Example methods and systems are provided for cross-cloud connectivity checks. One example method may include detecting a first connectivity check packet that is addressed from a first virtualized computing instance deployed in a first cloud environment; and determining that the first connectivity check packet is destined for a second virtualized computing instance in a second cloud environment reachable via the network device. The method may also comprise: generating a second connectivity check packet by modifying the first connectivity check packet to include one or more indicators that a connectivity check is required along a datapath towards the second virtualized computing instance in the second cloud environment. The method may further comprise: sending the second connectivity check packet to cause one or more observation points along the datapath to, based on the one or more indicators, generate and send report information associated with the second connectivity packet.