Ask your boyfriend where he'd like to go, but try to choose a location you both can enjoy. While it may be tempting to accommodate him when the relationship is new, it's important to be someplace you both want to be -- especially in case things go wrong. Choose a neutral location where neither has ties with a former partner.
Discuss ground rules before you go. For instance, if you've not yet been intimate, decide if you want separate rooms or if the vacation is the time to get closer. Make sure you're both on the same page to avoid misunderstandings and hurt feelings.
Schedule a loose itinerary. Select activities you'll both enjoy and maybe schedule some time apart as well. For instance, if he wants to spend a day golfing, schedule some spa time or a boat ride while he's on the links.
Keep your itinerary busy to avoid too much idle time. However, be flexible with your plans to accommodate any changes. For instance, if one of you is too tired to spend the afternoon on the go, opt for a nap and some window shopping instead of following the original plan.
Plan a balance of romantic elements with typical vacation activities. Make reservations for an intimate dinner, but also allow for meals on the go. Schedule activities that are quiet and allow the two of you to get to know each other, but also plan things that are fast paced and exciting.
Pay attention to your boyfriend throughout the trip process -- from planning through execution. The way he handles himself can give you insight into your compatibility and his personality. Spending the extra time together can really help you get to know him -- and vice versa.
