For history, boating, and good fun, you should put Hampton first on your list.

Even in an area as steeped in history as the Chesapeake Bay, Hampton stands a head taller. Here are a few quick examples. Hampton is the oldest continuous English-speaking settlement in the United States. Its prominent point at the entrance to Hampton Roads was given the name Point Comfort (now it’s Old Point Comfort) by the English colonists in 1607, before they sailed up the James to found Jamestown. Hampton was established soon afterward. And soon after that, the first fort was constructed on Point Comfort. It was here, in 1619, that the first enslaved people in North America were brought ashore. And it was here, at Fort Monroe during the Civil War, that three of the enslaved escaped and were given refuge by its commander, who declared them “contraband of war.” Hundreds more followed as the war continued.

On a completely different subject, Hampton was also where the first astronauts were trained.

Okay, we’ll stop with the history lesson and move on to just a few of the many reasons why Hampton makes the perfect Weekends-on-the-Water destination. Here’s a big one: The Hampton River leads right to the city’s doorstep, so coming in by boat is a snap, as is trailering or just driving in with your kayak on the cartop. Hampton has several excellent marinas and one of the friendliest yacht clubs around. It’s also easy to walk around the historic downtown where you’ll find one-of-a-kind restaurants and unusual shops, an excellent air-and- space museum and even a gorgeously restored carousel from the 1920s. We’ll get to all of that and more in just a minute. First let’s get the lay of the land.

Seeing the sights in Old Hampton is about as easy as it can get. And whether you arrive by boat and settle into the Hampton Downtown Public Piers or the Customs House Marina, or stay at Hampton’s waterfront, you will find yourself ideally situated, because the old town, with its pedestrian friendly, shaded streets of restaurants and shops, the imposing Virginia Air & Space Center, and that carousel we mentioned, are all within a few blocks of each other. The Hampton River is short, wide, deep, and welcoming. The main part of old town is located along the waterfront and just north and west of the U.S. 60 bridge. Most of the restaurants as well as an utterly charming stationery store (yes, that’s right) are located along Queens Way. If you opt to stay a little bit downriver at the Hampton Yacht Club, you make the easy walk or bicycle ride up Bridge Street into the old town. Or if you decide on the excellent Bluewater Yachting Center, also down the Hampton River, you can use their water-taxi service.

Across the U.S. 60 bridge, you’ll find Hampton University’s wonderful museum. A little farther afield, but a must-see site on your Hampton visit, is Fort Monroe, which you can visit by car, of course, but also by boat from Old Point Comfort Museum or by anchoring in adjacent Mill Creek, just east of the Hampton River at the entrance to Hampton Roads.

Hampton lies at the entrance to Hampton Roads, which is one of the principal reasons it has played such an important role in the history of the nation, first as a stop for early English settlers who were worried about attacks from the Spanish, then as a strategic toehold for the Union during the Civil War. Oops, back to history again. But we mention it because it also means that it is easy to reach, especially by boat. But, arriving by car offers no obstacles either. In fact, of the six destinations in this issue, it is the easiest, quickest and most straightforward to reach by land-yacht.

If you arrive by boat

If you keep your boat on the Elizabeth River or up the James, you will doubtless have passed the Hampton River dozens of times. If you keep your boat up the Bay, from Poquoson to Deltaville, you’ll find that the Hampton River is an easy cruise away. The same is true if you are in the Maryland portion of the Bay. You’ll just have to plan on a night or two anchored out or in one of the many marinas just off of the main stem of the Bay. Once you reach Hampton Roads, one of the world’s best and busiest natural harbors, you have only to pass by in the watchful shadow Fort Monroe to find the entrance to the Hampton River. It is, in fact, where the Hampton Roads Tunnel makes its dive underwater. From Hampton Roads, the channel is well marked. Just be aware of the shoal that sits just offshore of the entrance. Follow the markers, and you won’t even notice it.

As you come up the Hampton River, you’ll find Bluewater Yachting Center along the junction with Sunset Creek, followed quickly afterwards by Hampton Yacht Club. Both of these are to port, while handsome Hampton University lies along the starboard shore. With the U.S. 60 bridge ahead, you’ll find Customs House Marina and then Hampton Public Piers to port and a small anchorage to starboard. That’s it, you’re in Hampton.

If you arrive by car

If you are driving from Norfolk or Portsmouth, we don’t need to tell you the way to Hampton. If you are coming down from anywhere to the north, from Richmond to Baltimore, you’ll leave I-95 (or I-295) at I-64 for the drive down to Newport News and then Hampton. You’ll probably want to get off at LaSalle south to Settlers Landing Road east into the old town, but really that’s what Google Maps is for, isn’t it?

If you want to launch your boat, the only public ramp directly onto the Hampton River is on Sunset Creek upstream from Bluewater Yachting. The next two handiest ramps are off Back Creek to the north. Gosnold’s Hope Park’s ramps are on the Southwest Branch and Fox Hill-Dandy ramps are at Dandy Point near Belle Isle and Dandy Point marinas. From there, you’ll need to come out Back River and turn south to enter Hampton Roads and then Hampton River, about a 10- to 15-mile trip.

Launching a kayak or other paddle craft can be done conveniently from Mill Point Park, just under the U.S. 60 bridge, or a bit farther upriver at the River Street Park Canoe and Kayak Launch. The Hampton River, with its tiny tributaries, is a perfectly lovely and protected bit of water to paddle. You can also launch easily to explore the Fort Monroe area. No matter what size boat you are using, you can get quite close to the Fort Monroe bulkhead. It makes a great view.


Bluewater Yachting Center lies one mile upriver, at the intersection of Sunset Creek. You can’t miss it. This is a lovely marina, with friendly and efficient staff, extensive boat repair services, boat sales, and its very own Surfrider Restaurant—and if you’ve spent time in the southern Bay, you are probably already a fan. The marina also runs a water taxi into town.

Just upriver lie the docks of Hampton Yacht Club, which organizes a well-known series of races and regattas each year.

Then comes the Customs House Marina with docks right in front of the carousel and next door to the Virginia Air & Space Museum. The slips are easy to get in and out of, though mind the current, which, while not particularly strong, can provide a mild surprise to the unwary. The same is true of the Hampton Public Piers located just before the U.S. 60 bridge.

Hampton Public Piers is the city marina, and it has nice floating docks along its bulkhead. The shower and restroom facilities are located in the visitor’s center just up the ramp. Also up the ramp, we might add, is a friendly brew-pub which makes a delightful stop on the way back to the boat after a day of sightseeing. The docks also connect under the bridge to Mill Point Park, which is a good spot for dog-walking and, as we mentioned, launching a canoe or kayak. There is also a dog park next to the carousel.


There is one downtown hotel, and it’s a nice one—Hampton Marina Hotel—located right on the waterfront between Customs House and Public Piers. It has a pool and restaurant and, located on Settlers Landing Road, is easy to get into and out of.

We’ve already given you a bunch of hints on what to do and see while you’re in Hampton, but in case you’ve forgotten already, here’s a quick rundown.

Stroll around town

We know, we often start with this one, but it’s important to get the lay of the land, so to speak. We described the way in by water and interstate, but now that you’re here, you’ll want to enjoy the old town’s fascinating architecture, particularly Queens Way, from Mill Point Park abutting the river to old St. John’s Church just before you get to Franklin Street. Here, along this quiet centuries-old street, you find the heart of old Hampton. You will also find most of old Hampton’s bars and restaurants. But we’ll get back to that. We recommend that you wander through St. John’s grounds, particularly its old cemetery. The parish of St. John’s was established in 1610, though its location here dates only from 1728—still a respectably long time. The church itself includes a lot of firsts, but we’ll spare you those to discover on your own. We’ll just mention that the building includes the 1887 Pocahontas window, which was given, in part, by Native American students at what is now Hampton University, the first school in the country to admit Native Americans. Of course, you’ll also want to stroll along Old Hampton Lane, which curves around to intersect Settlers Landing Road. Stay on Hampton Lane and you’ll be on Bridge Street, which will take you past the working seafood plant, L.D. Amory & Co., and, across Salters Creek, the Victoria Boulevard Historic District, a fascinating residential area. If you cross Settlers Road, on the other hand, you’ll find the Virginia Air & Space Museum and the carousel as well as the downtown marinas.

Virginia Air & Space Museum

This is a must-see stop on your Hampton visit. The all-glass building is striking indeed, whether you are outside looking in or vice versa. Inside, though, you’ll find early aircraft, early space technology, and an IMAX theater with a wide range of choices. Here too you’ll find the welcome center for the NASA Langley Research Center and Langley Air Force Base.

Hampton Carousel

You are going to love this! Between the Air & Space Museum and the downtown marinas, you’ll find this charming, beautifully restored, gloriously detailed, perfectly executed carousel built in 1920. The mirrors and paintings at its center are original. The carousel is part of the Hampton History Museum. You’ll find its main building nearby on Queens Way.

Miss Hampton Harbor Cruise

Whether you arrived by boat or car, you will want to climb aboard the Miss Hampton for a cruise out of the Hampton River and into Hampton Roads to get a good look at Fort Monroe and its sister fort, Fort Wool, which never got got used. We promise you’ll learn something new.

Fort Monroe

Whether you take your boat, your dinghy or your car, don’t miss Fort Monroe. If you’ve trailered in, this makes a great excursion. We like to take the boat into Old Point Comfort Marina so we can spend the day, eat at the Deadrise Restaurant, which sits above the marina office, and spend the night. If you arrive by boat, you simply cross McNair Drive and walk through the grounds, across the boat and into the fort proper. Be sure to take a walk along the ramparts (we think they are called ramparts) as well as the grounds itself. See where Confederate President Jefferson Davis was briefly imprisoned after the war. See where young Robert E. Lee helped in planning the fort’s construction. Then, if they have reopened after the pandemic closures, be sure to treat yourself to the Casemate Museum and the new visitor center.


Hampton’s old downtown is stronger on restaurants than shops, but there are a few we want to mention. You’ll want to visit the Virginia Store and Best of British, both in the same block of Settlers Landing between Old Hampton Lane and History Museum Way. On Queen Street you’ll find a few antique shops, like Mint Julep and Salvage Boyz. Then, be sure to cross Queen Street and walk into Hampton Stationery. It’s just about our favorite stop in Hampton, and once you see it, you’ll know why. The shop was started in 1932 in a former photo studio belonging to Happy Cheyne. The Cheyne Building was constructed in 1890. The stationery shop was purchased in 1957 by the Ishon family and is now owned by John Cabot Ishon. If you’re lucky, he’ll be there to show you around. Aside from all that, you’ll find lovely pens, stationery, leather bags, office furniture, which, yes, you probably are not in the market for right now, and even some Gill boating jackets and bags.

Hampton University

Take a walk (or drive) across the U.S. 60 bridge and into the beautiful broad grounds of Hampton University, founded after the Civil War as an educational center for the area’s formerly enslaved people. We particularly recommend a visit to the Emancipation Oak on the northern edge of the campus and the Hampton University Museum, where you can add to our list of Hampton firsts. Founded in 1868, it is Virginia’s oldest museum, the nation’s oldest African-American museum and contains an extraordinary collection of art from all cultures, but particularly African American.


Hampton always draws a crowd for its two big annual events, the Blackbeard Pirate Festival in late May and the Hampton Jazz Festival in late June.


We are not recommending this nutritionally, of course, but your taste buds will thank us for mentioning Glazed Doughnuts, which is a block north of Queens Street on Wine Street. Another and potentially healthier breakfast option is Mango Mangeaux in the Phoebus neighborhood—open for lunch and dinner.

Everything else

Oh, how can we decide what to recommend when there are so many choices? We’ll just rattle off a few and let you decide for yourselves.

On Queens Way, we love to stop for a Reuben sandwich at Goody’s Deli & Pub, an absolute Hampton mainstay, and at Venture Kitchen & Bar for pizza, although we sometimes get tempted away for the tapas. Who could resist Brown Chicken Brown Cow, if only for the great name? But have a seat on the patio (dog friendly) and order a grass-fed happy-cow big burger and a cold local draft. You’ll be happy too. Then there’s Latitude 37 and Grey Goose . . . oh, gosh, there are so many, and they’re all good.

At Fort Monroe, be sure to eat at the Deadrise, especially for its fresh local fish and produce as well as fun twists to old favorites. Owner Joe Illes, who has two other Hampton restaurants, Fuller’s Raw Bar, and El Diablo Loco Cantina, opened Deadrise a couple of years ago. We love it!

Finally, we mentioned that Bluewater Yachts has its own Surf Rider restaurant. Owner Stanley Bennett just keeps customers coming in droves to his Surf Rider restaurants, and the Bluewater location is no exception. ⚓︎