Inside the S&S Bash: A Milestone Celebration in Costa RIca

There are trips you plan, and then there are trips you build. The kind where every detail, from the color of the ribbon on a welcome kit to the exact minute the sun sets over the Pacific, is chosen on purpose. The S&S Bash was the second kind.

In September, I brought together 14 travelers at Planet Hollywood Costa Rica on the Papagayo Peninsula to celebrate two milestones at once: Steve turning 60, and his sister Stacey turning 55. Five days, one resort, one big, beautiful reason to gather the people who matter most.

Here's how it came together and what it actually looked like once we landed.

Arrival Day: Settling In

The trip opened the way every good group trip should: no rush. Travelers checked into rooms placed together as one block, so from the first afternoon, this felt less like a hotel stay and more like a family compound. Welcome kits were waiting for each of the 13 honored guests; a small gesture that set the tone before a single toast was raised. Poolside cocktails and a casual dinner eased everyone into island time. No agenda, no itinerary in hand. Just the quiet permission to exhale.

The S&S Bash: An Earth-Toned Night to Remember

This was the night the whole trip was named for.

We took over a private terrace on the resort's third floor — ocean views, string lights, an earth-toned palette of greenery and gold that matched the invitation everyone had been sent months earlier. A custom "S&S Signature" cocktail. A birthday cake. Toasts that started light and got a little misty by the end, the way the best ones do. Appetizers offered at every dance turn, just to satisfy the hunger right before the celebration dinner. This is the kind of moment that makes you look around at who's in the room with you.

This is the part of hosting a trip that I love most: watching a plan on a spreadsheet become a room full of people who feel seen.

Adventure Day: Choose Your Own Costa Rica

Not every traveler wants the same version of adventure, and a good group trip makes room for that. So, we split the day:

• The Palo Verde group headed into the Tempisque River for a river boat tour gliding past crocodiles, howler monkeys, iguanas and other friends. Great excursion without ever breaking a sweat. A favorite with the 65-and up travelers in the group.

• The relaxation group opted for fun and games poolside with endless tropical drinks and food. Even participated in the resort games "find that item", pool volleyball, and team building, and more!

Both groups reconvened that evening with the same energy: tired, sun-touched, and full of stories to trade over dinner.

Stacey's Birthday: The All-White Catamaran Party

If there's one photo from this trip you'll see everywhere, it's this one: fourteen people in all-white, sailing the Pacific at golden hour.

We chartered a private catamaran for Stacey's actual birthday — snorkeling, open bar, music, and appetizers cut on deck as the sun started its descent. A "Happy Birthday Stacey" banner. A champagne toast mid-sail. It's hard to overstate what it does for a celebration to have the ocean as your backdrop instead of a banquet hall.

Spa & Leisure Day: The Exhale

By day five, this group had earned a slower pace. Massages on the beach and in our dedicated cabana, one last toast and quiet pool time before the evening ahead.

The Farewell Dinner: One Last Surprise

Here's the part Steve and Stacey didn't know: the "farewell group dinner" on their itinerary wasn't just a farewell. It was one more celebration, hiding in plain sight because the best way to close a trip like this is with one more toast, not a goodbye.

Heading Home

Last breakfast together. Group photos on the resort steps. A late checkout that bought everyone one more hour of Pacific air before the airport. Fourteen people who arrived as a family and left as a group with an inside joke, a shared banner photo, and — I'd bet — a group chat that's still active.

What travelers said

"This was an amazing experience. It was a fabulous trip. I recommend Arabia to any and everyone who wants a trip booked. Great job Arabia!"

- Steve Wright - Honoree

"Arabia has done an amazing job. This is my first time to Costa Rica, and she left no stone unturn with the information. Very informative, anything you needed to know she passed out all the information. Great, great job!"

- Stacey Wright - Honoree

"Arabia has done a fantastic job with organizing. As a person who likes to have a lot of information and things organized, from the emails that were sent out, to the questions that were asked, to making arrangements, to even asking about allergies or food preferences; she did a fabulous job. If anything changed, we were notified immediately via email and once we got our WhatsApp chat she would update us in there. She advised us on what to do, what to pack, what to bring. Great packing checklist... especially for someone who is visiting Costa Rica for the first time. A+ service!"

-Melissa Martin - Steve's wife

"I thank you for everything. This is our first time using a travel planner. We had a wonderful time. We wouldn't change a thing."

- Chris Swinson - Family

Planning your own milestone celebration

The S&S Bash didn't happen by accident. It happened because every detail, from the catamaran charter to the earth-toned décor to the exact resort request for a private terrace, was locked down months in advance by someone whose only job was making it seamless.

If you're sitting on a milestone birthday, an anniversary, or a "we just need an excuse to all be together" — that's exactly the kind of trip I design.

[Let's talk about what your version of the S&S Bash could look like →]