As an AI, I don’t have personal experiences or the ability to plan vacations. However, the time spent on planning a vacation itinerary can vary greatly depending on individual preferences, the complexity of the destination, and the level of detail desired. Here are some factors to consider when planning a 2-3 day city break itinerary:

1. Researching the Destination: Spend time researching the city you’ll be visiting. Learn about its top attractions, landmarks, cultural sites, and local experiences. Read travel guides, browse online resources, and check recommendations from reliable sources to get a sense of what interests you the most.
2. Prioritizing Attractions: Identify the must-visit attractions and landmarks based on your interests and the time available. Consider creating a list or ranking the sights you don’t want to miss during your visit.
3. Mapping Out Locations: Look at the map of the city and group attractions that are close to each other to optimize your time. Consider the proximity of different sites and plan your itinerary accordingly to minimize travel time between locations.
4. Setting Realistic Expectations: Keep in mind that 2-3 days is a relatively short time, especially for larger cities with numerous attractions. Be realistic about the number of places you can visit and the time it takes to explore each site thoroughly. Avoid overpacking your itinerary, as it can lead to rushing through attractions and missing out on enjoying the experience.
5. Flexibility and Free Time: Allow some flexibility in your itinerary to accommodate unexpected discoveries or spontaneous activities. Leave some free time for relaxation, exploring local neighborhoods, or enjoying the city’s atmosphere.
6. Dining and Local Experiences: Research local cuisine and popular eateries in the city. Consider adding dining experiences or trying local specialties to immerse yourself in the culture and flavors of the destination.
7. Practical Considerations: Factor in transportation logistics, opening hours of attractions, and any special events or festivals taking place during your visit. Consider pre-booking tickets for popular attractions or guided tours to save time and ensure availability.

The time you spend on planning your vacation itinerary can vary based on how much detail and thoroughness you desire. Some people may spend several hours or days researching and creating a detailed plan, while others might prefer a more spontaneous approach. Ultimately, the goal is to strike a balance between having a well-organized itinerary and leaving room for flexibility and enjoyment during your city break.