Kara Simmons
Based in Washington, D.C.
Ready, Set, Booked!
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Our Story
I have always believed in celebrating life, love, and everything in between. From my own milestones to helping loved ones plan theirs. I discovered that travel has a unique way of turning life’s chapters into unforgettable memories. Too often, milestones pass by unnoticed or are overshadowed by stress and uncertainty instead of celebration. That’s why I founded Ready, Set, Booked!—to help people celebrate life’s milestones with intention through travel.
Travel Style
Travel that marks the moment. Using travel as a way to help celebrate the beautiful parts of life with the people you love. A blend of immersive cultural exploration and leisurely indulgence—whether it’s savoring fine wine, diving into local cuisine, or swimming with manta rays, all the while celebrating an important milestone in your life.
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Reviews (8)
Edward J.
travel to San Sebastián
about 1 month ago
Kara is the absolute best! She made everything so easy and booked amazing excursions for us!
Amy C.
travel to Thailand
3 months ago
In the midst of wedding planning, working with Kara was the best decision I made. She is a very clear and timely communicator. She heard all of our preferences and wove tiny details into our trip to make it personalized to us and completely unforgettable, including pickleball on a tropical island! The two hotels she selected for us matched our requests perfectly - one more upscale and relaxing, while the other was a more traditional hotel that encouraged us to get out and explore more. The restaurants she reserved for dinners were all outstanding. Likewise the tours she scheduled were all different from one another and let us truly see all the island had to offer.
Due to the current conflicts in the Middle East, my husband and I were thinking of rescheduling our trip, and Kara took our concerns seriously, helped us navigate our options, and even offered to help us schedule a mini trip in the interim, should we have postponed. Her thoughtfulness and attention to detail really can't be matched.
I am happily recommending Kara to everyone I know, and I cannot wait to book more trips with her in the future!
Robert G.
travel to New York City
3 months ago
Kara was so attentive and even following when planning had slipped my mind and she made sure everything was going to go alright. Gave options and other templates in order to guide how we would like our trip to be planned. She made things feel special and gave it the work needed for us to have an incredible honeymoon.
Benjamin K.
travel to Chiang Mai
8 months ago
Kara was incredibly communicative and responsive throughout the planning process, making the end result seamless and an incredibly memorable and enjoyable honeymoon. We had a super smooth trip because of her partnership and were so grateful for so many of the small surprises throughout the trip from various accommodations that knew it was our honeymoon (because of Kara).
Karla Andrea P.
travel to Rome
8 months ago
Kara was so great to work with! She came highly recommended and was able to plan our trip with a pretty quick turnaround. She was very open to the feedback we provided based on the list of things and places we wanted to visit. Her communication and attention to detail was great and because of her we were able to enjoy the wedding planning process and not have to also worry about planning our honeymoon on top of that. We can't wait to entrust Kara with our next trip and continue recommending her to our friends and family.
Edward J.
travel to San Sebastián
about 1 month ago
Kara is the absolute best! She made everything so easy and booked amazing excursions for us!
Amy C.
travel to Thailand
3 months ago
In the midst of wedding planning, working with Kara was the best decision I made. She is a very clear and timely communicator. She heard all of our preferences and wove tiny details into our trip to make it personalized to us and completely unforgettable, including pickleball on a tropical island! The two hotels she selected for us matched our requests perfectly - one more upscale and relaxing, while the other was a more traditional hotel that encouraged us to get out and explore more. The restaurants she reserved for dinners were all outstanding. Likewise the tours she scheduled were all different from one another and let us truly see all the island had to offer.
Due to the current conflicts in the Middle East, my husband and I were thinking of rescheduling our trip, and Kara took our concerns seriously, helped us navigate our options, and even offered to help us schedule a mini trip in the interim, should we have postponed. Her thoughtfulness and attention to detail really can't be matched.
I am happily recommending Kara to everyone I know, and I cannot wait to book more trips with her in the future!
Robert G.
travel to New York City
3 months ago
Kara was so attentive and even following when planning had slipped my mind and she made sure everything was going to go alright. Gave options and other templates in order to guide how we would like our trip to be planned. She made things feel special and gave it the work needed for us to have an incredible honeymoon.
Benjamin K.
travel to Chiang Mai
8 months ago
Kara was incredibly communicative and responsive throughout the planning process, making the end result seamless and an incredibly memorable and enjoyable honeymoon. We had a super smooth trip because of her partnership and were so grateful for so many of the small surprises throughout the trip from various accommodations that knew it was our honeymoon (because of Kara).
Travel ideas (1)
Guide Around the Coast of Ireland
Ireland is a special destination for me, not just for its stunning landscapes but because it’s where both sides of my partner's family originated — we had the incredible experience of meeting his distant relatives, uncovering family stories and even visiting the cathedral where his ancestors tied the knot! In Ireland, you can explore the rugged cliffs of the Wild Atlantic Way, wander through ancient castles or take in the serene beauty of rolling green hills dotted with sheep. The cities, like Dublin and Galway, offer a lively atmosphere with traditional music, pubs and festivals that keep the Irish spirit alive. Whether you're sipping a Guinness in a cozy pub or driving along the scenic coastal roads, Ireland is a place where every moment feels like a story waiting to be told.
Guide Around the Coast of Ireland
Ireland is a special destination for me, not just for its stunning landscapes but because it’s where both sides of my partner's family originated — we had the incredible experience of meeting his distant relatives, uncovering family stories and even visiting the cathedral where his ancestors tied the knot! In Ireland, you can explore the rugged cliffs of the Wild Atlantic Way, wander through ancient castles or take in the serene beauty of rolling green hills dotted with sheep. The cities, like Dublin and Galway, offer a lively atmosphere with traditional music, pubs and festivals that keep the Irish spirit alive. Whether you're sipping a Guinness in a cozy pub or driving along the scenic coastal roads, Ireland is a place where every moment feels like a story waiting to be told.
Guide Around the Coast of Ireland
Ireland is a special destination for me, not just for its stunning landscapes but because it’s where both sides of my partner's family originated — we had the incredible experience of meeting his distant relatives, uncovering family stories and even visiting the cathedral where his ancestors tied the knot! In Ireland, you can explore the rugged cliffs of the Wild Atlantic Way, wander through ancient castles or take in the serene beauty of rolling green hills dotted with sheep. The cities, like Dublin and Galway, offer a lively atmosphere with traditional music, pubs and festivals that keep the Irish spirit alive. Whether you're sipping a Guinness in a cozy pub or driving along the scenic coastal roads, Ireland is a place where every moment feels like a story waiting to be told.
Guide Around the Coast of Ireland
Ireland is a special destination for me, not just for its stunning landscapes but because it’s where both sides of my partner's family originated — we had the incredible experience of meeting his distant relatives, uncovering family stories and even visiting the cathedral where his ancestors tied the knot! In Ireland, you can explore the rugged cliffs of the Wild Atlantic Way, wander through ancient castles or take in the serene beauty of rolling green hills dotted with sheep. The cities, like Dublin and Galway, offer a lively atmosphere with traditional music, pubs and festivals that keep the Irish spirit alive. Whether you're sipping a Guinness in a cozy pub or driving along the scenic coastal roads, Ireland is a place where every moment feels like a story waiting to be told.
Travel photos
