Chicago Wine and Cheese Cruise

Where an architecture cruise is about the buildings, a wine and cheese cruise is about the atmosphere. Boats leave the downtown dock and head out onto the river and the lakefront, giving passengers a long, unhurried look at the skyline while they sample wine and a spread of cheeses. It is a classic Chicago date night, a good choice for a celebration, and a gentle way to spend the evening with friends. The experience centres on sitting back and watching the city pass. The boat usually travels along the main branch of the river through the downtown canyon, then out through the lock to Lake Michigan for views of the skyline from the water. Seating is a mix of indoor and open-air areas, so you can move between shelter and fresh air. Staff serve the food and drink, and the pace is easy, with no need to queue. Because it is a social, relaxing cruise, it works well for couples, anniversaries, birthdays and small groups. The sunset departures in summer are particularly popular, as the light on the buildings can be spectacular. In cooler months, indoor seating makes the cruise comfortable, and the lit skyline at night has its own appeal. Check the operating season for your dates, as schedules vary.

There are a few things to consider before choosing your date. Sunset sailings bring the best light but also the largest crowds, so booking ahead is sensible, especially at weekends. Weekday evenings tend to be calmer. The boat's route can vary by season and conditions, so the cruise may spend more or less time on the lake. If you are visiting in spring or autumn, bring a jacket, as the air over the water is much cooler than on the street.

Age and alcohol rules apply. Wine service is for guests of legal drinking age, and identification may be requested. If you are travelling with children or someone who does not drink alcohol, ask the operator whether soft drinks are available or whether a different cruise would suit better. Some boats may allow families, but the atmosphere is geared towards adults. Check the policy in the product details before you buy.

The cruise is a good partner for other evening plans. Dinner before or after in River North, the Loop or Streeterville is easy, since the dock is central. If you want to see the architecture in more detail, an architecture river cruise earlier in the day will give you the story of the buildings you will then see from the lake in the evening. Couples might round off the night with a rooftop bar or a walk along the Riverwalk, which is lit and lively after dark.

A few tips make the evening smoother. Arrive early to choose a good seat, wear comfortable shoes for stepping on and off the boat, and keep your phone ready for photographs of the skyline reflected in the water. Seasickness is rarely a concern on the river, but the lake can be bumpier, so people who are sensitive to motion should sit near the centre of the boat and watch the horizon. Because the pace is slow, it also suits travellers who want a calm evening without a packed schedule.