Europe, Africa Trip Leader

David Monteiro

David Monteiro was born in Mindelo, Cape Verde, an archipelago on the west coast of Africa, and moved to Portugal with his family when he was a child. After working as a CPA for more than 20 years, he felt the need for a change and began to lead hiking, mountain biking, and rock climbing trips, all sports he had enjoyed since his childhood. When not guiding, David indulges in his passion for photography, literature, and history.

Our Team

Upcoming Trips with David

Hiking Cape Verde

Apr 3 - 12, 2026

Oct 23 - Nov 1, 2026

View Trip

Hiking in the Azores

Apr 27 - May 6, 2026

Aug 23 - Sep 1, 2026

View Trip

Hiker’s Journey to Portugal

May 12 - 21, 2026

Sep 8 - 17, 2026

Oct 6 - 15, 2026

View Trip

Client Testimonials

"My first trip with David but hopefully not the last. His knowledge and love of Portugal and his professionalism were spot on. No problem too large or too small for him to handle with patience and good humor. Another exceptional Trip Leader."

Anne J.

Long Beach, CA
Hiker's Journey to Portugal

"David was amazing in accommodating the needs, hiking abilities and individual interests of all of us. He clearly enjoyed showing us the terrains of his country, introducing us to the special foods and wines of the four areas we hiked in. He told us much about the characteristics of the land, the peoples, their habits, their culture, the history of Portugal. "

Antje N.

Los Altos Hills, CA

"David is a gem. He has limitless knowledge about the history and food and wine and all other aspects of we areas we traveled in. He was warm, humorous, and friendly. Another great WT leader experience for all of us."

David F.

West Stockbridge, MA

"David is in the very top echelon of all WT leaders I've had—and that is a high compliment. He is amazingly skilled at everything and beyond. He is courteous, responsive, and wonderful to talk with, due to his very broad life experience, thoughtfulness, and intelligence. Five stars and more."

Joe N.

Seattle, WA
Hiking in the Azores

"A perfect combination of knowledge, skill, and organizational ability all delivered with wonderful ease and friendliness and informality."

Judy L.

Mt Kisco, NY
Hiker's Journey to Portugal

"David is an excellent trip leader. His ability to share his love of Portugal, the history, culture, and people made this trip exceptional."

Karen H.

Gold Canyon, AZ
Hiker's Journey to Portugal

"David is an unbelievable personality and resource to have as a guide. His personality is charming, so pleasant, and so knowledgeable on so many subjects — history, landscape, food, and wine! Really a gem of a man and guide."

Ken C.

Natick, MA

"David was absolutely outstanding—lovely, concerned manner, very knowledgeable."

Lauren P.

Santa Fe, NM
Hiker's Journey to Portugal

"David is a delightful, thoughtful, and well informed guide. He provided a lot of depth to whatever the day’s experience was. His extensive depth of knowledge and local contacts were very evident. His hard work, concern, and attention to detail was most appreciated."

Leslie S.

Chicago, IL
Hiker's Journey to Portugal

"I cannot imaging doing this trip with anyone other than David. He has vast knowledge of the area with many personal connections which enhanced all our activities. He loves the islands and that passion really elevates the experience of being there and understanding the culture. He is personally very caring and congenial and a pleasure to be with. He is an excellent leader in every way."

Luisa F.

Westport, CT

"David is truly an impressive historian. His knowledge of the terrain, culture, and local practices always steered us in the right direction. His sense of humor was enjoyable, providing comic relief when needed."

Nancy O.

North Weymouth, MA

"David is an extraordinary guide, and an expert on his beloved country. Though I had traveled to Portugal before, I feel like this time, through his eyes, words, enthusiasm, knowledge, energy, and joyful spirit, I was able to really get to know Portugal. His organizational skills and attentiveness to all participants made it one of the top trips of my life. David created an atmosphere where he blended the goals of the individuals with his goals for sharing his country, its beauty, wonder, and richness. Anyone—even those who are well traveled—who is lucky enough to travel with him will have wonderful memories filled with new experiences."

Pam F.

Hermosa Beach, CA
Hiker's Journey to Portugal

"Such a pleasure to travel with David. He was very knowledgeable about the Azores and many other topics of conversation that spontaneously came up throughout the excursion."

Sue C.

Seattle, WA
Hiking in the Azores

Book Your Trip Today

Our Area Specialists know every detail about our adventures around the world. They will be happy to answer any questions and help you choose the journey that’s right for you. Contact us to learn more or book your trip today!

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