Day 1: Travel to the Azores
Enjoy a direct, overnight flight from Toronto to Ponta Delgada, the largest city in the Azores and the main gateway to São Miguel Island, the archipelago’s largest island.
Stay: N/A (in flight)
Meals:
D (on the plane)
Day 2: Ponta Delgada City Walking Tour
Upon arrival, meet your local guide and enjoy some free time for breakfast at a nearby café. Then, explore Ponta Delgada on a guided walking tour, discovering its cultural and historical landmarks, including Forte de São Brás, São Francisco Square, Convento da Esperança and the iconic Portas da Cidade. Visit historic churches, browse Mercado da Graça and enjoy views of the marina. After lunch, enjoy free time before checking in to your hotel. This evening, gather for a welcome dinner.
Stay:
Hotel do Camões, Ponta Delgada, PT (4 nights)
Meals: B (on plane), D
Day 3: Exploring the North & Central Coasts
In the morning, enjoy a guided hike along the Salto do Cabrito circular trail starting near the geothermal springs of Ribeira Grande. Follow forest paths to the impressive waterfall, learning about São Miguel’s freshwater systems and hydroelectric history along the way. After lunch, explore the volcanic landscapes of the Lagoa do Fogo Nature Reserve. Visit Caldeira Velha Natural Monument, with time to enjoy its surroundings or a thermal bath, weather and access permitting. Continue to Pico da Barrosa and the Lagoa do Fogo viewpoint for sweeping island views before visiting Cerâmica Vieira in Lagoa to discover traditional pottery making. Enjoy a free evening back at the hotel.
Meals:
B, L
Day 4: West Coast of the Island and Pineapple Plantation Tour
Today's hike takes us through the protected landscape of Sete Cidades, home to one of Portugal’s Seven Natural Wonders. Beginning near Muro das 9 Janelas, follow the Cumeeira Grande along the crater rim, passing Pico da Cruz and, weather permitting, enjoying views of Lagoa de Santiago and Lagoa Rasa. The approximately 9.7 km trail winds through Japanese Red Cedars and lush vegetation, with opportunities to learn about local flora, fauna, and the legends of the famous twin lakes. The hike concludes in Sete Cidades, with time to relax and visit São Nicolau Church. After lunch, visit a local pineapple greenhouse to discover how this distinctive fruit is grown, from planting to harvest.
Meals:
B, L
Day 5: South Coast of the Island, Tea Plantation Tour & Walk, and Funas Valley
After breakfast, visit Europe’s oldest working tea plantation and discover São Miguel’s tea-growing heritage. Enjoy a scenic hike through rolling tea fields and Japanese Cedar forests, following winding trails past agricultural fields and traditional farm buildings. At the highest point, take in panoramic views of the north coast before descending through the plantations to the tea factory, where you can enjoy a cup of tea and learn about its production. For lunch, savour traditional cozido, a local specialty slow-cooked underground using volcanic heat. In the afternoon, explore Terra Nostra Botanical Garden, renowned for its exotic plants, tropical vegetation and beautifully landscaped pathways. Enjoy time to wander through the gardens and relax in the thermal pool. On the return to the hotel, stop at Pico do Ferro viewpoint for spectacular views of the Furnas Valley.
Meals:
B, L
Day 6: Fly to Pico Island, UNESCO World Heritage Wine Trail (Northern Zone)
After breakfast, fly to Pico Island and meet your local guide for a half-day hike along the UNESCO-listed Santana to Lajido trail. Explore historic vineyard landscapes, pastures and agricultural fields, following ancient lava flows and traditional ox-cart paths. Much of the route follows the northern coastline, revealing the island’s volcanic origins and distinctive wine-growing heritage. The hike concludes in Lajido, one of Pico’s oldest wine-producing areas, where historic cellars and manor houses offer a glimpse into its winemaking past. Check in to your hotel and freshen up before gathering for an included group dinner.
Stay:
Hotel Pico Terramar & Spa, Pico Island, PT (3 nights)
Meals:
B, L, D
Day 7: UNESCO World Heritage Wine Trail (Western Zone), Wine & Tapas Tour
Today, explore Pico Island’s distinctive wine-growing heritage on a circular hike that begins and ends in Madalena. The approximately 10.8 km trail winds through UNESCO World Heritage-listed vineyards shaped by volcanic rock and centuries of tradition. Discover historic wine cellars, stone walls, tidal wells and remnants of traditional winemaking, including rola-pipas and relheiras. Enjoy views of Pico Mountain and the offshore islets along the way. After the hike, savour local flavours on a wine and tapas experience. Visit traditional adegas (wine cellars), sample local cheeses and renowned island wines, and learn about Pico’s rich winemaking heritage.
Meals:
B, L
Day 8: Calheta de Nesquim & Whalers Museum
After breakfast, discover the historic village of Calheta de Nesquim on a scenic circular hike through one of Pico’s more remote areas. Beginning at the harbour, where restored whaling boats recall the village’s maritime past, follow traditional paths past scenic lookouts, gardens and natural swimming pools. Learn how generations of islanders made a living from the land and sea, then follow the southern coast to Lajes do Pico. Here, visit the Whalers Museum to discover more about the island’s whaling heritage.
Meals:
B, L
Day 9: Faial Island Tour
In the morning, take the ferry to Faial Island for a day of hiking and exploring its remarkable volcanic landscapes. Begin with a guided hike around Caldeira do Faial, enjoying panoramic views and learning about the island’s unique geology and flora. Enjoy an included lunch at a traditional restaurant in Cedros before exploring Fajã da Praia do Norte and Capelinhos Volcano, where the 1957–58 eruption dramatically reshaped the landscape. Return by ferry to Pico Island and gather with fellow travellers for a farewell dinner.
Meals:
B, L, D
Day 10: Travel Pico Island to São Miguel Island
Enjoy a leisurely day on Pico Island before transferring to the airport for your flight to São Miguel. Upon arrival, transfer to your hotel for your final evening in the Azores.
Stay: Pedras do Mar Hotel, Ponta Delgada, PT (1 night)
Meals:
B
Day 11: Fly Home
After breakfast, transfer to the airport for your return flight to Toronto, taking home lasting memories of the Azores’ spectacular landscapes, volcanic trails, and unforgettable hiking experiences.
Meals:
B