A Long Weekend in Greater Williamsburg, VA

The following post is from a sponsored trip with Visit Williamsburg

Williamsburg, Virginia.

There’s over four centuries of history in this celebrated part of America. If you grew up on the East Coast, chances are you ventured to the Greater Williamsburg (including Jamestown and Yorktown areas) in grade school. You probably explored historic Jamestowne and Yorktown, and watched history come to life in Colonial Williamsburg.  But have you thought about returning?

Travel + Leisure named Greater Williamsburg as one of the top cities in the United States “to stay, travel, and more.” There’s everything from picturesque bike trails, to thrilling amusement parks, iconic golf courses, a Tasting Trail packed with breweries, wineries, and distilleries, and so much more in Greater Williamsburg. While you could pack a lot into a 24-hour trip, we highly suggest adding at least one more day (we’re sure your boss won’t mind) - there’s just too much to see!

Here’s what we think you should do:



Breakfast at Aromas Cafe: We can’t think of a better place to kick off your time in Greater Williamsburg than with breakfast at the cozy Aromas Cafe! You can’t go wrong with their Bacon & Eggs platter, and their French Press is top-notch. Sit outside and enjoy the sights and sounds of Williamsburg.

Explore Colonial Williamsburg: Just a five-minute walk from Aromas Cafe is Colonial Williamsburg, the world’s largest living history museum. Watch as history literally comes to life as you venture through

Can we eat at Aromas every day?

We loved exploring Colonial Williamsburg


Lunch at The Trellis Bar and Grill: Located in the heart of Colonial Williamsburg, The Trellis Bar and Grill has a fantastic seasonal menu and a welcoming patio that’s perfect for a warm, sunny day. Try the fish tacos!

Beer at Virginia Beer Co: Spend the rest of the afternoon at Virginia Beer Co, part of the Williamsburg Tasting Trail - it’s a brewery, tap room, and beer garden all in one! At 4pm on Fridays a new cask ale is tapped, and from 6-9 they have local singers, songwriters, and musicians playing in the beer garden. You’ll be tempted to stay all night! (They have rotating food trucks in case you stay for dinner!)

Yummy lunch at The Trellis Bar and Grill!


Dinner at Amber Ox Kitchen & Brewery: If you’re hungry and looking for a change of scenery, we highly suggest Amber Ox Kitchen & Brewery, another Williamsburg Tasting Trail brewery. From Fried Pimento Cheese, to Chicken & Waffles, to the popular AO Burger, it’s modern pub faire with a nod to local ingredients.

Stay at Woodlands Hotel & Suites: Comfy, conveniently located, and affordable. The perfect starting point to your Williamsburg adventure, the Williamsburg Woodlands is centrally located right next to Colonial Williamsburg. Their shuttle makes the trip stress-free and convenient! And Sally loved it!



Coffee at Mobjack Bay Petite Café and Coffee Roastery: You won’t find a more charming spot for coffee than Mobjack Bay Petite Café and Coffee Roastery, located in the Historic Cole Digges House on Main Street in Yorktown Village. This quaint coffee and tea house specializes in freshly roasted coffee (roasted on-site!) and mouth-watering pastries. Enjoy them in their pretty courtyard, or take them to go and explore the historic sites of Yorktown!

Sailing with Yorktown Sailing Charters: See a different side of Yorktown, from the water! Yorktown Sailing Charters offers daily 2-hour sightseeing cruises that take you along the banks of the picturesque York River, past Yorktown Battlefield, Victory Monument, naval warships, and more! It’s an awesome way to learn more about the area’s history, and you’ll even get the chance to help sail!


Lunch at Carrot Tree Kitchens: Steps from the Riverwalk Landing Pier is Carrot Tree Kitchens, a delectable little cafe that prides themselves on their baked goods and healthy (and hearty) sandwiches and wraps. Our favorite? “The York Town Onion”, a wrap filled with hummus, greek olives, lettuce, tomatoes, cucumbers, onions, and of course, carrots. It’s healthy, filling, and super delicious!

Segway Tour through Historic Yorktown: Right next door to Carrot Tree Kitchens is Patriot Tours and Provisions, an adventure company that offers daily Segway tours through Historic Yorktown! We suggest the one-hour “Breeze” tour, which gives you a quick, condensed look into Historic Yorktown, and is a great intro into riding a Segway if it’s your first time. They’re a blast!


Beer at Brass Cannon Brewing: If you haven’t already noticed, we’re big fans of the craft brewing scene in Williamsburg, and Brass Cannon Brewing (also referred to as “The Cannon”) is another brewery that shouldn’t be missed. It’s veteran owned and a favorite among locals, snag a seat at the bar and you’ll be making new friends in no time!

Dinner at Casa Pearl: Oysters and tacos may sound like an odd pairing, but this locally-sourced, latin-inspired, southern seafood joint sure pulls it off well! Casa Pearl is what we like to call “relaxed elevated”, serving fancy cocktails and small plates in a modern and surprisingly casual environment. We know you’ll love it just as much as we do!



Duck Donuts:  In our opinion, nothing says “Sunday Funday” more than donuts for breakfast! So before making the drive to Historic Jamestowne, take a detour to the famed Duck Donuts, that serves delicious made-to-order donuts that melt in your mouth. You’re welcome in advance.

Historic Jamestowne:  Walk in the steps of Pocahontas and John Smith! Historic Jamestowne is the original site of the first permanent English settlement in America. Seeing this up close is incredible, considering it’s over 400 years old! Taking it a step further, you can visit the Jamestown Settlement, a living history museum that brings it all to life. Fascinating!

Exploring Historic Jamestowne with Sally

Alli with Pocahontas


Beer &  Lunch at Billsburg Brewery:  You can’t beat the views of the James City County Marina at Billsburg Brewery, and the beer is especially tasty on a warm afternoon! They have daily rotating food trucks serving local grub, and occasional live music! See what they’re serving (and who might be playing) here!

Kayak James City County Marina:  If you’re feeling up for an adventure, rent a couple of kayaks (or a tandem), and take them around the historic Powhatan Creek and Jamestown Island! You can even bring your pup along for the ride (but they must have a life vest)!


Wine tasting Williamsburg Winery:  Situated on the 300-acre Wessex Hundred Farm, Williamsburg Winery is a quite the destination, and their tasting room is a stunning spot to sample some of Virginia’s best (and award-winning) wines!

Dinner at Cafe Provencal:  After you’ve sampled Williamsburg Winery’s many famous varietals, head to their on-site restaurant Cafe Provencal, where they take farm-to-farm dining to a whole new level. Showcasing the bounty of Virginia farms, their culinary team creates mesmerizing Provence-inspired dishes that are as pretty to look at as they are to eat!

It’s a perfect place to end your long weekend in Williamsburg… and we suggest planning your next trip back over one of Cafe Provencal’s tantalizing desserts! ;) Happy travels!