48-Hour Vacation By Boat

Portsmouth is located at the Zero Mile Marker of the Atlantic Intracoastal Waterway. It’s an ideal stopover location for long-haul travelers on the ICW, an excursion from the Chesapeake Bay, or a destination for boaters visiting from Richmond, Hampton, Virginia Beach, or any of the mid-Atlantic boating communities. Top of the line marinas with all the amenities and a walkable commercial neighborhood with great restaurants and plenty of things to do with out a car will make your trip easy to plan.  Portsmouth is Virginia’s Historic Seaport, welcoming seafarers since the 1600s.


4:00 pm

Arrive at Your Marina

Choose one of Portsmouth’s marinas. There are two in Olde Towne, Tidewater Yacht Marina and Ocean Yacht Marina, both operated by Suntex.  These are ideal if you want to be within walking distance to restaurants, bars, museums, and other attractions. Or if you have your own bikes on board, you can pull into one of the marinas located on Scott’s Creek. If you go out to the Western Branch marinas, you’ll find beautiful views in a tranquil setting but Uber will be necessary if you want to leave the area.  For even more R&R, leave your boat in the slip and enjoy the comfort of a local hotel or rental.

View Marinas
5:00 pm

Happy Hour on Land

Time to get off the boat and rediscover your land legs. There are plenty of places to consider in walking distance of your slip, like Guad’s for Margaritas or Olde Towne Public House for craft beers.  If you are not quite ready to venture away from the water, you can get happy hour drinks and apps at any of our two waterfront bars, Fish and Slips, or Foggy Point Bar & Grill

7:00 pm

Dinner in Olde Towne

If you didn’t fill up on appetizers during Happy Hour, treat yourself to a delicious chef-prepared meal in Olde Towne.  Feeling like a romantic dinner for two?  Try Cafe Europa, Stellar Wine, or Still. On Friday nights, Stellar Wine often has live music.  If your taste runs a bit more ethnic, you might enjoy Thai Basil or Bangkok Garden, possibly Cancun Fiesta, or German fare at the Bier Garden.  No matter what you might be craving, you can find it within walking distance of your slip.

View Olde Towne Restaurants
9:00 pm

Explore Local Nightlife

Friday nights are a good time to check out live music.  On most Fridays, you’ll find bands on the Roger Brown’s Live stage and inside Olde Towne Public House. You might find some jazz at Stellar Wine and  acoustic rock at Baron’s Pub. Hit up High on High for some hookah and the hottest DJs.

Who's Playing Tonight?


9:00 am

Breakfast on the Run

Start your day with coffee and a light breakfast (you’ll be snacking all day). Check out Olde Towne’s Coffee Shop on the corner of High and Middle or take a seven block walk up North Street to Starbucks and get your caffeine on! After breakfast, stop by the Portsmouth Welcome Center and pick up a map for a morning of exploration.

10:00 am

Explore Olde Towne

Olde Towne Portsmouth is both a neighborhood and a commercial district.  Within the bounderies, you find three centuries of architecture and history, along with over twenty public art pieces, and a variety of quaint shops to explore.  Take the self-guided Path to History tour or reserve a guided tour from one of Mary Veale’s costumed re-enactors or aboard the Olde Towne Shuttle.  Not into history so much? Download the guide and take an Art Scavenger Hunt to see the local public art.  Maybe you just want to shop?  Start with Olde Towne Portsmouth’s Farmer’s Market, visit Anderson-Wright Rooms and Gardens, the Kitchen Koop, or any and all of the other shops on High Street or any of the connecting cross streets.

12:00 pm


Your explorations will work up an appetite.  Pick any of the Olde Towne restaurants and enjoy.  Gosport Tavern is a Saturday lunchtime haunt but maybe you want to explore something you’ve never tried, so check out Beyond Vegan Cell Food or head over to District for authentic southern Soul Food. California burritos at 619 Cantina are always a good choice.  You can’t go wrong with any of these family-owned, chef-run restaurants.

1:30 pm

Take A Trip Across the Pond

Well, not that pond…but both Portsmouth and Norfolk do have roots in Great Britian!  The Elizabeth River Ferry runs every thirty minutes and takes about five minutes to cross.  Once on the other side, the choice is yours.  Take a cruise to the world’s largest Naval Base aboard the Victory Rover at 2pm.  If you want to stay on land, stroll over to Nauticus and visit the USS Wisconsin.  For the history lover, see the MacArthur Memorial Museum.  If you’re feeling energetic, stop by Pedigo Bikes and rent an electric bike for a ride along the Elizabeth RIver Trail (or bring the bike back to Portsmouth to explore places beyond Olde Towne).

6:00 pm

A Night Out on the Town

There’s always something happening on the banks of the Elizabeth River.  Get tickets for a show at the Atlantic Union Bank Pavilion.  See a movie at the 1945 art deco style, fully restored Commodore Theatre. Take the ballpark ferry to Harbor Park for an evening baseball game. Check out all the live entertainment on both sides of the water.

What's happening tonight?


10:00 am


Walk up to Washington Street and look for Yoolks on Us Southern Bistro.  They specialize in breakfast and if you like shellfish, the Crab Benedict is a must.  Yoolks offers a mimosa so large that is comes with a ladle.  You can also find a brunch at Foggy Point Bar and Grill.  Sit out on the patio and enjoy the view while you enjoy an amazing breakfast.

12:00 pm

Get Some Love to Take Home

No visit to Portsmouth is complete without a photo of you and your travel companion in front of the Loveworks sign.  Walk down to Crawford Parkway (you’ll need to walk off breakfast) near the Tidewater Yacht Marina and you’ll find the Love sign.  Take a photo with Crawford Bay and the Elizabeth River in the background.  You’ll be glad you did. If you post it on social media, be sure to tag #visitportsva

12:30 pm

Learn About Boats

Make a stop to tour the Lightship Portsmouth and see how the men of the Lightship Service lived for months at sea.  Go next door to the Naval Shipyard Museum and discover America’s oldest Naval Shipyard.  Portsmouth has been building and maintaining boats since the 1600s.  You might learn something here that will come in handy on your way home (let’s hope not).  From here, head back to your boat and begin your voyage home.  Come back to see us again very soon.

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