Narrow down the possibilities. Think about the kinds of activities your boyfriend enjoys or the places he has always wanted to visit. Create a short list of ideas, from river rafting to a winery tour. Compare all of your options by taking into account the cost of the trip and the amount of time you have to spend away from home.
Book the trip. Choose the trip you would like to take and go over all of the details before booking and paying for the various aspects of the trip, such as hotel, flight or rental car. Pay attention to all of the pricing details to eliminate any hassles or last minute fees when arriving to pick up a rental car or check into a hotel.
Clear his calendar. Enlist the help of his family, friends and coworkers in clearing his schedule. Ask a friend or family member, or several, to make various plans with your boyfriend for the days you will actually be taking a trip together. Keep it simple and mundane when creating the decoy plans, such as helping a friend paint or move over the course of a weekend.
Spring the surprise. Get creative and leave little hints, such as books about the location or activity, around the house or in his car leading up to the vacation. Consider various options for surprising your boyfriend, such as presenting him with airplane tickets when he arrives home from work. Pack his bags if possible and let him come home to everything ready to go for your adventure together.
