Kasey Winkles
Based in Columbia, South Carolina
Trip budgets start at $200/night
Kasey Winkles
Ask me about
My Story
My whole life I’ve had a love for travel. From family trips to mission trips to studying abroad to having a family of my own, I have always sought out the next place to travel to. After becoming a mom, I began designing stress-free, family-friendly vacations that create meaningful memories—plus babymoons and special getaways for every life season! I know the value of thoughtful planning and want to create a seamless, memorable, and joy-filled vacation for you! Whether you’re looking for a quick weekend away or a weekend with your kiddos, I’m here to help find what you’re looking for!
Travel Style
My travel style blends effortlessly luxury with a relaxed, coastal feel—think beautiful resorts, thoughtful details, and plenty of space to unwind. I design trips that feel elevated yet easy, where families can slow down, soak in the scenery, and make memories without the stress. Whether it’s a beachside escape or a Disney adventure, I combine elevated planning with a relaxed, feel-good vibe so trips feel magical, memorable, and refreshingly stress-free.
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Reviews (2)
Mary R.
a month ago
Super helpful! Kasey’s helped us plan the perfect weekend for my husband’s birthday. She was very attentive and helped our decision making for hotel and events in NYC when it felt like information overload with all of the options.
Peyton K.
2 months ago
Kasey made the entire booking process seamless! She was helpful following up to make sure our travel plans to the resort were set up and was able to get us an amazing room upgrade and free breakfasts. She also left a sweet note for us upon check-in. Overall, she made the booking experience easy and the stay feel extra personal (she even told the staff it was my birthday over the trip and asked them to do something special for me!). Will definitely use her again!
Mary R.
a month ago
Super helpful! Kasey’s helped us plan the perfect weekend for my husband’s birthday. She was very attentive and helped our decision making for hotel and events in NYC when it felt like information overload with all of the options.
Peyton K.
2 months ago
Kasey made the entire booking process seamless! She was helpful following up to make sure our travel plans to the resort were set up and was able to get us an amazing room upgrade and free breakfasts. She also left a sweet note for us upon check-in. Overall, she made the booking experience easy and the stay feel extra personal (she even told the staff it was my birthday over the trip and asked them to do something special for me!). Will definitely use her again!
Travel photos
