Key West Sunset Sail with Wine on a Classic Schooner

Most sunset cruises pour whatever's in the box. This sail takes the opposite approach. It's built around a proper wine selection, a generous food board and the quiet pleasure of being under sail on a traditional schooner. It suits travelers who want something a little more grown-up than a party boat, while still keeping things casual and warm.

The schooner leaves the marina in Old Town, and the crew raises the sails once you're in open water. Watching them haul the lines and set the canvas is part of the experience, so grab a seat where you can see the rigging. Once the engine goes quiet, the boat heels gently into the wind, and the evening settles into a slow rhythm of wind, water and conversation.

The crew pours eight different wines each evening, usually four reds, three whites and a sparkling wine, chosen from different regions around the world. It's essentially an informal tasting on the water. Take a small pour of each to compare, or settle on a favorite and stick with it. For a natural progression, start with the sparkling and the crisp whites while the sun is still warm, then move to the reds as the air cools after sunset. Beer drinkers have five premium imported and domestic options, and soft drinks and bottled water are always available.

Charcuterie boards come out early in the sail, loaded with cured meats, cheeses, crackers, fresh fruit, raw vegetables and a little chocolate. It's designed to pair with the wine and hold you over comfortably until a late dinner.

As the sun nears the horizon, the crew sets a course for a clear view west, and the sky over the water moves through gold, coral and violet. With a glass in hand, an open horizon and no crowds, this is about as relaxed as Key West sunsets get. The schooner returns to the dock in Old Town after about two hours, close to the area's restaurants and bars.

• The sail departs from and returns to the same marina. Parking in Old Town is paid and limited near sunset, so walk, bike or take a cab if you can.
• Bring a passport or photo ID. You'll need it to be served wine or beer, and the minimum drinking age is 21.
• Guests must be 13 or older. Teens are welcome to enjoy the sail, the food and soft drinks.
• The schooner isn't wheelchair accessible.
• Pace your tasting. Eight wines over two hours adds up quickly, so start with small pours, eat from the boards, and alternate with water.
• Pack a warm layer in winter. From December through March, evenings on the water can feel chilly once the sun is down, so bring a sweatshirt.
• Bring sunglasses. The low sun bounces off the water just before sunset.
• Departure times follow the sun. Sunset in Key West ranges from about 5:45 p.m. in late fall to about 8:20 p.m. in early summer, so check your ticket for the exact time.
• Tell the crew if you're celebrating. The quiet, intimate atmosphere is ideal for anniversaries and honeymoons, so let them know at check-in.