Jason Hair-Wynn
He/Him
Based in Boston, MA
Speaks English, Basic ASL, Basic Spanish
Jason Hair-Wynn
Ask me about
My Story
Type A about travel planning so that you don't have to be. Boston-based, with an insatiable curiosity to see the world, have memorable experiences that are culturally rich or cleanse the mind, body and soul. From luxury to budget. Everyone is VIP.
My Travel Style
I'm a foodie with a passion for travel and helping others create their dream vacation. I have a love of road-tripping and going off the beaten path to find hidden gems. I have traveled with budget-savvy tactics as well as VIP luxury. A lover of adventure, but also nourishing the mind, body and soul. A spa-addict, I tend to plan my own adventures around ensuring I have a place to relax when needed.
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My reviews (4)
Ally L.
8 months ago
Jason was the best part of our anniversary trip! He made planning a breeze, provided an enjoyable booking experience, and gave fabulous suggestions of things to do and see in the area. Communication was timely and crisp. I would book another trip with Jason in a heartbeat.
Tracy F.
8 months ago
Jason was amazing! He was knowledgeable, prompt to reply, flexible and went the extra mile to offer suggestions for food and leisure activities. We will definitely use Jason again for our future trips as he made the experience easy and seamless! Thank you Jason!
Timothy C.
10 months ago
Exceptional service. Personalized and a well-curated trip! I will use Jason for all of my travel!
Timothy C.
a year ago
Jason was a joy to work with from start to finish. He is working on a larger itinerary of mine, but I was pleased to find out that he was able to help me with my last-minute getaway. Not only is he very communicative, he leads with empathy and caring which is a great trait to have. Because I booked with Jason, I ended up getting room credits, free breakfast, and the best part — I was upgraded to a signature suite harbor view at no additional cost. I would trust Jason with any travel needs. Thank you!
Ally L.
8 months ago
Jason was the best part of our anniversary trip! He made planning a breeze, provided an enjoyable booking experience, and gave fabulous suggestions of things to do and see in the area. Communication was timely and crisp. I would book another trip with Jason in a heartbeat.
Tracy F.
8 months ago
Jason was amazing! He was knowledgeable, prompt to reply, flexible and went the extra mile to offer suggestions for food and leisure activities. We will definitely use Jason again for our future trips as he made the experience easy and seamless! Thank you Jason!
Timothy C.
10 months ago
Exceptional service. Personalized and a well-curated trip! I will use Jason for all of my travel!
Timothy C.
a year ago
Jason was a joy to work with from start to finish. He is working on a larger itinerary of mine, but I was pleased to find out that he was able to help me with my last-minute getaway. Not only is he very communicative, he leads with empathy and caring which is a great trait to have. Because I booked with Jason, I ended up getting room credits, free breakfast, and the best part — I was upgraded to a signature suite harbor view at no additional cost. I would trust Jason with any travel needs. Thank you!
My travel ideas (6)
Montepulciano, Tuscany, Italy
After arriving in Montepulciano, the first impression is overwhelmingly picturesque. The town is characterized by its medieval architecture, narrow cobblestone streets and breathtaking views of the rolling hills of Tuscany. The backdrop of the Val d'Orcia adds an enchanting touch to this charming hilltop gem.
Montepulciano, Tuscany, Italy
After arriving in Montepulciano, the first impression is overwhelmingly picturesque. The town is characterized by its medieval architecture, narrow cobblestone streets and breathtaking views of the rolling hills of Tuscany. The backdrop of the Val d'Orcia adds an enchanting touch to this charming hilltop gem.
Vibrant City and Culture in Porto, Portugal
Porto, Portugal's second-largest city, is renowned for its rich history, stunning architecture and vibrant culture. Nestled along the Douro River, this city is famous for its port wine, picturesque streets and the iconic Dom Luís I Bridge.
Vibrant City and Culture in Porto, Portugal
Porto, Portugal's second-largest city, is renowned for its rich history, stunning architecture and vibrant culture. Nestled along the Douro River, this city is famous for its port wine, picturesque streets and the iconic Dom Luís I Bridge.
Culinary and Cultural Wonders in Modena, Italy
Modena is a treasure trove of culinary experiences and cultural heritage. From savoring the rich flavors of aged balsamic vinegar to exploring the historical sites, every moment in Modena offers a unique insight into this captivating town. Whether you're a foodie, a history buff or an automotive enthusiast, Modena has something special to offer every visitor.
Culinary and Cultural Wonders in Modena, Italy
Modena is a treasure trove of culinary experiences and cultural heritage. From savoring the rich flavors of aged balsamic vinegar to exploring the historical sites, every moment in Modena offers a unique insight into this captivating town. Whether you're a foodie, a history buff or an automotive enthusiast, Modena has something special to offer every visitor.
Six Days in the Algarve Region of Portugal
I recently took a road trip down the Algarve region of Portugal and have curated an itinerary I think would be perfect.
Six Days in the Algarve Region of Portugal
I recently took a road trip down the Algarve region of Portugal and have curated an itinerary I think would be perfect.
Trip Report: Lisbon, Portugal
Lisbon is a charming and unique city with culture, history, fantastic food and heart.
Trip Report: Lisbon, Portugal
Lisbon is a charming and unique city with culture, history, fantastic food and heart.
The Palms Turks and Caicos Resort and Spa
The overall experience at the spa was nothing short of extraordinary. Each detail, from the soothing scents to the tranquil surroundings, was meticulously crafted to foster relaxation and rejuvenation. I left feeling completely refreshed and eager to return to this oasis of serenity.
The Palms Turks and Caicos Resort and Spa
The overall experience at the spa was nothing short of extraordinary. Each detail, from the soothing scents to the tranquil surroundings, was meticulously crafted to foster relaxation and rejuvenation. I left feeling completely refreshed and eager to return to this oasis of serenity.
Montepulciano, Tuscany, Italy
After arriving in Montepulciano, the first impression is overwhelmingly picturesque. The town is characterized by its medieval architecture, narrow cobblestone streets and breathtaking views of the rolling hills of Tuscany. The backdrop of the Val d'Orcia adds an enchanting touch to this charming hilltop gem.
Montepulciano, Tuscany, Italy
After arriving in Montepulciano, the first impression is overwhelmingly picturesque. The town is characterized by its medieval architecture, narrow cobblestone streets and breathtaking views of the rolling hills of Tuscany. The backdrop of the Val d'Orcia adds an enchanting touch to this charming hilltop gem.
Vibrant City and Culture in Porto, Portugal
Porto, Portugal's second-largest city, is renowned for its rich history, stunning architecture and vibrant culture. Nestled along the Douro River, this city is famous for its port wine, picturesque streets and the iconic Dom Luís I Bridge.
Vibrant City and Culture in Porto, Portugal
Porto, Portugal's second-largest city, is renowned for its rich history, stunning architecture and vibrant culture. Nestled along the Douro River, this city is famous for its port wine, picturesque streets and the iconic Dom Luís I Bridge.
Culinary and Cultural Wonders in Modena, Italy
Modena is a treasure trove of culinary experiences and cultural heritage. From savoring the rich flavors of aged balsamic vinegar to exploring the historical sites, every moment in Modena offers a unique insight into this captivating town. Whether you're a foodie, a history buff or an automotive enthusiast, Modena has something special to offer every visitor.
Culinary and Cultural Wonders in Modena, Italy
Modena is a treasure trove of culinary experiences and cultural heritage. From savoring the rich flavors of aged balsamic vinegar to exploring the historical sites, every moment in Modena offers a unique insight into this captivating town. Whether you're a foodie, a history buff or an automotive enthusiast, Modena has something special to offer every visitor.
My travel photos
