As gorgeous as Villa Montaña’s 35-acre setting is, it plays second fiddle to the pristine, three-mile secluded stretch of sand along the property’s edge. The beach is decidedly the main attraction here, and rightfully so. Wind your way through the flowers and palms, headed that general direction, then drop your beach bag near a few chairs and umbrellas for a day in the sun. The plantation-style architecture fits the overall Caribbean vibe, while handcrafted furniture and tiles add a nice artisan touch. The two onsite restaurants leave you little reason to venture any further for dinner. The Wine Spectator award-winning Eclipse delights with everything from filet mignon to fresh local catch – and the rustic-luxe décor is on point, with the antique silverware proving no detail has gone unconsidered. Meanwhile the Asian-inspired “O” dishes up spectacular Japanese, Thai, North African and Indian small plates made with fresh, seasonal ingredients – order several and share, then order seconds on table favorites. There are two lounge-worthy outdoor pools for lazy afternoons with a book. And spa treatments are available if you’re having a diva moment. Tennis racquets are complimentary, if you want to go hit on the synthetic grass courts. Or borrow cruisers for your whole crew and pedal around the lush property, looking for birds and geckos.

Casual Caribbean-style one-bedroom suites and two-bedroom villas are each styled in warm earth tones, dotted with unique art and artifacts. Terra cotta floors stay cool despite the balmy climate, and the detailed tiling in the bathrooms adds a local flair. Kitchens make low-key meals easy, but leave a few dinners open for the pros at the two onsite restaurants. (Be thee warned: it’s tough act to follow.) Wind down with drinks while you watch the sky put on its nightly show at sunset. Then see who’s up for a card game around the table. When the time comes to call it a night, crisp Egyptian cotton sheets and fluffy down comforters invite.

Tucked in the northwest corner of Puerto Rico, the quiet town of Isabela makes the perfect hideaway when all you want is sand and surf and maybe the occasional snorkeling excursion. If you’ve got an active crew, keep them entertained with kite surfing, windsurfing and actual surfing-surfing – and throw in some scuba diving and deep sea fishing just for kicks. Or if you prefer to stay land-bound, go horseback riding, ziplining or book ahead for a private beach picnic or plan a bonfire with s’mores.