After departing from the pier in a Hummer H2, you will be free to explore whichever sites you find most interesting. You can put together a list of destinations in advance, ask your personal driver to suggest favorite spots, or combine your ideas into a fun-filled itinerary.
Either way, Skagway is yours to explore, and there are plenty of attractions well worth your attention. You might drop by the Skagway Museum to see the wooly mammoth tusk and World War II memorabilia. Or head over to fragrant Jewell Gardens to stroll among the indigenous plants and watch the on-site glassblowers. Nearby, you'll find the Gold Rush Cemetery, where notorious con artist Soapy Smith was buried in 1898.
Skagway Overlook offers one of the best views of town and your cruise ship. If you want to see the attractions beyond the city limits, take the Klondike Highway. It leads to Pitch Fork Falls, Bridal Veil Falls and the unexpected Carcross Desert, the world's smallest desert. Before turning back, you should be able to reach Emerald Lake, a brilliant green body of water surrounded by dense forest. You might even spot a bald eagle soaring overhead.
With a personal driver at you beck and call for four hours, you can easily see the highlights of Skagway before returning to the pier.