Personalized trip recommendation attempts to recommend a sequence of Points of Interest (POIs) to a user. Compared with a single POI recommendation, the POIs sequence recommendation is challenging. There are only a couple of studies focusing on POIs sequence recommendations. It is a challenge to generate a reliable sequence of POIs. The two consecutive POIs should not be similar or from the same category. In developing the sequence of POIs, it is necessary to consider the categories of consecutive POIs. The user with no recorded history is also a challenge to address in trip recommendations. Another problem is that recommending the exact and accurate location makes the users bored. Looking at the same kind of POIs, again and again, is sometimes irritating and tedious. To address these issues in recommendation lies in searching for the sequential, relevant, novel, and unexpected (with high satisfaction) Points of Interest (POIs) to plan a personalized trip. To generate sequential POIs, we will consider POI similarity and category differences among consecutive POIs. We will use serendipity in our trip recommendation. To deal with the challenges of discovering and evaluating user satisfaction, we proposed a Serendipity-Oriented Personalized Trip Recommendation (SOTR). A compelling recommendation algorithm should not just prescribe what we are probably going to appreciate but additionally recommend random yet objective elements to assist with keeping an open window to different worlds and discoveries. We evaluated our algorithm using information acquired from a real-life dataset and user travel histories extracted from a Foursquare dataset. It has been observationally confirmed that serendipity impacts and increases user satisfaction and social goals. Based on that, SOTR recommends a trip with high user satisfaction to maximize user experience. We show that our algorithm outperforms various recommendation methods by satisfying user interests in the trip.