Azores Two-Island Adventure: São Miguel & Pico - 10 Days

Day 1: Arrive on São Miguel Island

Welcome to the Azores! These nine volcanic islands lie roughly 1,000 miles (1,600 km) west of mainland Portugal in the North Atlantic, and today you're headed for São Miguel, the largest and most central island of the archipelago. With a terrain of forest-wrapped volcanic peaks, azure lakes, and improbably perfect calderas, this is the perfect base to discover this extraordinary corner of Europe. Upon arrival at the airport, you'll be met by a private driver who'll transfer you to your hotel in the capital of Ponta Delgada. The rest of the day is yours to relax or start exploring the charming town at your leisure.

Take a stroll to the striking Convento de Nossa Senhora da Esperança, a 16th-century convent with an opulent Baroque altar. Wander to the port and explore the Forte de São Bras, an imposing fortress erected in 1552 to guard the city, then stop for a bite and sink your teeth into the island's famous pineapples. If natural history's your thing, consider a self-guided tour of Museu Carlos Machado. It's the oldest museum in the Azores, dedicated to the 19th-century naturalist Carlos Machado and offers exhibits on geology, mineralogy, and an array of local flora and fauna. 

Day 2: Whale Watching Excursion

The Azores are among the best whale watching destinations in the world—their location in the middle of a key migratory route means that over 25 species of cetaceans are found in the archipelago's cool, deep waters. Since there is no continental shelf around the islands, several deep-sea species swim next to the coastline, including sperm whales, beaked whales, and dolphins.

After breakfast, meet your guide as you board a boat to spot these fantastic creatures with the help of biologists and naturalist guides. Search for whales, dolphins, turtles, and more while discovering the islands' scenic coastline and sandy beaches. Then take a tour around the islet of Vila Franca do Campo for a closer look at this volcanic marvel and its resident wildlife.

Day 4: Half-Day Diving Adventure

The cool, deep waters of the Azores are home to an incredible diversity of marine species, and this combined with its fascinating underground lava formations, make it one of Europe's best diving destinations. You'll get to discover some of the archipelago's underwater treasures yourself this morning as you board a boat for a guided diving adventure.

You'll visit two of São Miguel's dive sites, which include the Lourenços, where you can dive with mobulas (rays) during summer, and other pelagic (open water) fish like carangidae and barracudas. Panela, on the island's south coast, is another favorite dive site, formed by large boulders that have created caves where marine life thrives, from octopus to moray eels and damselfish. 

Day 6: Sete Ciudades Jeep & Hike Adventure 

Escape the usual tourist routes and head for adventure with an off-road excursion to Sete Cidades. Located on the western side of São Miguel, this remarkable area of natural beauty is considered one of the Seven Wonders of Portugal. Lush hillsides and volcanic craters rise between numerous tranquil lakes, each with its own distinctive character. Along today's 4WD trip, you'll stop at several viewpoints, such as Carvão and Vista da Princesa, where you can admire this breathtaking landscape off the beaten track.

Weather permitting, stop for a hike along the iconic Cumeeiras Trail, which follows the volcano's rim and offers stunning views from both sides. Continue to the charming local church and enjoy a cup of tea or coffee in the village located inside the crater. On the way back to Ponta Delgada, a trail around the lake's edge passes through a small peninsula shrouded in trees and flowers—giving you one last chance to capture the wilderness of this pristine landscape with your camera. The hike usually takes around 40 minutes but can be adjusted for younger kids or more adventurous travelers. 

Day 7: Fly to Pico Island, Guided Island Tour

You're in for a change of scene today as you rise early and transfer to the airport, where you'll catch a 1.5-hour flight to the neighboring Pico Island. Located 161 miles (258 km) northwest of São Miguel, Pico is the second-largest island in the archipelago but also one of the least populous. Its rocky, volcanic terrain is crowned by Ponta do Pico, a towering stratovolcano that has lain dormant since 1720.

Upon arrival, a driver will be waiting to take you to your hotel in the picturesque island capital of Madalena. Once you've settled in, discover more of this unspoiled island paradise with a full-day guided tour. Set out from the town's port and head into the countryside, passing through the UNESCO-listed wine-growing landscapes as you learn about the island's unique terroir and how its vineyards are still cultivated and harvested by hand. Continue along the rocky coast to reach Pocinho Bay, home to various migratory birds, and make a stop to taste some traditional Pico cheese at the oldest cheese factory on the island.

After lunch at a local restaurant known for its excellent fresh fish, squid, and shrimp, you'll visit the Whalers' Museum, a fascinating glimpse into the archipelago's past that displays several model ships. Then it's on to the north coast, where you can admire the views of the neighboring island of São Jorge and stop for a refreshing swim. Your day ends in the small village of Lajido, known for its distinctive lava-rock houses, where you'll taste some of the local white verdelho wine before returning to your hotel in time for dinner.

Day 8: Hike to the Summit of Montanha do Pico

Grab your best hiking boots and fuel up with a hearty breakfast—this morning you're off on a full-day, guided trek to the summit of Montanha do Pico. The 7,713-foot (2,351 m) dormant volcano is not just the highest point in the Azores but in all of Portugal, and its rocky terrain and spectacular views make for a challenging but rewarding hike. 

Your certified guide will share fascinating insight into the island's biodiversity and geology along the 5-mile (8 km) trek, stopping near the top to overlook the vast central crater. Continue another 30 minutes to reach the peak, where you'll be met with breathtaking vistas over the surrounding islands and sea. Following your descent, your driver will take you back to your hotel in time for a well-earned dinner and an early night.

Day 9: Discover Pico's UNESCO-Listed Wine Region

The penultimate day of your trip takes you on a trip back in time as you discover the ancient winemaking traditions of Pico's UNESCO-listed Criação Velha growing region with a half-day guided tour. The island's history of viticulture dates back to the 15th century, when the first settlers from Portugal planted vines suited to the mineral-rich volcanic soil. Growers today still use traditional methods to grow grapes like verdelho, arinto, and terrantez—utilizing distinctive black basalt walls to protect the vines from ocean winds and harvesting entirely by hand. 

You'll learn all about this rich growing heritage on today's tour as you visit local wineries, stroll through the unusual vineyards, and cap off the experience with an exclusive wine tasting.

Day 10: Fly to São Miguel Island, Depart 

It's time to bid farewell to the Azores! When the time comes, a driver will be waiting to take you to the airport on Pico Island to catch a flight to your final destination via São Miguel Island. Safe travels!