Southwest Airplane Taking OffPlanning for Vegas seems simple to the uninitiated. However, you can become quickly overwhelmed when you begin to consider the multitude of hotels, restaurants, shows, pools, spas, golf courses, roller coasters, bars, nightclubs, casinos, buffets, shopping locations, people-watching venues, old Vegas sites, new Vegas sites, and so forth.

I spent several weeks researching logistics, costs, rankings, texture, timing, and ambience to arrive at my weekend plans for two. My methodology included cross-referencing a multitude of sources including the Internet, word of mouth, and travel guides to reach a detailed three-night/four-day weekend agenda, beginning Friday afternoon and ending Monday afternoon.

When to Visit Vegas

The time of year you visit Vegas depends on what you’re going to be doing outdoors. November through February can be downright cool if not cold (believe it or not). Check out weather.com and take a look at the average temperatures for the numbers that match your needs. If you despise unbearable heat, then I’d recommend skipping the summer months.

Once you arrive in Vegas, however, you quickly learn that if you absolutely had to (such as if you were a Vampire), you could go for many days (if not years) without ever encountering actual daylight. That’s because Vegas is a massive interconnected system of physically adjoined structures with various conveyances that can get you to and fro without ever exposing you to the rugged desert sun.

Booking Your Flight

At two months out, I’d begin searching for your airfare. Start with Kayak.com and play with various dates. Vegas is a weekend haven so prices for everything will be higher on Friday, Saturday, and Sunday (Sunday night through Thursday are considered off times). That’s the premium price you pay for partaking in the weekend action. You could visit on the weekdays and have fun, but trust me, go on a weekend and participate in the debauchery. (If you want a quiet get-away, wish to utilize Vegas facilities to the fullest, enjoy the sites without a multitude of others, and save some money, then you should definitely book a Sunday-Thursday trip.)

To find the best weekend airfare, I’d also run Orbitz, Travelocity, and other engines like Travel Zoo in addition to Kayak.com. Don’t forget to check Southwest.com directly so you don’t miss out on their considerable discounts. Unfortunately, Southwest doesn’t share flight information with search aggregators. Like Orbitz and several others, Southwest.com also provides package deals so it’s often the overall price winner when you factor in flight and room.

A multitude of airlines use McCarran Airport (Las Vegas/LAS) so finding something that works for you shouldn’t be a problem.

Picking a Hotel

Most people who go to Vegas for the first time pick a hotel based on price and features alone. As a result, they either end up downtown, mid-strip, or north strip without ever thinking about logistics. While each location has its pluses and minuses, I highly recommend a hotel mid-strip. This location includes hotels such as Paris, Bellagio, Venetian, Palazzo, Mirage, Treasure Island, Wynn, Caesars, or any other big name establishment adjacent to these. Mid-strip is where most of the activities occur and staying in this area will save you a lot of time and money. For my trip, my girlfriend and I stayed at the Venetian. While the Venetian’s hotel room prices run higher than the average, it’s worth the extra money based on location, room, size, and hotel amenities. Other hotels work, too. On the high-end, I’d pick Wynn. On the low-end (but very nice) is the Mirage. All of the hotels that I mentioned are very nice and will serve you well regardless of which one you select.

Booking Your Flight and Hotel via Southwest Airlines

I booked my Vegas flights and hotel through the Southwest website. The website seems dated but it’s straightforward, simple, and quite good. (The Southwest website is the USA Today of airline booking sites.) I received the paperwork in just a few days.

Here’s one thing you should know about booking via the Southwest website, though: if you book a Southwest vacation package, you’re mailed a paper ticket that you must produce at the airport Southwest ticket counter (not the gate) for a boarding pass. And, as anyone who flies Southwest knows, 24 hours prior to your flight you can go online and print off the much-coveted boarding pass and receive a high letter and the corresponding number that allows you to board ahead of those who waited to get their boarding passes (or did not know this).

On Southwest, you board according to letter (A, B, or C) and an attached number indicates where in the queue you stand for boarding. If you get an A, you can pretty much sit wherever you want. B, is iffy. C, enjoy the middle row and possibly no place for your overhead carry-on.

The issue here is that with the Southwest Vacation Package ticket, I couldn’t go online 24-hours ahead and print the boarding pass. So I unless I chose to drive the 60 miles roundtrip to the airport the day before my trip, I was forced to get the boarding pass upon my arrival at the airport and all but ensure that I’d get a “C” boarding pass. Needless to say, I did, and my girlfriend, a Southwest first-timer, was slightly disappointed when we were forced to sit ten rows apart on the first leg of our flight.

Other Booking Tips

I did most of the bookings on my own (air, hotel, shows, and a few restaurants via OpenTable). I did cheat a little by employing my American Express Platinum Card Concierge service. By using AMEX Platinum, you’ll end up paying a little more, as they include a few amenities with your hotel (which are quite nice) for a few extra bucks. In fact, AMEX Platinum would make booking your trip so simple that if you read them my entire agenda and provided the times, they’d book everything for you — you wouldn’t need to worry about one single detail. They’re knowledgeable and efficient, and once they’re done doing all your work, they email you the itinerary with all the corresponding confirmations. Being a cheapskate and a micromanager, I booked a couple of shows and any restaurants not on OpenTable myself. Since I booked the air and hotel via Southwest.com, I didn’t get the AMEX Platinum upgrades, but I did save a couple of hundred bucks.

If you plan to go to any Cirque du Soleil shows, order your tickets via their easy-to-use website or go through the host hotel’s link; the tickets will be available for pick-up at ANY Cirque box office. No need to stand in a long line the evening of; merely waltz up to any Cirque ticket box office at Bellagio, MGM, Mirage, Treasure Island, etc. during the day and presto, you’ll have your tickets.

Buffets are a free-for-all so you can’t typically reserve a table ahead of time. Unless you have a high-roller comp card, you’ll have to wait in line, but not for very long if you take my stern advice and avoid the peak dining hours (6:00-7:30ish). Roll-in at 5:45 PM and head to the front of the line.

I only had one logistical glitch during my trip. When I checked-in to a restaurant at a previously reserved time, they claimed to have no record of my reservation. It was a non-issue as they seated us in 10 minutes anyway. Make sure you keep ALL of your confirmation numbers, the name of the person you spoke with, and any other details that might help in the event your reservation is lost.

Regardless of how you book all your fun, it’s relatively easy due to the fact that Vegas knows what it’s doing. Vegas makes it quick and fast so you can get to the casino and lose, lose, lose (or win, then lose).

Summary

Pick the time of year that works for you temperature wise, book early for a low airfare, pick a hotel located mid-strip, purchase show tickets and make restaurant reservations ahead of time, keep record of all your confirmation information, arrive on a Friday afternoon, and depart mid-to-late Monday. Getting in on a Friday afternoon allows at least a couple of hours to get geared-up. The time on Monday gives you the freedom to enjoy the things you missed during your Friday, Saturday, and Sunday drunken fiesta.

Image credit: Philip / Picasa

###

Post updates:
- August 12, 2008 at 8:15 PM ET: Southwest NOW allows you to check in online and reserve your boarding position 24 hours in advance of your departure when you book a vacation package. Click here to see the announcement details.