I think your business model might be wrong. As Iaks points out below, the $5 price point is not far from that of a used travel book.
Perhaps offer the content free, then work with top restaurants and retailers on the 'tours' you recommend and get them to offer coupons / deals or advertising, of which you can get a cut. People touring a city will get hungry, and if you can point them to a great place, they'll thank you.
We're running a small test with essentially this approach. We're giving away the itinerary for free and then trying to upsell/cross-sell other related services -- such as a San Francisco CityPass, tours and p2p experiences. If you'd like to take a look you can check it out here (you'll have to enter your email address to get the free itinerary) -- http://bit.ly/enWxWz
My concern with partnering with restaurants and retailers is that I feel like it's a slippery slope to disingenuous recommendations. Plus, why would a restaurant offer a coupon to a traveler (at least a coupon of value)? There's no chance of repeat business. Just some thoughts, would love to get more feedback, if you have any.
Priority #1 is to remain genuine. That's what you stand for.
Restaurants might actually be more open to offering coupons to travellers - in a sense, those customers are not repeat business, so they shouldn't be worried about impacting their long term pricing with the local market.
Ultimately, I think you need to focus first on building enough value here with consumers - I don't like to suggest making things free, but in this case I think it's something you have to give away and monetize in other ways. There's nothing bad about that approach (Google does it), but it does require a higher volume of users for it to make sense.
I don't think this product entirely competes with travel books.
I think the value is that it makes the decisions for you. You already have your itinerary set in logical/geographic order.
If I'm running through a city for 2 days, I know I can't squeeze in everything. I can either waste time deciding what to do or I can buy this and see something I know will be awesome.
Not to say that there isn't room for other revenue streams or that other revenue streams may be better, but I don't think direct sales should be discounted before a proper test.
Yes...you absolutely nailed the value we believe we're providing. Thanks :-). In fact, we've thought about re-marketing ourselves as "last minute travel guides" or something to that affect.
....ImpromptuItinerary.com? It's available. I don't know if I like it though. Too many vowel sounds, not enough hard consonants. Though the name is a pretty good description of the product.
Perhaps offer the content free, then work with top restaurants and retailers on the 'tours' you recommend and get them to offer coupons / deals or advertising, of which you can get a cut. People touring a city will get hungry, and if you can point them to a great place, they'll thank you.