• San Miguel and Pico Islands
  • Hike to famous caldeiras, hot springs, volcanos, and caves
  • Visit Pineapple and Tea Plantations
  • Whale watching and wine tasting

The Azores archipelago sparkles like a string of jewels in the Atlantic Ocean, some 900 miles west of Portugal. Blessed with a temperate ocean climate, these islands are a work of art, crafted by mother nature herself with lush forests and volcanic lakes, hot springs, thermal baths, dramatic waterfalls, fertile plantations, ancient vineyards and wonderful locally sourced foods and wines. This is a place that values its old ways and works to preserve its unique way of life. Nature is #1 here. Our visit begins on the island of San Miguel and ends beyond the lava rock walls and vineyards below Mount Pico. We hike in beautiful green landscapes and lush forests, swim in thermal baths and picnic beside jewel-toned caldeiras, with a chance to see a great variety of flowers and birds, maybe even a whale. This wonderful spot, so easily reached by Europe and the eastern US, is slowly on its way to becoming a top vacation destination. Now is the time to savor each moment.

Saturday Overnight: Hotel do Colegio

Meet the group at our hotel in Ponta Delgada, on Sao Miguel island. Enjoy a wonderful welcome cocktail and dinner with the group.

Sunday Overnight: Hotel do Colegio

We begin with a gentle hike along the ridge of the Caldeira das Sete Cidades, a protected landscape dominated by four spectacular lakes. It's one of the most iconic views in the Azores. After lunch we head for an enlightening (and tasty!) visit to the historic Arruda Pineapple Farm, then return to Ponta Delgada to explore its historic center. Dinner tonight is at a nearby restaurant.

Monday Overnight: Terra Nostra Garden Hotel

Begin with a visit to Miradouro do Castelo Branco for panoramic views and a short hike to Furnas. We'll stop for lunch at a local restaurant, then walk on to see the geysers and boiling mud springs of Caldeiras das Furnas. It's quite a sight. We'll continue our walk in the stunning green hills of Ribeira do Faial da Terra, then board the shuttle in Outeiro, stopping at the spectacular Achada Waterfall enroute to our Furnas hotel. Dinner tonight is at a favorite local restaurant.

Tuesday Overnight: Terra Nostra Garden Hotel

The day begins with an easygoing loop walk to the hot springs and waterfalls of Salto Do Cabrito. After lunch, we head out for a more challenging hike to the tea factory in Cha Gorreana. After a visit we stop for a well deserved healing hot bath at the lush Caldeira Velha Interpretation Center.

Wednesday Overnight: Hotel Aldeia da Fonte

Our morning walk takes us to the fascinating Fabricas de Luz trail to see remnants of the country's industrial past. After, we walk to the beautiful Lagoa do Congro, where we'll enjoy a picnic lunch before exploring the charcoal cave at Vila Franca do Campo. Later this afternoon, we'll head to the airport for a late-afternoon flight to Pico Island. Enjoy dinner at our Pico Island hotel.

Thursday Overnight: Hotel Aldeia da Fonte

Pico Island is famous for its long history of grape growing and wine making, and home to Mount Pico, the volcano that dominates the skyline. Opt to hike Portugal's tallest mountain with an altitude of 7713 ft, or choose instead to enjoy a wonderful hike among the old vineyards of Pico. This afternoon we'll travel inland to walk in more of the island's beautiful landscapes.

Friday Overnight: Hotel Aldeia da Fonte

This morning if the seas are calm, we hop onto a small boat and head out to sea for an exciting bit of whale watching. After a fun trip and a good lunch we'll hike near the coast in an area designated as a World Heritage Site. We end the day with a wine tasting at the Pico wine cooperative. Dinner tonight is a favorite Azorean restaurant in Madalena.


After breakfast The Wayfarers will transport you to the Pico Airport for onward travel.
Walking to the thermal pools and taking a dip .... heaven!
Small dirt roads and paths through forests and valleys. A mix of easy and vigorous walks, sometimes rocky trails. Once challenging day up Portugal's highest mountain. 5-8 miles per day.


US $4,895.00
Per Person, Double Occupancy
(Single Supplement US $695.00)
Our Wayfarers friends' Price is US $4,650.00


From Apr 18 to Apr 25 (more dates)
Request booking
Begins: Sao Miguel Island, Azores
Ends: Pico Island, Azores
The Azores April 2020 Map

Hotels - Where we stay

Hotel do Colegio

Hotel do Colegio

The recently updated Hotel do Colegio was originally built as a 19th century manor house for a wealthy orange merchant at the height of the island's orange trade. Since then it has served as a private school, and more recently as the Regional Conservatory of Music of Ponta Delgada. Reminders of the building's rich history have been retained in the thoughtful restoration. The hotel has an outdoor pool and Wi-Fi throughout. Guest rooms feature private bath, minibar, cable TV, and air conditioning.
Hotel Terra Nostra

Hotel Terra Nostra

The Terra Nostra Garden Hotel is a four-star luxury hotel nestled in the Terra Nostra Garden, one of the world's best green retreats. This award winning hotel features Art Deco style, a wellness spa, and restaurant. Wi-Fi is available throughout. Guest rooms have a private bath, flat screen TV, mini bar, air conditioning, and other amenities.
Hotel Aldeia da Fonte

Hotel Aldeia da Fonte

The Aldeia da Fonte hotel offers luxury accommodation in a unique natural setting. Comprised of six volcanic rock houses, it sits on the cliffs overlooking the Atlantic Ocean, surrounded by stunning landscaped gardens. The eco-friendly hotel has a beautiful outdoor pool, sauna, observation tower, Tai Chi garden, beach access, and on-site hiking trails. WiFi is available throughout the property. Guest rooms have a private bath, minibar, safe, and flatscreen TV.

Start planning your trip

What Is Included in the Price of My Vacation

  • Full-time services of two staff - a Walk Leader and Walk Manager
  • A backup vehicle for resting walkers and moving luggage
  • Comprehensive Travel Information Package and Reading List
  • Diverse itineraries with an emphasis on history, geography, culture, peoples, flora and fauna
  • Demonstrations, wine tasting, admissions to museums and historic sites
  • All ground transfers (ferries, cable cars, trains, etc.)
  • Maps and unique souvenirs to commemorate your trip
  • First-class accommodations with cultural and historical interest
  • All meals - with choices - (Special dietary requirements? No problem!)
  • Wine with dinner
  • On-trail snacks and refreshments
  • All gratuities at hotels and restaurants