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I think the most appealing aspect of Old San Juan is the architecture and design of the city. Residential apartment buildings have been converted to designer boutiques or little B&Bs, and interior courtyards invite hungry guests to relax and unwind in the shade.... I’ve been to this area multiple times and still I manage to find a street I’ve never wandered down. Some are more popular than others, in particular Calle San Sebastian, which hosts eateries, bars, and shops, and Calle San Francisco. At the corner of this street is my particular favorite, Franky’s antiques. It’s in a four-story building, loaded with vintage goodies. There’s so much to see, one trip is not enough. If you want to shop, consider wandering all morning and into the early afternoon. You’ll be delighted by all the unique shops. Then, take a break at my favorite restaurant, Triana, for Spanish-style tapas and their famous sangria. It’s a must-stop place any time I’m in the old city. You don’t need a car to get around. Just park at one of the garages and explore by foot. There’s lots to see and do in Old San Juan.

“We hope you adapt to our bohemian philosophy,” say the staff at Hotel La Semilla, by way of explanation when guests ask why rooms have no televisions (there is, however, Wi-Fi and AC). With distressed walls and furniture, the hotel has a shabby chic feel (or, as they describe it, “rough luxe”), and owners Alexis and Angie treat all guests as friends. Part of the room rate is earmarked as a donation to the Friends of Sian Ka’an, a conservation group dedicated to the preservation of the nearby Sian Ka’an Biosphere Reserve.

On this episode of Where to Go, Aislyn Greene speaks about Menton with Jenn Rice to uncover the lemon groves, three‑star dining, and seaside charm that make this Riviera town a top pick for 2026.

On this episode of Where to Go, Aislyn Greene talks with Katherine LaGrave about navigating Sweden’s Stockholm Archipelago: ferry logistics, sauna rituals, island bakeries, and how to plan a restorative multi‑island hiking itinerary.

On this episode of Unpacked, we guide you to wonder-filled, outdoor adventures and teach you to tap into the magic of off-season travel, all year round.