Sri Lanka serves as the perfect segue between Southeast and South Asia: a laid-back island where Buddhism is the dominant religion and dhal curry is the dominant dish. A 3.5-hour flight from Singapore’s Changi will deposit you at Colombo’s Bandaranaike International Airport; from there, it's on to the capital city and Galle Fort—just come ready for a walking tour or two.
Day 1: Explore the capital
It’s an hour-long drive from the airport to the Galle Face Hotel, a colonial-era grande dame on the beach that's the city's most storied retreat. Check in and have a quick lunch on the verandah overlooking the sea, then head off to the restored 1681 Dutch Hospital in Old Colombo to meet Mark Forbes of Colombo City Walks for a stroll through the erstwhile Dutch Fort, looking for traces of the city’s Dutch and British legacies. Forbes’s enthusiasm for his hometown is infectious, and his stops include the stately Edwardian General Post Office, the ornate Cargills department store, the striking pomegranate-inspired Red Mosque in Pettah, and the Grand Oriental Hotel for a gin-and-tonic break. Forbes’s tours will bring you right back to the Dutch Hospital, which these days is better known for curative treatments in the form of shopping and dining. Browse the Ayurvedic skincare balms at the cult favorite Spa Ceylon before heading a few doors down to the city’s hardest-to-book reservation (though Forbes can try to pull a few strings to get you a table if need be): Ministry of Crab, a temple to seafood opened by Sri Lankan cricket icons Mahela Jayawardene and Kumar Sangakkara. Wrap yourself tightly in a bib and get your hands dirty as you dig into the sloppy, delicious garlic chili crab.
Day 2: Head south for some colonial history
While Colombo alone would make for a fun long weekend, if you’re wondering where the locals head when they need a break, look a bit farther down the map. For centuries, Sri Lanka was coveted among international traders thanks to its prized cinnamon, and the seaside town of Galle (pictured at top) is a testament to that: The Portuguese, Dutch, and English all staked their claim at some point, and now the still-inhabited Galle Fort, a two-and-a-half-hour drive from Colombo, is a UNESCO World Heritage site. The narrow lanes have immaculately preserved buildings in a hodgepodge of architectural styles, many of which now house hip restaurants, boutique hotels, and shops. (Don’t miss the Sudarmalaya Buddhist Monastery, which still has strong traces of its roots as a Catholic convent, complete with a bell tower.) Pick a hotel in the heart of the fort: It’s hard to beat Amangalla, Galle’s finest address, for style and history—its origins date back to a Dutch residence from the 1600s. Others might want to consider the charming Mango House Hotel, a sweet stay done up with pink and orange textiles and colonial-style furniture, as well as a collection of vintage Bollywood posters on the walls. For dinner, walk over to Fort Printers, an 18th-century villa converted into a small hotel with one of the best restaurants in the fort. Whether you’re in the mood for Sri Lankan or Mediterranean fare, one thing isn't up for debate: You have to order the lobster curry.
Day 3: One more walking tour
After breakfast at Heritage Cafe, get ready for a walking tour of the fort. I know, I know: Another walking tour? But think of Shanjei Perumal, who left his career as an ad exec in Colombo to start Galle Fort Walks, less as a guide and more as your quirky Sri Lankan BFF. He’ll be at your side as you meander through the streets, always ready with a fun fact or hilarious story that somehow involves his mother. He’ll spill centuries worth of Galle’s secrets before treating you to a scoop of gelato at Pedlar’s Inn Gelateria, the most authentic ice cream in town—as it should be, considering its owner hails from a four-decades-strong gelato-making lineage back in Italy. Squeeze in a stop for a quick swim at nearby Unawatuna Beach, then hightail it back to Colombo to catch your flight out.