its impressive façade and elaborate floors I Relax in the main piazza of the town and learn about the famous horse races there I Transfer to the Florence airport the morning of day 8


    Religious Houses & Hotels

     We stay mainly in the guest accommodations of religious houses (monasteries, convents, sanctuaries, etc.).  The culture and history of these places really adds to the character of our pilgrimage.  The rooms are clean, comfortable, and nice, but not “luxurious'”. Normally 1 or 2 roommates of the same gender.  Air conditioner is generally not available.


     We eat mainly at restaurants. Menus may be limited to fixed options or set menus. We can accommodate most food allergies.


    You may bring any type of luggage with you on this trip.  This particular itinerary is not a backpack-only pilgrimage.  We will provide a detailed packing list.


    Prayer is at the heart of the pilgrimage.  Mass, the rosary, and other prayer opportunities are available throughout the trip.  




    • 7 nights lodging
    • All breakfasts
    • All dinners 
    • Ground transportation
    • Airport shuttle at the beginning and end of the pilgrimage
    • Entrance fees for the Uffizi, Siena Cathedral, and San Gimignano Church
    • Outdoor activities (guides, rental equipment, luggage transfers, tips)
    • Pilgrimage materials (reading packet, prayer booklet, maps, group gear)
    • Masses and other spiritual activities
    • All tips and service charges to drivers, restaurants, etc.


    • Flights
    • All lunches
    • Single room supplement ($650)
    • Fee if paying by credit card
    • Anything else not listed



    march 7-14, 2025

    Sign-up Deadline: November 30, 2024


    Day 3: Hiking

    Level 1:  2.3 miles, 656ft elevation gain
    Level 1:  1.2 miles, 659ft elevation gain
    You can choose to do either, both, or neither of these hikes.

    Day 4: Biking

    Level 1: 3 or 6.5 miles, mainly flat
    You can choose to hike the path or take the train instead of biking.

    Day 5: Hiking

    Level 2: 5.2 miles, 875ft elevation gain

    Day 6: Hiking

    Level 1: 4.2 miles, 300ft elevation gain

    Click here to learn more about how we determine our activity levels. Activities are weather dependent. Distances may vary from the information given above


    Arrival & Departure

    Florence Peretola Airport (FLR) . HRA will be giving more information on a group flight option. Please wait for a confirmation to buy any plane tickets.


    We will be using a variety of transportation on this pilgrimage, both private and public.   


    Each pilgrim should have health insurance. We highly recommend purchasing traveler’s insurance as well



    Step 1: Sign up

     Fill out our short online form. Please direct any questions you have to Mr. Kevin Quain (kquain@hraak.org)

    Step 2: Registration

    We will send you the registration packet to complete and send back to us

    Step 3: Payment & Confirmation

    Please wait to buy your plane ticket until you recieve a confirmation

    Contact Us

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