Sailing can be done with ships or small craft.
- Cruising on small craft provides advice for cruising on a vessel you can afford to buy or charter by yourself.
- Hitchhiking boats are such small craft in need of crew, often for long legs across the ocean. Usually costs are shared between the owner and crew.
- Cruise ships are usually large motor ships, but some companies run sailing ships with the same overall concept.
- Sail Training International and related organisations give youth (and some adults) the chance to sail remaining tall ships of the age or sail, newer purpose built ones, or large sailing yachts. Some of the ships in the Tall Ships' Races are school ships, usually for the navy, but many allow outsiders to join some of the trips.
- Smaller sailing ships may also be operated commercially, offering possibilities to join shorter cruises, sometimes having customers do most of the sailing. Some of these can be found in the destination articles.
- Some expensive destinations also have niche markets for sailing vessel expeditions, as a small vessel can reach places were you cannot go by ship. Several operators offer sailboat expeditions e.g. to Antarctica.