(15 Reviews)
100% Recommended

Gwynne Chafer

La Crosse, WI

Luxury Travel Experience Planner

Traveling the world allows us to gain insight into different cultures, religions and food, as well as explore ancient ruins, natural wonders & historic landmarks that most people only read about. I pride myself in my attention to detail & the knowledge I have gained throughout my years of traveling. My travels have not only made me a better travel agent, but a better person, with a deeper understanding of how people live & survive around the world. I recently visited Saudi Arabia, which was about as different to my life as could be. I found myself fascinated by the women of the country. 90% of the women encountered were fully veiled, even though wearing a Niqab is not required. However, it is an important part of Saudi culture & in most Saudi cities (including Riyadh, Mecca, Medina, etc.) the vast majority of women do cover their faces. The Saudi niqab usually only leaves a long open slot for the eyes…their eyes are the only thing the world sees of them.

My Travel Specialties

Luxury Vacations Experiences

What is a luxury? Webster’s definition defines it as the state of great comfort and extravagant living. Does this define what a luxury travel experience is? Some clients might define a luxury travel experience as a very expensive trip, with 5-star accommodations along the way. Other...
Read more from my Luxury Vacations Experiences bio.

Italy Extravagant Escapes

Visiting Italy is a feast for your senses … from the scent of lemons in Capri, to the delicious flavors of the many pastas and sauces which is known for, to viewing the crumbling ruins of the Roman Empire. Did you know that Italy has the most UNESCO World Heritage Sites of any country in the world?...
Read more from my Italy Extravagant Escapes bio.

Asian Adventures

Asia is a fascinating area of the world that I think everyone should visit at least once in their life.  In my quest to learn as much as I can about the culture, food and religions throughout Asia, I have visited China and Thailand twice, Japan, Bhutan, Cambodia, Vietnam, Hong Kong and India.  I include...
Read more from my Asian Adventures bio.

Escape to the Big Apple

I have traveled to New York City MANY times, yet I still seem to find a new place to explore and a new restaurant to dine at every time I go. Needless to say ... you will never run out of things to do!

Here are just a few things that I have personally experienced in New York:

My Travel Albums

Incredible Italy
Luxurious Travel Experiences

My Travel Stories

Authentic Experiences with Il Chiostro

Il Chiostro was established by Linda Mironti and Michael Mele, both Italian Americans with backgrounds in the arts. At Il Chiostro their goal is to bring Italy to people. They are all about “Slow Travel” and full immersion travel experiences. You will stay in one place long enough to become familiar...Read more.

Customer Testimonials

Everything went like Clockwork

"Hello, Gwynne. Everything went like clockwork. Thank you so much for everything you did to make our trip so wonderful. Your expertise and organizational skills were greatly appreciated."
Richard R.

GREAT Vacation

"Gwynne - Because of you, we were able to quickly turn what could have been a not-so-good vacation into a GREAT vacation. I will be recommending you to all my friends!"

On Top of it All

"Hi, Gwynne. We had an awesome trip and have you to thank for it. You were so 'on top' of things and kept us advised of everything. On the trip, I heard horror stories from other couples that didn't have the neat experience we had with you. It was a trip of a lifetime. Thank you for all you did to make this a very memorable trip."
Jan H.

My Reviews

42 of 70 people found this review helpful
Magnificent 50th Anniversary family trip
Gwynne was very accommodating in planning a rather complex family trip for 14 people, 5 of whom live overseas. All of Gwynne's arrangements went off without a hitch.
We are totally satisfied and highly recommend Gwynne's services. We'll use her again.
By  LJ  from  Genoa, Wisconsin
Traveled to  Italy ~ Europe
I would recommend this agent to my family and friends
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37 of 64 people found this review helpful
The Trip of a Lifetime!!
Gwynne was recommended to me by a friend when they learned we planned on visiting Italy. We had many details such as meeting my daughter who was already in Italy, and having my son leave earlier than the rest of us, and also having a large number of people making different payments and also needing various different requirements while traveling...a bit overwhelming for me to plan since I had never been to Europe before!! Gwynne was invaluable to the process of planning our trip!! She provided everything we needed even before I knew it was needed...She recommended beautiful hotels and priceless experiences. We visited Florence, Rome and Paris, and Gwynne provided us with private tours with lovely, knowledgeable tour guides. She arranged a cooking class and food tastings, gave us lists of restaurants in different price ranges with all of their contact information. Everywhere we went we had transfers to and from our hotels, airports, train stations and tours! Best experience ever!
By  Colleen R  from  Sun Prairie, WI
Traveled to  Florence ~ Italy ~ Europe
I would recommend this agent to my family and friends
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43 of 77 people found this review helpful
Our Travel Agent for many years
Gwynne has been our travel agent for many years. She is a delight to work with, is attentive, thorough, and proactive. Our most recent trip was to France. She arranged air, hotel, train tickets including detailed guidance on verifying tickets prior to boarding, and a map. She has always made whatever travel arrangements we needed even if she was under a deadline for other responsibilities. If she is away, she provides a backup plan "just in case." All details are efficiently handled well in advance of the start of any trip. Several times over the years, when some misadventure befell our flight plans, she rescued us by re-booking for us so we could journey on. It's just so nice to know, whatever travel arrangements I might need, Gwynne will handle it.
By  Traveler  from  Tomah, WI
Traveled to  Europe
I would recommend this agent to my family and friends
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25 of 42 people found this review helpful
The easiest planned vacation ever!
Gwynne was amazing. From day one she answered every question I had. She was able to get me a deal that I couldn't come close to getting with any online site. She is truly wonderful at her job. When I was concerned about a flight due to a hurricane coming in, she promptly changed my flight and sent me the updated itinerary. Thank you again Gwynne.
By  SandiR  from  Athens, Ohio
Traveled to  Cancun ~ Quintana Roo ~ Mexico
I would recommend this agent to my family and friends
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30 of 55 people found this review helpful
Fantastic Family Trip to Switzerland
Having known Gwynne for many years, when our entire family of 15 wanted to plan a trip to Switzerland she was the only call we made. She offered great advice from the very beginning as we were planning our itinerary, selecting cities and fine tuning the details. She was quick to reply to any questions or concerns we had through the entire process. You could feel she wanted to make sure we had the best travel experience possible - and we did. Thank you Gwynne!
By  Thompson Family  from  Lake Mills, WI
Traveled to  Switzerland ~ Europe
I would recommend this agent to my family and friends
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Destination Expert:

  • China
  • Italy
  • New York City
  • India
  • Thailand
  • Cambodia
  • Ireland
  • East and Southeast Asia
  • Vietnam
  • Europe
  • Hong Kong
  • London
  • Caribbean

Travel Specialist:

  • Adventure
  • European Culture
  • Luxury
  • Food & Wine
  • Couples & Romance
  • Escorted Tours
  • Family Vacations
  • Historical Sites
  • All Inclusive

Top Travel Partners:

  • Delta Vacations
  • CIE Tours
  • Funjet Vacations
  • Globus
  • Avalon Waterways
  • Palace Resorts
  • Viking
  • Celebrity Cruises
  • Le Blanc Spa Resorts


  • Alitalia Travel Specialist (Italy)
  • Sandals Certified Specialist
  • Avalon Waterways Specialist
  • College of Disney Knowledge Graduate
  • Travel Leaders Certified Travel Specialist

Industry Affiliations:

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