Alternative title: A Love Letter to the Croatia Crew

If you’re anything like I was earlier in life, the words “group travel” conjure up haunting images of people packed into mega buses like sardines, tour guides shouting into microphones, and crowds of tourists blocking pedestrian streets in metropolitan capitals.

I hated it.

Luxury, to me, meant the freedom to get lost. I wanted to dine in restaurants that only sat 10 people, get to know the locals, and spend hours wandering narrow alleyways without having to anxiously check the clock and stay in close enough proximity to the ‘meeting point.’ The idea of traveling with a group seemed like the antithesis of everything I wanted out of my personal travel.

Until one summer in Croatia, when I set sail with 34 perfect strangers on a private yacht charter through the Adriatic to explore the Dalmatian Coast.

We were an eclectic bunch: teenagers and grandparents, oil tycoons and artists, party animals and quiet readers. Most had never met before stepping foot on the ship, with the only obvious commonality between us all being a shared travel advisor. For me, it was a trip of convenience more than anything, a way to check off a destination that had long been on my list.

It became the journey that singlehandedly changed my mind about group leisure travel.

Yes, I still fulminate against big box group tours that promise luxury and deliver nothing but sweat and agitation. But I also have developed a stalwart belief in the power of group travel done right to augment unforgettable experiences with unbreakable connections and bonds that last far beyond the return flight.

If you are considering planning a group trip, be it with friends, family, or colleagues, here are some of the many lessons I learned about what it takes to do it well.

Lesson 1: Setting is everything

Choosing the right location and format will make or break the experience. For 34 strangers, a yacht in Croatia was the perfect choice, building in seclusion and exclusivity from day one. It created moments for genuine group connection — jumping off the back of the ship into the sea, planning spontaneous small group dinners — while still giving guests the space to connect with their partners, family members, or other chosen travel companions.

While a yacht in Croatia was perfect for us strangers, it would not be the right setting for every group. For an executive retreat, you might look for something that creates even more seclusion from the outside world, but also more space between the guests (like one of our favorite properties in Norwegian fjord country or a private game reserve in South Africa). For a multi-generational family trip, you might go the opposite direction and choose a private villa to experience the ultimate luxury of having everyone under one roof. For a bachelorette trip, a traditional resort offering more amenities and opportunities for socialization would create the perfect backdrop for an unforgettable party.

Lesson learned: There is no one-size-fits-all approach to group travel. Work with a professional who can understand the needs and composition of your group, then help you find the perfect fit.

Lesson 2: Balance Togetherness and Independence

One of the biggest mistakes that group organizers make is planning too many group events. They think that for a group to feel closer, they need to spend every moment together. Often, we find that the opposite is true: packing the itinerary with group activities can create tension between conflicting personalities, leave little time to recharge, and end up creating a trip that feels exhausting more than rejuvenating.

In Croatia, we had group activities scheduled daily, but allowed guests to opt out of every single one. This ensured that there were always things to do for those who preferred group activities, but no pressure to participate for those who would rather have more time to themselves. At every destination, there was choice: bike the island or take a guided historical tour, visit a fortress or enjoy a wine tasting on the water, stay with the group or wander on your own. This made the few moments when we did come together as a full group – like our all-out farewell costume dinner – even more impactful and memorable.

Lesson learned: Curating the perfect group energy is about quality over quantity. Focus on maximizing the value of a few shared “wow” moments, then give your guests some breathing room to customize their days to feel like the trip was made for them.

Lesson 3: Details matter more than you think

Anyone can put together a solid itinerary. Most tour operators can execute on it sufficiently well. Transforming a fine vacation into a seamless, unforgettable experience requires more than getting the basics right.

I will never forget our first day in Dubrovnik before the yacht departed. As I sunbathed on the deck and tried to get over my jet lag, Jenene and Dave (a guest and dear friend who we affectionately referred to as the Captain) returned to the ship with paper bags filled with snacks, water toys, and more. I gave Jenene a look, and she laughed at me: “You’re going to want these soon, you’ll see.”

She could not have been more right. The initial arrival gifts the Travel with Awestruck team had prepared were beautiful, but I would argue that those midnight snacks passed among the group were more meaningful. Those little brown bags were passed from guest to guest, building bonds over shared affinities for Pringles and sparking debate over the superiority of select cuts of charcuterie. It was the first of multiple shopping trips Jenene made. While it was a minor moment on the surface, it was a masterclass in executing on the true hallmark of luxury: knowing what people will need before they do (and having it ready long before they ask for it).

Lesson learned: In luxury group travel, details are the experience. Think beyond the itinerary to anticipate the needs of the group before they arise.

Lesson 4: Prepare for the unexpected

Travel is unpredictable, doubly so if it is group travel. Even the most skilled group travel expert cannot control airlines, weather, unpredicted local strikes, and the free will of dozens (or hundreds) of people.

We had our share of unexpected moments in Croatia: shouting, “Bye Eddie!” off the back of a transfer as Eddie (one of our guests) missed the boat, bouncing through choppy seas and unexpected winds on a small speedboat into Hvar, getting caught in the rain in Korčula.

What made these moments funny, rather than stressful, was knowing that the professionals on our team had it covered. No matter the situation, Jenene and Colleen were at the ready to resolve it, whether that meant finding a bandage, coordinating alternatives with Croatian locals, or fiercely negotiating for a bottle of Clase Azul (yes, this did constitute an emergency).

Lesson learned: The unexpected needs to be expected. Have a professional supporting your group, so they can help you navigate the challenges.

Lesson 5: Leave room for spontaneity

Overscheduling is the successful group travel planner’s enemy. A vacation shouldn’t feel like a business conference, where guests need to rush from place to place to meet some arbitrary clock.

I have wonderful memories of all of the scheduled group activities that appeared on the itinerary from our Croatia trip, but the moments I will never forget are the ones I didn’t see coming: a 3-hour spontaneous dinner with friends who became family, last-call at a local bar in Dubrovnik, dances at a nightclub in Hvar with people I didn’t know three days prior, a group night swim in the Adriatic with midnight far in the rearview.

Those moments cannot happen if they have been scheduled over (or if guests are so exhausted from the day that everyone is asleep by 9).

Lesson learned: Memories are made in the in-between moments. Don’t suffocate them with scheduling.

Closing thoughts

Croatia converted me to become a group travel aficionado (and gave me the first thought of leaving my prior career and joining the Travel with Awestruck team). That trip was a crash course in how luxury group travel, when done thoughtfully, creates a level of joy, connection, an shared experience that cannot be replicated with individual trips (without a single tour bus in sight).

Part of what made that group so memorable for me was the effortlessness of it all. I was able to show up as a participant — not as a group organizer — and it allowed me to disconnect from the logistics to fully connect with my travel companions.

Now, as someone who luxury travel with a specialization in events for a living, I cannot stress enough how important it is to put a professional in that role, so that you can fully enjoy the moment. Whether you’re planning a milestone birthday, a corporate incentive trip, or a bachelorette for the ages, we are here to support you in putting on a group trip that is as effortless as it is extraordinary.