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When you're visiting a city for the first time, are you armed with a list of attractions and a map to find your way, or do you go one step further to plot a customised sightseeing itinerary of the city you're visiting?

While the first option works fine (we recently reviewed City Maps 2Go, which has an added perk of working offline), the latter could help you choose to stop by the art galleries at London’s Tate Modern after visiting St Paul's Cathedral, instead of the Tate Britain (which is 40 minutes away on the Thames River by ferry).

Mapping out your favourite attractions will give you an idea of the best course to chart around town. Here are some free digital tools for planning an itinerary quickly.

Your Tour
Your Tour
is the best tool for creating multi-day road trip itineraries, and this Belgian-based start-up stands out for its deep coverage of Italy, France, Spain, Andorra and, randomly, Florida. The site recommends hotels via Booking.com and includes airport and rental car information, too, so you can truly hit the ground with a comprehensive itinerary. In a nice touch, it provides estimates of the fuel costs for driving each stretch of distance, in case you want to alter your itinerary to incur less road time.

After you plug in your arrival and departure points and your travel dates, the site suggests a "greatest hits" itinerary. You can then customize the suggestions based on your level of interest in various categories (like nature or culture), and then you can refine the results further by telling the site you are only interested in animal attractions and parks. The itinerary list provides detailed information like hours of operation, admission and related practical concerns, plus you can print the itinerary, e-mail it to yourself, or share it via social-networking sites.

The site is far from perfect. Its itineraries aren't formatted to be easily viewed on mobile devices, and the printout versions lack maps and driving directions. The site's other main drawback is its limited geographic relevance. It doesn't include street level information on how to sightsee on foot and ignores major cities like Paris and Miami. Additionally, it fails to offer restaurant recommendations or even to account for the amount of time lunch might take.

Plnnr
This Israel-based website focuses on providing street-level advice for planning a trip to one of the 20 cities most popular with leisure travellers, such as Paris, London, New York City, Rome, Barcelona, San Francisco, Berlin, Prague, Dublin, Toronto, and Washington, DC.

Like YourTour, Plnnr has a questionnaire, and it will customize its sightseeing suggestions based on your answers. Tell Plnnr how much walking you're willing to do, which hotel are you staying at (if you already booked one), whether you are more of a museumgoer or an outdoors person, how many days you're in town, and so on. Then you can pick and choose, buffet-style, the places that are relevant to you, rather than running a lot of web searches. If you like one of its hotel suggestions, you can book it at the rate quoted via HotelsCombined.com.

Like a GPS device, Plnnr also provides step-by-step walking (or taxi or public transit) directions, with recommended times to spend at each spot. Accounting for how long it will take to get from point A to point B has never been simpler. Itineraries can be printed out with all of the relevant information (such as street addresses, opening hours and phone numbers) and multiple micro-maps of each relevant part of the route.

Plnnr has a couple of downsides: Its itinerary is not easy to view in a mobile phone or tablet browser, so the print out option is best, which limits a traveller's ability to make changes on the fly. As with YourTour, the site also overlooks functionality for planning for lunch or dinners, with no space allowed in the proposed schedules.

GoPlanIt
Similar to Plnnr, GoPlanIt is focused on helping you plan trips around cities, supplying daily sightseeing schedules and maps based on your answers to a questionnaire where you prioritise what's most important to you. This San Francisco-based start-up only covers the US, providing trip tips for the eleven largest US cities. The site then whips together a recommended schedule of sites to see according to their proximity to each other.  As with the above-named sites, you can customise your itinerary item-by-item. In the cleanest interface of the three sites, you can drag and drop – or cut – items, just as if you were using a typical electronic calendar. In another excellent touch, GoPlanIt provides restaurant recommendations based on your budget, something the other two sites fail to do. Print out the resulting custom map, which comes with relevant contact information for each attraction, or access this map and related information from your smart phone.

GoPlanIt's interface is more cluttered than Plnnr's, but it deserves praise for including restaurant information, with ratings from Yelp and similar review sites. It's also unique for having mobile access that allows you to adjust a plan on the fly, with great compatibility with an iPhone.

In selected large cities, the site is experimenting with offering deals — like 30% to 70% off restaurants or attractions — via group-deal site HomeRun. In a recent look at the deals being offered in Washington, DC, I was impressed: the offers were for restaurants I have been to and would actually recommend to friends, and the discounts on offer were substantial. Overall, GoPlanIt was a slicker site for planning a city-level trip than Plnnr, but either of these sites is only relevant if it actually covers the destination you're visiting. I hope GoPlanIt expands its reach to overseas destinations, which is currently Plnnr's turf.  

Google’s My Places
As wonderful as these three competing itinerary-planner services are, they share a common Achilles Heel: they're only as flexible as their databases. If you want to add an attraction or a hotel that isn't on their computerized list, you're out of luck. In this sense, the only site with true flexibility is Google Maps, which in mid-July revised its My Maps feature to make it easier to build a custom itinerary. Now called My Places, the tool lets you star attractions you're interested in seeing, which saves them to a My Places tab on Google Maps. You can also add these places to a customized map, both of which are viewable via your mobile device's web browser.

New integration with the year-old Google Places functionality lets you instantly see user ratings, opening hours, user-generated photos and other relevant information about major attractions, which is relevant data lacking in other online map planners, like Mapquest's year-old tool. Yet while creating a custom Google map offers the ultimate flexibility to a traveller, it is also the most time consuming option. If you would like to speed up the process with the help of knowledgeable advice about your destination, try YourTour for driving tours of sunny European spots, Plnnr for walking around major European cities, and GoPlanIt for explorations of the largest US cities.

Sean O'Neill is the tech travel columnist for BBC Travel

 

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