While cruising the Chesapeake, it pays to get off the beaten path. Cruisers commonly complain that everything in the Bay takes too much time to get to — that you must plan an extra 5 – 10 miles out of your way just to get into marinas and anchorages. But sometimes it’s worth it, and Urbanna, Virginia, is one of those out-of-the-way ports you should visit. Founded in 1680, the town was a major port in the area for cargo (tobacco going to Europe, then steamers traveling the Bay. Now, the town is the tourist center for Middlesex County. And, unlike the rest of the towns in the region, it’s convenient for boaters to visit with everything clustered right near the protected harbor.
Urbanna is located on the banks of the Rappahannock River, about 16 nm upriver from Stingray Point and Deltaville. Yes, it’s a bit of a trek off the “highway” up and down the Bay, but it’s worth it. Friendly marinas with bargain prices, fuels (including propane!), several excellent walkable restaurants, and even a good-sized IGA grocery store.
Hundreds of migrating boaters beeline through Chesapeake Bay every year, leaving some of the country’s best cruising grounds for the locals. There are a ton of great cruising towns around the Lower Bay, but Urbanna is our favorite. Unlike other destinations in the area, everything is within walking distance from the marinas and harbor. The dinghy dock is free and easy for everyone to access.
Urbanna is the perfect Chesapeake boating destination for cruisers
Urbanna Creek is a lovely spot for paddling or sailing small boats. It’s wide and protected, with room to stay out of the channel and away from boat traffic. At the mouth of the creek is a lovely beach for walking. You’ll see kayakers and dinghies landing throughout the day to let their dogs romp or stretch their legs. On low tides, you can walk a considerable distance (maybe 0.2 miles), but there are private property signs once you reach the Rosegill property.
It’s a quick three-minute walk up Virginia Street from the harbor to a welcoming downtown area with historic buildings. We particularly like the burgers at Small Town Burger, and Little Jimmy’s has some great salads and sandwiches. The Virginia Street Cafe has diner food emphasizing fried seafood, and Something Different has barbeque. Within a few steps, there’s an old-time drug store, boutique, two art galleries, the post office, an ABC liquor store, an inn, and several cafes. A five-minute walk takes you to the IGA supermarket. In the middle of town, you’ll pass the 1740 farmhouse, Landsdowne. It’s a private residence, but it’s a lovely sight.
Boaters will be interested to stop by the town visitor center and museum to see the John Mitchell map. The Urbanna Oyster Festival is big business in these parts, attracting boaters and tons of car traffic to the area. It’s on the first consecutive Friday and Saturday each November and includes a carnival, arts show, parades, beer and wine tastings, live music, and a shucking contest.
Setting course for Urbanna
The trip up the Rappahannock is well marked. Even the strongest ebb tides do not exceed about three-quarters of a knot and are usually between 0.3 and 0.5 knots. Coming into the channel at Urbanna requires caution as shoals surround it. Thankfully, it has been surveyed by USACE and is available on the AquaMap app. The first extends east into the river from the stone breakwater and is marked by both a fixed red and a red nun — give these a good margin, at least 100 or 150 feet, and more if you are approaching from the north. Once aligned in the channel, maintain the center as you pass the beach area, with its shallow sandbars, to port. After making the 90-degree turn into the harbor area, favor the marina side until you reach the anchorage area.
There are two transient marinas in town: The town docks (sometimes called Upton Point) and URBBY (Urbanna Boatyard and Marina). The anchorage area is protected from nearly all directions and lies in the bight across from the town marina. In spring 2025, there were two derelicts and an unattended mooring ball, but plenty of room for 4 or 5 to anchor. If you can clear the 21′ fixed bridge upstream, you’ll have access to even more anchoring options.
If you’re interested in a long-term stay, the rates at the town marina are a reasonable $400 per month for transients — it’s a nice place to tie up in the summer and run your air conditioner. Both marinas have pump-outs, and URBBY has diesel, gas, and propane fills.
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