(20 Reviews)
100% Recommended

Gwynne Chafer

La Crosse, WI
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 UNES...
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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? 58 sites have been designated for either their natural beauty or historic significance!


I love selling Italy, from the archaic ruins of Rome to the hidden beauty of Venice. Roam the ancient streets of Pompeii and explore the medieval walls of Assisi. It is hard to describe the feeling of standing in the Colosseum, where so many years ago the gladiators fought for their lives. Wake up to the sound of a Venetian gondolier, warming up his voice as he meanders through the cobbled sidewalks of the island. These are all things I highly suggest you experience for yourself.


If you have been to Italy before and would like to go back, I can suggest visiting some lesser-known areas of the country, like Matera and Alberobello. I recently visited these areas myself and would highly recommend. There are countless destinations to travel to in Italy and I still have more to check off my bucket list.


For all of my foodie travelers, I had two of my favorite meals in Italy. They were both on this last trip in Matera! My taste buds rejoiced when taking the first bite of Pistachio Pasta at Baccus in Matera and Panzerotti. I am still dreaming of these meals 4 months after eating it!


I have over 30 years of experience as a travel professional. I have visited Italy numerous times. I have traveled from north to south and from east to west. I really enjoy selling the different areas of the country. Let's start planning your Italian dream vacation. 


 

My Travel Albums

Incredible Italy

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.

See more travel stories

My Reviews

43 of 72 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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39 of 67 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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27 of 45 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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44 of 79 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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32 of 58 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:

  • Italy
  • India
  • East and Southeast Asia
  • Ireland
  • London

Travel Specialist:

  • European Culture
  • Luxury
  • Couples & Romance
  • Escorted Tours
  • All Inclusive

Top Travel Partners:

  • Delta Vacations
  • CIE Tours
  • Palace Company
  • Le Blanc Spa Resorts
  • Viking

Certifications/Awards:

  • 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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