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Finding Your Family’s Kefi: The Best Multi-Generation Vacations in Greece

A santorini caldera sunset over whitewashed buildings shows why multi-generational vacations in greece are unforgettable.

In this article, I share how Greece offers multi-generational families the chance to discover their own “kefi”—that spirit of joy—through simple, meaningful moments. From Athens to Crete to hidden islands, I highlight how grandparents, parents, and kids can each find their rhythm while weaving a shared family story. “Papou, tell us about the octopus again!” […]

Costa del Sol

Height of bliss exterior

Costa del Soul A family haven above the Mediterranean First, you see Africa . . . floating like a mirage across the strait. A reminder that some views haven’t changed since the Moors ruled these hills. Then the sweep of coastline unfolds before you – the precise spot where three worlds collide: Europe, Africa, and […]

Provence

The ancient olive tree patio

Under the Provençal Sun Living like the Masters in the heart of Provence First, you smell it. Lavender and wild thyme, carried on the breeze that whispers through ancient olive branches. Then the warmth of sunbaked stone welcomes you home – the magnetic pull that drew Van Gogh, Renoir, and Matisse to this light-blessed corner […]

Tuscany

The tuscan castle outdoor dining area

500 Years of Sunsets A luxury castle experience in Tuscany’s heart Stone and cypress. Some things in Tuscany never change. The fortress rises from the hillside like a memory, its medieval walls the color of honey in the late afternoon sun. Five centuries of sunsets have painted these stones. Your morning coffee comes with a […]

10 Multi-Generational Travel Trends

10 multi-generational travel trends for 2025

This article explores how multi-generational travel is evolving, highlighting ten key trends—from villa stays, destination dupes, and off-grid escapes to ancestral discovery and wellness retreats—that are reshaping the way families vacation together, and showing why private villas are emerging as the preferred choice to support these new travel styles. According to a report from Virtuoso […]

The Secret to Booking Your Perfect Villa: 7 Things Smart Travelers Always Check

The secret to booking your perfect villa

In this article, I share seven key things to check before booking a villa—drawn from my own hard-learned lessons around the world—to help travelers avoid common pitfalls and ensure their villa delivers on comfort, privacy, and value, making the process of finding the perfect villa simple and stress-free. Picture this: You’ve just arrived at your […]

3 Villa Rental Horror Stories – And How to Avoid Them

Infinity pool at a luxury villa under dark storm clouds, foreshadowing villa rental horror stories.

This article shares three true villa rental horror stories that reveal how easily family vacations can go wrong, and offers practical tips on how detailed vetting, reliable local support, and asking the right questions can help you avoid these pitfalls and enjoy a smooth, stress-free getaway. Remember those carefree college backpacking days? When a last-minute […]

Together Time: How Multi-Generational Travel is Redefining Family Vacations

Two generations of women share a hug overlooking sleeping bear dunes national lakeshore, mi, during a multi-generational vacation.

This article explores how multi-generational travel is reshaping family vacations, moving beyond backyard reunions to shared adventures that bridge generations. From Tuscany villas to Caribbean getaways, it shows why grandparents, parents, and kids are choosing immersive experiences that strengthen bonds, create lasting memories, and turn family trips into new traditions. Jenny stood in her mother’s […]

Best Multi-Generation Vacations in Italy: Top Spots for Family Bonding

Original photo by paul partridge of the colosseum in rome with crowds—an iconic stop for the best multi-generation vacations in italy.

In this article, I share the top spots in Italy for multi-generational family vacations, from iconic landmarks and scenic coastlines to hidden gems and villa stays. With tips on accommodations, activities, and planning, it shows how Italy’s mix of culture, food, and landscapes creates the perfect setting for families to bond across generations. Italy beckons […]

How Luxury Villa Stays Are Secretly Teaching Kids About Conservation

How luxury villa stays are secretly teaching kids about conservation

Who knew that your family’s luxurious getaway could turn into a masterclass in environmental stewardship? Luxury villas are becoming unexpected classrooms, teaching your kids or grandkids vital lessons about our planet. Nature’s Playground: Learning Through Exploration Forget stuffy classrooms. In a luxury villa, the great outdoors becomes a child’s learning lab. Kids dash through lush […]

Why Your Family Deserves More Than Just a Hotel Room on Vacation

Why your family deserves more than just a hotel room on vacation

Picture this: You’re sipping an espresso on a sun-drenched terrace, watching your kids and their cousins splash in your private pool. Beyond the pool sits the ocean. You and your spouse just finished a workout in the private gym. Nana and Papa are taking a bike ride. The aroma of freshly baked croissants wafts from […]

How to Hack Your Way Into the Most Exclusive Family Villas in the World

How to hack your way into the most exclusive family villas in the world

Picture this: You wake up to the sound of waves crashing in the distance. You slide open the door to your private terrace and gaze out at the horizon, where the ocean meets the sky in an endless expanse. You take a deep breath, feeling the cool breeze against your skin, and dive into your […]

The Together Letter

Get The Together Letter — stories and ideas for turning “We should all get together” into a trip everyone still talks about years later.