These Are the Most Underrated Places to Celebrate Your Next Milestone, According to a Travel Advisor

Travel + Leisure

4 days ago

The best destinations aren't always the most popular ones. When it comes to celebrating major milestone—whether it's a birthday, your honeymoon, or retirement— under-the-radar spots take the lead. As a lifelong traveler who plans destination celebrations for a living, I know that going somewhere out of the ordinary makes for a truly one-of-a-kind experience—think bioluminescent lagoons or towering baobab trees. Here are some of my favorite underrated destinations, plus top hotels at each.
Madagascar
Madagascar is the ultimate combination of untouched natural beauty and beachy luxury. Isolated from the African continent, the island has evolved on its own terms, giving rise to wildlife found nowhere else on Earth—like the aye-aye, lemurs, and rare species of chameleons.
The best way to take in the otherworldly landscapes is from above, which is exactly how an arrival at luxury resort Miavana by Time + Tide begins:with a cinematic helicopter ride over ancient red earth, touching down on a private island edged by clear blue waters. With room for up to 40 guests, it's an extraordinary place to gather, but what makes it unforgettable is its in-house cultural center. There, guests can learn about the island's deep Indonesian roots, shaped by centuries of migration, trade, and myth.
On the other side of the island, Tsara Komba and Voaara offer more bohemian stays. They're relaxed, artistic, and rooted in nature, yet undeniably well-appointed.
African Safaris
A bush dining set up by Arijiju Retreat.
Tom Martienssen/Arijiju Retreat
For travelers seeking intimacy with scale, Africa's safari lodges are the ultimate all-inclusive. In Kenya's Borana Conservancy, I love Arijiju and Lengishu House—stays that marry design and conservation, offering horseback safaris and community visits alongside world-class chefs and wellness teams.
Botswana delivers a cinematic range of settings, from the salt pans near Jack's Camp to the Okavango's lush waterways surrounding Xigera Safari Lodge, or the combination of land and water safari at Wilderness Duma Tau.
In Namibia, Shipwreck Lodge in the desolate Skeleton Coast National Park and the secluded Hoanib Valley Camp are oases of luxury in otherworldly settings. They're hauntingly beautiful, comfortable, and conservation-focused.
Wine Country
The wine cellar at La Chartreuse de Cos d'Estournel.
La Chartreuse de Cos d'Estournel
Celebrations in wine regions are a natural pairing. Imagine starting with a bubbly toast at the Royal Champagne—a T+L reader favorite in Champillon, France, a tiny village less than an hour from Paris—followed by dinner in the vaulted cellar at Château de la Commaraine. Or head to Bordeaux for a sleek takeover of La Chartreuse de Cos d'Estournel, an eight-bedroom house where modern art and old-world elegance collide amongst renowned vineyards.
In South Africa's Franschhoek Valley, celebratory wine trips take on a restorative quality. At Sterrekopje Farm, guests are invited to slow down through biodynamic farming, communal feasts, and holistic rituals. La Residence's Franschoekk House offers an opulent villa setting with butler services for a secluded and spectacular fête.
Underrated Cities
The Suite Royale at the Royal Mansour Casablanca.
Royal Mansour Casablanca
Cities like Cape Town and Casablanca offer the cosmopolitan energy of your go-to cities, but they have just enough edge and cultural depth to feel truly unique. Casablanca is quietly cool: there, elegant Art Deco design meets North African timelessness. A few nights at the timeless Royal Mansour Casablanca paired with live jazz, spice market strolls, and rooftop sunsets makes for a buzzy, energetic trip.
Cape Town, too, balances urban energy with natural grandeur. With exclusive-use accommodations like Villa Leeukoppie or Ellerman House as your home base, paired with hikes up the iconic trails of Lion's Head and a behind-the-scenes look at Cape Town's influential contemporary art scene, your celebration will feel both grounded and glamorous.
The Ends of the Earth
An overhead of White Desert's pods in Antarctica.
White Desert
For the group that's done it all, it's time to head to the Earth's last frontiers. Work with a travel agency to charter your very own expedition vessel to the poles: whether the fjords of the Arctic to toast champagne under the midnight sun, or Antarctica to chase the aurora australis. The voyages are cinematic and deeply intimate. Similarly, White Desert's private polar pods in Antarctica reframe luxury in stark, extraordinary terms, redefining what's possible at the edge of the world.
Erina Pindar is a member of Travel + Leisure's A-List and specializes in destination celebration trips. You can create a tailor-made itinerary with Pindar by contacting her at [email protected].