From bucket-list gorilla treks to Grand Canal sunsets, these are the trips our World Playground team keeps returning to in their daydreams.

Everyone has a trip they keep coming back to. Not the one they're actively planning, but the one that lives somewhere quieter, the destination that shows up in a saved photo or a conversation with a friend or a random Tuesday afternoon when your mind wanders somewhere warmer. We asked the World Playground team to name theirs. The one they'd book tomorrow if nothing stood in the way. Here's where they'd go.

Tuscany, Florence, and Rome, Italy

Brooks Laich, World Playground’s Founder & CEO, surprised himself with this answer. “What I’m craving most right now isn’t adventure,” he says. “It’s stillness and ease.” Coming from someone who built a career around competition in the NHL, that admission carries weight. The trip he keeps returning to is a month in Italy to simply be present with his fiancée and their daughter. 

He’d begin in the Tuscan countryside with no real agenda. Renting a classic car, wandering through villages, stopping wherever the pastry or the conversation earns it. From Tuscany, the plan moves to Florence for a few days of art and architecture, then on to Venice for a long weekend of aimless wandering through streets and canals.

The final stop is Rome, and for Brooks, one specific moment: standing on the floor of the Colosseum. “There’s something about that structure — the scale, the history, the ambition — that calls to me,” he says. Having spent much of his life performing in front of crowds in NHL arenas, he feels a particular pull toward it. He wants to stand there and try, even for a moment, to understand what it felt like in the “arena of all arenas”. 

Where he’d stay: Rosewood Castiglion del Bosco for the Tuscany stretch, where he'd set up in a suite with an outdoor patio that doubles as a workspace during his daughter's nap, then hand the rest of the day back to the family. From there, Aman Venice for the final long weekend in the city.

Image credit: Rosewood Castiglion del Bosco

Volcanoes National Park, Rwanda

Jenna Long, World Playground's Social Media Manager, has had one destination on her radar since she was a little girl, and it has never changed: Rwanda. "I've always wanted to experience Africa in a real way," she says, "the people, the culture, the wildlife, with nothing between you and it." Seeing mountain gorillas in the wild at Volcanoes National Park is, in her words, about as bucket list as it gets. Her plan when she gets there is intentionally simple: into the forest as early as possible, camera in hand, no over-scheduled itinerary and no chasing highlights, just the kind of slow, full presence that only comes when you've wanted something for a long time and finally let yourself have it.

Where she’d stay: One&Only Gorilla’s Nest is set right on the edge of the national park. The property feels intentional in the same way she loves about her favorite hotels: design that connects you to the place, and an experience built around Rwanda’s people and culture rather than insulating you from them.

Image credit: One&Only Gorilla's Nest

Savannah, Georgia

Kevin Santos, World Playground's Hotel Business Development Director, keeps arriving at the same answer: Savannah. He's been multiple times but never in spring, and he's convinced that's the version of the city he's been missing all along. "It's my favorite US city," he says, "famous for its old-world charm, history, and walkable downtown and squares." His first move upon arrival is already decided: a praline from Savannah's Candy Kitchen, or the Pecan Chicken from The Pirate House, the city's oldest building and, according to local lore, a former pirate haunt. From there, the plan stays loose, which is exactly how Savannah is best experienced. The squares reward wandering, the architecture earns a second look around every corner, and the pace of the city has a way of doing most of the work for you.

Where he'd stay: Hamilton-Turner Inn, a historic southern mansion turned bed and breakfast that fits the character of Savannah so naturally, it's hard to imagine the city without it.

Image credit: Hamilton-Turner Inn

Southern Caribbean

Lauren Liebert, World Playground's Director of Cruises and Business Development, knows exactly what she needs right now. Her last cruise was to Alaska, and by her own description, it was absolutely fantastic, but Lauren is a sun person at heart, and she's ready to trade glaciers for crystal-blue Caribbean water and a snorkel in her hand. The itinerary she'd build covers San Juan, Tortola, St. Kitts, Barbados, St. Lucia, Dominica, and St. Maarten across eight nights of island-hopping, with two days tacked on before departure to explore San Juan properly rather than rushing straight to the pier. The moment she boards, she's heading straight to the hammock on her balcony with an umbrella cocktail, watching San Juan disappear behind her as the ship clears the harbor.

Where she'd stay: Virgin Voyages' Scarlet Lady for the eight-night sailing roundtrip from San Juan, and Hotel Rumbao for the two nights prior, sitting directly across from the cruise pier so the move from city to ship couldn't be easier.

Image credit: Virgin Voyages

Venice, Italy

Jeff Shafar, World Playground's COO, has one destination he keeps circling back to: Venice. "The architecture, atmosphere, and food make it unlike anywhere else," he says, and his timing is deliberate about it. Late spring, May through early June, is his window of choice, when the crowds have thinned, the weather is comfortable, and the risk of flooding is almost nonexistent. It's the version of Venice that most travelers want but few actually plan around carefully enough to get. The city is the main event, but Jeff's itinerary doesn't stop at the water's edge. After a few days wandering the canals and neighborhoods, he'd rent a motorcycle and head north into the Dolomites for a day of riding through the mountain passes, a completely different kind of beautiful from everything he'd just left behind.

Where he'd stay: The Gritti Palace, a Luxury Collection Hotel, dating back to 1475 and sitting directly on the Grand Canal with unobstructed views of Santa Maria della Salute. Its restaurant, The Club del Doge, is one of the finest dining settings in the city, and staying there puts you inside Venetian history rather than just passing through it.

Image credit: The Gritti Place, a Luxury Collection Hotel