Join us as we set off to explore three of the most captivating islands in the Azores — São Miguel, Pico, and Faial. From shimmering crater lakes to UNESCO-listed vineyards, steaming hot springs, and whale-filled waters, this journey blends adventure with culture, history, and unforgettable food. Each day invites us to hike through dramatic landscapes, taste the flavors of the islands, and soak in the laid-back rhythm of Azorean life.
Dates: September 18-24, 2026 – max participants 4
Starting location: Ponta Delgada, San Miguel Island; Ending location: Lisbon, Portugal
Itinerary:
Day 1 – Friday, September 18 – Arrive in Ponta Delgada, São Miguel Island
We’ll arrive in Ponta Delgada and dive right into the charm of the Azores. Together, we’ll wander the old town, passing through the iconic Portas da Cidade, exploring the Forte de São Brás, and browsing local artisan shops for handcrafted treasures. In the evening, we’ll come together for a festive welcome dinner, raising a glass to the adventures ahead.
Overnight: Ponta Delgada (3 nights)
Day 2 – Saturday, September 19 – Sete Cidades: Lakes & Legends
This morning we lace up our hiking boots for the breathtaking Sete Cidades Crater Rim Trail (7 km / ~2.5 hrs), where we’ll enjoy sweeping panoramic views of the twin lakes glistening below. Afterward, we’ll wander through Sete Cidades village, visiting its small church and artisan pottery shops. In the afternoon, we’ll relax by the water, swimming or sunbathing at Mosteiros beach or the black sands of Praia dos Moinhos.
Day 3 – Sunday, September 20 – Lagoa do Fogo & Tea Traditions
Today’s adventure takes us along the Lagoa do Fogo trail (11 km / ~4 hrs), a spectacular hike into the heart of São Miguel, where emerald ridges circle a luminous crater lake. Afterward, we’ll step into history at the Gorreana Tea Plantation, Europe’s oldest tea estate, and sip fresh brews in its tasting room. To end the day, we’ll unwind with a soothing soak in the warm waters of Caldeira Velha hot springs.
Day 4 – Monday, September 21 – Vineyards & Lava Landscapes of Pico
An early morning flight brings us to Pico Island, where we’ll walk the Lajido – Criação Velha Wine Trail (7 km / ~2 hrs), winding through lava-walled vineyards in a UNESCO World Heritage landscape. Our cultural stop includes the Pico Wine Museum or a visit to traditional adegas for tastings. In the afternoon, we’ll marvel at the dramatic Arcos do Cachorro, a coastline shaped by wild lava rock formations.
Overnight: Madalena, Pico Island (2 nights)
Day 5 – Tuesday, September 22 – Peaks, Whales & Farewell Feast
Today we hike the Prainha – Lagoa do Capitão Trail (9 km / ~3 hrs), a serene lake walk with sweeping views of Mount Pico, Portugal’s highest peak. In the afternoon, we’ll embark on a thrilling whale & dolphin watching trip, spotting some of the many species that call these waters home. We’ll gather in the evening for a farewell dinner, celebrating our Azorean journey.
Day 6 – Wednesday, September 23 – Departure from Pico Island
Ferry to Faial Island & Lisbon Finale
This morning we’ll take the short ferry across the channel to Faial Island, a quick and scenic 30-minute ride offering beautiful views of Mount Pico rising behind us. On arrival in Horta, we’ll store our luggage and with our hands free, we’ll spend the morning exploring Horta — strolling the vibrant marina, where sailors from around the world leave colorful murals of their voyages, and visiting the Peter Café Sport, an iconic sailors’ bar and museum. We’ll take in the Porto Pim Bay area and perhaps visit the Scrimshaw Museum, a small but fascinating collection celebrating the island’s whaling history.
After a relaxed seaside lunch, we’ll transfer to Horta Airport (HOR) for our evening flight to Lisbon. After checking into our Lisbon hotel, we’ll settle in for a good night’s rest — ready to reflect on our incredible week of island adventures.
Overnight: Lisbon (1 night)
✨ This trip is designed to balance hikes, cultural experiences, and relaxation — perfect for travelers who love active days paired with delicious food and authentic encounters.
Includes: 6 nights’ accommodation (3 nights in Ponta Delgada (San Miguel Island); 2 nights in Madalena (Pico Island), 1 night in Lisbon); meals included: 6 breakfasts, 2 dinners (welcome and farewell); ground transportation on the islands; ferry from Pico Island to Faial Island; flight from San Miguel Island to Pico Island and from Faial Island to Lisbon; whale and dolphin watching boat trip.
Personalized additions either before or after the noted itinerary are possible and gladly accommodated for additional costs.
Price: $4100 USD pp single occupancy; $3500 USD pp double occupancy. (Trip subject to modification as necessary.)
Not included: international airfare, tips, meals, and activity costs other than those noted, “optional” activities, travel insurance.
If you’re interested, please contact me with any questions or to book your spot. Space is extremely limited.
Hope you can join us!!!