7 Luxury Escapes That Are Perfect for Milestone Celebrations

Forget predictable birthday dinners and restaurant reunions. Today’s travelers are letting their YOLO flags fly, craving celebrations that go bigger, bolder and far beyond the bland in destinations so rich in history and experience that they become another treasured guest at the party.

Whether it’s an eco-lodge tucked into Costa Rica’s jungle, a romantic Mexican hacienda, a catered Caribbean yacht or a luxury dude ranch in Big Sky country, Ciao Bambino’s Travel Advisors can book a milestone getaway for you that feels both deeply personal and delightfully over-the-top. After all, you deserve it!

Here are seven extraordinary places to add sparkle and shine to your big day.

Best Luxury Properties for Milestone Celebrations

Paws Up Montana

Set across 37,000 wild acres in Greenough, Montana, Paws Up turns birthday parties, anniversaries and graduations into monumental milestone memories. Families and friends can bond over fly-fishing, explore more than 100 miles of horseback riding, hiking, mountain biking and ATV trails, or choose from 70-plus year-round activities, from horseback adventures to restorative wellness experiences. Evenings are made for private dinners, stargazing from outdoor hot tubs and stories around the campfire as you perfect the art of the s’more.

Accommodations range from one- to three-bedroom luxury cabins that blend Western-chic design with all the comforts of home, offering the luxury of privacy and space. For larger celebrations, the historic Bull Barn provides event spaces ideal for weddings, graduation trips and other unforgettable gatherings, Big Sky-style.

Origins Astral Lodge, Costa Rica

Brand-new to Costa Rica (opened in December 2025), Origins Astral Lodge is a celestial-inspired luxury boutique hotel tucked high in the volcanic highlands of Bijagua, where cloud forest, lava-formed landscapes and sky all seem to merge. Set between the Miravalles and Tenorio volcanoes at 2,625 feet, the lodge offers 360-degree views that stretch all the way to Lake Nicaragua.

The intimate retreat comprises just seven private villas, each with two to four guest rooms, making it ideal for buyouts, girls’ wellness getaways, family reunions, milestone birthdays and other intimate celebrations. Spacious two-bedroom villas feature kitchens, airy living areas, private hot tubs and lush terraces designed for cloud-watching by day and stargazing by night.

Families are especially well cared for, with a family pool, outdoor gym, firepit gatherings and the whimsical, dome-shaped Astral Kids Club, where rainforest-inspired workshops and adventures spark curiosity and connection. Dining centers around El Cosmo, a brasserie-style, farm-to-table restaurant rooted in the lodge’s own gardens, while evenings slip by at the Stellar Saloon Bar with expertly crafted cocktails beneath a star-filled sky.

Hacienda de San Antonio, Mexico

If the looming Volcán de Colima doesn’t quicken your pulse, Hacienda de San Antonio will. Here, old-world grandeur collides with warm hospitality, set against a landscape straight out of a mystery novel. Surrounded by western Mexico’s rolling hills, 100-year-old-trees, verdant forests and a breathtaking view of the volcano, this historic family hacienda provides the perfect stage for a destination wedding, an anniversary party or a private gathering with your closest circle.

Every corner and window in the hacienda’s 25 rooms and suites showcases something special. Adorned with handwoven wool rugs from Oaxaca, carefully selected European textiles and curated art pieces, rooms exude personality and warmth.

By day, you can wander sun-dappled courtyards and fragrant gardens, or saddle up for a scenic horseback ride or thrilling ATV adventure across the region’s dramatic landscapes. For the ultimate swoony moment — marriage proposal, anniversary toast — the staff will organize a floating picnic on a handcrafted bamboo raft to the center of Laguna Jabalí.

Return to the hacienda’s terraces to clink glasses over candlelight and gourmet cuisine inspired by the region’s freshest ingredients, and let the soft glow of lanterns and colonial architecture frame your occasion.

Gurney’s Montauk Resort, The Hamptons

Perched on the edge of the Atlantic Ocean, Gurney’s Montauk Resort is a seaside sanctuary and Hamptons mainstay, and for multigenerational families who like to stay and play together, the resort has something for every age group: surfing lessons, paddleboarding and kayaking; beach bonfires and sandcastle building; guided nature walks along the rugged coastline.

If it’s a celebration with friends, the sunset cruises, intimate beachside dinners and marine-based wellness therapies and treatments (housed in the recently renovated 30,000-square-foot Gurney’s Seawater Spa) might be the perfect party favors. Better yet, pop some bubbly with your toes in the sand at the resort’s private Beach Club.

With 158 ocean-facing rooms, suites and cottages, Gurney’s Montauk is the place to bring the whole family together for adventure, indulgence and relaxed coastal memory making.

Airelles Château de la Messardière, France

Set high above the glittering Pampelonne Bay in Ramatuelle near Saint-Tropez, Château de la Messardière taps into every French Riviera fantasy: grand, sun-soaked, hedonistic and unapologetically glamorous. No wonder the folks behind White Lotus decided to set Season 4 here.

With its Belle Époque architecture, 25 acres of lush Mediterranean gardens, pine groves and olive trees, and sea and vineyard views from every corner, the hotel is a scene-stealer in a place where parties have been elevated to an art form for decades.

Head to the exclusive private beach club Jardin Tropezina for leisurely seaside lunches paired with local rosé; book a private yacht charter along the coast; or arrange exclusive wine tasting tours to nearby vineyards. Back at the estate, multiple pools and the Airelles Spa by Valmont set the tone for relaxation. A festive dinner can be arranged at Matsuhisa Saint-Tropez, where Chef Nobu Matsuhisa’s celebrated cuisine blends the best of Japanese and Provencal flavors.

The estate offers 86 exquisitely appointed and expansive rooms, suites and residences, ideal for romantic gatherings, sophisticated sunset aperitifs and living your best life in one of the most beautiful places in the world.

Dream Yacht Charter, The Bahamas

For a barefoot adventure with your sea-loving plus-one, get off the cruise circuit and opt for a private yacht. Dream Yacht Worldwide operates more than 800 vessels across 35-plus dazzling destinations, from the Caribbean to Greece and Sardinia to the South Pacific and the Indian Ocean.

For travelers craving salty indulgence, it’s the ultimate power move: a professional crew, custom routes tailored to your whims and first-class service that carries you from sunrise swims to Champagne-soaked birthday beach bashes.

If you want the experience without the price tag, Dream Yacht is also offering several by-the-cabin options in select destinations. Among them: the Abacos in the Bahamas, a reef-fringed wonderland where technicolor fish, turquoise coves and pink swimming pigs steal the show.

Launched in January 2026, their 42-foot Lagoon catamaran has been refurbished to feature six queen ensuite staterooms, bookable individually — perfect for small celebrations with another couple, grown kids or just your one-and-only. Expect all the perks of luxury yachting, such as water toys, alfresco gourmet meals and happy hour as the sun sinks beneath the watery horizon.

Grace La Margna, Switzerland

Is there a more glamorous ski resort in Europe than St. Moritz? The very name is synonymous with old-world charm and slopeside champagne, which makes the arrival of  the Swiss enclave’s newest hotel in 50 years, Grace La Margna St. Moritz, a perfect place for your high-altitude revelry. As one of the few hotels in St. Moritz open 365 days a year, the hotel offers plenty to do for travelers in all seasons.

Grace Hotels undertook a full transformation, extension and rebranding of the historic Hotel La Margna, a St. Moritz institution dating to 1906, and reopened it in 2023. Guests will now find a sleek new wing, a 7,500-square-foot spa, gourmet dining and a picturesque setting beside Lake St. Moritz. The 74 rooms exude modern mountain elegance with clean lines, neutral tones and tactile touches like faux-fur throws.

Celebrate with a cocktail at N/5 – THE BAR, relax in the spa’s saunas and steam baths or rent an e-bike from the hotel shop. Want to plan something extra-special? Inquire about individually tailored indoor and outdoor activities, including hiking, climbing, pizza making, cocktail mixing and fondue feasts, to name just a few ways to fête any occasion.

NIHI Sumba Island

It’s rare to find 5-star luxury that still feels genuinely wild, but NIHI Sumba Island delivers exactly that, making it an incredible backdrop for life’s milestone celebrations. Tucked along the remote western coast of Sumba in eastern Indonesia, the resort sits on an island twice the size of Bali with a fraction of the people, where rural farmland, grasslands and rice paddies give way to pristine beaches famed for world-class surfing.

The journey itself sets the tone: Guests are whisked from the airstrip in open-air safari-style vehicles for a 90-minute drive into another world. NIHI’s 28 cliffside and hillside villas, ranging from one- to multi-bedroom layouts, are ideal for friends or multigenerational gatherings, with private plunge pools and pinch-me ocean views.

Days unfold with waterfall hikes, cultural encounters and legendary surf sessions, while the equine program at Sandalwood Stables includes horseback rides, a rare experience to swim with horses and a Kids’ Pony Club. Even the spa at NIHI, carved into the lush landscape, feels like a once-in-a-lifetime getaway.

Meals here are included and feel celebratory by design, from intimate omakase dinners at Kaboku to barefoot feasts grilled on the beach.

Relevant Links: 

Browse all luxury family vacation ideas on Ciao Bambino 

Reunited at last! 7 amazing U.S. hotels for a family reunion

Birthday wishes come true at Tuscany’s Castello di Casole, A Belmond Hotel

10 best places for multigenerational family vacations

12 luxury family hotel brands we love

Why use a Travel Advisor to book hotels? 5 key benefits

Editor’s note: This post was accurate when published. We advise checking independently for the latest information and updates. Ciao Bambino does not accept responsibility or liability for any errors or omissions in, or for any actions taken based on, the information presented.