Turning 50 is not “just a birthday.” It’s a milestone that deserves a trip with meaning—equal parts joy, glow-up, and life-is-good energy. Whether you’re celebrating with your closest girlfriends (the “we’ve-seen-each-other-through-everything” crew) or planning a romantic reset with your partner, the best 50th-birthday trips share three traits:
- A bucket-list setting (the kind that makes your camera roll look unreal)
- A hotel/resort that feels like an experience (not just a place to sleep)
- A rhythm that balances celebration + restoration (spa mornings, sunset dinners, a little adventure)
And yes—these types of trips book out early, especially the best resorts, the best room categories, and prime dinner reservations. Planning ahead is how you get the “wow” suite, the perfect location, and the seamless itinerary.
Below are five of the most in-demand, bucket-list-worthy destinations right now—aligned with what luxury travelers are prioritizing for 2026: iconic culture destinations (Italy, Greece) and high-touch, experience-driven trips (like safari + city).
1) Santorini, Greece
Best for: sunset glamour, milestone photos, chic pool days, and “we’re really doing this” energy
Where to stay (top resorts)
- Grace Hotel, Auberge Resorts Collection (Imerovigli) – cliffside romance and polished luxury.
- Canaves Oia (Oia) – iconic caldera views and classic Santorini style.
- Sandblu Resort – plenty of natural light, soft color palettes, and elegant interiors.
- Katikies Santorini (Oia) – legendary whitewashed aesthetic and dreamy plunge-pool vibes (a go-to for milestone trips).
What to do (besties or partner)
- Private catamaran cruise with stops for swimming and snorkeling (sunset option is non-negotiable)
- Wine tasting (Assyrtiko is the local star) + a winery lunch
- Golden hour photo stroll through Oia + Imerovigli (I’ll map the best, least-crowded timing)
Don’t miss
- Pyrgos village (more authentic, less crowded)
- A caldera-view dinner timed to the sunset
Local gem to eat
- Metaxi Mas (Exo Gonia) – beloved for elevated local Greek flavors; reserve ahead.
2) Tuscany, Italy (Chianti + Val d’Orcia)
Best for: wine-country romance, villas and countryside views, cooking classes, and slow-luxury living
Italy remains one of the most-requested destinations for luxury travelers heading into 2026—especially for food, culture, and scenery.
Where to stay (top resorts)
- Rosewood Castiglion del Bosco (Montalcino/Val d’Orcia) – iconic estate stay with serious “anniversary trip” energy.
- Borgo Santo Pietro (near Siena) – intimate, design-forward countryside luxury.
- COMO Castello Del Nero (Chianti) – a castle retreat with a Michelin-starred restaurant on-site.
What to do
- Private winery day (Brunello + Chianti Classico) with driver
- Hands-on cooking class in the countryside
- Vespa tour through vineyards (or convert to a vintage Fiat tour if you want it more relaxed)
- Truffle hunting (seasonal)
Don’t miss
- Sunset in Val d’Orcia (think: rolling hills + cypress roads)
- Siena (for a beautiful day trip with history and shopping)
Local gem to eat
- Officina della Bistecca (Panzano in Chianti) – Dario Cecchini’s legendary, celebratory dining experience (book well in advance).
3) The Maldives
Best for: the ultimate “I made it to 50” splurge—overwater villas, spa days, and barefoot luxury
Where to stay (top resorts)
- The Ritz-Carlton Maldives, Fari Islands – modern, design-forward luxury with that next-level service.
- Cheval Blanc Randheli – ultra-luxe, fashion-house polish, exceptional dining.
- St. Regis Maldives Vommuli – iconic overwater villa energy and a very celebratory vibe (great for groups who want both relaxation and a little scene).
What to do
- Private sandbank picnic (yes, it’s as surreal as it sounds)
- Snorkel with manta rays (seasonal) or book a private marine biologist excursion
- Sunset dolphin cruise
- Signature spa journey + a “recovery day” after your celebration dinner
Don’t miss
- A private boat day (snorkeling + lunch + golden hour return)
- A villa category upgrade (this is one destination where room choice changes everything)
Local gem to eat
In the Maldives, the “local gem” is often your resort’s destination restaurant—and the best reservations are snapped up early. (I’ll pre-book dining, experiences, and transfers so you don’t land and realize everything is waitlisted.)
4) Bali, Indonesia
Best for: wellness, culture, girlfriends’ reset trips, and luxe villas at strong value
Where to stay (top resorts)
- Four Seasons Resort Bali at Sayan (Ubud) – iconic jungle serenity and wellness focus.
- Alila Villas Uluwatu – cliffside architecture + sunset views.
- Bvlgari Resort Bali (Uluwatu) – ultra-luxe, very “special occasion.”
What to do
- Private temple + rice terrace day with a guide (I’ll time it to avoid peak crowds)
- Sunrise hike at Mount Batur (active option) or a spa + beach club day (relaxed option)
- Balinese cooking class
- Sound healing / yoga (perfect milestone-trip ritual)
Don’t miss
- Ubud art + café scene
- Uluwatu sunset (clifftop views are a core memory)
Local gem to eat
- Locavore NXT (Ubud) – celebrated for sustainability and creative dining; reservations are essential.
5) South Africa: Cape Town + Luxury Safari
Best for: a once-in-a-lifetime “two-trip-in-one” itinerary—city, wine, coast, then Big Five safari
Africa continues to trend strongly for 2026 travel planning, especially when paired with standout lodges and conservation-forward experiences.
Where to stay (top hotels/lodges)
Cape Town
- Ellerman House – boutique, art-forward luxury with iconic views.
- Mount Nelson, A Belmond Hotel – timeless, classic, and perfect for a celebratory stay.
- The Silo Hotel – design lovers’ dream, positioned above Zeitz MOCAA.
Safari (Sabi Sand/Kruger area)
- Singita (multiple lodges) – top-tier safari luxury.
- Londolozi – known for exceptional guiding and an elevated lodge experience. (I personally have a girlfriend who is doing one of the week long retreats in this amazing location!)
- Royal Portfolio’s Masiya’s Camp (Thornybush) – a newer, design-forward option for something fresh and distinctive.
What to do
- Cape Town: Table Mountain / Lion’s Head hike, waterfront cocktail hour, art + design shopping
- Cape Winelands: private tastings + long lunch
- Safari: twice-daily game drives, sundowners, and the most unforgettable “pinch me” wildlife moments
Don’t miss
- Zeitz MOCAA (especially if you stay at The Silo)
- A Winelands day (Franschhoek is a favorite for a reason)
- At least 3 nights on safari (2 feels rushed; 3+ is where it becomes transformational)
Local gem to eat
- The Pot Luck Club (Cape Town) – one of the city’s most talked-about reservations.
Planning Notes (So Your 50th Feels Effortless)
- Start early: The best resorts and the best room categories often sell first—especially for peak seasons and milestone dates.
- Create your want list: I will always want you to be in the best location possible, but where you stay and for how long can be fluid. Prices are the same way. You may want to splurge in one area and save in another. Make sure you have time to enjoy the moment.
- Celebrate strategically: I’ll build an itinerary that includes one “big moment” (private boat, chef’s table, safari surprise, etc.) plus plenty of downtime.
- Make it personal: Spa preferences, activity levels, food priorities, and your “non-negotiables” shape the trip.
Ready to Plan Your 5-0 Trip?
If turning 50 is your sign to go big—I’m here for it.
I’ll match you with the right destination, lock in the best-fit resort, and design a trip that feels elevated, fun, and completely you (whether it’s girlfriends, your partner, or both). And because these bucket-list stays book out early, the best time to start planning is now.
Reply to this post or contact me through my website to get your 50th celebration on the calendar—before the suites, villas, and prime dining times disappear.
She Travels in Style 