Ready, Set... TOTO!

We begin on Terceira, one of the most colorful and historic islands in the Azores. After landing, you’ll be greeted at the airport and brought straight to our hotel, the Azores Book Hotel, where you’ll have time to settle in, refresh, and shake off the travel day. In the evening we gather for a warm welcome dinner at QB Restaurant, our first chance to connect, raise a glass, and start building the little community that always forms on Toto trips.

Our morning unfolds in Angra do Heroísmo, a UNESCO World Heritage city filled with vivid façades, cobblestoned lanes, and a rich maritime past. A local guide leads us through its elegant squares and viewpoints, setting the tone for the days ahead. In the afternoon, we trade the city for the sea as we board a boat out to Ilhéu das Cabras. These twin islets sit just off Terceira’s coast, beautiful, dramatic, and home to some of the clearest waters in the region. The evening is yours to enjoy dinner wherever you choose.

Today we dive deeper into Terceira’s wild side. A full-day island tour takes us through volcanic caves, sweeping coastal viewpoints, and pockets of local life that most visitors never see. Along the way, we enjoy a hearty Azorean lunch, the kind that reminds you how proud the islands are of their traditions. You’ll return to the hotel with plenty of stories and a new appreciation for this island’s dramatic geology.

This morning we take a short flight to Faial, known as the “Blue Island” for its hydrangeas and ocean vistas. After checking in at Pousada Forte da Horta—a historic fortress-turned-hotel overlooking the marina—we head out for a full-day exploration. The highlight is Capelinhos, the site of the Azores’ most famous volcanic eruption. Standing on this lunar landscape feels like stepping onto another planet. The rest of the tour winds through scenic viewpoints and the charming town of Horta. Dinner is open for you to enjoy at your own pace.

We cross the water by ferry to São Jorge, an island known for its dramatic cliffs and its fajãs, the lush, flat coastal plateaus created by ancient lava flows. It’s one of the most breathtaking landscapes in the archipelago. A full-day tour gives you time to soak in the island’s quiet beauty, learn about its unique geology, and, of course, sample the island’s famous cheese, which locals will proudly tell you is the best in Portugal.

This morning’s ferry carries us to Pico, home to Portugal’s highest mountain and vast fields of black lava rock that shelter UNESCO-protected vineyards. The contrast between the deep green landscape, the dark volcanic stone, and the blue Atlantic is unforgettable. We spend the day exploring Pico’s wine culture and volcanic scenery, and later we enjoy a special dinner at Genuíno Restaurant, the home of the first Portuguese sailor to circumnavigate the globe solo. His stories are woven into the space, and the food is worth the trip alone.

We say goodbye to Faial and board a short flight to São Miguel, the largest island in the Azores. After checking in at the DoubleTree by Hilton Lagoa, we enjoy a relaxed afternoon before gathering for a lively Gin & Sushi Night at The Gin Library, a quirky, one-of-a-kind bar that celebrates gin with almost scientific enthusiasm.

Our morning begins with a gentle city tour of Ponta Delgada, where we taste local wine and cheese and wander through charming historic districts. In the afternoon, we let loose and enjoy a playful picnic filled with games, laughter, and a few surprises. It’s a low-key, joyful day that fits perfectly into the middle of our journey.

Today we visit one of the most famous sights in the entire archipelago: the twin-colored lakes of Sete Cidades, set inside an enormous volcanic crater. The landscape is spectacular from every angle. For those who want a little adventure, optional kayaking or biking is included. A delicious lunch rounds out the day before we head back to the hotel to unwind.

We spend the day exploring Nordeste, a region known for its waterfalls, lush hillsides, and almost impossibly green scenery. After lunch, we return to Lagoa for a quick refresh before boarding a speedboat in Rabo de Peixe for a sunset cruise. Drinks, sushi, and local bites are served as the sun drops toward the Atlantic, one of those quietly perfect travel moments you remember long after the trip ends.

Our final full day brings us to Furnas, a valley alive with geothermal activity. We stroll through Terra Nostra Park, soak in the beauty of its enormous thermal pool, and enjoy a traditional Cozido lunch cooked slowly underground by volcanic heat. In the evening, we gather for our farewell celebration, an easy, heartfelt closing to our journey together, full of good food, warm light, and the shared feeling that something special just happened.

After breakfast, we transfer to the airport for our return journey. Saying goodbye to the Azores is never easy, but the islands have a way of lingering with you through the views, the quiet moments, and the sense of connection we build as a group.