Background: Annually, approximately 10 million pilgrims travel to the Kingdom of Saudi Arabia (KSA) for Umrah from more than 180 countries. This event presents major challenges for the Kingdom’s public health sector, which strives to decrease the burden of infectious diseases and to adequately control their spread both in KSA and pilgrims home nations. The aims of the study were to assess preventative measures practice, including vaccination history and health education, among Umrah pilgrims in Saudi Arabia. Methods: A cross sectional survey was administered to pilgrims from February to April 2019 at the departure lounge at King Abdul Aziz International airport, Jeddah city. The questionnaire comprised questions on sociodemographic information (age, gender, marital status, level of education, history of vaccinations and chronic illnesses), whether the pilgrim had received any health education and orientation prior to coming to Saudi Arabia or on their arrival, and their experiences with preventative practices. Results: Pilgrims (n = 1012) of 41 nationalities completed the survey. Chronic diseases were reported among pilgrims (n = 387, 38.2%) with cardiovascular diseases being the most reported morbidity (n = 164, 42.3%). The majority of pilgrims had been immunized prior to travel to Saudi Arabia (n = 770, 76%). The most commonly reported immunizations were influenza (n = 514, 51%), meningitis (n = 418, 41%), and Hepatitis B virus vaccinations (n = 310, 31%). However, 242 (24%) had not received any vaccinations prior to travel, including meningitis vaccine and poliomyelitis vaccine, which are mandatory by Saudi Arabian health authorities for pilgrims coming from polio active countries. Nearly a third of pilgrims (n = 305; 30.1%) never wore a face mask in crowded areas during Umrah in 2019. In contrast, similar numbers said they always wore a face mask (n = 351, 34.6%) in crowded areas, while 63.2% reported lack of availability of face masks during Umrah. The majority of participants had received some form of health education on preventative measures, including hygiene aspects (n = 799, 78.9%), mostly in their home countries (n = 450, 44.4%). A positive association was found between receiving health education and practicing of preventative measures, such as wearing face masks in crowded areas (p = 0.04), and other health practice scores (p = 0.02). Conclusion: Although the experiences of the preventative measures among pilgrims in terms of health education, vaccinations, and hygienic practices were at times positive, this study identified several issues. These included the following preventative measures: immunizations, particularly meningitis and poliomyelitis vaccine, and using face masks in crowded areas. The recent COVID-19 pandemic highlights the need for further studies that focus on development of accessible health education in a form that engages pilgrims to promote comprehensive preventative measures during Umrah and Hajj and other religious pilgrimages.