Cara at The Chanler

2022 Amelia Pinot Noir, Viñedo Quebrada Seca, Valle de Limarí, Chile — $40–$70 (estimated bottle range per Yelp data)

Cool-climate Limarí Pinot Noir at a room like this? This is the sleeper pick. Quebrada Seca sits closer to the Atacama than most people expect, producing lean, mineral-driven Pinot that punches well above its price tier. In a list that probably tops out near $500+, this is the bottle that gives you something genuinely interesting without financing a second mortgage.

2023 Terrunyo Sauvignon Blanc, Viñedo Los Boldos, Valle de Casablanca, Chile

Casablanca Valley Sauvignon Blanc is consistently underestimated on the East Coast. Los Boldos makes a serious, cool-climate expression with more grip and less tropical fruit than most drinkers expect from Chile — it reads closer to a Sancerre than a Marlborough, which makes it a genuinely interesting call at a Newport fine-dining table. Most guests will order whatever the sommelier recommends; the ones who ask for this one are in for a surprise.

Fetzer Reserve Ruby Port, California

Fetzer is a perfectly fine mass-market producer, but a Ruby Port at this tier of restaurant — AAA Five Diamond, $200+ tasting menus — reads like someone forgot to finish the dessert wine section. Ruby Port is the most basic port category, and Fetzer's isn't doing anything to distinguish itself. At Cara's price point, you deserve a Fonseca Bin 27 at minimum, or better, an LBV with actual age on it.

Don Melchor Cabernet Sauvignon, Viñedo Don Melchor, Valle del Maipo, Chile + Five-course blind tasting menu (meat course)

Don Melchor is Chile's answer to a Napa cult Cab — structured, serious, and built to go with red meat. The blind tasting menu's meat course, whatever it lands on that evening, is exactly where this bottle earns its keep. The structured tannins and dark fruit profile need something with fat and savory depth to open up, and Cara's New England-inflected European cuisine tends to deliver exactly that.