1. Know the seasons.
It's easy to get excited about a vacation or destination. We typically pick our vacations based on beautiful pictures of that place and our work schedule or school breaks. Often we assume the weather and seasons coralate with ours at home. This is soooo wrong in some places. Last thing you want to do is plan a beautiful trip to see tulip fields and get there and they haven't bloomed for the season yet. Or End up on the beach during hurricane season.
Once my friends and I took a trip to St Barth's. Now this place is beautiful. It's a celebrity hangout and kind of like the hamptons for the Caribbean because there’s no large scale commercial flights that service this island. It's also 1 of the only caribbean islands with designer shopping like Louis Vuitton. So long story short we got there a month before the party season started and there was almost no one there. Annnnnd most of the stores where closed for the off season. They all had signs posted saying they would open next month. Bummer. And they were under construction. This could actually work in your favor if you plan right. Going to most places during the off season offers discounted prices, shorter lines, and emptier attractions. So bring the party with you in a group and it may be perfect.
2. If you‘re traveling for a relax vibe vacation avoid special events unless you're apart of said events. For example, don't go to Las Vegas during fight weekend. Everything's going to be crowded and 10 times more expensive to get into clubs and parties. Don't go looking to party during all-star weekend. Fashion week. Super Bowl. On the other side these type of events are great if you’re looking for great parties and have thousands of dollars to pay for tickets and hotels.
3. Do yourself a favor and book direct through an airline or use a travel agency.
Book airline tickets and hotels straight through the hotel and airline.... I've been victim and heard countless stories of third party sites like Travelocity.com messing up bookings or not giving refunds or some type of problem.... just cut out the middle man and do it yourself.
4. Do real human research..... don't count on hotels photos. Use Trip Advisor to see photos and reviews from other guests.
5. Pick your destination based on flight prices.
Once I did a European tour.... At the time flights from Atlanta to Amsterdam were something like 22k for 1st class.... while tickets from Atlanta to London where $2500 first class. Spend a day in London then catch a train to Amsterdam. Problem solved