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.

Good luck!

Thanks! I think you're right and a great idea. We've discussed a redesign for a while now. We couldn't justify the cost when we were bootstrapping. Now that some cash will begin to roll in again I think it would be worth it.

Email me at inlith@gmail.com. I might be able to help you out with the site redesign.

I am a freelance web designer and i love helping out startups with tight budgets. My portfolio is at madebyargon.com

Thanks Rishi -- I really appreciate the feedback. That's interesting and not something we had thought about.

Unfortunately we don't have anything in Hawaii yet. Thanks for checking it out though.

Thanks, will do.