Kerrylynn Regan
Based in Nashville, Tennessee
English
Kerrylynn Regan
Ask me about
My Story
I grew up in the Northeast and have called Nashville home for the past 10 years. Travel has always been a passion of mine—from international adventures to the breathtaking beauty of the US (especially the National Parks!). Whether it’s a family vacation, a girls’ getaway, or a romantic escape, I love planning trips that feel seamless, personal, and unforgettable.
Travel Style
My travel style is all about meaningful experiences. I design trips that feel organized, well-paced, and intentionally planned, with just the right balance of adventure and relaxation.
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Reviews (9)
Chris J.
5 months ago
I had a fantastic experience working with Kerry for our trip to Vermont. She made the entire process easy and stress-free, finding the perfect hotels that matched exactly what we were looking for in both comfort and location.
Janelle M.
9 months ago
Kerry was absolutely amazing to work with! Communication was clear, timely, and always so friendly — I felt completely taken care of throughout the entire booking process. She really listened to my travel preferences and made thoughtful suggestions that I wouldn’t have discovered on my own. Every detail was handled with care, and her recommendations were spot on and made my trip even more special. I truly appreciate her expertise and dedication — I can’t wait to plan my next adventure with her!
Haley S.
9 months ago
Great, friendly agent!
Lauren M.
9 months ago
Kerry is kind and caring and will get you the best rates. She is so easy to work with. She is always flexible with our travel plans and changes and does everything she can to make each trip amazing!
Morgan O.
9 months ago
Kerry was friendly, communicative, and timely. It was so nice to just relax and enjoy vacation knowing Kerry thoughtfully provided recommendations based on our preferences. I can’t recommend Kerry highly enough for anyone looking to make travel seamless, personalized, and stress-free. I’ll absolutely be booking through her again!
Chris J.
5 months ago
I had a fantastic experience working with Kerry for our trip to Vermont. She made the entire process easy and stress-free, finding the perfect hotels that matched exactly what we were looking for in both comfort and location.
Janelle M.
9 months ago
Kerry was absolutely amazing to work with! Communication was clear, timely, and always so friendly — I felt completely taken care of throughout the entire booking process. She really listened to my travel preferences and made thoughtful suggestions that I wouldn’t have discovered on my own. Every detail was handled with care, and her recommendations were spot on and made my trip even more special. I truly appreciate her expertise and dedication — I can’t wait to plan my next adventure with her!
Haley S.
9 months ago
Great, friendly agent!
Lauren M.
9 months ago
Kerry is kind and caring and will get you the best rates. She is so easy to work with. She is always flexible with our travel plans and changes and does everything she can to make each trip amazing!
Travel ideas (6)
A Cozy Vermont Fall: Burlington, Stowe & Woodstock
Vermont is especially magical in the fall, with its small-town charm that feels straight out of a Hallmark movie. As the temperatures drop, cozy bars and restaurants glow, serving amazing food that makes lingering inside just as appealing as being outdoors. Quiet hikes bursting with colorful foliage offer moments of peaceful escape.
A Cozy Vermont Fall: Burlington, Stowe & Woodstock
Vermont is especially magical in the fall, with its small-town charm that feels straight out of a Hallmark movie. As the temperatures drop, cozy bars and restaurants glow, serving amazing food that makes lingering inside just as appealing as being outdoors. Quiet hikes bursting with colorful foliage offer moments of peaceful escape.
Canadian Rockies Road Trip: 4- to 6-Day Guide to Banff National Park & Beyond
This was a girls' trip we will never forget! The Canadian Rockies are absolutely breathtaking, with turquoise lakes (truly have never seen a color like them), towering peaks, and abundant wildlife. We were able to fit a lot into a few short days without it feeling rushed or overwhelming.
Canadian Rockies Road Trip: 4- to 6-Day Guide to Banff National Park & Beyond
This was a girls' trip we will never forget! The Canadian Rockies are absolutely breathtaking, with turquoise lakes (truly have never seen a color like them), towering peaks, and abundant wildlife. We were able to fit a lot into a few short days without it feeling rushed or overwhelming.
Passing Through Portugal: An 8- to 10-Day Guide to Porto, Lisbon & Algarve
Portugal is beautiful, with 300+ days of sun. In addition to fantastic weather, Portugal offers delicious food and wine, gorgeous beaches, and welcoming and kind locals. The cities are walkable (if you don’t mind hills). Public transportation is easy and convenient. Portugal is also known for being more affordable than other popular areas of Europe.
Passing Through Portugal: An 8- to 10-Day Guide to Porto, Lisbon & Algarve
Portugal is beautiful, with 300+ days of sun. In addition to fantastic weather, Portugal offers delicious food and wine, gorgeous beaches, and welcoming and kind locals. The cities are walkable (if you don’t mind hills). Public transportation is easy and convenient. Portugal is also known for being more affordable than other popular areas of Europe.
3-Day Guide to Bozeman & Yellowstone National Park (Baby & Family-Friendly)
This was our first national park trip as a family of eight, including a 9-month-old. We vary largely in our hiking abilities and love of the outdoors. Fortunately, everyone absolutely loved this trip! Yellowstone is magical and unlike anywhere else we have been.
3-Day Guide to Bozeman & Yellowstone National Park (Baby & Family-Friendly)
This was our first national park trip as a family of eight, including a 9-month-old. We vary largely in our hiking abilities and love of the outdoors. Fortunately, everyone absolutely loved this trip! Yellowstone is magical and unlike anywhere else we have been.
A Solitary Stroll Through Edinburgh
This was my first solo trip abroad, and it was truly an unforgettable experience! I highly recommend it to anyone looking to escape for a few days to a magical city full of history, stunning architecture, and gorgeous landscapes. Everywhere you turn is a charming view, whether it’s a castle, quaint cobblestone street, or miles of rolling hills.
A Solitary Stroll Through Edinburgh
This was my first solo trip abroad, and it was truly an unforgettable experience! I highly recommend it to anyone looking to escape for a few days to a magical city full of history, stunning architecture, and gorgeous landscapes. Everywhere you turn is a charming view, whether it’s a castle, quaint cobblestone street, or miles of rolling hills.
Wild Peace: A Weekend in Jackson, Wyoming
I felt immediate peace stepping off the plane in Jackson Hole. What a special destination to unplug and make lifelong memories. We had an amazing trip and wouldn't change a thing (other than packing some binoculars!).
Wild Peace: A Weekend in Jackson, Wyoming
I felt immediate peace stepping off the plane in Jackson Hole. What a special destination to unplug and make lifelong memories. We had an amazing trip and wouldn't change a thing (other than packing some binoculars!).
A Cozy Vermont Fall: Burlington, Stowe & Woodstock
Vermont is especially magical in the fall, with its small-town charm that feels straight out of a Hallmark movie. As the temperatures drop, cozy bars and restaurants glow, serving amazing food that makes lingering inside just as appealing as being outdoors. Quiet hikes bursting with colorful foliage offer moments of peaceful escape.
A Cozy Vermont Fall: Burlington, Stowe & Woodstock
Vermont is especially magical in the fall, with its small-town charm that feels straight out of a Hallmark movie. As the temperatures drop, cozy bars and restaurants glow, serving amazing food that makes lingering inside just as appealing as being outdoors. Quiet hikes bursting with colorful foliage offer moments of peaceful escape.
Canadian Rockies Road Trip: 4- to 6-Day Guide to Banff National Park & Beyond
This was a girls' trip we will never forget! The Canadian Rockies are absolutely breathtaking, with turquoise lakes (truly have never seen a color like them), towering peaks, and abundant wildlife. We were able to fit a lot into a few short days without it feeling rushed or overwhelming.
Canadian Rockies Road Trip: 4- to 6-Day Guide to Banff National Park & Beyond
This was a girls' trip we will never forget! The Canadian Rockies are absolutely breathtaking, with turquoise lakes (truly have never seen a color like them), towering peaks, and abundant wildlife. We were able to fit a lot into a few short days without it feeling rushed or overwhelming.
Passing Through Portugal: An 8- to 10-Day Guide to Porto, Lisbon & Algarve
Portugal is beautiful, with 300+ days of sun. In addition to fantastic weather, Portugal offers delicious food and wine, gorgeous beaches, and welcoming and kind locals. The cities are walkable (if you don’t mind hills). Public transportation is easy and convenient. Portugal is also known for being more affordable than other popular areas of Europe.
Passing Through Portugal: An 8- to 10-Day Guide to Porto, Lisbon & Algarve
Portugal is beautiful, with 300+ days of sun. In addition to fantastic weather, Portugal offers delicious food and wine, gorgeous beaches, and welcoming and kind locals. The cities are walkable (if you don’t mind hills). Public transportation is easy and convenient. Portugal is also known for being more affordable than other popular areas of Europe.
Travel photos
