Travel Advisor

Jason Hair-Wynn

He/Him

Expertise

Wellness & Spa,
Honeymoon,
Caribbean,
Europe,
Cruises,
Disney/Universal

Based in

Boston, MA

Languages spoken

English, Basic ASL, Basic Spanish

Travel Advisor

Jason Hair-Wynn

Profile details

About

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.

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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.

Jason's travel guides & trip reports

Guide

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...

Guide

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...

Guide

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...

Guide

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

Trip Report: Lisbon, Portugal

Lisbon is a charming and unique city with culture, history, fantastic food and heart.

A view from the spa at The Palms overlooking a reflecting pool surrounded by palm trees under a clear sky.

Trip Report

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...

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Favorite hotels

The Palms Turks & Caicos

Beach time holiday perfection with white sands and azure waters great for sauntering and unwinding.

Fora Perks

★
$100 hotel / resort credit.
★
Breakfast daily.
★
Upgrade & extended check-in/out whenever possible.

Aruba Ocean Villas

Blissful and quaint retreat with overwater villas and authentic beach bungalows in Aruba.

Disney's Animal Kingdom Lodge

African-inspired resort at Walt Disney World offering immersive savanna views with exotic wildlife, themed dining experiences and richly designed accommodations that transport guests to the heart of Africa.

Atlantis Bahamas

Nassau’s vacation kingdom is home to five hotels, two marinas and endless beach and watersports entertainment.

Fora Perks

★
$100 food / beverage credit.
★
Breakfast daily.
★
Upgrade & extended check-in/out whenever possible.

Jason's travel photos

View of a beautiful resort spa in a tropical area on a sunny day

View of a seagull flying over a rocky shoreline and waves crashing at sea under cloudy skies

Aerial view of a lush green coastal area on a cloudy day

View of a beautiful open-air room with bed and hanging swing, right beside the sea

Advisor side by side with a Mickey Mouse dressed in wizard robes

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Jason's reviews

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!

Timothy C.
Booked travel to Massachusetts
August 2024

Jason Hair-Wynn curated by Jason Hair-Wynn

Get in touch with Jason

Reach out to customize and book your own experience. Or, just to chat about travel in general.

You can normally expect a response from Jason within a business day or so. You’ll also be subscribed to our travel newsletter (you can unsubscribe at any time).