Fall foliage season (September through October) draws crowds for the leaf peeping - shared trolley tours run regularly then. Summer is peak for Lake Champlain sailing and water activities. Winter skiers use the city as a base for Killington and Okemo, so book airport transfers well ahead if you're coming during ski season.

Private sailing charters and group packages fill up faster during peak season, so 2-3 weeks out is safer for summer weekends. Brewery tours and wine-cider experiences are usually bookable with shorter notice, but check before you go for exact availability.

Not necessarily. Most visitors either book private transfers from the airport to their destination (Killington, Okemo) or use trolley tours to explore the area. If you're staying downtown and doing boat charters and brewery tours, you can get by without driving, but having one gives you flexibility for exploring beyond the city.

Yes - especially brewery tours (the local craft scene is substantial) and foliage trolley tours where someone else navigates the best viewing spots. Private boat charters are worthwhile if you want to learn about Lake Champlain's ecology and history rather than just floating around.

Multi-day Vermont packages usually cover lodging, some meals, and guided activities - check your specific booking for details. Day tours like brewery tastings often include tastings and a guide but may not include lunch. Private boat charters typically include the captain and boat; food and beverages vary by tour.

Lake activities and trolley tours work well for kids. Group picnic boat cruises are designed for families and small groups. Check age policies and whether specific charters (especially the smaller 6-passenger ones) accommodate children before booking.

Killington and Okemo are roughly 1.5 to 2 hours south, which is why airport-to-mountain transfers are popular here. If you're flying in to ski, book your transfer when you reserve your trip.