Puerto Rico

RTJ Sr.'s 1958 original, restored by RTJ Jr. in 2011 and the reason most groups fly down. The closing stretch hugs the Atlantic, and the par-4 13th — the famous double-dogleg over water — is still one of the better thinking holes in the Caribbean. Tee times are tight in season; book the second you commit to the trip.

Same property, same pedigree, fraction of the wait. Also an RTJ Sr. layout, more inland and tree-lined than the East, with water in play on roughly half the holes. If the East is fully booked or twice the price, you're not settling — you're just being smart.

Arthur Hills design that climbs and falls 200+ feet across the cliffs of Fajardo with the Atlantic in your face on the front nine. The views off the upper holes are the best on the island — bring a camera and a few extra balls. The course was renovated and reopened after Hurricane Maria knocked it out for years; conditioning has come back.

Tom Kite design in Río Grande, between San Juan and El Yunque, with a Championship and an International course on property. Big, generous fairways, wind that picks up by mid-morning, and a closing stretch that bites if you got cute earlier. Solid fourth round of the trip — doesn't feel like filler.

RTJ Jr. set this one between the El Yunque rainforest and the Atlantic, and it's the prettiest round on the island that nobody's lining up to play. Iguanas on the cart paths, mountains on one side, ocean on the other. If Dorado is the headliner, this is the round you'll remember.

Greg Norman design tucked against the foothills of El Yunque, more strategic than the resort's older Ocean Course and usually in better shape. Worth a round if you're basing on the east side and want a fifth course in the rotation. Not destination golf, but a fair price for what it is.

Two and a half hours west of San Juan on the cliffs above the Atlantic — and the most ambitious course on the island. The Pasarell brothers built it themselves, walking-only, with five holes on the cliff edge that rival anything in the Caribbean. It's a haul to get out there, but it's the one course you can't replicate anywhere else.

The play if golf is the priority and budget isn't. On-site access to both RTJ courses, three miles of private beach, and the kind of service that makes you forget you're 45 minutes from anywhere. Pricey in season — expect $1,500+ a night — but you're paying for the address.

Quieter alternative to Dorado, on the northeast coast against the El Yunque rainforest. Bahia Beach golf is on property, and you're 20 minutes from Trump and El Conquistador. Smaller, less corporate than the Ritz — better for groups that want privacy without the price tag of a Reserve.

Old San Juan's best hotel — a converted 17th-century convent with a rooftop pool, two blocks from Calle San Sebastián. If you're following the advice and splitting nights between resort and city, this is the city base. Walk to dinner, walk home, do it again.

Beachfront in the Condado district — closer to nightlife and restaurants than Old San Juan, with a real pool and beach scene that some groups prefer. Great middle-ground base if you want city access without the cobblestones-and-no-parking situation.

Best value play on the east side. Two on-site courses, big pool complex, beach access, and rooms at a fraction of the Reserve or St. Regis price. Not as polished, but if you're spending six rounds outside and only need a bed, you're fine here.

For groups of 6+, a private villa inside or near the Dorado Beach community is usually cheaper per head than booking five Ritz rooms. Look for properties with a pool and a kitchen — you'll save real money on breakfast alone.

José Santaella's restaurant in the Santurce market district is the best dinner in San Juan, full stop. Modern Puerto Rican — start with the mofongo croquettes, get the lechón, and let someone else figure out the cocktail menu. Reservations, and not the night-of variety.

Tasting-menu spot in Old San Juan that punches above its weight on a small island. Four to six courses, smart wine pairings, and a chef (Peter Schintler) who actually cooks every night. The big-dinner option if Santaella's full.

The original San Juan destination restaurant — handwritten menu, no reservations, and a line that's worth standing in. Whatever fish came in that morning is what you order. If you only get one truly local meal, this is it.

Multi-room cocktail bar in Old San Juan that's been on every 'World's 50 Best Bars' list for a reason. Each room has a different vibe — back rooms get loud and salsa-heavy after 11. The post-round drink stop turns into the post-dinner everything stop.

Casual Puerto Rican spot near Dorado Beach for the round-day lunch or low-key dinner. Mofongo, churrasco, plantains, cold Medalla. Fraction of resort prices and twice the flavor.

Old San Juan breakfast spot with strong coffee, full Puerto Rican plates (mallorcas, tripleta, the works), and a courtyard that doesn't feel like a hotel buffet. Get there before 10 in season or you're waiting.

BBQ joint in Fajardo run by an ex-NYC chef in a converted gas station. Best stop on the way back from El Conquistador — ribs, jerk chicken, pulled pork, all done over wood. Casual, no pretense, ice-cold beer.

Inside the Condado Vanderbilt — the one fine-dining hotel restaurant on the island that's actually worth the price. Tasting menu or à la carte, ocean views, jacket-optional but you'll feel underdressed in shorts. Right call for the closing-night dinner.

Hole-in-the-wall in Santurce serving the kind of fritters and street food you'd otherwise hunt down at a roadside stand. Alcapurrias, bacalaítos, pinchos, $4 beers. The cheap, honest lunch the resort can't replicate.