Would You Book A Flight To An Unknown Destination?

Destination Unknown
Flickr, Nico Hogg

Earlier this year, new booking engine GetGoing began offering deep discounts to travelers with flexibility and a sense of spontaneity. You tell the site what type of trip or region you want, and it will give you two destinations and the airfare you’ll pay, up to 40% off. The catch? You won’t know *which* place you’ll go or which airline you’ll fly until after you purchase.

Now how about booking a trip where you won’t know where you’re going until a few days before departure? FlyRoulette launched this week, taking spontaneous travel to the next level. With FlyRoulette, you’ll tell them your budget, maximum trip length, and type of trip (does “weird and exotic” sound appealing?) and it will create an itinerary for you. But you won’t know where you are going until 12-48 hours before you depart, which means you can probably rule out anywhere that requires an advance visa, but the whole world is fair game. In exchange for your flexibility, you’ll get great hotel and flight deals, but it’s not for those who want some degree of control over their travels.
Would you book a trip without knowing where you are going? While it’s an intriguing concept, there are a few issues I can see arising for even the most intrepid travelers. Without knowing what destinations are in their arsenal, a trip to go somewhere “to party” could just as easily be Daytona Beach or Berlin, two very different tastes. There could be reasons why a destination is discounted: even if you wanted a “quiet” trip, what if everything of interest is closed for the season? While you specify your maximum budget, you don’t know what portion is going to airfare or hotel, so you might prefer a destination with a more expensive flight but cheap accommodations. The site allows you to book for groups up to 25 people and was founded by recent college graduates, which may indicate their ideal demographic. It might be best for INexperienced travelers, who are more open to anything and carry less baggage (no pun intended) about how they travel and where they end up.

PackLate.com’s newest idea: sleeping with strangers

I’ve never been skiing and I’ve never heard of PackLate.com. And yet, here I am, hopping from ski shop to ski shop in Austin, Texas of all places. I’m trying to nail down a ski jacket worth the money, but I’ve already assigned more than five hours to this task and I’m beginning to work out the math of my time vs. my money vs. my ski jacket as I pull into the sixth store. I don’t think my orders are especially tall. I think they’re simple. I just want a jacket that’s black and warm. That’s it. I find it unreasonably difficult to match a jacket to my criteria and I’m getting the impression that all of these skier-by-weekend, ski-shop-worker-by-weekday guys think I’m just inexperienced. And they are, of course, correct. I’ve never been skiing before. I’ve never even seen anyone ski before.

“This purple jacket is pretty rad. It’s one of our most popular ladies jackets”, explains the employee of the sixth store, who is, I’m pretty sure, still in high school.

While I have explicitly said I’m looking for a no-frills black jacket, he seems to think I just don’t know what I want. Truth of the matter be told, I lived in New York City for 8 years–black is my default go-to color. What he’s showing me is not a go-to color. It’s fuchsia.

“I just want something I can wear when I’m not skiing, as well”, I say, becoming more hopeless with every exasperated conversation like this I find myself having. “I’m not a skier. I’m trying it for the first time ever this weekend”.

“Oh yeah? Where ya goin'”, he asks while hanging the fuchsia jacket back up on the perforated wall.

“Tahoe”, I say. “I leave tomorrow morning”.

“Tahoe!” he exclaims, suddenly attentive. “Tahoe is sick. Are you just going to ski?”, he asks, seeming genuinely curious now.

“Kind of. I’m also a part of this vacation rental experiment that this website, PackLate.com, is hosting. So I’ll be staying in a big house with a bunch of people I’ve never met before. Lets hope none of them are axe murderers”.

%Gallery-118787%As I watch the landscape unfold before me, 30,000 feet below me, from my window seat on the plane, I realize it’s not axe murderers I’m really worried about. It’s the ordinary button-pushing people I hope to avoid this weekend. I’ve caught glimpses of anonymous personalities through internet comments, ones I often find myself perusing, and I’m a little bit nervous. If I’m stuck sharing a bathroom with someone who represents one or more of my people-fears, birthed largely from the internet, this weekend might not be a good one. And thus, the risk of shacking up with random people from the online sphere.

The topography becomes more rigid, more barbed with slicing mountain tops, and soon after, the plane descends into Sacramento. I proceed to:

1. Rent a car, one with seats that will fold down. I’m staying in Northern California a week longer than my housemates in Tahoe and I don’t yet know where I’m going or when I’m going there. And I don’t think the ability to sleep in my car will be a bad thing.

2. Locate, purchase, and devour In-N-Out Burger. There’s no choice in this move; it’s inarguably necessary.

3. Drive east until I stop at a CVS to purchase: hand and foot warmers.

4. Pull over to take photos of the striking views from the road leading into town, South Lake Tahoe.

5. Arrive at the vacation rental house in Tahoe.

PackLate.com is a website that offers low last-minute prices on vacation rentals to travelers willing to leave town at the drop of a hat. But CEO Steve Barsh has been thinking–something he seems to be very good at doing. While in Park City, Utah recently for none other than the Sundance Festival, Barsh found himself in a unique situation: alone in a big house. Being alone in a towering living space can be disenchanting for most people, but Barsh did something about it: he put out an S.O.S. on the PackLate Facebook page. Here’s how it looked:

“The CEO of PackLate is staying in a huge, gorgeous 3 BR condo in Park City this weekend (1/21-1/23). Inviting any PackLate.com fans to stay for FREE and come enjoy skiing or Sundance Film Festival. LIKE this post if you want to stay and we’ll reach out to you go try to get you in! Room for 2 other couples / 2 pairs of friends. Uploading photos in a moment.”

And then, as promised, the photos were released. Actually, you can still check them out right here. With only five photos up for the viewing, PackLate fans did respond to this outcry and, on their own dime, a few of them flew out to Park City for the weekend of January 21st. Their incentive? The free lodging, naturally. But there were also other appealing elements present for fans who were interested in this weekend: spontaneity, experience, and the prospect of making a new friend. And according to firsthand reports, these thirsts were quenched. The end result was good. Good enough for Barsh to want to do it all over again.

Just three weeks later, Barsh was at it again. The logic was this: if his random mingling of strangers in his Park City condo that January weekend had gone so well, it could go well again. Without much time to put it all together, PackLate soon after announced another opportunity to share a vacation rental with Barsh–in Tahoe. His marketing whiz, Stephen Daimler, would also be on the trip this time around. Photos of a well-to-do vacation rental with half a dozen or so bedrooms were posted on Facebook and fans were asked to leave wall comments explaining why they wanted to spend the weekend in Tahoe. Again, fans would have to pay for plane tickets on their own, but the lodging would be covered–and shared.

Over 100 fans clamored for the weekend getaway this time. The winners were eventually chosen and invited to bring a guest. Rob, an absolutely cool guy from Florida, wound up in Tahoe, but he had first been one of the guests in Park City. Happy with the way things had gone in Park City, he and his son Scott arrived in Tahoe cradling several bottles of von Strasser wine–a little house warming gift they transported from their own vacation home in Napa.

Four other guests eventually poured into the the spacious open kitchen; two couples from San Francisco. The savory wine helped break the ice, but ice-breaking with this crowd was already easy. At my initial detection, I ascertained that there weren’t any axe murderers nor walking manifestations of my other worst fears among us. And so I found myself engaged in truly interesting conversation whilst dismantling an impressive hors d’oeuvre spread laid out by Barsh.

“So Elizabeth. You’ve never been skiing before?”, asked Barsh, without a single presumptuous inflection in his voice.

“Nope! This is my first time. I’m excited”, I said, reminding myself that I was, in fact, excited and not terrified.

“You’re going to have so much fun!”, he responded with a bit of authoritative enthusiasm, as if my fun-having was non-negotiable–a fact of skiing.

There was a tangible excitement in the air of the house the following morning. We were all waking up and dressing for the mountain while the two Steves were making bacon in the oven, scrambling eggs, and arranging cut fruit, juice, and other morning grains on the wide-spanning kitchen bar. Rob used a coffee filter cone to fill my cup with Ritual Coffee, which is, as it turns out, damn good coffee. Daimler offered to drive to Kirkwood Resort–about 45 minutes south of South Lake Tahoe.

I discovered myself feeling something I had felt at other times in my life… during choir camp, volleyball conditioning, freshman orientation: instant camaraderie. I’ve spent much of my adult life living with people who were complete strangers before I lived with them. By and large, the thanks for this goes to Craigslist; a matter-of-fact necessary tool when trying to nail down roommates in New York City. And while things don’t always go swimmingly well with strangers I suddenly find myself camped out with, things usually go acceptably well. Most people, I believe, are not bad. Most strangers, I believe, are not threats. Had I believed anything other than, I wouldn’t have wound up in Tahoe for this social experiment to begin with.

And so we skied.

And so I fell.

And so I got back up, repeatedly, and skied some more.

When we finally left the hills of Kirkwood late that afternoon, we gathered around a large picnic table style booth at a nearby pub and dug into several plates of deep-fried appetizers and we chased the food with well-deserved beverages. Amid our dinner conversation, Barsh requested our thoughts on the concept we were, at that moment, practicing: vacationing alongside perfect strangers.

Unbeknownst to Barsh, our collective voices spoke loudly on this topic. Not only were we all fully supporting the concept at hand, and having fun doing so, but we were suddenly brainstorming. How could PackLate do this again? How could PackLate do this again without PackLate employees present? Would people pay substantially lower rates for a vacation rental they would be sharing with (hopefully) like-minded travelers? Our answer was: yes. Our recurring question was: why not?

The hot tub’s water spilled onto the deck that night with our over-occupancy. But the stars were bright and the cold mountain air had a certain holistic breath to it, one I inhaled slowly and deeply before running (while screaming and laughing) up to the master bedroom’s in-room sauna/steam room.

We went to Heavenly Resort the following day.

And so we skied.

And so I fell.

And so I got back up, repeatedly, and skied some more.

Our respective departures were genuinely a little bit sad and definitely a little bit too soon and PackLate’s vacation-with-strangers concept was still rumbling around in my head when I arrived in San Francisco much later that night. I thought, and still think, they’re really onto something. I mean… why not?

Why not match yourself by way of interests, like skiing, with like-minded people who are also seeking like-minded people?

Why not save a significant amount of money and shack up together in a vacation rental?

Why not have an unexpected adventure?

Why not make some new friends?

PackLate’s idea is still zygotic. They’re still thinking on, polling, and tweaking the concept. But this ‘share a vacation rental’ idea may soon be integrated into the travel services they offer on their site.

And according to Justin, one of the PackLate fans along for the Tahoe trip, this idea is a good one. When I asked him what he thought about the weekend once he’d been settled back into his home in San Francisco for a few weeks, this is what he said:

“Tahoe via Packlate was a really great experience where we were able to enjoy amazing accommodations, ski fantastic slopes, and meet great friends in the process. I would definitely use and or join a group using Packlate again in a heartbeat!”

Barsh had some comments, as well.

“PackLate is experimenting with pairing together people with strong common interests, who don’t know each other, in the same home”, says Barsh when I ask him to describe to this concept. He continues on to describe the current state of the concept, “We’ve gotten tremendous direct feedback and it’s a thrill to experience it with our customers and learn from them. It’s something we’ll continue to test”.

And while PackLate is still testing, my advice is to keep your eyes peeled. Hostels, B&Bs, airbnb.com, couchsurfing.com–these are all accommodations options playing off of the success of introducing strangers with a common bond in travel. If PackLate can narrow those interests down even further, the success, I presume, should be larger. If they wind up generating enough support to offer vacation rentals for music festivals, I’ll see you in Tennessee for Bonnaroo. And I’ll leave my ski jacket at home.

Early Christmas gift from the airlines – no advance purchase surcharges

After several years of adding additional fees and rules to our tickets, the airlines are finally giving us something back for the Holiday season.

Seven of the major carriers (American Airlines, United, Delta, Northwest, US Airways, Frontier, AirTran and Midwest) announced that they would waive all advance purchase rules for tickets between today and January 4th 2010.

What this means to last minute travelers is that an $1800 ticket will be about $1500 cheaper when purchased for same day travel.

Of course, the airlines wouldn’t be the the money makers we know them to be, without a bunch of restrictions on their sales:

The cheapest tickets are available on Dec. 16, 17, 25 and Jan. 1 and 4

The second cheapest level airfares are about 30% higher than the lowest fares. Travel for this level is valid on December 18, 20, 21, 24, 30 and 31.

The third cheapest level is about 55% higher than the lowest fares. Travel dates will be December 19, 22, 23, 26, 28 and 29.

December 27 and January 2 and 3 have not been included in the holiday fare sale – and those tickets could end up being substantially more expensive.

(Source: USA Today / Bestfares.com)

Bottom line is that even though the airlines appear to be the good guys, their complicated fare structure could end up costing passengers more. Travelers tend to book flights for the holiday season in advance, so removing last minute purchase rules really only benefits those that suddenly decide to go somewhere for Christmas or who run into sudden changes that require a last minute ticket purchase.

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Last minute flights may be cheaper than the bus

Searching for travel deals feels like playing a game show where how to get a winning number is unclear. It’s like hunting in a jungle where the frequent hunter has the edge. Timing remains the wild card.

Being flexible and not assuming the outcomes makes the difference between snagging a deal or paying more than you feel happy paying. The one that makes you whine.

Case in point: A friend of mine bought a round-trip ticket to New York City from Columbus for $240 two weeks ago for a trip next week. He smacked his forehead when I told him I bought a ticket last Saturday for $138 total. My trip is tomorrow.

The price surprised me as well. Before buying a bus ticket, expecting Greyhound would be much cheaper since it usually is, I searched plane fares last Friday “just in case.” Surprise, surprise.

But, I also learned–again– the importance of not hesitating. I waited until Saturday to buy the ticket while ironing out life’s logistics, thus missed out on the flight I wanted. Delta’s prices had almost doubled.

Another search found the $138 price on American. The hesitation, though, means flying out at 5:40 in the morning. Blech! Still, the less than two hour plane ride is $30 cheaper than the 14 hour bus ride. Factor in the cost of the bus from LaGuardia into Grand Central Station and I’m still $8 ahead.

While hunting for your own deal, keep the following points in mind.

  • Don’t assume you know prices before you check. You may be surprised.
  • The more often you check prices, the more you’ll know what is a price you’re willing to pay. (This is my 6th trip to NYC since June. This is the 2nd time I’ve flown. The bus has been the best option three times and two weeks ago we drove.)
  • When you see a price you want, don’t waffle. Your life can adjust to the decision you’ve made. (The beauty of bus travel is that it’s more flexible than flying.)
  • Don’t pay too much attention to headlines that talk about the price of travel. In the travel business, so much depends upon timing. What’s true in the morning could have shifted by the afternoon. Keep looking. Hunt out every corner of options and stay flexible.
  • If you’re flying to New York City, the airport you fly into can make a difference into the cost of a flight. Pick the option that checks the price of all NYC airports. Once you know which airline has the cheapest price, book your ticket through that airline.

Good luck hunting out the best travel deal for you. It could be the bus.

Airlines roll out last-minute sales for Labor Day

There are just two weeks left until Labor Day, but it’s not too late to plan a getaway for the holiday weekend. In fact, waiting until now to book your trip might even save you money with some of the great last-minute deals that are available.

American Airlines Flights
American Airlines has several destinations on sale for Labor Day. Buy your tickets to Belize by August 28th and travel Monday through Thursday, starting September 1st, for as low as $217 each way. Book a trip to Jamaica by August 24th for travel any day of the week after September 1st, and prices will start at $84 each way. Tickets to Cancun, booked by August 25th for Saturday and Tuesday travel after September 1st, start at $88 each way.

United Airlines Flights
If you can stretch your weekend until Tuesday (departing on Saturday), book tickets to destinations within the United States on United Airlines by August 25th to save. Prices vary by departure and destination cities, but sample fares include Chicago to New Orleans for $89 each way, Atlanta to Denver for $109 each way, and Miami to Washington Dulles for $69 each way.

Spirit Airlines Flights
Spirit is well known for its near-constant sales to destinations within the United States, Central America and the Caribbean. It’s like the Gap of airlines – never pay retail because, just as the Gap will knock 50% off those jeans in two weeks, chances are that Spirit will soon offer a better deal for the flight you want. Their current sale ends tomorrow, August 25th, and discounts some of their more popular routes to as low as $33.90 each way. As with all of their sales, $9 Fare Club members and those in hub cities like Fort Lauderdale and Detroit save the most and have the most options. But even the rest of us can still get some good deals for Labor Day. For example, New York to Medellin, Colombia is $138.90 each way, Boston to Myrtle Beach is $68.90 each way, and Atlanta to San Jose, Costa Rica is $128.90 each way.

Expedia.com Deals
Beyond flights, Expedia has deals on just about everything else – hotels, cars, cruises, package deals – for your Labor Day travels. Deals vary widely by location, but some of the highlights include discounts of up to 50% off hotels in Las Vegas, Orlando and Chicago (among other cities) and 3-night Royal Caribbean Bahamas cruises for as low as $262 per person for an inside cabin.

If these deals don’t work for you, there’s still plenty of time to plan your perfect Labor Day vacation at a great price. Check out Hotwire’s Travel Ticker, peruse the sale list on Travelzoo and follow your favorite airlines on Twitter. JetBlue and Southwest regularly post their top deals on twitter, so you’ll be the first to know about great fares.