Exploring Historic Portsmouth, VA: Ultimate Trip-Planning Guide

Portsmouth, Virginia, is one of our favorite destinations for its small-town feel, located in an urban and industrial area. Nestled along the Elizabeth River across from Norfolk, Portsmouth combines its rich maritime heritage with a vibrant local culture made up of annual festivals, live music bars, and friendly locals.

In this guide, we’ll share our favorite activities in Portsmouth, VA, as well as the top spots to eat, when to visit, and more travel tips! If you’re arriving by water, stay tuned for our dedicated Boater’s Guide to Portsmouth at the end where we share info about free docks, where to get provisions, the best remote working spots, and more!

About Portsmouth, VA

Portsmouth, VA, founded in 1752, boasts a rich history as one of America’s oldest seaports, with deep roots in naval and maritime heritage. This city played key roles in both the Revolutionary and Civil Wars, and many historic sites still echo its past, like the Portsmouth Naval Shipyard Museum and the iconic Lightship Portsmouth. Today, Portsmouth is a melting pot of historic charm and modern attractions, where one minute you’re exploring a historic ship, and the next you’re sipping on a specialty coffee on the High Street. With each visit, we are more and more blown away by its incredibly walkable streets, well-kept historical architecture in the old town, and mouthwateringly good eats!

Our 7 Favorite Activities in Portsmouth VA

In this section, we’ve put together our top 7 favorite activities in Portsmouth, VA, featuring a mix of both free and paid attractions. From our favorite movie theatre in Portsmouth to a guided walking tour, there’s something here for everyone! At the end, we’ve included some honorable mentions of the other top activities in Portsmouth, VA, that you might be interested in!

1. Start Your Day Off at the Portsmouth Welcome Center

Kick off your day in Portsmouth with a stop at the Portsmouth Welcome Center, where you can get the inside scoop on everything happening around town. The friendly staff can provide maps, recommend local hotspots, and let you know about any seasonal activities taking place. It’s the perfect spot to get oriented and avoid missing out on any events happening while you’re in town.

Location: 206 High St, Portsmouth, VA 23704
Hours: 9 am – 4 pm Sunday to Thursday, 9 am – 5 pm Friday and Saturday
Price: Free

2. Take a Lively Walking Tour through Olde Town with Guides in Historical Garb!

This Olde Towne Portsmouth Tour is a fun guided walking tour led by experts dressed as historical figures from Portsmouth’s storied past. These knowledgeable guides don’t just wear the costumes—they bring history to life with engaging stories, colonial songs, and fascinating insights into the origins of words and traditions. You’ll walk the same streets once trodden by historical figures like Benedict Arnold, Chief Black Hawk, and Martin Luther King Jr. This tour concludes at the Portsmouth Arts and Cultural Center, where a rotating array of exhibits showcases local art and history.

Location: The tour starts at the Portsmouth Welcome Center
Hours: Saturdays at 11 am
Price: $30 per adult

3. Watch a Movie at the Commodore Theatre

Watching a movie at the Commodore Theatre is truly a one-of-a-kind experience and hands-down one of our favorite activities in Portsmouth, VA.

Housed in a beautifully restored state-of-the-art Art Deco theatre from 1945, the Commodore Theatre combines classic cinema with a full dining experience, making it feel like a delightful step back in time.

As you’re seated at your private table, you can then order dinner and drinks through the table’s telephone up until the movie starts. It’s easy to see why this has become one of our favorite stops on the Great Loop and a must-visit when in Portsmouth!

The food isn’t anything to write home about, but the experience as a whole, the friendliness of the owner and the staff, makes seeing a movie at Commodore Theatre one of our top things to do in Portsmouth!

Location: 421 High St, Portsmouth, VA 23704
Hours: Depends on show times
Price: $12 per adult

4. Visit the Portsmouth Art & Cultural Center

The Portsmouth Art and Cultural Center is where you’ll find local art, history, and culture, all in a beautifully preserved courthouse from 1846 in the heart of Olde Towne. This center hosts rotating exhibits that highlight a wide range of creative works, from contemporary art pieces to historical displays of Portsmouth’s past. In addition to exhibits, the center often hosts community events, performances, and lectures—consult their events page for upcoming events!

Location: 400 High St, Portsmouth, VA 23704
Hours: 10 am – 4 pm Wednesday to Sunday (Closed Monday and Tuesday)
Price: $3

5. Visit Portsmouth’s Naval Museums

Portsmouth, VA, is home to two main naval museums that highlight the city’s rich maritime history and cost close to nothing to enter!

1. Lightship Portsmouth Museum – This unique museum is housed in a retired lightship from 1915, the Lightship Portsmouth, which served as a floating lighthouse guiding ships safely along the East Coast. Visitors can explore the crew’s quarters, see original equipment, and learn about the challenging life of lightship crews.

Location: London &, Water St, Portsmouth, VA 23704
Hours: Saturday and Sunday 10 am – 4 pm ONLY
Price: Free admission, suggested $3 donation

2. Portsmouth Naval Shipyard Museum – Located on the waterfront, this museum showcases over 250 years of naval and shipbuilding history. It features artifacts, models, and exhibits on Portsmouth’s role in shipbuilding and the Navy, including sections on the Revolutionary and Civil Wars, as well as modern naval advancements.

Location: 2 High St, Portsmouth, VA 23704
Hours: 10 am – 4 pm Wednesday to Sunday (Closed Monday and Tuesday)
Price: $3

6. Go on a Free Walking Tour

The Underground Railroad Tour and Architecture Tour are two free self-guided walking tours that you can go on in downtown historic Portsmouth. Read or listen to the information in either of those two links, provided by Portsmouth Visitor Center, as you walk. Both tours allow you to explore at your own pace while still providing all the info you’d get with a paid tour! The Underground Railroad Tour takes you down the very streets that once served as vital paths to freedom, while the Architecture Tour highlights Portsmouth’s remarkable collection of historic buildings.

7. Walk the Waterfront Trail

We’re always on the lookout for scenic trails or pathways to explore with our dog, Ollie. In Portsmouth, we discovered the Portsmouth Waterfront Trail, a laid-back, picturesque path that follows the Elizabeth River with views of ferries, barges, and tugboats gliding by.

Along the trail, you’ll encounter unique landmarks like a massive Fresnel lens that once guided ships, the historic Lightship Portsmouth (an actual floating lighthouse!), and plenty of informative panels detailing Portsmouth’s history.

For finding more trails around Portsmouth, we always turn to AllTrails for reliable recommendations and easy-to-follow maps.

We love using AllTrails to download maps offline so we can always stay on the trail. Sign up for AllTrails+ so you too can download maps offline before your hike!

Even More Activities in Portsmouth VA

• The Children’s Museum of Virginia is a hands-on museum for kids, with interactive exhibits on art, science, and more! It’s ranked as one of the top activities in Portsmouth VA on Trip Advisor!
• Hill House Museum is a preserved 19th-century home showcasing period furniture, artifacts, and local history from four generations of the Hill family.
• The Elizabeth River Ferry to Norfolk is a passenger ferry offering a quick and scenic trip across the Elizabeth River, connecting Portsmouth and Norfolk with frequent daily departures.

Where to Eat and Drink in Portsmouth, VA

High Street is where you’ll find the majority of trendy restaurants, bars, and coffee shops in Portsmouth. So head here if you’re looking to bar-hop or want to choose a restaurant in person!

Restaurants

• Still Worldly Eclectic Tapas is your classic speakeasy bar serving up appetizers and mains from around the world—from potstickers to penne alla vodka. Their drinks include whiskeys, cocktails, wines, and more! Closed Mondays.
• Thai Basil is a Thai restaurant in downtown Portsmouth serving up flavorful vegetarian and non-vegetarian dishes from Tofu Pad Thai to Seafood Hot Pot. Open daily for lunch and dinner.
• The 619 Cantina is a Mexican restaurant that lets you design your own tacos, burritos, bowls, and more! If you’re craving Chipotle, this is your place! Open daily for lunch and dinner.
• Beyond Vegan Cell Food is a vegan restaurant that will satisfy both carnivores and veggie eaters alike! They serve up creative dishes from Chicken and Waffles to Crunchy Crab Cakes—100% plant-based! Closed on Sunday and Monday.

Drinks and Breweries

• The Bier Garden is a unique German beer hall and garden pouring out over 300 global brews and serving German-style lunch and dinner classics, from pretzels to Schnitzel. Closed on Mondays.
• Roger Brown’s Restaurant and Sports Bar is a local favorite known for its comfort food, over 20 draft beers, and welcoming atmosphere in their indoor dining area and outdoor patio. This lively spot hosts regular live music events and is a go-to for catching live games. Open daily.

Breakfast, Coffee, and Sweets

• The Coffee Shoppe is a local coffee house serving hot and cold coffees, smoothies, breakfast plates, lunch sandwiches, and more! Open daily.
• Cure is a modern coffee shop that serves up everything from classic cappuccinos to peanut butter and jelly lattes as well as breakfast and lunch options. Open daily.
• Yoolks On Us is a rustic breakfast and lunch spot serving up South comfort food and extra large mimosas. Open daily.
• ELG Sweet Boutique is an ice cream shop in downtown Portsmouth with classic as well as more inventive ice cream flavors. They even serve up several vegan ice cream options! Closed Monday and Tuesday.

Map of Portsmouth, VA

How to use this map: We have saved the locations from this guide on this map. You can save this map to your Google Maps by pressing the star icon. In your Google Maps, click the menu icon and then Saved Maps, where this map will appear.

Farmers Markets and Festivals in Portsmouth, VA

We used to pass by farmers markets and festivals while traveling, but now they’re must-dos! Farmers’ markets have especially become favorite stops for meeting locals, discovering regional specialties, and picking up fresh veggies (especially useful when boating).

Farmers Markets

• Portsmouth Olde Towne Farmers’ Market runs every Saturday from 9 am – 2 pm in downtown Portsmouth. Here you can find everything from local produce and baked goods to artisan soaps and handmade crafts!

Festivals

• Olde Towne Holiday Music Festival is the signature holiday event in Portsmouth, which is celebrated in December.
• Seawall Music Festival is celebrated over a weekend in June, with food, local and national entertainment, and a fireworks show.
• Umoja African-American Culture Festival happens in May and celebrates African American culture with food, music, fun for kids, traditional arts and crafts, and more.
• First Fridays Concerts in the Courtyard from April to October at the corner of High and Court Streets in Olde Towne Portsmouth. You can expect live entertainment, drinks and snacks, an art market, and free admission to the Portsmouth Art & Cultural Center. 

Is Portsmouth Worth Visiting?

By now, you’ve probably already gotten a feel for why Portsmouth, VA, is such a memorable destination. Whether you’re exploring its historic ship museums, gazing at its unique architecture, or grabbing a dinner and movie at the one-of-a-kind Commodore Theatre, Portsmouth offers something for every visitor. Many tourists’ main destination is Norfolk, which is just a quick ferry ride across the water, but we encourage you to give this small historic city a visit as well!

When to Visit Portsmouth

We’ve visited Portsmouth three times by now in various seasons. When to visit Portsmouth depends on what activities you’re interested in and your temperature sensitivity.

• Spring offers comfortable sightseeing weather and the chance to enjoy the city’s vibrant festivals like the Umoja Festival and Seawall Music Festival. This is our favorite season to visit with the mild temperature.
• Summers in Portsmouth, though quite hot and humid, are still fit for indoor activities and evening outdoor events, like the First Fridays Concert Series that continues through the summer.
• Fall provides a cooler, scenic backdrop and smaller crowds, perfect for exploring historic neighborhoods or taking the ferry to Norfolk. This is our second favorite season to visit Portsmouth.
• Winter brings a quieter charm, with mild days in the 40s to 50s and festive events around the holidays.

Getting to + around Portsmouth, VA

How to get to Portsmouth

Here’s a quick rundown on how you can get to Portsmouth, Virginia, by the main means of transportation:

• By Ferry: If you’re already in Norfolk, you can quickly hop on the ferry across Elizabeth River to reach Portsmouth for just $2. You can purchase tickets online ahead of time or at the ferry; however, the exact cash/change is required.
• By Plane: Fly into Norfolk International Airport (ORF), just 20 minutes from downtown Portsmouth. ORF offers numerous flights from major cities and has convenient ground transportation options, including rental cars and shuttles.
• By Train: Amtrak services nearby Norfolk, Virginia, via the Northeast Regional line. From there, it’s a short drive or ferry ride to Portsmouth.
• By Bus: Greyhound makes stops at Norfolk, making Portsmouth easily accessible then by ferry for budget travelers.
• By Car: Portsmouth is conveniently located near major highways, including I-264 and I-64, making it easy to reach by car from most East Coast cities. There are tunnels that connect Portsmouth to Norfolk as well.
• By Boat: Consult our Boater’s Guide to Portsmouth, VA, below!

Getting around Portsmouth

Once you’re in Portsmouth, we found that you can comfortably walk or bike throughout the downtown. There is no need for a car to get around Portsmouth.

If you want to explore areas outside of Portsmouth and Newfolk, like the Great Dismal Swamp or First Landing State Park, during your trip, that’s where a car would be useful. But if you’re planning on staying local, you can 100% get by without one.

Rental cars are available locally as well, mainly out of Norfolk.

Where to Park in Portsmouth

There’s plenty of free and paid (usually $1.25 an hour) street parking throughout downtown Portsmouth, but here are two parking garage options, both for $12.50 per day, if you’re looking for a bit more security:

• Water Street Parking Garage is closer to the waterfront
• Middle Street Garage is closer to the downtown

🚶🏼‍♀️ Portsmouth has a walk score of 84/100 and a bike score of 51/100 making it a very walkable city and also fit for getting around by bike!

How Much Time Do You Need in Portsmouth?

To fully enjoy Portsmouth, Virginia, without overstaying, we recommend a trip of 1-2 days. With this time, you’ll be able to explore historic sites like the Portsmouth Naval Shipyard Museum, stroll along the scenic waterfront, and check out Olde Towne. Add in a visit to the Children’s Museum of Virginia or the Hill House Museum for more local history, and enjoy some of the great dining options in town. If you’re looking to explore neighboring Norfolk as well, we recommend extending your trip to 3-4 days.

Where to Stay in Portsmouth

Portsmouth offers a variety of hotels and campgrounds to fit any budget. Here, we’ve listed the top accommodations that stood out to us at each price point. For a more private or unique stay in Portsmouth, consider browsing VRBO and Airbnb, where you’ll find options ranging from cozy apartments to full home rentals.

Hotels

• Super 8 by Wyndham Portsmouth – Norfolk – Budget, 0.5 miles from downtown Portsmouth, lowest price
• Quality Inn & Suites Old Town – Budget, 0.5 miles from downtown Portsmouth, breakfast included
• Renaissance Portsmouth-Norfolk Waterfront Hotel – Moderate, 0.2 miles from downtown, right next to the ferry stop in Portsmouth

Campgrounds

• Chesapeake Campground is the closest tent and RV campground to Portsmouth, a 23-minute drive from downtown.
• JEB Little Creek Campground is the second-closest tent and RV campground to Portsmouth, at a 29-minute drive from downtown.

Boaters Guide to Portsmouth, Virginia

We visited Portsmouth 3 times while we lived on our boat and traveled around America’s Great Loop and loved the free docking options, provisioning, and all things boat life quite uncomplicated. Here’s all the information we have for any of you fellow boaters looking to sail into this charming Virginia coastal city!

How to Approach Portsmouth

The Elizabeth River provides well-marked channels and easy access to Portsmouth’s waterfront, but boaters should be mindful of commercial vessel traffic and check for bridge openings when necessary. This area has a LOT of marine traffic with large military ships, commercial traffic from cargo ships, and pleasure craft. Please be cautious of your speed and wake!

When approaching Portsmouth, you’ll either be navigating from the Chesapeake Bay down into the Elizabeth River.

Portsmouth’s waterfront includes multiple marinas with transient docking options, as well as proximity to popular spots like High Street Landing for easy access to restaurants, shops, and all the main activities in Portsmouth, VA.

Download the free Waterway Guide App to locate marinas, services, anchorages, free docks, navigation alerts, bridges, locks, and more!

Where to Dock in Portsmouth

• Tidewater Yacht Marina is a full-service marina with all your standard amenities, right off the Elizabeth River and next to downtown Portsmouth. If you’re staying at the nearby anchorage, there is a $12 fee to tie up your dingy for the day.
• Ocean Yacht Marina is a Marina with all your standard amenities right by downtown Portsmouth.
• Waterside Marina is a Marina with all your standard amenities on the Norfolk side of Elizabeth River, you can tie up your dinghy for up to 4 hours for $9 and have easy access to downtown Norfolk.

Use our Referral Code 450ZMS3 for a $15 discount on your Dockwa reservation!

Free Docks in Portsmouth

• High Street Landing Free Dock is a 100% free dock in Portsmouth for boats up to 40 feet. This is where we docked our boat, Pivot, each visit to Portsmouth. Dockage is limited to 3 days within a 30-day period. The basin can get rocky and rolly from the Portsmouth-Norfolk ferry. The dock is a fixed dock, so be sure to tie your boat up accordingly. The water can rise above the docks during King Tides.

Check out our Great Loop Anchorages and Free Docks Spreadsheet with 600+ anchorages!

Where to Anchor in Portsmouth

• Hospital Point Anchorage is an open river anchorage where you can anchor anywhere between the red channel buoy and the white warning buoy. You can take your dinghy to Nauticus dinghy dock in Norfolk or the High Street Landing in Portsmouth. This is a great spot for boaters who prefer anchoring over a free wall or as a backup plan if the free docks are full. We anchored here and found the anchorage a great alternative to the free dock if it’s full. Most boats are courteous and go slow, but there are a few boats that are disrespectful and throw a large wake. We recommend locking up your dinghy as this is an urban area with a lot of people.

Check out our blog post on Dinghy Essentials, which we always keep in our dinghy!

Wifi in Portsmouth

• Portsmouth Public Library is a great free option to work from your laptop in Portsmouth, only closing on Sundays and Tuesdays.
• The Coffee Shoppe offers free wifi to customers, just consult their staff about any rules for working on your laptop, especially during peak hours.
• Cure is another coffee shop that offers free and fast wifi to customers, always good to ask staff before setting up to work!

Check out our blog post on Boat Internet!

Provisioning in Portsmouth

During our visits to Portsmouth, we didn’t reprovision in town. We picked up groceries at the Food Lion near the Deep Creek lock on the northern side of the Dismal Swamp Canal. Here is a list of some of the nearby grocery stores:

• Olde Town Food Mart is the closest place to the river to pick up a few basic provisions, just a 9-minute walk from the harbor.
• Food Lion is your closest large grocery store, about a 30-minute walk or an 8-minute bike ride from the harbor.

Hardware + Marine Supplies in Portsmouth

• Mile Zero Marine is the main marine supply store in Portsmouth, conveniently located right by Elizabeth River.

Watch Our Trips to Portsmouth, VA on YouTube!

You Might Also Be Interested in:

• Top 10 Beautiful Chesapeake Bay Towns & Cities on the Shore
• A Detailed Guide to Boating the Dismal Swamp Canal

Ready to Explore Portsmouth, VA?

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