2026 three-island Azores Adventure Seeker journey
april 18 - 26, 2026

pricing from $2,750/person*

Embark on an exhilarating 9-day Azores Islands adventure with Holiday Travel’s own Aimee, exploring São Miguel, Faial, and Pico through thrilling outdoor activities and stunning landscapes. From the lush greenery of São Miguel, where you’ll hike, kayak, and whale-watch, to the dramatic caldera rim hikes on Faial, this tour is for the true adventure seeker.

Travel by ferry to the island of Pico for a relaxed sightseeing tour, and enjoy breathtaking views, including the iconic Mount Pico, the highest point in Portugal. Your itinerary also features a full-day Sanguinho hike, a day trip to Pico, and more scenic hikes in Sete Cidades and Caldeira do Faial. And as the crowning touch, you’ll be treated to guaranteed early check-ins and luxurious accommodations, including 5 nights in Ponta Delgada and 3 nights in Horta. With daily breakfasts, inter-island flights, and seamless airport transfers included, this active adventure is the perfect way to experience the Azores’ natural beauty and rich culture!

Included in the cost:

• 8-night guided tour, including full professionally-guided sightseeing tour as outlined in the itinerary below, all accommodations, inter-island flight from São Miguel to Faial, and 11 meals (8 Breakfasts, 3 Lunches)

  Not included in price: International Air from Boston to/from Azores, Guide/Driver Gratuities, and Travel Insurance. Valid US Passport will be required.

Get in touch with your favorite member of the Holiday Travel team today to secure your spot!

Day to Day Itinerary

April 17, 2026: Depart from Boston on your overnight flight to The Azores!

April 18, 2026 - Day 1: Welcome to the Azores and São Miguel!
Upon arrival at Ponta Delgada International Airport, you’ll be met by a private driver and brought to your hotel in the city's center. The rest of the day is yours to explore the cobblestone streets of the Azores’ largest city. Visit the Portas da Cidade (city gate), the historic St. Sebastian Church, and Forte de São Brás, or simply relax in a café near the marina. Included Meals: None

April 19, 2026 - Day 2: Sanguinho Guided Hike
Start today’s full-day hike in the parish of Faial da Terra, following the trail to the former village of Sanguinho. Here you will find abandoned buildings and traces of traditional farming, along with a panoramic view of the village below. The highlight of the day will be a stop at the magnificent Salto do Prego waterfall, famous for its fresh, glittering, crystalline water. 3 hours of hiking, 5 km, 172 m elevation change, intermediate/moderate. Included Meals: Breakfast & Picnic Lunch.

April 20, 2026 - Day 3: Whale and Dolphin Watching Tour
Today, you’ll set out on a semi-rigid boat for a whale watch to spot bottle nose dolphins, pilot whales, and as many as 21 other marine species that call these waters home. Visitors are practically guaranteed to spot marine life every day of the year! Included Meals: Breakfast

April 21, 2026 - Day 4: Kayaking on Lagoa das Furnas and Visit to Terra Nostra Park
Today you will head to the eastern side of São Miguel for a day of peace and tranquility. Take in the beautiful natural landscape as you spend the morning kayaking on Lagoa das Furnas, a crater lake. While you paddle, your traditional cozido lunch will be cooking in the ground on the banks of the lake. After lunch, you will head to Terra Nostra Park to visit the award-winning botanical gardens and also relax in the hot springs. A truly relaxing day spent in a beautiful place! Included Meals: Breakfast & Lunch

April 22, 2026 - Day 5: Sete Cidades Guided Hike
Today is a shorter hike in the Sete Cidades area of the western part of the island. Walk along beautiful trails at the top of a volcanic crater and see the various lakes and wetlands that have formed in the valley below. The highlight of the trail is a stop at Mata do Canário, which is one of the most photographed parts of the island. 2.5 hours of hiking, 4.5 km, 54 m elevation change, easy. Included Meals: Breakfast.

April 22, 2026 - Day 6: Welcome to Faial
After a quick inter-island flight over to Faial, take the afternoon to explore the main town of Horta, the ruins of the Santa Cruz Fort, the Faial Botanical Gardens, or just relax poolside and get ready for tomorrow’s great adventure. Included Meals: Breakfast.

April 24, 2026 - Day 7: Caldeira do Faial Guided Hike
Today you will enjoy a guided hike around the rim of Faial's Caldeira. The Caldeira Volcano is a massive stratovolcano that formed the island of Faial. The floor of the crater is two kilometers wide and is 400 m (1,300 ft) in depth below the rim. Your hike will feature spectacular views, both of the inside of the Caldeira and of Faial. 3-3.5 hours of hiking, 7 km, minimal elevation change, easy/moderate Included Meals: Breakfast.

April 25, 2026 - Day 8: Day Trip to Pico
Dominating the view out to sea from Horta, the island of Pico is just a short, 30-minute ferry ride away. Home to Mt. Pico, the highest peak in Portugal, Pico offers breathtaking landscapes, dark black basalt cliffs, lava flows, and historic vineyards. On this full-day tour, you will learn how grapes are grown in ancient lava flows, stop at viewpoints along the dramatic coastline, and see the endemic flora in the laurel forest. After lunch in one of the island’s small towns, the tour continues in Lajes, visiting the Museu dos Baleeiros (the whaling museum). At the day's end, return to Faial by ferry, enjoying the late afternoon sun on the ocean. Included Meals: Breakfast & Lunch.

April 26, 2026 - Day 9: Until Next Time, Azores!
After breakfast, transfer back to the airport for your flight home (airfare not included). Safe travels! Included Meals: B

*Pricing is per person, based on double occupancy (limited triple occupancy rooms are available). Pricing does not include international air, driver/guide gratuities, travel insurance, or anything not specifically mentioned as included. A non-refundable deposit is required to confirm space. Space is limited and space/discounts are subject to availability until deposit is made. Please note that the schedule of excursions listed in the itinerary is tentative and the days on which excursions will take place may change. Excursions are not scheduled on travel days.