Day 1: Sunday, July 11, 2027: Arrival in Kauai

Our pilgrimage begins as we make our way from across the United States to the island of Kauai, Hawaii’s oldest and northernmost island, known as the Garden Isle for its lush, unspoiled landscapes and dramatic natural beauty. Upon arrival, we check in to our oceanfront resort at the Sheraton Poipu. This evening we gather on the beach lawn for a welcome reception with Chris and Natalie Stefanick, enjoying appetizers and drinks as the sun sets over the Pacific. It is the perfect beginning to our time together on this remarkable island. (Appetizers included)

Check-in guaranteed at 4:00PM, welcome reception begins at 7:00PM

Day 2: Monday, July 12, 2027: Kalalau Lookout, Waimea Canyon, Spouting Horn Park & Luau

We open the day with Mass on the beach lawn, followed by a group breakfast at the resort. Our Mercedes Sprinter vans then take us to two of Kauai’s most breathtaking natural landmarks. At the Kalalau Lookout, we gaze out over the vast Kalalau Valley and the Pacific beyond, a view often framed by rainbows arching across the ridgelines. We continue to Waimea Canyon, known as the Grand Canyon of the Pacific, where layers of deep red cliffs, green valleys, and cascading waterfalls stretch across miles of untouched terrain. We then make our way to Spouting Horn Park before sitting down together for a group lunch at RumFire. The afternoon is free to enjoy the resort and its surroundings at your own pace. In the evening, we attend the Aulii Luau, an authentic Hawaiian celebration featuring traditional food, music, and the Rhythm of Aloha show. (B/L/D)

Day 3: Tuesday, July 13, 2027: Hanalei & the North Shore

Following Mass and group breakfast at the resort, we make our way up to Hanalei, one of Kauai’s most beautiful and storied coastal towns, set beneath dramatic green peaks along the island’s north shore. The morning is spent on the water, with options to kayak or paddleboard on the Hanalei River, paddling beneath the historic Hanalei Bridge and into the Hanalei National Wildlife Refuge, where native birds and lush tropical foliage line the banks, or heading out toward Hanalei Bay, where sea turtles are a common sight along the golden sand shoreline. Lunch is on your own, with a variety of local cafes nearby. We rejoin as a group in the late afternoon for the return journey to the resort, where we gather for dinner and an evening session with Chris Stefanick, Josh Kapika, and Dallas Carter. Dinner and overnight at Sheraton Poipu. (B/D)

Day 4: Wednesday, July 14, 2027: Allerton Garden, Ziplining & Mountain Tubing

After Mass and breakfast at the resort, we make our way to the National Tropical Botanical Garden for a guided Best of Both Worlds tour of the McBryde and Allerton Gardens, two of the most extraordinary botanical collections in the United States. Set along the Lawa’i Valley, the Allerton Garden was developed over decades by the Allerton family and features a series of garden rooms, rare tropical plantings, and Moreton Bay fig trees made famous by the film Jurassic Park. We return to the resort for a group lunch before heading out for our afternoon adventure. Guests choose between a thrilling zipline experience or mountain tubing through the historic irrigation tunnels of Kauai’s former sugar plantation highlands. We return to the resort for dinner and an evening group session. Dinner and overnight at Sheraton Poipu. (B/L/D)

Day 5: Thursday, July 15, 2027: Helicopter Tour & Day at Leisure

We begin the morning with Mass and breakfast at the resort. Today offers one of the most extraordinary optional experiences of the pilgrimage: a doors-off helicopter tour over Kauai. Soaring above lush rainforests, hidden waterfalls, Waimea Canyon, and the dramatic Na Pali Coast, this flight offers a perspective on God’s creation that few ever witness. Those who prefer a quieter day may enjoy the resort, the beach, or optional surf lessons at Kauai Surf School, located steps from the Sheraton Poipu. Lunch is on your own today. We close the evening together with dinner at the resort, followed by Adoration. Dinner and overnight at Sheraton Poipu. (B/D)

Day 6: Friday, July 16, 2027: Na Pali Coast Catamaran & Kauai Coffee Estate

We depart early this morning for Port Allen Marina to board our catamaran with Captain Andy’s Sailing Adventures. A light continental breakfast is served onboard as we set out along the Na Pali Coast, one of the most spectacular stretches of coastline in the world, with towering sea cliffs, hidden sea caves, and cascading waterfalls accessible only by water. The morning includes time for snorkeling in the warm Pacific waters, and a BBQ lunch is served onboard before we return to shore in the early afternoon. On our way back to the resort, we make a stop at the Kauai Coffee Estate, home to the largest coffee farm in the United States, for a brief visit and a chance to sample the island’s own harvest. Back at the resort, we gather for Mass, followed by a group dinner and time for shared reflections to close the day. Dinner and overnight at Sheraton Poipu. (B/L/D)

Day 7: Saturday, July 17, 2027: Farewell & Departure

We gather one final time for breakfast together at the resort before saying our farewells and departing for Lihue Airport. We carry home with us the beauty of these islands, the grace of the sacraments celebrated together, and the friendships deepened along the way. (B)

Those who wish to linger a little longer are warmly invited to join us for three additional nights at the Sheraton Poipu. The extension is open to all pilgrims and offers a slower, more relaxed pace after the main program concludes. Spend your days exploring the island at your own leisure, returning to favorite spots, or simply resting on the beach. Daily Mass continues each morning, and Chris Stefanick will offer evening reflections on select nights.

For those selected for the optional Kalaupapa Saints Day Trip, one of these days will include an extraordinary excursion to the island of Molokai. Space on the Kalaupapa tour is limited to 24 participants, with 8 departing on each of the three extension days. Participants will be randomly assigned to a departure day. Those not visiting Kalaupapa on a given day will enjoy that day fully at leisure.

Day 1: Saturday, July 17, 2027: Extension Begins

The extension begins with Mass this morning and the first of three unhurried days on the island. The day is yours to enjoy as you please. Those assigned to today’s Kalaupapa departure will head out early for Molokai (see Kalaupapa Day Trip description below). Chris will offer an evening reflection for the group. Dinner this evening is on your own.

Day 2: Sunday, July 18, 2027: At Leisure

Another day to rest, explore, or simply take in the beauty of Kauai at your own pace. Mass is celebrated this morning. Those assigned to today’s Kalaupapa departure will head out early for Molokai (see Kalaupapa Day Trip description below). Chris will gather the group for an evening reflection. Dinner this evening is on your own.

Day 3: Monday, July 19, 2027: At Leisure

Our final full day on the island. Whether you spend it on the beach, out exploring, or quietly enjoying the resort, savor these last hours in Kauai. Mass is celebrated this morning. Those assigned to today’s Kalaupapa departure will head out early for Molokai (see Kalaupapa Day Trip description below). Chris will gather the group this evening for a final reflection together. Dinner this evening is on your own.

Day 4: Tuesday, July 20, 2027: Farewell & Departure

We gather for a final breakfast at the resort before checking out and making our way to Lihue Airport. We carry home the gifts of these extra days, the quiet grace of Kauai, and the friendships and faith deepened along the way. (B)

Visiting Kalaupapa is not easy, and that is precisely what makes it so rare. The Kalaupapa peninsula on the island of Molokai sits at the base of some of the tallest sea cliffs in the world, accessible only by small aircraft, mule trail, or sea. Access to the peninsula is governed jointly by the National Park Service and the Hawaii State Department of Health, which strictly limits the number of visitors permitted each day to protect the small community of remaining residents. Public tours were suspended entirely for five years during and after the COVID-19 pandemic and only resumed in late 2025. Even today, tours are limited to a maximum of 30 visitors per day, and most of the public has no way of securing a spot. This is not a destination you can simply book on your own.

For the 24 pilgrims joining us on this excursion, the visit carries a significance that goes well beyond its difficulty. The Kalaupapa peninsula on the island of Molokai is one of the most sacred Catholic pilgrimage sites in the United States. From 1866 until 1969, this remote, cliff-bound settlement served as a government-mandated isolation colony for those diagnosed with leprosy, known today as Hansen’s disease. Into this place of suffering came St. Damien de Veuster, the Belgian priest who arrived in 1873 and gave his life in service to the patients there, dying of the disease himself in 1889. He was canonized by Pope Benedict XVI in 2009. St. Marianne Cope, a Franciscan sister from New York, arrived in 1888 and continued his work for more than three decades, caring for the most vulnerable with extraordinary compassion and joy. She was canonized in 2012. Together, their witness transformed Kalaupapa into a place of hope and holiness that still speaks powerfully to all who visit.

A box breakfast will be provided on the day of your visit. The day follows the schedule below.

4:00 AM – Motorcoach pickup at Sheraton Poipu
4:30 AM – Arrive Lihue Airport (LIH)
6:00 AM – Depart LIH on Alaska Airlines flight 1004
6:36 AM – Arrive Honolulu (HNL)
8:45 AM – Depart HNL on Mokulele Airlines
9:34 AM – Arrive Kalaupapa Airport

Upon arrival, we receive a welcome and safety briefing before setting out on a guided tour of the peninsula.

Morning, Kalaupapa Side: The tour takes in the Kalaupapa Lighthouse and Peninsula, Ocean View Pavilion, Papaloa Cemetery, historic patient homes and community churches, the Visitors’ Quarters, and the historic pier.

Midday, Kalawao Side: We visit Paschoal Hall, Staff Row, Siloam Church, St. Philomena Church, the graves of Father Damien and Brother Dutton, the Baldwin Home for Boys, and the ruins of the Leprosy Investigation Station. Views across the Kalaupapa Crater and Waihanau Valley offer a striking sense of the peninsula’s dramatic geography and isolation.

Lunch is enjoyed at Judd Park. Please bring your own lunch, as no food is available for purchase on the peninsula.

Afternoon, Legacy Sites: The tour continues to the Kalaupapa Bookstore, Mother Marianne’s gravesite and memorial, the Bishop Home Complex, St. Francis Church, and Historic Damien Hall.

4:00 PM – Return to Kalaupapa Airport
4:54 PM – Depart Kalaupapa on Mokulele Airlines
5:37 PM – Arrive HNL
7:31 PM – Depart HNL on Alaska Airlines flight 1163
8:13 PM – Arrive LIH
9:00 PM – Motorcoach pickup, transfer to Sheraton Poipu

Dinner will be provided upon your return.