Emily Boles
Your next international adventure begins here! 🇵🇹🇮🇹✨
I specialize in creating personalized journeys through Italy and Portugal with a focus on meaningful, local experiences that go beyond the typical tourist path. I believe travel is at its best when it creates genuine connections, whether that’s sharing a meal at a family-run trattoria, discovering small coastal villages, or learning the stories behind a destination from the people who call it home. My approach is thoughtful, immersive, and tailored to each traveler, blending authentic experiences with seamless planning to create unforgettable trips.
How did you get involved in travel?
"My love for travel started when I was just 16 and got the chance to visit Costa Rica on a school trip. As soon as I returned, I knew I wanted to explore the world as much as I could! Since then, I’ve traveled to 15 countries, whether it was with groups of strangers, friends, or even solo. Each adventure has opened my eyes to different cultures and ways of life, and I’m so passionate about helping others have these amazing, transformative experiences, too!"
Please share a unique travel experience you will never forget.
"One of my favorite travel experiences was spending a day like a local in Porto. The people in Portugal have a wonderful balance between work and leisure, taking the time to enjoy life. I strolled through the Mercado do Bolhão, where I picked up some fresh bread, cheese, and olives for a lovely picnic. Then, I headed to Ribeira Square to sit by the water while I read a book, enjoyed my snacks, and watched the boats go by on the Douro River. I'll always remember how I took a moment to appreciate the beauty of my surroundings."
Emily's favorite itineraries and travel advice
Top itineraries and travel advice
You don't have to travel far to see, taste, and experience the best of Portugal. Start your adventure in Lisbon to explore the city's art, cuisine, and hills. From Lisbon,...
This itinerary includes Portugal's two biggest cities, a slew of historic villages, and some spectacular beaches for an epic adventure to remember. Start in up-and-coming Lisbon...
See the highlights of Portugal's cities, beaches, and gorgeous towns on this fantastic itinerary that takes you through the country's must-see gems. Explore the urban centers of...
Family itineraries
Check off some of Portugal's most famous sights on this seven-day family adventure. Start in Lisbon with a guided tour via electric tuk-tuk and a ride on an amphibious...
Take your family for a week-long adventure in Portugal, where you'll find the ultimate mix of sightseeing, nature, culture, history, and good food. Start in postcard-perfect...
Honeymoon itineraries
Recent trip reviews for Emily
Overall, the experience exceeded our expectat...
Italy
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Sep 22 - Oct 5, 2026
Everyone was amazing and showed up on time.
Portugal
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Sep 7 - Sep 16, 2026
Everyone was amazing and showed up on time. The trip went perfectly! It really allowed us to get some local experiences that we would not have been able to do on our own. This saved us so much frustrations. I am not sure what they put on top of everything but whatever it is worth it.
Thank you so much for writing a review, Christopher! I'm so glad you had an amazing time and were able to enjoy your trip without any stress. We love taking care of everything for you so you can just relax and enjoy the beauty of Portugal! I hope you returned with amazing memories and are already dreaming up your next international adventure together. We're looking forward to seeing you again in the future! - Emily
Family trip to Portugal
Portugal
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Sep 5 - Sep 12, 2026
Thank you so much for the kind review, Hanh! I'm so glad you and your family had such a wonderful time in Portugal, even despite the slight hiccup with the Fado Dinner & Walk activity. We'll be ready for you when it's time for your next adventure. Can't wait to see where you go! - Emily😄
Emily helped us to plan a terrific vacation
Portugal
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Aug 13 - Aug 21, 2026
Thank you so much for the wonderful review! I love all the photos. 🤩 It was such a pleasure helping you discover Portugal and put together a trip that felt both enjoyable and memorable. I’m so happy to hear that you loved the guided tours and had such great experiences with your guides. I'm sorry to hear about the Flores Boutique Hotel, but I'm glad it didn't put a damper on the whole experience. Can't wait to see where you go next!
This was an AMAZING trip, From start to fini...
Portugal
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Aug 15 - Aug 23, 2026
From start to finish everything was perfect.
All the hotels were stylish, well equipped, functional, staff very accommodating.
Breakfast was delicious everywhere, and just got better at each location.
The intimate feel of a boutique hotel is very welcoming.
The excursions were so well coordinated, our guides were very knowledgeable about the country’s history, the landscape, food, wine, and we appreciated the fun Lisbon/ Porto rivalry…
Dennis from the... Read more
Olá, Nicola! Your review warmed my heart, thank you. 😊 I'm so happy the trip was so incredible, especially for the birthday girl. I remember my time traveling abroad when I was 16, and it stuck with me forever! Meeting people from all over is also what makes traveling so special. We'd love to help plan your next international adventure, wherever it may be. Can't wait to see where you and your family go next!🇵🇹 -Emily
Overview
Portugal
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Jul 19 - Jul 25, 2026
- Recommendations of restaurants or areas... Read more
Thank you so much for your thoughtful review, Lauren! I'm so glad to hear you enjoyed your guides, accommodations, and experiences throughout Portugal. I also really appreciate your detailed feedback. Your suggestions about restaurant recommendations, arrival day planning, tour timing, and the Douro Valley are incredibly valuable, and I'll be sure to share them with our local team as we continue improving our itineraries. I'm so happy you had a wonderful trip overall, and I hope we have the opportunity to help you plan another adventure in the future! - Emily
Wonderful trip
Portugal
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Jul 15 - Jul 21, 2026
Thank you for your review, Michael! 😊 I'm so glad you and Abby had such a wonderful time in Portugal. Fado is truly such a special tradition in Portugal with a deep history -- it's so great you got to experience and learn about it! We hope to see you again, whether it's back to Portugal or trying somewhere new. - Emily
Two must do trips in Portugal
Portugal
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Jul 5 - Jul 10, 2026
Thanks for writing a review, Lori! I LOVE the pictures you included. 🤩 I'm so glad you had such a fun time in Portugal, even though it was just a few days. Hopefully, you can return one day to see more of this beautiful country! - Emily
Portugal......i'll see you again
Portugal
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May 17 - May 24, 2026
As usual i had Emily as backup for everything . Everyone showed up on time. I can't wait to use Kim Kim for my next adventure 👍😄 Read more
This is such an awesome review, Edward! Connecting with local guides is certainly a great way to learn more about Portugal and find lesser-known spots in the places you're staying. I can't wait to see where you go next on your Kimkim adventure—I know it's going to be a great trip! - Emily
Southern Portugal Add On..
Portugal
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Apr 25 - Apr 29, 2026
I'm sorry to hear you caught a cold at the end of your trip, Ami! I appreciate you taking the time to share your thoughts on your trip. The Algarve is such a gorgeous place, and I'm glad you enjoyed your driver for the ATV drive -- the local guides are so fun to talk to! Looking forward to seeing where you go next on your international adventure! 😄🙌 - Emily