It’s the summer of 2024, and I’m sitting on the porch of a sun-washed mansion in Martha’s Vineyard, champagne flute in hand, watching my toddler chase her goddaughter around a splash pad. The ocean breeze smells faintly of salt and sunscreen. It’s the kind of perfect summer day you want to bottle and keep forever.

This was the first real group trip I’d managed since my daughter was born, and I was glad it happened. I was grateful to be here surrounded by friends, giggling kids, and a view straight out of The Summer I Turned Pretty.

But underneath the joy, that familiar frustration was bubbling up again. I knew exactly how many reminders, follow-ups, and “Hey, can you just…” messages it had taken to get us here. I knew who booked the house, organized the meal plan, and figured out the daily clean-up schedule (spoiler: it wasn’t everyone). And while I adore my people, it was hard to ignore the truth: some of us had worked a whole lot harder than others to make this “relaxing” getaway actually happen.

How the planning unfolded

Martha’s Vineyard is a picturesque island off the coast of Massachusetts, long celebrated as a summer haven for the Black community, especially since the early 20th century, when Black families began establishing vacation homes there. With its coastal charm, rich history, and vibrant social scene, it’s a place where you can unwind by the ocean in the afternoon and mingle at a networking event by evening. For young professionals like us, it offered the perfect mix of relaxation, culture, and connection.

So thankfully, deciding on the location for this trip was easy. In the past, just agreeing on where to go could take weeks of back-and-forth in the group chat. This time, August was the obvious choice, not just for the weather, but because of the island’s well-known networking events that draw people from all over.

And as always, in every friend group there’s that one person who makes things actually happen. If you’re reading this, there’s a good chance it’s you. In our case, one of our planner friends finally got tired of waiting for consensus and just went ahead and booked a $10k+ villa on Airbnb. He emailed us all with a payment deadline, instructions for booking the ferry, and a neat little list of everything we’d need to know before arrival. Somehow, though, I ended up booking everyone’s ferry tickets, managing the grocery plan, covering the upfront expenses, and surprise, surprise not getting reimbursed on time.

During the trip, it became pretty clear who was actually keeping things running, who was in the kitchen cooking, who was tidying up, who was wrangling everyone for golf outings and dinner reservations. Spoiler: it was the same three of us who always seem to end up in that role… all while juggling our kids at the same time 🙃. Needless to say, it wasn’t the “kick back and relax” vibe we’d all pictured.

That’s when it hit me, how amazing it would be if we could just hire someone to handle all of it. Not just the cooking or the cleaning, but the coordination, the scheduling, the making-sure-everyone-has-what-they-need part. Basically, someone to take care of ALL of us for once.

How a travel advisor could have helped

Imagine this trip but without the stress headaches, passive-aggressive group chats, or the “wait, did someone bring drinking water?” panic.

Here’s how a travel advisor could have made things easier for us:

Before the Trip

• Idea wrangling – Even with the destination set, a travel advisor could help find a property that fits everyone’s budget, schedules, and travel style, potentially preventing issues like late reimbursements.
• Curated options – Instead of sending a flood of links, a tailored list of rentals or activities helps everyone prepare financially **and emotionally** for the trip.
• Payment coordination – No more chasing friends for deposits; a third party can handle it securely and fairly.
• Itinerary design – Balances group time with personal downtime, so both introverts (me!) and extroverts get what they need.

During the Trip

• Logistics handled – Transportation, room assignments, and check-in details all sorted ahead of time.
• Local recommendations – Restaurants, hidden gems, and can’t-miss activities.
• On-call support – For anything that goes sideways.
• Helpful add-ons – Like a private chef, cleaning service, or curated experiences.

After the Trip

• Trip debrief – Checking in with everyone individually to see what worked and what to improve for next time.

Now, these are exactly the services I provide for friends, families, and small groups. From planning and coordination to on-the-ground support, I take care of the logistics so you can focus on the memories. If you’re ready to finally relax on your next getaway, reach out and let me handle the details, your only job will be to show up and enjoy.