Going Back, But Deeper: How to Revisit Your Favorite Places

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.

This is exactly how I plan: we start with what you already know you love, then build a stay, a pace, and a set of experiences that feel like the “next chapter” of that destination.

Below are some ideas for putting a fresh twist on your favorite spots.

Step 1: Choose the version of the place you want to see

Hotels are often the best entry point for seeing a beloved destination in a different way. The right property can:

• Put you in a neighborhood you haven’t explored

• Shift the overall pace (more relaxed, more lively, more local)

• Build in experiences you haven’t tried before

When we plan together, I’ll ask what you loved last time—and what you’d change. Then we match you with a hotel that reflects the version of the place you want to experience now.

If you love Hawaii…

Maui is one of those islands that rewards repeat visits. There’s always more coastline to explore, a new vantage point on the Road to Hana, or another waterfall to discover.

Where to stay: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.

Who it’s for:

• Families returning with kids who are now old enough to snorkel

• Couples who want a beachfront base that doesn’t feel like a scene

When we plan your return to Maui, we’ll decide how much time you want to spend exploring versus staying put, then build in the right mix of ocean time, drives, and downtime.

If you love Florida…

Most clients who come back to Florida have already done Miami, Naples, or the theme parks. Sarasota distinguishes itself with a serious arts scene and easy access to Siesta Key, which consistently ranks among the best beaches in the country.

Where to stay:The Ritz-Carlton, Sarasota is intimate by the brand’s standards and puts you within reach of downtown’s restaurants and galleries while still feeling like a proper resort.

Who it’s for:

• Travelers who want a more cultural, less theme-park-focused Florida

• Repeat visitors ready to see a different side of the state

Together, we’ll decide how you want to split your time between beach, art, and dining—and I’ll line up the right reservations and experiences so it all flows.

If you love Spain…

First-timers tend to approach Spain in one of two ways:

• Major culture hubs like Madrid and Barcelona, or

• Beachy getaways like Ibiza and Mallorca

Marbella, on the Costa del Sol, tends to get overlooked, but it actually blends the best of both worlds: ample sunshine, a stunning coast, distinctly Andalusian culture, and a thriving food and nightlife scene.

Design-forward and culinary-focused:

• La Zambra sits in the hills above Mijas, built on the bones of the legendary Hotel Byblos. It’s now a minimalist, Moorish-inspired retreat. Basque chef Iker González Ayerbe oversees four restaurants that bring a serious culinary sensibility to the region’s best coastal ingredients, and the spa is among the largest in Andalucía.

Relaxed and low-key:

• Kimpton Los Monteros Marbella channels a more laid-back sensibility, with a beach club that never tips into the scene-y.

Classic and lively:

• Puente Romano Beach Resort is grounded in classic Andalusian architecture, with a world-class tennis club, a Six Senses spa, and more than 20 dining outlets, including a Nobu and a Cipriani.

When we plan your return to Spain, we’ll talk about whether you want more design, more food, more nightlife—or a quieter, resort-forward stay—and choose the property that fits.

If you love the Mediterranean…

If you’ve already done Italy and Greece, there are two very different directions you can go.

Undervisited and historic: MaltaValletta 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.

• Where to stay: 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.

• Who it’s for: Travelers who want something genuinely different in the Med, with real history and fewer crowds.

Iconic and glamorous: Monte-CarloMonte-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.

• Where to stay: 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.

When we plan, we’ll decide whether you’re craving “new and under the radar” or “classic and glamorous”—then build the right length of stay, transfers, and experiences around that.

If you love Italy…

Clients who have done Rome and the Amalfi Coast are often ready to go further south or explore a completely different coastline.

• Sicily: Below Taormina, Atlantis Bay sits right on the water, with a combination of history, landscape, and seclusion that’s hard to match.

• Ligurian Coast: Royal Hotel Sanremo brings a different era of Italy into focus—a Belle Époque grande dame set in terraced gardens with a saltwater pool and a private beach.

• Sardinia: W Sardinia in Porto Cervo delivers some of Europe’s most beautiful coastline in a design-forward package.

In my planning structure, this is where we talk about what “Italy, but different” means to you: more coastline, more history, more food, or more quiet. Then we choose the region and hotel that match that vision.

If you love Greece…

Santorini and Mykonos get a lot of attention, but clients who want to go deeper into Greece often find the most rewarding experiences on islands that see far fewer visitors.

• Kéa: About an hour and a half from Athens, Kéa feels like the Greece most people imagine but rarely encounter—unspoiled, quiet, beautiful coastline, and very few tourists. One&Only Kéa Island is designed to feel like a natural extension of the landscape, with exceptional food and genuinely personalized service.

• Crete: Crete offers real depth: its own distinct culture, extraordinary food, and Minoan history that predates the classical world. Phaea Blue Elounda sits on one of Crete’s most beautiful bays, with design and service that make it easy to stay put and explore at your own pace.

Here, we’ll decide how “off the radar” you want to go, how much you want to move around, and how much time you want to spend simply staying put and soaking it all in.

If you love London…

Clients who think they know London well tend to be the most surprised by what’s opened in recent years.

• Raffles London at The OWO: Housed in the Old War Office building in Whitehall, this is Churchill’s former office, transformed into a hotel with nine restaurants, exceptional service, and a setting at the center of the city’s most historic corridor. It’s a reason to come back to London even if you’ve been many times.

• L’oscar London: A boutique hotel in a converted Victorian Baptist chapel in Holborn—richly designed, theatrical, and unlike anywhere else in the city.

When we plan your return to London, we’ll talk about what you haven’t seen yet—neighborhoods, restaurants, galleries—and choose a base that makes those easy to reach.

How I plan these “second chapter” trips

Every itinerary I build follows the same basic structure:

1. Start with what you loved last timeWhat stood out? What felt rushed? What did you wish you had more time for?

2. Decide what you want more of nowSlower pace, better food, more culture, more beach, more time in one place—this becomes our north star.

3. Choose the right home baseWe pick a hotel and neighborhood that match that vision, so your day-to-day experience naturally supports the trip you want.

4. Layer in the right experiencesPrivate guides, day trips, restaurant reservations, spa time, or nothing at all—we build a rhythm that feels good to you.

5. Handle the logistics so it feels seamlessTransfers, timing, and small details are taken care of so you can simply arrive and enjoy.

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.

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