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“Twenty years from now you will be more disappointed by the things you didn’t do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover.”

Recognition and Awards

Dreams

Wherever Your Dreams May Take You

What Our Customers Are Saying

  • I would love to return someday and thank you again Private Trade Winds for the recommendation and all the little touches that make working with you such a pleasure.
    David K.
  • Portrait Of Positive Family On The Sunset BeachMy expectations were more than met on our vacation. We can't wait to come back and bring our 3 boys with us. Thanks again for all you did to help make our trip booking easy!
    Mike R.
  • Group of young divers showing ok using their hand gesture.We just got back from our trip, and it was so fabulous, I can't even believe what a great time we had!!! After our wonderful week there. None of us wanted to come home.
    Mrs. Bouvier
  • Beach Luau_HualalaiFirst and foremost I want to thank you for being responsible for providing my family and me with one of the greatest experiences of our lives. Not only did we find the villa and resort to be absolutely breathtaking, but everyone we spoke to was friendly and beyond helpful. We enjoyed the villa and resort in its entirety, and we also went off campus to explore and participate in manta ray snorkeling, zip lining, and surf lessons.

    Linda Cohn, Television Sports Anchor
  • I was very satisfied with the villa and felt it was accurately depicted in the listing. Views were tremendous; location superb. Looking forward to our next visit at a similar property.
    Brandon S.

Here’s What the Kid’s Say

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    I am blessed to have traveled with my best friend since I was 4 months old!  Our families always share a house or get two condos so we can all stay close and enjoy each moment of our trips.  We have been to beaches around the world and enjoyed the snow on several mountains.  Each with its distinct memories.  Italy was one of the best because 4 families traveled together through Tuscany and Lake Como was an adventure but staying in a Tuscany villa was the best!

    Katarina C.
    Age 17
  • girl1We were certainly in the lap of luxury and enjoyed every minute we were there. I asked my eight-year-old how she liked her first villa vacation while we were on our flight home, and she said, “I feel like it was a great blessing to stay in such a beautiful place. It made me feel closer to my family.” You can’t ask for more than that from a vacation. We created memories that will last a lifetime. With most vacations, we are usually ready to head home as we near the end of our stay, but this one was different – nobody wanted to leave!
    Greg C
  • Hugo and Friends Group BoatCabo was such a fun trip for surfing and fishing.  I’m glad we stayed in a condo so all my family and friends could be together!  I can’t wait to do it again.
    Robert C.
    Age 15
  • Hugo and Friends GolfI like to golf, surf and play volleyball which I can do even on vacation.  I’ve enjoyed travelling to Pebble Beach, Hawaii, and Cabo with my favorite friends plus we can play video games in the living room till late at night while our parents enjoy cooking dinner.
    David L.
    Age 14
  • Italy was the most amazing trip I have ever been on!  From touring the cities to sunbathing in the vineyards and on Lake Como, only the food and shopping were an equal match.  My favorite memory of Tuscany was having an outdoor dinner on our patio (all 17 of us!)  overlooking the rolling hills and listening to Andre Bochelli.  Well, at least all the moms and daughters were in heaven!
    Ariana K.
    Age 18

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