A 48-Hour Small Town Couple’s Getaway in Portsmouth, VA

As the state slowly begins to open its doors again, Portsmouth is taking care and caution to safely welcome visitors back for much-needed getaway time. Only a short drive away for the majority of Virginians, Portsmouth is the perfect small town to explore, without the worry of big crowds. We’ve rounded up a whole weekend’s worth of activities to enjoy during a visit to stretch your legs, refresh your mind and rediscover what it means to take a vacation.


4:00 pm

Check into Your Accommodations

Spend the weekend overlooking the Elizabeth River at the Renaissance Portsmouth – Norfolk Waterfront Hotel or, if you’re traveling on a budget, at the Quality Inn and Suites Olde Towne. Both properties are within walking distance of bars, restaurants, shops, and historic sites. Rest easy knowing these properties are being maintained with the best safety standards as set forth by Marriott and Choice Hotels.

5:30 pm

Happy Hour

The High Street entertainment district offers 22 hot spots for drinks and social gatherings when visiting historic Olde Towne. From the very first block when arriving by water and west for eight blocks, there’s an abundant supply of High Street pubs and restaurants as well as waterfront places to enjoy happy hour. It’s an easy walk with things to see and places to visit along the way. Historic churches, the old Norfolk County Courthouse, murals, sculptures, and ancient oaks come together to make the walk almost as much fun as the drink at your next stop.

7:00 pm

Dinner on the Town

The Olde Towne Waterfront and sidewalk dining experiences in Olde Towne are a great way to take in the views or people-watch while enjoying your meal. Check out the outdoor seating and menus at places like Café Europa, Still, The Bier Garden, and Thai Basil.

9:00 pm

Enjoy a Nightcap

Finish the night with a drink at any one of Portsmouth’s popular locations serving your drink of choice like Barons or Longboards.


9:00 am

Rise and Shine with Coffee Time

Start your day in the best way – with a cup of coffee from a local shop! Grab a specialty latte and danish from The Coffee Shoppe on High Street and stroll along the water’s edge, taking in the beautiful views while you greet the day.

10:00 am

Farmer’s Market

What better way to shop local than the Farmer’s Market. Every Saturday you can enjoy regional produce, goods and items as you make your way through Olde Towne.

11:00 am

Explore the Olde Towne Historic District

Take a step back in time when you stroll the tree-lined streets of Olde Towne Portsmouth, Virginia. A variety of architectural styles span three centuries and include Georgian, Colonial, Federal, Gothic Revival, and more. Tour the area on your own or meet up with History Alive for a guided tour from a troupe of storied characters from Portsmouth’s past will guide you through the streets of Olde Towne while telling tales and singing songs about the life and times of the era. Or, head to the Farmer’s Market to support local craftsman, enjoy fresh produce and take in the surrounding murals that line the buildings.

12:30 pm

Grab Some Lunch

If you’ve worked up an appetite, head to for some great seats and eats at local favorites like Guads, JoJacks, Amici’s, Beyond Cell Food, and Gosport Tavern.

2:00 pm

Play Outside

While Portsmouth is mostly a suburban destination, the city boasts several beautiful nature parks where you can enjoy fishing, golf, kayaking, hiking, and more. Fish from the piers on the Elizabeth River, rent a kayak at Hoffler Creek Wildlife Preserve, or get 18 holes of golf in at Bide-a-Wee Golf Course.

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4:30 pm

Sample Some Craft Beers

After a busy day of play in Portsmouth, take a break with a cold, refreshing brew from one of our craft breweries, MoMac Brewery Company, Harbor Trail Brewing Co., or Post Secondary Brewing.

7:00 pm

Dinner and a Movie

Pair a unique dining experience with the latest movie release a movie at the Commodore, a luxuriously restored 1945 Art Deco-style motion picture theater that shows first-run movies while serving light dinners. Among the many features are a 42-foot screen, THX Digital sound system, upholstered seating and crystal chandeliers.

9:30 pm

Take an After-Dinner Walk

After your dessert, view the city lights across the water with a stroll along the Seawall or the lanterns along High Street in Olde Towne.


10:00 am


After checking out of your accommodations, start the day off with delicious brunch offerings from hot spots like Yoolks on Us, Griffs, Hometown Diner, and Twisted Pig – known for their Bloody Mary Bar on Sundays.

12:00 pm

Explore the Region

After discovering Portsmouth, explore the rest of the region and its offerings. Take a ferry across the water to downtown Norfolk, be charmed with main street Smithfield, or make your way to the oceanfront in Virginia Beach.

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