In 1489, Roger Machado led an Embassy to Spain and Portugal for Henry VII of England. The account he gave following his return includes an interesting description of both sea crossings, from Southampton to Laredo and from Lisbon to Padstow (Cornwall). Offering the viewpoint of a landsman travelling as a passenger rather than that of a mariner, the account given by Roger Machado provides insight into the different stages of a sea voyage at the end of the 15th century: lodging on land before boarding, chartering a ship, a rough crossing or easier conditions depending on the weather encountered, landing and leaving the ship.