As the week dawned rainy and a bit chilly in NYC,  my mind turned immediately toward sunny Florida –I knew I needed a vacation. And that’s just what I got, as I spent these past few days celebrating Memorial Day weekend in style. I always relish the chance to hop a quick flight south to my parents’ adopted home of Fort Myers, that much is true.  Close to pristine beaches and blue water, near to a great craft beer brewery or two, and surrounded by great times, close friends and family and a hearty helping of gourmet home cooking — it’s always a treat! Of course, if you follow me on Instagram, you’re familiar with my visits. And if not? Settle in for a few tips on men’s travel style from my trip. I last trekked down to Florida with my favorite #menswear during a Style Guide spring break visit this past March, and that came not long after I celebrated Christmas in style in Fort Myers. That being said, it never gets old ditching rugged spring outerwear for a bit of much-needed sun! And as always, this trip put my packing mettle to the test.

My last major trip took me to Pittsburgh to see Local Natives — needless to say, conditions were a little bit different (in a great way!), as I hopped a quick flight to Fort Myers. To take on a breezy NYC day and travel thereafter, my Levi’s Trucker Jacket in a seasonally friendly light wash was an easy-to-wear outer layer — and it was just as easy to cram into my trusty Owen and Fred Voyager Waxed Weekender when getting off the plane in Fort Myers. Thanks to my casual office dress code, I was able to sneak in two great pieces from my pals at JACHS NY — the breathable, comfortable Striped Pocket Tee and sharp Red Cropped Stretch Cotton Chinos, featuring a single pleat for modern style. Be on the lookout for similarly easygoing pieces for your next jaunt to a warm-weather locale — and perhaps bring along your own pair of the Abercrombie & Fitch x Tretorn Nylite Sneakers, as I did. When teamed up with my rugged-yet-crisp Nautica SYD Leather Date Watch and my reliable Huckberry Explorer’s Cap, the combo worked for the plane ride … and then grabbing a Corona shortly after arrival.

As it so turns out, Friday was a bright, beautiful and sunny day in Florida — the absolute perfect day to hit the beach and kick off a mini-vacation. No matter where your travels take you, you should start the day with men’s grooming essentials — as it were, I styled my ‘do for the day with the clean and sharp Sea Salt Pomade from Brooklyn’s own Fatboy Hair. And on the apparel front: Simple style always starts with the basics — like a stylish Flint and Tinder T-shirt, made in America with marled fabric. It was a classic complement to my new favorite pair of swim trunks, the beach-ready 311 Boardshorts from the excellent Birdwell Beach Britches for Todd Snyder collaboration.

And it wouldn’t be a day of exploration without my Legend Sneakers from the fine folks at SeaVees — effortless style finely accented by the durable, handsome and functional MVMT Watches Calypso Watch.  And for kicking back on the beach, I needed a few more items. Step one: Enter the stylish headphones via the Vibes Box from Bespoke Post. Step two: Enter my wearable and sharp Component sunglasses . The next time you head to the beach, don’t leave behind your stylish beach gear. And with a day of beach-going and pool relaxation in the books, it was time for a classic Hayhoe family cookout. I’d tell you all about my dad’s ribs, but that recipe is a secret!

Of course, no trip to Florida would be complete without a Saturday trip to Fort Myers Beach — teamed with seasonal style that fit right in, of coruse. In this instance, that meant my new Volcom Surf n’ Turf Hybrid Shorts were a comfortable, transitional style move — able to move seamlessly from water to land thanks to quick-drying technology. The tailored fit also nicely complemented my slim, tailored and classic Criquet Shirts Slim-Fit Player’s Shirt in a crisp shade of white. You might recognize the Slim-Fit Player’s Shirt from a recent Style Pick of the Week entry — I can vouch that it performed admirably in the heat as I soaked up the sun and sipped a few Coronas.

And the next time you want to inject a bit of continental style into a polo-and-shorts combo, take the Clarks Reazor Drive Loafer in a bright shade of Blue Nubuck — mine proved quite comfortable and very easy to slip on and off. And when matched up with stylish accessories (specifically, the Electric Leadbelly Sunglasses and the well-priced CHAPS Bransen Diver, courtesy of the brand), I was more than set for a full day of exploration in the Florida sun. A dive watch and versatile shades will work anywhere you travel this summer — especially Florida.

It should come as no surprise that a day of rest and relaxation — along with another backyard BBQ — was in order on Sunday following two busy days in the sun. I still took on the heat in style though, starting with my slim-fitting and uniquely designed United By Blue Wenlock Chambray Shirt. You might recognize this United By Blue summer essential from my Style Pick of the Week series — with a tailored fit, soft fabric and a cool pattern, the Wenlock Chambray Shirt proved a Florida winner. Particularly when matched up with my cotton-linen blend Bridge and Burn Roark Olive Trousers, I stayed quite cool in the sun. Getting around was also made easier thanks once again to my Component sunglasses, mixing vintage inspiration and a modern edge. I was pleased once again with the tough functionality of my Nautica SYD Leather Date Watch, and I injected a bit of dressy detailing into the ensemble with the Sebago Legacy Penny Loafers in a head-turning shade of red leather. Look for similar day-to-night, transitional pieces the next time you’re searching for a full-day, warm-weather outfit.

Monday so far promises a full day of Florida relaxation — and a crucial day off work — before heading back to NYC. I brought more on-point gear to fight off the heat, starting with another Criquet Shirts Slim-Fit Player’s Shirt — the organic cotton  of the Slim-Fit Player’s Shirt is breathable and comfortable. My Ministry of Supply Going Places Shorts also do a fine job at wicking sweat in a tailored silhouette. And my Gola Classics Comet Plimsoll Trainers add a dash of sporty style to this classic look. Of course, my durable and rugged Timex Waterbury Chronograph (in a cool matte black) has so far paired up nicely with my Electric Leadbelly Sunglasses for one last day in the Florida sun.

Looking back on this weekend, it absolutely brought with it everything I had hoped for — relaxing beach time, some much-needed sand and sun (as always), and plenty of meaningful time with family. In the hustle and bustle of New York City (and in the hustle and bustle of planning for these trips!), life can sometimes fly by very quickly, and yet … this weekend was simply the ideal way to kick off summer. I hope you experienced much of the same on your end this weekend. Know that there’s plenty more travel and plenty more menswear to come on The Style Guide, including a look tomorrow at what to wear to a music festival.

Thanks, as always, for reading!

-Beau