Travel Agency Located in Arlington, VA

travel that marks the moment

From romantic escapes to group celebrations and luxury journeys, we design unforgettable travel experiences tailored to your story.

At Ready, Set, Booked!, we believe every milestone deserves to be celebrated in style. Whether it’s a honeymoon, a milestone birthday, or a well-earned retirement trip, we take the stress out of planning so you can focus on making memories.

Why Choose Us:

  • Milestone-focused travel planning
  • Personalized itineraries that reflect your unique story
  • Exclusive luxury perks and insider access
Newlywed couple on romantic beach swing overlooking ocean during expert-planned honeymoon celebration

Celebrate Life’s Milestones with Seamless Travel

Happy retired couple enjoying boat excursion during empty nest travel adventure planned by celebration travel experts

Know Where & When You Want To Celebrate?

Milestones We Love to Mark with Travel

Honeymoons

Start your greatest adventure together with a seamless, stress-free honeymoon tailored to your love story. From tropical escapes to romantic European getaways, we’ll handle every detail so you can focus on celebrating.

Our clients love celebrating their honeymoons in Europe and the Caribbean. In the Caribbean, they love all-inclusive resorts!

Retirement

You’ve been waiting for this. Now it’s time to explore the places you’ve always dreamed about without the constraints of a vacation calendar. Let’s plan that bucket-list journey that marks the beginning of your next chapter.

Our clients love traveling with fellow retirees, often enjoying cruises or luxury train journeys with their loved ones. Many also dream of spending a few weeks in a long-awaited destination — whether it’s exploring Tahiti or simply relaxing on a new beach.

Birthdays

Turn a milestone birthday into a trip no one will forget. We handle the logistics of getting everyone there, coordinating schedules, and creating experiences that make the birthday honoree feel truly celebrated.

Our clients love celebrating their birthdays surrounded by friends and family! Some of the most popular ways include gathering everyone at an all-inclusive resort or enjoying a group cruise. Others plan their trips around special events — like Oktoberfest, major sporting events, or concerts abroad.

Destination Weddings

Say “I do” somewhere unforgettable while we manage the details of getting your guests there, housed, and entertained. From welcome dinners to post-wedding brunches, we’ll ensure your celebration feels effortless for everyone.

Our clients love celebrating their destination weddings in the Caribbean at stunning all-inclusive resorts, or opting for a more curated European experience — think a private villa, historic estate, or romantic castle.

Anniversaries

Mark another year together with a getaway that feels as special as the commitment you’re celebrating. Whether it’s your first or your fiftieth, we’ll create an experience that honors your journey and gives you time to reconnect.

Our clients can’t get enough of Europe and the Caribbean for their anniversaries, with many also look at French Polynesia, Fiji, or the Maldives. While honeymoons are often seen as a once-in-a-lifetime trip, we believe there’s something truly special about celebrating love year after year — making time to escape together, not just right after “I do.”

Family Reunions

Bringing the whole family together shouldn’t feel like herding cats. We coordinate accommodations, activities, and dining for groups of all sizes so everyone can actually relax and enjoy the time together.

Our clients love choosing an all-inclusive property where every family member’s preferences are taken care of — no need to manage all the details! Others prefer traveling somewhere meaningful, like a destination tied to their family roots in Europe.

WHY WE EXIST

Our founder, Kara Simmons, has always believed in celebrating life, love, and everything in between. From her own milestones to helping loved ones plan theirs.

Kara 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 Kara founded Ready, Set, Booked! – to help people celebrate life’s milestones with intention through travel.

“When we rush through our greatest milestones without creating the space to slow down, we do our minds and souls a disservice. In our opinion, there is no better way to cement these core memories than through intentional travel. We don’t just plan trips; we curate the space for you to savor your story.”

What our clients are saying

Picture from clients of the view from their room on their honeymoon to Portugal at Les Suites

Honeymooners to Madeira, Portugal

We used Kara to book our honeymoon – she was so wonderful to work with, and we had the most unforgettable honeymoon! She worked with us to understand what both my husband and I were looking for in the trip, and gave us a few different options to choose from. We ended up choosing Madeira, a Portuguese island that we were not familiar with before she suggested it to us. Once we chose the location, she helped design and book an amazing itinerary. The hotel she chose for us was outstanding, and every excursion she recommended was flawless. We are so happy we chose Kara to plan our honeymoon – when you plan so much for your wedding, there are no words for how nice it feels to have someone plan such an incredible getaway to celebrate. Thanks Kara!!

Picture from trip to Hawaii for an anniversary from Ready, Set, Booked!'s clients

Anniversary Trip to Hawaiian Islands

Kara helped plan a perfect anniversary trip. Both my husband and I felt like our interests were heard and beautifully woven into the trip design. Very grateful for Kara’s help!

Picture representing clients trip to a destination wedding on the Amalfi Coast

Destination Wedding Guests to Amalfi Coast

Everything coordinated through Ready Set Booked went as planned. Kara ensured we were prepared and was very detailed + responsive. All this to say, I have no recommendations for improvement because it went so well.