The Greek islands have sounded their siren call to maritime-minded adventurers since the days of Homer, topping the list of the world’s great sailing destinations from ancient times through present day. The isles offer stunning beaches, crystal-clear seas, world-class nightlife, lip-smacking eateries, and worthwhile shops – and island-hopping from the comfort of a cruise ship makes it possible to thoroughly sample their bounty with absolute ease. Consistently featured on some of the most coveted cruise itineraries on the high seas, the popularity of the Greek isles during the high season months of summer is illustrated by suffocating crowds and inflated costs for cruise bunks, boutique booty, and everything in between. Having just completed a shoulder season autumn sailing to the Greek isles (aboard the sleek sailing yachts of Windstar; read on to nab discounted fares for sailings with them in spring 2012), I’ve rounded up some firsthand tips on the pros and cons of crafting your own custom-tailored, cost-effective, crowd-reducing Greek island odyssey à la shoulder season in spring (March and April) or fall (September and October).

SHOULDER SEASON CROWDS
Pros: There are fewer people. For cruisers in search of a little slice of Greek island paradise all to themselves, shoulder season marks that magic “sweet spot,” when ships can pull into ports delightfully devoid of crowds. Families and students are tied up with the school year, keeping the pitter-patter of little feet and the raucous rambling of college kids at bay, and far away from prized island attractions.
Cons: There are fewer people. Light crowds work well when visiting key sites, but can translate to bit of a yawn if it’s nightlife or a bustling restaurant or beach scene that you’re after. Keep in mind that you’ll miss out on most of the more energized mood and party atmosphere that the isles are famed for under the summer sun (and stars).

SHOULDER SEASON CLIMATE
Pros: Cooler temps are primed for sightseeing. If you like sweater weather and are prepared to forgo long days at the beach, spring and fall temperatures are perfectly lovely (our time in Santorini, Mykonos, and Rhodes in mid-October offered daytime temps in the low 70s), and well-suited for outdoor sightseeing and simple sunbathing (if not so ideal for swimming). Rainfall remains relatively rare and the slightly cooler temps can be a welcomed respite from the oppressive heat of summer.
Cons: Sweater weather means leave the bikinis behind. Summer is prime time for a reason: The sun shines the brightest, the waters are their most welcoming, and both daytime and evening temps ensure optimum conditions for a blissful vacation spent in the great outdoors. Weather during the shoulder season months – especially on the fringes in early April and late October – can cool down considerably, especially in the evenings. You’ll need a jacket and can expect nighttime temperatures to dip into the 50s.

SHOULDER SEASON COSTS
Pros: Save money on sailings, nab bargains in port. Sailing on the shoulder of the summer high season can easily translate to savings of 20 to 40 percent off cruise fares, with the most substantial discounting done towards the very start and tail end of the Greek island cruise season (in April and October). Once disembarking on the island itself, expect shopkeepers, tour operators, and car rental agencies to be more willing to haggle as they prepare to wind down their business for the season.
Cons: Avoid holiday periods, even during shoulder season. Rates can spike considerably during holidays and school breaks, even during shoulder season – expect boosted rates when the kids are out of school or when the workforce gets a break, particularly around Easter.

SHOULDER SEASON SIGHTS & ACTIVITIES
Pros: You’ll have them all to yourself. Light crowds can translate to sheer delight when sampling island museums, archaeology sites, and sunsets, without having to bump elbows with tourist throngs.
Cons: Expect reduced hours or closures. Many establishments and tour operators offer limited hours, decreased services, and sometimes entirely shut down for the season; be sure to verify information and plan your itineraries carefully ahead of time to avoid disappointment.

Save 35% Off Spring 2011 Greek Isles Cruises on Windstar: With a recently expanded capacity in the Greek isles for 2011 (all three ships in its sailing yacht fleet are now operating in the region), look for itineraries incorporating several stops in Greece (Athens, Mykonos, Santorini, and Rhodes), as well as a trio of ports in Turkey (Bodrum, Ku?adasi, Istanbul). Save 35 percent off June 2012 week-long sailings aboard the Wind Star, with the discounted rates we dug up on VacationsToGo.com priced from $2,799 per person.

See our Greek Islands Travel Guide and our Mediterranean Cruises 101 for more helpful trip-planning information, then visit Travel Search tool to book your cruise on the cheap.