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Rebecca Walker embarks on a spontaneous journey to Bulgaria, guided by locals she connected with both virtually and in real life.

One of the world’s most epic drives, the Hana Highway connects Kahului with Hana in eastern Maui. The scenic stretch is just 64 miles long but can take up to three hours to drive, thanks to 62 twists in the road as it winds through rain forests and past waterfalls, natural pools, and seascapes. Plan at least a half day to properly experience the drive, or slow it way down and spend a night in Hana so you can linger at places like Twin Falls, the Keanae Peninsula, the Garden of Eden arboretum, and the black sand beach at Waianapanapa State Park. Sun worshippers should also budget plenty of time for stops at Hamoa Beach and Ho’okipa Beach Park Beach Park.

Poised on sheets of 440 million year old granite, the view across the ocean from Halibut Point seems to go on for ever. The quarry itself is a dramatic site and the surrounding tidal pools and hiking trails a great spot to explore. The Visitors Center {closes after Columbus Day} spotlights the history of this former Cape Ann industry where granite that now lines the streets and buildings of Boston was quarried.

Giving new life to an old haunt, the Cayman Spirits Company has turned the onetime bar area of the historic Pedro St. James into a rum-centric saloon and café: the Outpost Bar. Go for a tasting, and you’ll try as many as five local rums, one of which—the 1780—is aged and available exclusively on-site. The next most important variety to sample here is the Seven Fathoms, if only so you can say you’ve tasted rum that’s been anchored and aged 42 feet (i.e., seven fathoms) below the Caribbean’s surface. Of course, considering the Outpost’s view—prime, uninterrupted seascape—you could have pretty much any drink in hand and be happy.

This little private church is probably the most photographed stop in Oia. Our rented house was right next to it but lower on the steps so we could see lots of people getting lots of photos. Married couples would take their photos next to it, photographers were offering workshops that included this spot. I woke up at 5.30AM to wonder when nobody else was around. Best time of day to walk around this very busy tourist destination.

This three-day itinerary caters to different travelers’ tastes with a smorgasbord of fun, from beach time and golf to water sports and tours—on land and in the island’s dazzling blue waters.

Enjoy lively festivals, tranquil beaches, and marine adventures across St. Thomas, St. John, and St. Croix—no passport required.

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.