As a general rule, I haven't seen good results for my brides who have chosen to book group travel for their destination weddings. That doesn't mean that you can't get the cheapest deals by working with a travel agent for a group package — sometimes you can get better airfare or additional perks at the hotel. The question is whether the perks make up for having to travel en masse throughout the wedding.
Sometimes, brides and grooms try to create their own group travel without using a travel agent — frequently, that doesn't end well. I did it for my own wedding and, although it wasn't a complete disaster, I'm pretty sure the people whose flights arrived on time in San Juan were not thrilled about waiting in an airport for a few hours for the guests whose flights had been delayed. Some lost a half day of vacation that way.
The moral of the story: If you're going to do group travel, let a professional arrange it. If something goes wrong, your guests will be blowing up the travel agent's phone and not yours. Helping friends who missed flights can suck up a lot of your playtime during the first days of your destination wedding weekend.
Nowadays, most people travel, and some of your guests probably travel frequently, for business and for pleasure. They have their own preferred airlines and hotel chains, and they like to take advantage of their miles and points whenever they can. If they use travel agents, they have one they prefer and trust. They know what time they prefer to fly, and how long they like to stay, and whether they want to turn your wedding weekend into their own extended vacation. It's hard to personalize your trip when the bride and groom are trying to arrange your travel schedule in a manner that accommodates a larger group.
Another complaint I've heard from guests roped into group travel packages is that they didn't get anything close to direct flights. Depending on who is offering the package, some group rates will give you the cheapest airfares the most roundabout way. It may not be worth the savings to people who just want to get where they're going quickly.
If you have a travel agent you trust and want to offer discounted group rates to your guests, don't sign up for something that requires an unrealistic number of participants to get the pricing you want. Some guests will appreciate your efforts and will jump right on board. The rest can do whatever they like as long as they get to your wedding on time!
Sandy Malone is the owner of Sandy Malone Weddings & Events, a full-service traditional and destination wedding planning company and Do-It-Yourself wedding planning consulting service for DIY brides and grooms based in the Washington, DC area. Sandy is the star of TLC's reality show "Wedding Island," about her destination wedding planning company, Weddings in Vieques. Sandy's book "How to Plan Your Own Destination Wedding: Do-It-Yourself Tips from an Experienced Professional," will be released on March 1st, but is available online for pre-orders now where books are sold.