I don't think there is any perfect approach but we have found it works for our family to spend an extended amount of time together - work and school keep us very busy during the year and we have taken our son out of school for long vacations from kindergarten to Grade 8 (currently) - he isn't the greatest student and struggles with ADHD and social skills but his teachers are very supportive and see this as an alternative learning opportunity for him - the improvement to his social skills and other exposure he gets on these trips is very beneficial - when he was younger he would do a "trip report" type of assignment and math and language sheets. In older grades their work is on Google Classroom so he is able to log on and keep up with a lot of the work - yes, he misses the in-class instruction but honestly, his grades would likely not be better even if he was there - the one on one time we have with him to go over his lessons a bit each day on vacation actually seems to help him improve - this is the last year we plan on a big trip as he heads to high school next year and it will be harder for him to keep up/catch up but i wouldn't trade our time together for anything and the travel has had a huge impact on his world view - we have sailed 5 transatlantic and 3 panama canal cruises during the school year (he has visited Spain, Portugal, Italy, the Canary Islands, France, UK, Denmark, Norway, Iceland, The Netherlands, Mexico, USA (including Hawaii), Columbia, Aruba, Costa Rica as well as other Canadian Maritime Provinces) - we have cruised primarily in May or over a time when there are some school holidays to minimize the impact. If it works for you and you are comfortable, do what is best for your family.