7 Places to Celebrate a Big Birthday, According to T+L's A-List Advisors

Planning a celebration for a milestone birthday? Consider one of these amazing destinations for a trip to remember.

No matter your age or stage of life, every birthday can be celebrated with a big trip. Some exciting destinations are perfect for visiting in your 20s, like backpacking through Southeast Asia or road tripping the Pacific Coast Highway. Others, like a relaxing beach vacation in Hawaii or Thailand, might be better suited to those 50 and over.

We asked our trusted A-List of top travel advisors for their recommendations on the best places to celebrate a milestone birthday, whether you want to go alone or with a larger group, stay in one place or visit multiple locations. Here are their suggestions for over-the-top destinations to celebrate your big day.

Cayo Espanto, Belize

aerial view of Cayo Espanto private island
Cayo Espanto

Three miles off the coast of Belize, this private, luxury Robinson Crusoe-style island offers just seven villas. Each one is luxuriously furnished with hardwood floors, mahogany beds, and crisp white bed-linen. Enjoy panoramic views from your private pier and plunge pool, and world class diving and snorkeling.— Will Bolsover, Natural World Safaris

Havana, Cuba

Start with a sunset convertible car ride through breezy Old Havana, soaking in the culture, colors and sounds of this enigmatic island destination. Then, have dinner at a private table at the city's best rooftop restaurant with 360 degree views of the city—start with a rum and cigar tasting then dive into fresh fare caught locally. After dinner, head to the Tropicana nightclub for a taste of 1950s era cabaret, or ask for front row seats to a sold out live local music concert.— Chad Olin, Cuba Candela


Horseback Riding in San Carlos De Bariloche, Argentina
Derio Ilari/EyeEm/Getty Images

Renting an authentic Patagonian Estancia with gauchos and all, and crossing the Andes on horseback, is a once-in-a-lifetime thrill. — Maita Barrenechea, Mai 10


A private ranch in Kenya hands down would be my recommendation, something like Ol Jogi or Arijiju, they provide the clients with everything they need at their fingertips, from tennis courts, wildlife interactions, ATVs, to private chefs. You name it they have it here.—Leora Rothschild, Rothschild Safaris

Grand Teton and Yellowstone National Parks

Jenny Lake at Grand Teton National Park
Shardul Rao/Getty Images

There's nothing better than going all-out for a travel-related birthday bash! The Jackson Hole area in Wyoming, right near Grand Teton National Park and not far from Yellowstone National Park, is an incredible destination -- it's rugged yet still luxurious. If the birthday adventurer is really looking for a once-in-a-lifetime bash, they would enjoy a private helicopter ride between the Tetons and Yellowstone. Who all can say they've flown into Yellowstone on a private helicopter? On a trip like this, they can travel to multiple locations with their group to get the best of what the Rockies have to offer. Hike, bike, maybe a little fly fishing near Grand Teton National Park, and a private air balloon ride at dawn for an unforgettable bird's eye view! The accommodation options are quite lavish in this famous ski hub, and the celebrated traveler can enjoy modern or more historic downtown bars and restaurants for their special night in Jackson.—Dan Austin, Austin Adventures

Tanzania and Rwanda

I suggest a Tanzania/Rwanda combination. Land at Sasakwa Airstrip and transfer directly to Singita Serengeti House, set at the base of Sasakwa Hill overlooking the 350 000 acre Grumeti Reserve. Settle in, with all private services and your very own 4-suite villa in the heart of game-rich terrain. Laid-back luxury with various outdoor living areas including outdoor sala, 25-meter lap pool, private tennis court and pavilion, a tented wellness suite, and a full fitness center as well as access to the Singita Boutique and Gallery at nearby Singita Sasakwa Lodge. And if you're keen to add another aspect to this trip, private charter from Sasakwa Airstrip to Kigali, Rwanda and travel onwards to Singita Kataza House, set on the edge of Volcanoes National Park. Relish in the exceptional views, the privacy, heated pools, food and wine journey and in-villa cinema. And of course location, location, as you're within easy access to gorilla trekking. Tamsyn Fricker, Travel Artistry Africa

Monsaraz, Portugal

The perfect birthday trip in Portugal would include heading out to the deep countryside to the very small town of Monsaraz. Here, depending on the size of the group, we would do a buyout of the luxury countryside retreat São Lourenço de Barrocal and plan quite a few special activities: a hot air balloon ride at sunrise overlooking the Alentejo's rolling hills and castles; a private horse back riding lesson along the streets of the 12th century castle of Monsaraz; a private stargazing session in complete darkness led by one of the leading Portuguese astronomers. A weekend full of activities, tranquility and authenticity!—Gonçalo Correia, Tours For You

The medieval and historic village of Monsaraz at twilight. Alentejo, Portugal
Mauricio Abreu/Getty Images/AWL Images RM
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