Tripshare, an iPad application for travel planning, is joining a crowded space. But its CEO knows a little something about the industry – Bob Dana was the former employee No. 1 and first CFO of Virgin America. He once wrote the business plan and feasibility study for Sir Richard Branson in 2003. And now he’s doing a travel startup.

Dana tells us the inspiration for Tripshare was based on a personal experience he had years ago. As CFO, he spent 10 hours on a plane each week flying back and forth from New York to California. In 2006, Dana was trying to convince his family to come out to California for a vacation, so he put together a proposed itinerary to help sell the idea.

“I ended up preparing this 10-page Word document that included text and photos I cut and pasted from various websites. It was intended to be persuasive in nature, and collaborative, too,” he explains. “I thought afterwards, that collaborative travel planning was something that was rather difficult to do.”

But not only was it difficult to plan, it was also hard to move from the point of inspiration and discovery to actually booking the trip. This idea later formed the basis for Tripshare, which he founded two years ago.

The app was originally built in conjunction with then co-founder and CTO Ken Goto, a former director of engineering at Apple. Goto has since moved on but his ex-Apple development team, including acting CTO Eric Kapke, now continues the work.

The app itself has actually been live in the iTunes App Store as unpublicized beta since August 2012. However, though that app was functionally similar, it drew some criticisms from early users because of its user interface. Today’s version is an overhaul and much improved.

Still, despite having done no publicity or marketing, Tripshare has been downloaded nearly 20,000 times while still a work in progress. In other words, today’s release is technically a version 2.0, but for all intents and purposes, this is the big debut.

Designed for those planning vacations or other complex trips with multiple destinations or activities, Tripshare allows you to browse, collect and share information with others before booking. Using the iPad’s big screen, you can flip through photos of destinations and lodgings, create itineraries and discover flights, hotels, restaurants, activities and more.

Today, the app allows you to explore more than 20,000 cities worldwide, plus 500,000+ lodging options, thousands of flights, and more than 200,000 tours, activities and restaurants.

After creating a sample itinerary, you can then share it to other Tripshare iPad users, or via email, Facebook, and Twitter. For those not using the iPad application, the shared trip displays in the web browser. These trips can include all the details, too – photos, descriptions, reviews and prices – so your family and/or friends won’t have to redo the work on their end before giving you their feedback. Pricing and availability also update in real time, something another new planning app, Pintrips, offers as well, but on the web.

Users can also communicate with the trip organizer within the application using an IM-like chatting function, or leave suggestions if the trip’s planner is offline.

While there are quite a few trip planning applications and services on the market (and that’s an understatement ) what makes Tripshare stand out is not the uniqueness of the idea, but the overall package. The app’s user interface is easy to use, which is critical when planning complicated trips where you’re trying to pack in a lot of activities and outings.

At first glance, Tripshare seems inspired by Khosla-backed social travel app Jetpac, which uses smart technology to index photos from social networks, allowing you to see where friends have traveled in order to find inspiration for trip-planning purposes. It has the same general layout, and it shares some common features, such as the idea of making a list of places you want to go.

But Tripshare’s photos don’t come from Facebook. They’re high-resolution images from its travel partners, including HomeAway, Fly.com, the Expedia Affiliate Network, and Viator.com. Plus, the overall vision for the application is not one of just inspiration, but converting that inspiration into an actionable itinerary by actually allowing you to book the trip, including the flights, hotels, outings and more, directly in the app.

Dana says the company plans to integrate content from more travel aggregators and services into the app in time, including things like vacation rentals from Flipkey, car rentals, restaurant reservations, cruises, safaris, and even travel insurance. By year end, the plan is to have many of these live, as well as an iPhone-optimized application. Afterwards, the goal will be to further build up the social community.

Tripshare is backed by $1.47 million in angel funding; some of that is founder money, and the other part comes mainly from the New York angels community, including David S. Rose.

The app itself is free to users, as it will earn revenue via a percentage of the bookings users make. Tripshare is live here on iTunes.

Continue reading here: Social Trip Planning App Tripshare Converts Travel Inspiration To Bookings