Travel · virginia

A Beautiful Weekend Getaway in Portsmouth, VA

Dustin and I had an amazing weekend exploring Portsmouth, VA and I am thrilled to share it with you! I was able to work closely with Keith Toler through The City Of Portsmouth’s Parks, Recreation, and Tourism Department in the creation of this exciting Itinerary for A Romantic Weekend Getaway in Portsmouth.

Portsmouth is an absolutely gorgeous historic seaport town. If you are looking for a unique, waterfront weekend getaway – then look no further! Here’s our itinerary:

Itinerary for a Weekend Getaway in Portsmouth, VA

Day 1:

  • Check-in at The Renaissance Portsmouth Waterfront Hotel
  • Dinner at The Foggy Point Bar & Grill
    • Located inside the hotel – The Jerk Chicken and Fried Wings were absolutely delicious!
  • Drinks & S’mores by the Fire
    • Request the S’mores package at the bar
  • Grab a Nightcap from one of the many bars on High Street
    • Roger Browns, Stellar Wine, and Baron’s Pub are a few options

Day 2:

  • Brunch at Yoolks on Us
    • An INCREDIBLE brunch spot – we highly recommend the Eggs Benedict and the Fiesta Chicken Omelet
  • Walking Tour of Olde Town with Mary Veal & The Colonials
    • This was so much fun! I don’t always get excited about history and tours of this nature, but this company does a great job. They make it very fun and educational; plus, walking around Old Towne Portsmouth is absolutely beautiful!
  • Get in the car and head to Hoffler Creek for exploring the trails or do some kayaking!
    • We chose to do the Kayaking and highly recommend it! It’s very calm and very peaceful – a great way to unwind and admire nature in a unique way.
  • Grab a flight at MoMac Brewing
    • MoMac has a nice outdoor patio. The Brown and The Purple Lady Fruited Sour were our favorites!
  • Lunch and a Beer at the Bier Garden (& German Restaurant)
    • This place was one of our absolute favorite spots in Portsmouth. They offer traditional German food and a huge variety of beer. We enjoyed a Large Pretzel, which came with the most delicious Beer Cheese that you could ever imagine! We also split a Knackwurts, German Potato Salad, and Red Cabbage. I would not typically order any of these things, but for something different – it hit the spot!
  • Relax at the Hotel
  • Dinner & a Movie at The Commodore Theatre
    • This was actually a Bucket List experience for me! The Commodore Theatre is a historic theater that operates as a full-service dinner theater. You sit at a table, order your food and drinks through a phone located on each table, and your food is brought to you throughout the movie!

Day 3:

  • Breakfast & Coffee at The Coffee Shoppe on High Street
    • This Coffee Shoppe sells “Bagel Nutz” which was founded in Portsmouth. They are delicious cream cheese filled dough balls, offered in a variety of styles; My favorite was the Everything Bagel style! I also had an incredible Iced Raspberry Mocha.
  • Explore Downtown Shops, Wall Art, Museums, Waterfront, etc. I also recommend stopping by the Portsmouth Visitor Center, as they have a unique gift shop that sells a variety of locally made foods, art, clothing, etc.
  • Lunch on the Marina at Fish & Slips
    • I’m a sucker for any restaurant that’s on the water, and Fish & Sips did not disappoint! Dustin had the Wings and I had the Buffalo Shrimp Tacos that were SOO GOOD that I forgot to take a picture of them.
  • If time permits, take the Ferry to Norfolk and explore Waterside
    • We didn’t have enough time to do it – but the Ferry stop is located right outside of the hotel. The trip over there isn’t far at all!

Another huge thank you to Keith Toler and the City of Portsmouth for helping me plan this trip! It’s truly a beautiful place and would make a great getaway weekend for people of all ages and interests! There is so much rich history in the area, but yet today’s Portsmouth is the most beautiful mix of both historic and modern.

There is so much to do and see within the area, you can read more about The history of Portsmouth and surrounding areas here. It’s a great town for history buffs, art lovers, foodies, and travel lovers of all types!

Thank you all for reading about my Weekend Getaway in Portsmouth VA! Please don’t hesitate to reach out with any questions about the trip. You can find me on Facebook or Instagram.

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Until next time,



One thought on “A Beautiful Weekend Getaway in Portsmouth, VA

  1. It’s great to visit, terrible place to live! The court system is a nightmare for family issues, there seems to be a “catch and release” policy if anyone is ever actually caught, gunshots are a nightly occurrence in more neighborhoods than not… did you stay over a weekend? I’m shocked you didn’t hear a few in Olde Towne. Property taxes that don’t match city investments. Schools that are almost all Title I with teachers underpaid, under supported, and generally not where I’m happy to send my kids. Corrupt local government we can’t seem to flush out. Not a single hospital in the city with an operational labor and delivery unit. Glad you enjoyed your visit and wish I could leave with you. This isn’t a place I’d encourage anyone to visit. Olde Towne is a cute little bubble but it ain’t Portsmouth by a long shot. It’s like the commercial version of the Whopper versus the soggy bun they hand you that an angry teenager hastily threw together with half your condiments splashed on the wrapper and the cheese you paid extra for is missing.

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