Friday, February 25, 2011

Group Vaycays Done Right

Part of our fabulous and amazing group at Marquee at the Cosmopolitan in Las Vegas, NV
[Nightcap Clothing lace dress, Shotwell earrings]

Planning a vacation for a large group is a task that should not be taken with folly.  The person tackling this daunting but worthwhile job should be aware that the role requires due-diligence, a TON of patience (something I could still improve on), some savvy-know how, string-pulling, and a love for organization.  I'll have you know; however, that it is COMPLETELY worth it.  Group vacations are some of the most amazing, memorable and FUN experiences to have  if the trip goes well (AKA – not a complete disaster).  Someone in every group of friends should (wo) man up and take on this role, because every group of friends should go on at least one or two big vacations! Once travel and check-in is complete, most of the stress is over, and you can then relish in all your hard work as group coordinator.

1.  The group.  When planning a group vacation, take into consideration the people you are including in the trip.  Some peoples' personalities are not going to do well with situations that may be stressful, physically or emotionally demanding, and keep in mind that when people travel our personalities tend to shift a bit -as we are all a tad more elevated on varying levels when we are away from home.  In addition, consider how  personalities will react with each other, and re-examine whether or not you want to bring any and everyone on your trip.   Keep this in mind when choosing who's rooming together.  Try not to stick one person who may not be as close with others in a room just because it might be convenient for you - this often ends up being awkward and in my experience, the person could bail on the trip entirely because they don't want to be in a weird rooming situation, understandably.  This will aid in encouraging a welcoming atmosphere and to help keep them happy.

2.  Your expectations.  One of the most important things I've learned while planning group trips over the years is: everything is not going to go as planned.  Things will have last minute changes, and in the past (more early on) this has upset me.  I now know that the trip planner can only do the best that they can to create a perfect trip, and only about 60% of what was planned for is actually going to happen.  I say, embrace it!  This is one of the many fun aspects of a group trip.  Think about how a flock of birds fly together - going any which way - sometimes splitting up, but usually blending back and moving forward together.  You can only do so much to keep it all tied in, and in many ways it is like being a kindergarten teacher - it is very difficult and virtually impossible to keep everyone in the same place.  Know that people are going to branch off to do the various activities they want to.  Allow this to happen, but plan a unifying group activity for each day (lunch, dinner, drinks, nightclub) that will bring everyone back together.  You want to be the group point person, not the planning group Nazi.

3.  The location.  Choose a location that is going to have many different outlets for all kinds of personality types.  Some people will want to sleep in and wander down to the pool or spa to relax, others may want to go out exploring, shopping or for a hike. Choosing a fun location with options will help keep everyone happy.  In addition, make sure everyone has hotel rooms booked at the same hotel and with rooms on the same floor or connecting if possible.  Explicitly specify when booking the rooms that you would like all rooms to be linked together, even if under different names.  Many times hotels offer discounts or benefits for booking multiple rooms at the same time, so make sure to inquire about this as well.  Also, encourage your party people to book their itinerary as soon as you do.  Prices will only go up over time (can’t stress this enough) - and if you've gotten them to commit, nudge a bit to have them book ASAP or else they'll be tempted to cancel on you when prices go up after they've procrastinated booking their tickets and rooms.  If someone is being particularly unreachable or non-enthusiastic, drop ‘em early on.  Enthusiasm is an important thing to bring on a group trip, and after years of getting on people for this, I now say don’t waste your energy and efforts on someone who is being flaky. You’ve got enough on your plate.

4.  The vehicle.  It is ideal if most people are on the same flight to encourage the group atmosphere, however there will always be a few stragglers that plan their own flights.  I recommend flying Southwest Airlines WHENEVER possible. They are the only airline that does not charge a change/cancel fee if your dates change and they do not charge for checked bags.  Believe it or not, this adds up.  Yes, Virgin America has cool-looking planes, but you will be pissed off and regretting booking with them when you have to pay $75 per flight to change your itinerary AND $25 per checked bag. It adds up!  If you are driving, encourage everyone to meet at one spot, all leaving at the same time.

5.  Foresight.  Make sure to always anticipate change, and having enough room on your credit card (or in your wallet) for any unexpected mishaps or change in events is usually a good idea.  For example, on our most recent group excursion, we ended up having to switch hotels at the very last minute.  I was able to book 3 rooms at our new hotel immediately on my credit card, but in the meantime, I was still waiting for my deposit funds to be released by the old hotel.  Had I not had enough room on my card to re-book, this could have made things a lot more complicated.  In addition, expect a lot of confusion when paying for any and every group activity.  The best way to go about it is by having one person pay the venue, with everyone paying that person back.  It is that person's responsibility to do the math correctly and make sure they are being reimbursed appropriately.  Taking turns between bill payers each time ensures not one person in particular is paying for everything, over and over again.  This usually applies to dinners and bottle service only.  And, if you're feeling risky – try credit card roulette.  Heh heh heh. ;-)

-Another tip: when booking restaurant or nightclub reservations, always give an estimate of how many people are going to be coming, for example 10-12.  One or two people are always going to drop off or add to the party, and the venue should be aware that the party size may fluctuate.  However, when going to a nightclub – make sure to provide a guest list with full names to your host – this is the #1 thing a lot of nightclubs request going forward with your reservation, and if you dilly-daddle on it they will probably put you on the back burner thinking you’re not serious (this is our attitude at the club I work at).  Just let them know that a few people may add on or drop off.  Planning large dinners is probably the most difficult part of a group vacation - many restaurants require a credit card to hold the reservation and the seating setup is often awkward as well when it's groups of more than 8.  I would really only suggest doing a large dinner if the group is 10 people or under.

Advice for the group goers:

-Be on time to any planned events.
-Expect to contribute a fair and equal amount of money to dinners or other planned events. Don’t be the group cheap ass, scrutinizing every detail of the bill and asking tons of questions – great way to get on the fast track to annoying everyone in the group. If you end up paying $20 more than you should have, make a point to pay $20 less at the next dinner/lunch etc.  Do NOT make a scene at the restaurant when everyone wants to just get out of there and party.
-Don't be afraid to suggest or partake in any planning! The more ideas the merrier. Being a vacation planner is much like being a party host -any help is always welcome.
-Realize that people are going to act a little differently on vacation, and things are subject to change at any point.  Embrace this!
-Whatever you do, don't back out at the last minute!
-Take pictures!  The more people taking pictures, the more likely that everyone will actually get to see them!  Picture posting laggers, you know who you are!  ;-)

And most importantly, have fun and be patient.  I'd do it again in a heartbeat!  So worth it.


My friends enjoying our trip!


  1. commented. I am not surprised you were in charge. There is a reason why I ask you to do everything.

  2. well said! I would totally do it again in a heart beat! Pictures pictures pictures!

  3. So much fun with your best buddies is definitely worth every effort and must repeated as often as possible