As summer approaches, I’m hearing something a little different from clients who haven’t booked yet. They’re not asking me to find somewhere new, they’re asking to go back.
Back to Italy. Back to Greece. Back to places that left an impression the first time, but that would benefit from a different lens or slower pace.
That instinct makes a lot of sense. Familiarity means you’re not spending energy orienting yourself or trying to hit the highlights. Instead, you can actually settle in and go deeper on the aspects you love most. And when you work with me on a second (or third, or fourth) visit, the creativity goes into finding the right place to stay and the right experiences to layer in.
Here are some ideas for putting a fresh twist on your favorite spots.
going deeper
Hotels can be a great entry point for seeing a beloved destination in a different way. They might situate you in a neighborhood you haven’t explored or offer an activity you haven’t tried before.
If you love Hawaii…
Maui is one of those islands that benefits from repeat visits. There’s always more coastline to explore, a new vantage point on the Road to Hana, or another waterfall to discover.
The Sheraton Maui Resort & Spa
sits at the northern end of Kaanapali Beach, right above Black Rock—one of the best places on the island to see sea turtles and tropical fish. It’s been thoughtfully refreshed in recent years and strikes a tone that feels relaxed, rather than overly produced. It’s a strong choice for families returning with kids who are now old enough to snorkel or couples who want a beachfront base that doesn’t feel like a scene.
If you love the Mediterranean…
Malta is one of the most undervisited places in the Mediterranean—especially among American travelers—and that’s exactly what makes it interesting right now. Valletta is a UNESCO World Heritage city with millennia of history layered into its narrow streets: Knights of Malta, Baroque architecture, ancient temples just outside town.
The Westin Dragonara sits on its own peninsula in St. Julian’s with a private beach and a pool that feels like a world apart. For clients who have done Italy and Greece and want to add something genuinely different, Malta is the answer.
Monte-Carlo is the opposite of undiscovered, but it rewards a longer stay—the Formula One circuit, world-class dining, views over the harbor from the casino gardens. Monte-Carlo Bay Hotel & Resort has a more relaxed, resort-oriented feel than the grande dames in the principality, with a lagoon pool, direct beach access, and a softer pace that makes it easier to settle in.
Whatever’s been pulling you back—a place you loved before, or a version of it you haven’t seen yet, I’d love to help you put it together.
