Some of the world's most appealing destinations are also some of the most complicated places to visit. Here, eight places where even the most streetwise traveler would be smart to enlist guidance.

The words "group travel" can conjure up visions of busloads of tourists roaring past sites, checking off a strict itinerary. But not all group tours are created equal. More importantly, there are some places where you'd be at a distinct disadvantage without a guide. Each of the destinations on our list comes with its own charm--and it's own set of challenges. In these places a guide can help with everything from navigating a complicated bureaucracy to sidestepping common scams to getting your point across in a foreign language. For each place we've identified here, we also recommend a tour, and most of them offer free time and some customization. Some of the tours save you money, others cost a little bit extra, but all of them include airport transfers, entrance fees, and a few meals--not to mention a hefty dose of protection against anxiety. Yes, it is possible to go all of these places on your own, but it's a lot smarter to go with a group.

Russia

Back before the fall of the USSR, Americans traveling to Russia had to book through Intourist and stay at state-run hotels. Restrictions have become less and less limiting over the past two decades, but bureaucracy and red tape are still huge obstacles for a trip to Russia. You still need an "invitation" from a hotel or tour company to even apply for a visa, and it's not unheard of for travelers to be sent back home--or even stuck in Russia--because of "problems" with their paperwork. Corruption continues to be an issue, with guidebooks still warning travelers about being stopped to show "papers," a legitimate question that could be veiled as an intimidating request for a bribe. It is advised that all travelers have a local contact to navigate the confusion, and tour operators have trusted contacts with local knowledge.

Sample tour: Travel to Russia isn't cheap--and neither are the tours. SmarTours 10-night Cruise of the Czars package includes airfare from New York, time in St. Petersburg and Moscow (including tours of the Hermitage and Red Square), and a cruise down the Volga River.