Be Your Own Travel Agent: Planning Group Travel On Your Own

I’ve always loved planning group travel, and while certainly not the easiest task ever, it’s quite rewarding.

  • My sophomore year in college, I took 6 other students to New York City via Mega Bus for a weekend of broadway and sites.
  • My junior in college, I took close to 20 students to Chicago via Amtrak for a weekend of museums, comedy and more.
  • Last year, I took 4 other friends via plane to Walt Disney World in Orlando, visiting the theme parks and attractions.

Pros of Organizing Group Travel

  • If you have other pay you for the cost of their expenses, you can pay for the purchases on your credit card, accumulating points.
  • You can generally have control over the accommodations, flight routings and more.
  • You’ll have friends for life if you plan things correctly. 🙂


  • When traveling with a group, accommodations can be a bit tricky since you’re either looking for large suites to fit enough people or rooms with two double beds.
  • I generally prefer larger suites or condominiums, since they provide more flexibility. In New York, I packed the 7 of us into an Embassy Suites hotel room, splitting up sleeping arrangements amongst a pull-out couch, and two double beds in the back. For Disney, we were lucky to have a condominium at Old Key West where there was a master bedroom with one king bed, a second bedroom with two double beds, as well as a living area with a pull-out sofa.
  • I try to find locations downtown or close to transportation, since you want to minimize extraneous movement that would otherwise be easy with one person. I look for free transportation to and from hotels to airports and other locations, or hotels that are within walking distance of major attractions, since you don’t want to be inconvenienced having to train into the big city, even though it might be a tad cheaper.
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  • Depending on the group you are taking, your transportation options may depend on the tolerance of everyone else. If things are close enough, consider the bus since it’s cheaper. When I went to NYC with my friends from college, we were fine on the Mega Bus not only because it was cheap, but because it did have reasonable departure and arrival times. For Chicago, I maximized time by utilizing an overnight Amtrak train departing Washington in the late afternoon and arriving into Chicago early the next morning. By that point, everyone was able to hit the ground running.
  • When I traveled to Disney, I used one of my companion passes off of my US Airways Dividend Miles MasterCard to transport two friends at $99 a person, as my companion. What I ended up doing is dividing the cost of airfare amongst all of us, so everyone would receive a portion of this discount.

Attractions and Entertainment

  • With Disney, I had a hard time finding discounts since Disney is so stingy on them, and we weren’t large enough for a group rate. Since I had AAA, and none of my other friends did, I used them to book the tickets, and we received the discounts for all of us, saving money.
  • For major cities such as New York and Chicago, I used CityPass booklets since it exposed everyone to the major sites, but saved money on admission fees and time on getting inside.
  • In places with a public transit system, I purchased all-access, all-you-can-use passes to minimize time and ticket machines and expedite getting from one location to another.
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  • Dining is another tough thing since everyone has a different budget, but at the very least, I like to plan at least one meal that’s “nice” or culturally relevant. In Disney, we went to Le Cellier, my favorite steakhouse in EPCOT. I try to build this expense into what I charge people, since I feel a nice dinner is worth it for camaraderie. Otherwise, I try to stick with simple, or buffet style options since they’re cheaper. I try to plan out the locations of these restaurants in advance that way reservations can be made, and it blocks out a time on the schedule.

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