Planning the Ultimate Guys’ Weekend in Cape Charles

Whether you’re planning a fishing trip, a laid-back bachelor party, or you’re just in dire need of some “bro time,” Cape Charles is tailor-made for a mancation to remember. This beach town on Virginia’s Eastern Shore offers a wealth of outdoor activities, great dining, and an award-winning brewery, so gather your friends and pack your bags for the ultimate guys’ weekend in Cape Charles.

When to Plan Your Guys’ Getaway

Cape Charles is a great destination any time of year, so you’ll want to schedule your guys’ trip based on what you want to do with your time. If watersports and lounging on the beach are your idea of a good time, be sure to book your accommodations early for the popular summer months. If you’re into fishing and more of a relaxed vibe with fewer crowds, plan to visit in the off-season — this saltwater fishing guide will tell you what’s in season when.

Where to Stay

Your accommodations of choice will largely depend on the size of your group. A local hotel, B&B, or inn may be ideal for smaller groups, while larger crews may prefer to book a vacation rental home. You can find more guidance on where to stay in Cape Charles right here. There are also lots of places that are listed for rent through VRBO or AirBnB like this home situated just .3 miles outside of Cape Charles Historic district Fish Tales. If you’re willing to stay a bit futher out of town, there are great motel options including Cape MotelPeacock Motor InnShore Stay Suites, Edgewood Motel, Cape Charles Milestone Lodge and for a unique experience Cape Charles Tiny Livin’

What to Do

You guessed it: Fishing is a huge draw for many visitors to Cape Charles. Head to Bailey’s Bait & Tackle shop for the lowdown on what’s biting and to pick up the supplies you need. You can keep it simple by heading to the free town fishing pier, or if you’d like to target some big fish, consider booking a fishing charter either out to sea or in the Bay. Tidewater Charters and Top Dog Charters are just a couple of options that depart from Cape Charles Harbor. Is fishing not your forte? Depending on the time of year, you can plan to fill your days lounging on the beach, hiking or biking local trails, or touring the local watering holes. Speaking of which…

Where to Drink

Cape Charles isn’t a party town, but if cozy pubs and high-quality craft beer and cocktails are more your style, you’ll feel right at home here. With a diverse lineup of brews, a crowd-pleasing menu, and a sprawling outdoor space, Cape Charles Brewing Company is a favorite stop for beer lovers. Cider fans will have fun exploring the creative options at Buskey Cider by the BayKelly’s Gingernut Pub and AJ’s Bar & Grill are popular picks for pints with a side of darts and wings. For something stronger, Cape Charles Distillery has an excellent whiskey selection — enjoy a craft cocktail by their fire pit or pick up a bottle to drink at home.  

Where to Eat

No guys’ trip would be complete without a few memorable meals, and luckily there are plenty of restaurants to choose from in Cape Charles. For a night in, order a stack of pizzas from Deadrise Pies, or head out for a casual seafood dinner overlooking the water at the Shanty or the Oyster Farm. Find pub fare at Kelly’s, AJs, or Cape Charles Brewing Company. Find more info on where to eat in Cape Charles here

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