Hi First name / friend!

 

Question for you: 

 

When was the last time you prioritized big-time family time? Not just the usual weekend get-together or holiday dinner—but a real, uninterrupted stretch of days where everyone, from the littlest to the oldest generation, got away together?

 

Life moves fast, and it’s easy to assume there will always be another chance to make it happen. But the truth is, there’s never a perfect time—only the time you decide to take. Maybe it's Grandma's 80th, a 25-year vow renewal, or a high school graduation. Or maybe no excuse is needed at all. A family trip isn’t something to put off—it’s something to make happen.

 

Of course, pulling off a big family getaway takes more than good intentions. Different ages, travel styles, schedules, and interests can make planning feel overwhelming—so it helps to go in with a strategy.

 

Key Things to Keep in Mind When Planning a Multi-Generational Trip👇

 

 

Now, let’s get inspired with some destinations and a few tips to get it done. Below, we've highlighted the kind of places where family stories get written. Where generations connect over meals, adventure, and the kind of moments that turn into lifelong memories.

🇮🇹 Umbria, Italy

Picture the whole family gathered at a long wooden table, passing plates of handmade pasta, the evening stretching on under the glow of string lights. Mornings are slow—espresso in a quiet piazza, kids running through olive groves. Afternoons are for e-biking through medieval hill towns or learning to make pasta with a local nonna. Stay: Hotel Reschio, a 3,700-acre estate where you can spread out in beautifully restored farmhouses or castle rooms, then come together for meals and time by the pool.

 

🇭🇷 Istrian Peninsula, Croatia

A verdant triangle jutting into the Adriatic where truffle-rich forests meet Roman ruins and Italian-influenced coastal towns. The peninsula's diverse landscape creates natural separation of activities—beachgoers can swim in crystalline coves while others explore medieval villages or cycle through lavender fields. Stay: San Canzian Village & Hotel, a hideaway of stone buildings and quiet courtyards, offering just the right mix of togetherness and retreat.

 

🇫🇷 Provence, France

A landscape of lavender fields, hilltop villages, and ancient olive groves where markets burst with seasonal produce and the light changes hourly across limestone cliffs. Multi-gen groups thrive among the varied activities—from grandparents exploring antique markets to children hunting for fossils in quarries, each day ending with family meals on terrace tables under plane trees. Stay: Hôtel Crillon le Brave, a village-within-a-village where 17th-century stone houses link through secret passages, offering both quiet corners and communal gathering spots.

 

🇩🇲 Dominica

More waterfalls than beaches, volcanic hot springs bubbling up through the rainforest, and lush mountains that tumble straight into the sea. Families explore together—morning hikes through the jungle, afternoons floating in emerald pools, grandparents sharing stories over sunset drinks. Stay: Secret Bay, where treehouse-like villas perch between two beaches, each with a kitchen and plenty of space for the whole family.

 

🇨🇷 Nosara, Costa Rica

A laid-back surf town where jungle grows right to the shoreline, yoga studios outnumber bars, and sea turtles nest by the thousands on protected beaches. Multi-generational groups find natural rhythms here—grandparents joining morning yoga while teens catch waves with local instructors, families gathering for sunset walks along Playa Guiones' four-mile stretch. Stay: Silvestre Nosara, a collection of design-forward jungle residences that bring everyone together while offering enough space to breathe.

 

🇪🇸 Marbella, Spain

A sophisticated stretch of Andalusian coastline where Mediterranean beaches meet Moorish architecture, with the Sierra Blanca mountains providing a dramatic backdrop. The region balances tradition and modernity—from grandparents exploring Old Town's flower-filled plazas to teens joining beach volleyball matches, families reconnecting over multi-course lunches that stretch into the afternoon. Stay: Marbella Club, a beachfront oasis with multi-bedroom villas, lush botanical gardens, and a dedicated kids’ club.

 

An ancient highway flowing through golden desert where temple ruins tower above palm-lined banks and village life continues much as it has for centuries. Sailing between legendary sites brings history alive for all ages—from Luxor's open-air museum atmosphere to the Valley of the Kings where hieroglyphics still burst with color after 3,000 years, each stop offering experiences that burn into memory banks regardless of age. Stay: Nour El Nil dahabiyas, traditional boats with just 8-10 cabins, creating a private family atmosphere while cruising between Esna and Aswan.

 

Heather-covered moors, mist-shrouded castles, and glassy lochs unfolding outside your window as you glide through Scotland's wildest landscapes. The Belmond Royal Scotsman is classy and FUN. No stuffiness here. It's a joy fest on rails. They welcome children 10+ (ideal for older families), with off-train excursions tailored to different energy levels—from falconry demonstrations to whisky tastings for adults. Stay: Belmond Royal Scotsman, where family groups can book connecting cabins and shared experiences create natural conversation starters across generations.

 

A landscape of dramatic mountains encircling historic farmsteads, where Dutch colonial architecture meets cutting-edge sustainable design and world-class vineyards line scenic valleys. The region offers rich experiences across generations—from grandparents enjoying wine tastings to teens joining conservation activities, families exploring together on horseback rides through lavender fields and mountain trails. Stay: Babylonstoren, a 300-year-old Cape Dutch farm where contemporary glass-walled cottages look onto working gardens, offering hands-on experiences from harvesting to bread-making that connect generations.

P.S. Seriously, friends…don't put off your most important asset––your time with loved ones. Whether it's near or far, get it in the works. 🖤 If you want help, you know where to find me! (just reply here or click below 😊)