The perfect port city to anchor your weekend on the water

The charming old city of Portsmouth, a center of maritime activity for nearly four hundred years, stretches out along the busy Elizabeth River, named for Queen Elizabeth I, at the extreme southern end of the Chesapeake Bay. The heart of this riverfront city, and the center of its many attractions, is known as Olde Towne. This is where you’ll want to concentrate your weekend visit.

But don’t think of Olde Towne Portsmouth as a fusty old place, sleepy with age. Along with a world-class collection of historic buildings, churches and homes, Olde Towne has a vibrant nightlife with several first-rate entertainment venues, a dozen highly regarded restaurants and and weekends full of music, art, markets, crafts, and antiques. 

In addition, Portsmouth is directly across the river from Norfolk, a fact that makes it doubly attractive to visitors because a simple water taxi or ferry boat ride makes Norfolk attractions such as Nauticus and Waterside delightfully easy to reach. 

So, whether you come by boat or car, you’ll soon fall under the spell of Olde Towne Portsmouth and its fascinating maritime heritage.

Just to orient you, here is a quick tour of Portsmouth from the water. You might want to keep a map open in your other hand. Stick with us, it will all make sense in the end.

The city of Portsmouth lies south of Craney Island (an ever-growing spoil island) and Hampton Roads at the south end of the Chesapeake Bay. Like its neighbor Norfolk, it traces the Elizabeth River and its northern tributaries, in Portsmouth’s case encompassing by its own count 90 miles of shoreline. You will see right away why this area has been a base of shipbuilding and all things maritime right from the beginning. And by beginning, we mean within a decade or two of the founding of Jamestown.

On its north end, just south of Craney, you’ll find the historic U.S. Coast Guard Base, followed soon afterward by the Western Branch of the Elizabeth. The Portsmouth Marine Terminal on Pinner Point comes next, and then, jutting well out into the river and creating a bay popular with ICW cruisers, is the historic Hospital Point, site of the historic Naval Medical Center, and the location of the ICW Mile “0.” Then along comes another creek, Scotts, and finally the heart and soul of Portmouth, Olde Towne, its northern boundary marked by Tidewater Marina’s breakwater and docks, and the Crawford Trail and Parkway. Here the Elizabeth River splits with the Eastern Branch continuing into the Norfolk side and the Southern Branch forming the eastern border of Olde Towne as far as Ocean Marine docks and large yacht repair facility and then meandering off past the sprawling Norfolk Naval Shipyard. Why is it called the Norfolk Shipyard when it’s in Portsmouth? Glad you asked. When the old Gosford Shipyard was renamed by the Navy in 1862, there was already a Portsmouth Naval Shipyard in New Hampshire, so they named it after the county (Norfolk) instead. Whatever the reason, this is where famous ships such as the USS Chesapeake, the CS Virginia (better known as the Merrimack) and the USS Enterprise (world’s longest naval ship) were constructed. 

From here things stay very industrial and shippy, on both sides of the river, until the Albemarle & Chesapeake (“Virginia Cut”) and Dismal Swamp Canals split.

Whew, got all that straight? Good, now we can get back to Olde Towne, which is where pretty much everything you’ll want to see is located anyway. Happily for those arriving by boat, Olde Towne is bookended by two major marinas, Tidewater to the north and Ocean Marine to the south. Everything in between is within walking distance. Most of the restaurants and many of the shops are located on High Street. To the north and south of High are quiet, tree-shaded residential areas, punctuated by historic squares and churches. Within this area you’ll find most of the museums. Here too you’ll find some lovely and historic bed and breakfasts. And if an elegant riverside hotel is on your wish list, Olde Towne just happens to have one, the Renaissance Hotel.

If you are arriving by boat

The trip into Hampton Roads and down the Elizabeth River to Portsmouth is one of the most fascinating trips you will ever make on the Chesapeake Bay. And in some ways most nerve-wracking. Other than trying to negotiate Annapolis Harbor at 3 p.m. on a Saturday afternoon during race week, we are unaccustomed to much boat traffic on the Bay. Generally, wide open space is the rule. The trip into Norfolk and Portsmouth is the exception. In addition to the increased commercial shipping traffic headed in to and out of Norfolk and Portsmouth terminals as well as tugs and barges coming and going from docks up the Elizabeth River, boaters here must contend with U.S. Navy ships, which come with their own set of security requirements—most of which involve staying well out of the way. Once you get used to watching every which way in the manner of a hoot owl, you’ll find it’s quite exciting. 

After we’ve made the turn into the Elizabeth River at Sewell Point, we like to run just outside the channel markers on the western side, or just inside the markers on the eastern side. The eastern side will of course give you the best view of the U.S. Navy’s Atlantic Fleet, but you definitely don’t want to wander outside the channel here. You’ll be plenty close enough for a good view.

Once you are past the Navy ships, you’ll come to a series of ship terminals and then the coal black Norfolk Southern Pier 6 we mentioned above. Now you are nearly into the passage between downtown Norfolk to port and Portsmouth to starboard. Once you pass Hospital Point on the Portsmouth side, watch for Tidewater Marina’s breakwater and docks.

If you are trailering in

Your best (and pretty much only choice) for a public boat ramp is Portsmouth City Park, which has three docks and two ramps, as well as restrooms and other park facilities. Launching here will put you about 2.5 miles up the West Branch of the Elizabeth River. The West Branch joins the main river at Pinner Point, north of Olde Towne and just south of Craney Island. From there, turn to port for a cool cruise past the U.S. Navy Atlantic Fleet; turn to starboard for an equally nifty cruise through bustling Norfolk and Portsmouth as well as a good look at the Navy Yard’s impressive dry dock facilities and “hotel boats” for crew in dry dock. Continue down the Southern Branch another few miles for the novel experience of locking through the Great Bridge Lock. If you’ve time, continue under the Great Bridge Bridge to the Great Bridge Park’s free dock. Take a walk, have lunch, read the historic markers and then head back to Portsmouth. Want to go fishing? Head out the Elizabeth River into Hampton Roads, then head to port up the James River or to starboard to get out onto the Bay and some great fishing.

If you are launching a kayak, canoe or SUP

Yes, even in the midst of busy Portsmouth and Norfolk there are several places to put in your paddle-craft on your visit to Olde Towne. The first is Portsmouth City Park on the West Branch of the Elizabeth River. As we mentioned above, the park has two paved boat launches, but it also has a beach launch for kayaks, canoes and SUPs. You can drive within 20 feet of the beach to drop your craft for an easy launch. From there it is a 2.5 mile paddle to the Elizabeth River. Along the way, you can explore any number of creeks and salt marshes on both sides that invite exploration. Once you reach the main river, traffic in number and size will increase dramatically, so paddler discretion is advised. City Park is located on Cpl. J.W. Williams Ave.

South of Olde Towne and at the south end of the Naval Shipyard, you’ll find a lovely new kayak launch area at Paradise Creek Nature Park. This one is even handicap accessible. Here you can paddle through 11 acres of restored wetlands opening into Paradise Creek or you can join a guided tour. The Elizabeth River Project has been working to restore this area since 2001.

Finally, put in your kayak at Hoffler Creek Wildlife Preserve. There is a $10 launch fee for the park’s floating dock. Although the dock is half a mile from the parking area, there is a shuttle with kayak caddy that runs from one to the other. You can rent a
kayak here or join a guided paddle. Hoffler is located at the north end of the city near Craney Island. Its adjoining Hoffler Creek opens into the James River.


Tidewater Yacht Marina

A favorite choice for its location at the north side of Olde Towne and its extensive facilities, it is probably the most convenient for a weekend visit. Tidewater has its own restaurant and bar, a floating pool and party deck, fuel and repair facilities. And good WiFi.

Ocean Yacht Marina

At the south end of Olde Towne is a very pleasant choice as well. And it is nearest to the Union Bank & Trust Pavillion. So if you have tickets to an event, this might be your best choice. To get to Ocean Marine, follow the channel past Tidewater and into the Southern Branch while keeping an eye out for criss-crossing water taxis and the ferries. Just beyond the two city docks, you’ll spot Ocean Marine’s basin and piers. 

Free docks

There is a third option for Olde Towne dockage, and that is to choose either of the city’s two basins—North Basin and South Basin, which are cut into the seawall. These also serve as water taxi stops. The ferry leaves from the South Basin. You won’t find power or water hookups, but you will find free dockage here for up to 36 hours on a first-come first-served basis. Of the two, we find South Basin a little bit more comfortable. The free docks may lack the comfortable facilities of the marinas, but they are indisputably in the center
of everything.


Our first choice for an Olde Towne hotel would certainly be the Renaissance Portsmouth-Norfolk Waterfront Hotel which is located directly on the South Branch of the Elizabeth River and right in the middle of everything you are going to want to see. The views are impressive, especially from the rooftop bar. The hotel has its own restaurant and is within walking distance of many others. In fact, all of Olde Towne is just outside your door. 

If you are planning to come and go with your trailered boat, you might find the Quality Inn & Suites Olde Towne more convenient. It is located at the western edge of Olde Towne on Effingham Street. 

Bed and Breakfasts

A special weekend in a historic Olde Towne bed and breakfast seems like a natural. Here are two we recommend.

The Glencoe Inn

Located on the Elizabeth River just a couple of blocks south of Tidewater Marina. The home was built in 1890 and the rooms feature antique furnishings, private baths and high-speed internet. Our favorite part: the Scottish breakfast, including fresh homemade scones.

The Mermaid’s Porch

A Queen Ann Victorian with a lovely big porch featuring mermaids and a siren swing. There is also a courtyard, large welcoming living room and locally sourced breakfast.

Take a walk into history

Don’t worry, this won’t hurt. If you are in love with history, we don’t have to tell you more than to get hold of a copy of the city history walk and indulge your passion. You won’t find a better place to do it than Olde Towne. Three hundred years of historic homes and buildings. Leafy city squares. Churches awash in the past. Splendid architecture. Tiffany windows. Echoes of a violent past. Struggle for a brave future. It’s all here. And plenty of places for lunch.

If you consider architectural history more of an inconvenience than a long road to the future, we urge you to wander the streets of Old Towne and let the history of the place wash over you like a pleasant breeze. Enjoy the shady streets, the quiet neighborhoods, the perfect flowerbeds. Now, wander over to High Street and have a cold beer or a cup of tea. Then go shopping. We’re coming to that next.

Go shopping

Yes, let’s get right to shopping. We can get back to more elevating activities later. But where to begin? Here are a few of our favorites. We never visit Plymouth without a long and lingering look through the endless temptations of Skipjack Nautical Wares and Gallery. Antiques nautical stuff, nautical art from a well-known artists, jewelry, folk art, and even marine salvage. Make a boater happy! Then there’s Stellar Wine, the Kitchen Koop and the Little Shoppes on High. You get the idea. Go to it!

Visit a museum or two or three

Two or three? Isn’t that a bit much? Not at all. We’re not talking about the Louvre or the Smithsonian Museum of Natural History here. No, Olde Towne’s museums are all a nice manageable size, not too big. Just right for a nice relaxing weekend in a new town. Take the Portsmouth Lightship Museum. It’s a ship: How long can that take? Okay, the USS Wisconsin across the river in Norfolk takes a long time. This one, a lightship, carried about 15 crew when not sitting for months or years on end in one place, which is what it mainly did. Lightships were like lighthouses that moved. They were placed in dangerous places to warn off passing ships. This one was built in 1915 and didn’t return until 1964. Then it came here to be a museum. Then there is the Naval Shipyard Museum, which saves you a trip to the shipyard, and just outside Olde Towne, the Railroad Museum, which has artifacts of the railroading days and an old steam engine, passenger car and caboose. 

By the way, Norfolk Southern Railroad has a small museum of its own a water-taxi ride and a short walk away.

And if you’ve packed a few children for the trip, you’ll want to be sure to take them to the Portsmouth Children’s Museum. There they can produce very big bubbles, learn to be a tugboat captain and a banker, and be dazzled by the stars in the Beazley Planetarium. Sure, it’s in Olde Towne too.

Many of these museums are open only on weekends, so check the times.

Be entertained

During the season—roughly May through December—you’ll find plenty of special events around Olde Towne to keep you royally entertained. Here are just a few:

While you are still planning your weekend in Portsmouth, check the schedule for the Union Bank & Trust Pavilion. This is the area’s venue for top-name performers. Sit under cover or under the stars and enjoy the concert. And if you are staying at Ocean Marine, you will be only steps away.

If you are in town on a Thursday, walk over to High Street Landing and listen to great local musicians as you enjoy the evening along the Elizabeth River. Like to mix art with your music? You’ll love concerts in the courtyard and free admission to the Cultural Arts Center, all on High Street, of course, on the first Fridays of the month. 

Finally, don’t pass up the opportunity to take in a first-run movie at the 1945 art deco Commodore Theatre. The theater features a whopping 41-foot screen and state-of-the-art Dolby sound. Sit in the balcony and enjoy a great sandwich or pizza and a glass of beer or wine while watching the movie. Sweet!

Oh, there’s more. On the first Saturdays, be sure to catch Portsmouth’s famous Antiques & Flea Market on County Street, just south of High Street, and hunt for treasure among the rows upon row of antiques and collectibles. Finish off the morning with a visit to the Farmers Market at Court and High streets.

Take a boat ride

Here’s a special treat. We know that there are more than enough activities to pack a weekend full in Olde Towne alone, but if you can squeeze in the time, we recommend taking either the paddle-wheel ferry or the water taxi across the Elizabeth River to Norfolk. Visit Nauticus Marine Museum and the battleship Wisconsin if you can—Norfolk is full of great things to do—but our favorite thing to do is to catch a ride on the tour boat Victory Rover for a narrated trip out the Elizabeth River to visit the Atlantic Fleet, the largest collection of U.S. Navy ships docked at the world’s largest naval base, Naval Station Norfolk. Taking the tour will let you know what’s what. You’ll also pass the Norfolk shipping terminals and Norfolk Southern Railroad’s Pier 6 at Lamberts Point—the largest and fastest loading coal facility in the Northern Hemisphere.


Who wouldn’t recommend a restaurant named Yoolks on Us for breakfast? This Southern bistro, located on Washington Street just off High Street, not only has a great name, it also serves a great breakfast and does it all day. How could you go wrong? Okay, it also serves lunch and dinner. Whatever you order, make sure you’ve got grits on the side. Omelet and grits. Shrimp and grits. Fried eggs and grits. You get the picture.

Lunch and Dinner

We just couldn’t decide. Olde Towne has too many good restaurants to pare it down to a couple. We love all of these. It just depends on the day of the week and what we’ve got a yen for. All of these places serve lunch as well as dinner. We suggest you stroll down High Street and follow your nose.

Café Europa

For lunch, think mussels provençale, polenta with mushrooms and gorgonzola or shrimp Pernod. For dinner, imagine a medium rare steak fritte, shrimp puttanesca or lobster ravioli in a shrimp and brandy sauce.

Still Worldly Eclectic Tapas

How about seared scallops with balsamic strawberry jam, salmon bacon and goat cheese crumbles or bison meatloaf with caramelized onion and port wine ketchup gravy? Just reading the menu boggles the mind. We just close our eyes and point.

Bier Garden

We’re running out of steam. Let’s just say we love German food and you’ll find none finer than here. Bratwurst, rouladen, goulash. Sehr gut!

Want more? How about Gosport Tavern, Stellar Wine, and Lobscouser, which is apparently Norwegian for fixing food on a boat—how could we leave it out? And the same goes for Fish and Slips at Tidewater Marina. Just one more: Barons Pub with its famous burgers and beers. No, really, we’ve got to stop. Our advice is just arrive hungry. ⚓︎