There are certain types of trips it seems you only get to take once in a lifetime, honestly. This coming weekend, I’ve got the great opportunity to embark on one such trip, as luck would have it. The Hayhoe family (Mom, Dad, sister, brother and sister-in-law) is heading overseas for a cruise through the Mediterranean — starting in the glorious city of Rome and swinging through Greece (Santorini, Mykonos, Athens and Katakolon, to be specific). It’s sure to be scenic and extraordinary, despite the economic tensions gripping Greece. But I face a decidedly more trivial challenge — what the heck am I going to wear? And how am I going to get it all there?

While I’m absolutely a Lean Wardrobe advocate, a slightly longer trip and variety of situations has me raiding my (somewhat extensive) closet to come up with outfit solutions. Formal cruise dinners, casual excursions, time spent by the pool and on the water and of course, some extensive travel. Yes, this trip has it all. So I’m hoping what I throw in my Navali Stowaway Weekender (a companion on other trips) sticks. To carry the rest of my gear, I’ll be toting along a durable

For the everyday wear, I’m bringing along a selection of T-shirts both more plain (like my heather burgundy Steven Alan pocket tee, an American Apparel tee and a new Ace Rivington crewneck, not pictured) and ones with a bit more visual cues (like my Pistol Lake henley and a J. Crew sailboat tee — unfortunately sold out). For time spent by the pool and heading ashore, any option should work within reason. And when I travel, I’ll be throwing on my favorite Everlane pocket tee under my older (circa 2013) J. Crew blazer for easygoing travel style. I’m packing a vintage ballcap for a bit of extra protection from the sun, too — courtesy of the excellent folks at Goorin Bros.

Those tees should be a  nice complement to the selection of casual shorts you see above– my Pistol Lake sweatshorts, pictured at left, are proving to be a personal favorite, comfortable yet functional and relatively tailored for a pair of sweatshorts. I’m also tossing some technically advanced Athletic Propulsion Labs basketball shorts in my bag for work-outs and hiking through the mountains of Greece. My Frank and Oak linen blend shorts should be ever-reliable in the heat, too (read more about them and the brand here), and I’m also packing my Banana Republic khaki shorts (similar to these). On the swimwear front, I’m looking forward to taking my Orlebar Brown Setter trunks out for a dip (as featured here – haven’t been working out as much as Bond though).

Which brings me to my steadfast decision to bring perhaps more pairs of pants to a Mediterranean cruise than you might expect — what can I say? I prefer pants. For the flight there, I’ll undoubtedly be wearing my new pair of Mott & Bow white denim — they’re exceedingly comfortable thanks to a hint of stretch and will hopefully allow me to blend in stylishly once I land in Italy (I’ll also be bringing along some olive Washed Chinos from Bonobos for comfortable travel). And because one can never bring enough jeans on a trip, my grey selvedge Billy Reid denim should do the job nicely for more dressed-down dinners and travel days, while some sky blue Combat Gent chinos in a versatile slim-straight cut should do the trick for both casual and more crisp wear. For pairing with those jeans, I’ve got both a brown leather J. Crew dress belt  and more casual striped and braided options. The number of pairs of pants I’m packing means I’m actually dialing in my shirts (somewhat) – a white Combat Gent Oxford, a blue Bonobos Oxford, my trusty GAP chambray shirt and my breathable and airy Stock Mfg. Co linen shirt should work well within a rotation. I plan to complement those with a patterned Saturdays NYC short-sleeve shirt and a vintage thrift store ‘Drinks’ shirt (check it out in more detail here).

But for those occasions that call for a significantly upped style game, I’ll be pulling out the big guns. As this is a Mediterranean cruise and all, I enlisted my friends at Combat Gent to set me up with perhaps the most fashion-forward number in their arsenal, the Steel Blue Glenplaid Double-Breasted suit as you can see above. I’m looking forward to breaking up the blazer with some custom grey suit pants and a crisp white Endurance Shirt via Combat Gent as well — and the rest of the time, my J. Crew blazer should certainly be able to pull double duty when worn with accessories like a red floral pocket square (similar to this one).

And given the variety of outfit pairings I’m hoping to line up, my shoe ensemble is stretched a little bit more than usual. For travel, my Timberland Coulter Chukka boots (courtesy of my day job, in full disclosure) will likely get the job done while the rest of my footwear is packed — neatly — away. I’m also bringing along my versatile G.H. Bass leather loafers (read more on them here) as well as my trusty GREATS Brand Wilson sneakers. I’m planning to pair the loafers with everything from chinos and T-shirts to jeans and short-sleeve shirts. And on the athletic and shore exploration front, I’m quite excited to try out my Athletic Propulsion Labs sneakers (a GearHungry post on those sneakers will be up soon!). But the footwear that might best fit in with the continental style one sees throughout Greece and Italy is coming on the trip courtesy of start-up loafer brand Andre Coton. These jute fabric loafers are without a doubt the most unique footwear style I’ve tried, but I’m hopeful (confident?) they’ll go well with my more formal outfit pairings.

Rounding out what looks to be a very full set of bags is a great Travel Kit courtesy of Baxter of California (read more on the brand here; I’m told the Travel Kit restock is imminent, so keep your eyes peeled). And while I’m not packing many socks, a few pairs of Richer Poorer no-show socks and a pair or two of patterned socks (for matching with shades of blue) should fit right in. A few everyday carry accessories, like a handy pair of American-made sunglasses, my black rubber Stuhrling Aquadiver watch, my stainless steel Invicta dive watch and my new Daniel Wellington Classic Bristol watch will also be with me as options for daily rotation. Luckily other than my blazer for travel, I’m leaving outerwear behind — which will hopefully prove to be the right choice. To protect my laptop, I’m stowing my computer in my new Issara leather laptop sleeve (available now on the brand’s site), while a reliable Field Notes Brand steno book should more than help me keep track of my travels.

That marks just about everything I’m bringing with me — whether it’ll prove foolish or a wise choice to forgo (somewhat) the Lean Wardrobe philosophy, time will tell. Just because I’m jetting off doesn’t mean the site will be forgotten, however — look out for another guest post via Madhav of Wardrobe Domination, as well as a Style Q&A with my buddy Barron from the excellent menswear site Effortless Gent. Of course, we’ll still close out the week here with the Friday Read and a good ol’ Style Pick — stay tuned, stay stylish!

Are you taking any big trips to close out the summer? What are your go-to travel essentials?