Step by Step Start researching for your trip destination by getting inspiration from guides or travel books, travel blogs, articles, or even families or friends. How many days do you need? Choose the best day regardless of the season. It's better offpeak or shoulder season, though. You can start with looking at or comparing accommodations, transportation, food, activities, etc. – both offline and online. Prepare your paperwork, automate bills, hold mails, tell your families, friends, or neighbors. Don’t over-packing, unless you go for months. Don’t forget the essentials. How to Plan Your Dream Trip