Over the years, Sarah and I have had the joy of photographing more than 25 surprise proposals as we watched young men ask a single question that would change the course of their lives. Between that and my own experience of proposing to Sarah, we’ve learned a lot! I certainly wish I had all this information before I got down on one knee!

 

But now it’s our turn to pass along our experience and wisdom to every guy out there wondering to himself, “How do I propose to my girlfriend?” Every week throughout this Spring, we’ve posted an updated version of this 2018 blog series. It’s mostly written as a note directly from me, Hunter, to all the guys out there who are exactly where I was back in 2016: head over heels in love with a girl, with absolutely no plan on how to ask her to be yours! Sarah even chimed in with some of her input to the ladies who think the big question might be coming soon!

 

A Guy’s Guide to Proposing Well Part 7: How to Make a Weekend Out of It

 

Well, well, well, here we are! The final post in this series! Last week, we talked about the most important part of the entire process, the proposal itself! This week we’re rounding things off with a few thoughts on how to turn a ten-minute-long proposal into a weekend-long celebration!

 

 

Why Make it a Weekend?

Although the day you propose will be a one-of-a-kind memory no matter what, we’ve had many of our HSP couples turn their proposal into a full out-of-town weekend event! We know that our couples have loved the extended time away from their normal lives, and it can even preempt the proposal by making the weekend a romantic getaway from the very start!

 

We know not everyone will make a weekend out of their proposal, but at the very least, take some time out of your busy lives to spend one meal celebrating together. If you can spend 48 hours celebrating, even better!

 

 

Best of C’ville (As Judged By Us)

While we certainly won’t claim to be experts on all things Charlottesville, here are just a few of our favorites in each category as you plan a weekend getaway here in town. We’ve focused mainly on the downtown area since that’s where we live and what we know best! We’ve also arranged each category (roughly) from least to most expensive for your convenience. If you think we left somewhere out, just let us know!

 

If you aren’t planning on proposing in Charlottesville, but have been reading this blog for all it’s more widely-applicable advice, hopefully this will help you think through all that there is to do and see (and eat) in whatever town you’ll be proposing in!

 

Awesome Places to Stay

• Our Basement Apartment – No joke! Want us to be your photographers AND your AirBnB hosts? Sarah and I spent the winter of 2020 turning our unfinished basement into an adorable 2-bedroom apartment! If it isn’t already rented for your weekend, check it out!
• Residence Inn Downtown – This is your classic upscale hotel experience, complete with indoor pool, hotel bar and fitness center. It’s also located one block from the Downtown Mall, making it the most frugal of the four options while still giving an experience worthy of your proposal weekend!
• The Huntsman – This “unhotel” has no front desk, no check-in, and only four rooms. They keep costs low with AirBnB-style check-in, but are located on the Downtown Mall. For the foodies and bar-hoppers who will spend a lot of time on the Mall, this might be the best choice.
• The Oakhurst Inn – If you’re looking to go all-out with a boutique hotel experience, the Oakhurst Inn is your best bet. They’re located a block away from UVA’s Grounds, and have a wonderful little café that’s open to guests and the public alike.

 

 

A Few of Our Favorite Places for Dinner + Drinks

• Now and Zen – If sushi and Japanese food is your thing, this is the place to be! They have tons of options, and the portions are really reasonable for a sushi restaurant! Get here early though, because their space is tight.
• Orzo – Orzo serves up innovative Mediterranean food with great wine and cocktail pairings. Their restaurant somehow perfectly combines an industrial feel with an intimate “date-night” ambiance.
• Lampo – This absolutely TINY eatery is probably one of the most upscale Pizza restaurants you’ll ever eat at. Their authentic Neapolitan brick pizza oven was imported from Italy, and the restaurant often boasts waits of 1-3 hours on busy nights.
• Tavola – This is one of the only Italian restaurants that Hunter will eat at (his family is Italian – it’s a whole thing). But their food and drinks are incredible! Not to mention, they have an adorable hidden bar around the back where you can share a drink while you wait on your table. It’s our favorite for date nights, anniversaries and other special occasions! All four of these restaurants are within an easy walk of downtown.

 

 

The All-Important Brunch Spot

• Bodo’s Bagels – This New York-style bagel shop has three location and is as Charlottesville as Thomas Jefferson himself. Stop in and grab yourself a great bagel sandwich for only a few bucks, and don’t sweat it if the line is out the door – you’ll still be in and out in minutes.
• Bluegrass Grill – This very classic American diner gets so busy on weekends that you should expect to show up well before 10 am or prepare for a long wait. Despite the fact that they only accept cash and check, it’s a favorite for many C’ville natives.
• Brazos – Just because YOU never imagined that scrambled eggs, mashed potatoes and brisket would go well in a taco together, doesn’t mean that you aren’t 100% wrong. This taco joint is straight out of Austin, Texas, who’s unofficial mantra “Keep Austin Weird” fits perfectly into Brazo’s location: The IX Art Park.
• Farm Bell Kitchen – If New Orleans and Charleston had a brunch-baby, this would be it. Their upscale twist on southern classics makes them a local favorite. Luckily, they accept reservations online! It’s also the only brunch spot on this list where you can also get espresso drinks (which is a MUST for Sarah).

 

 

For the Sweet Tooth (Or Teeth)

• • La Flor Michocana – A very authentic Mexican ice cream shop. Their “paletas” (ice cream popsicles) are absolutely killer and only cost a couple bucks. But bring cash unless you’re planning on getting a LOT of ice cream!
  • Pie Chest – Excellent pie and a full espresso bar, right on the Downtown Mall. Need we say more?!
  • Splendora’s Gelato – If you’re into the richness of authentic Italian gelato, Splendora’s on the Downtown Mall is hard to beat.
  • Iron Paffles – An unexplainable cross between a pastry and a waffle, stuffed with everything from apple pie to cannoli cream. (Pro tip: go in at meal time for the bacon, egg and cheese paffle or the chicken & paffles. Thank us later.)

 

 

Charlottesville-Unique Activities

• Hiking – With the southern entrance of Shenandoah National Park only 30 miles from Charlottesville and dozens of other free hiking spots nearby, you could spend months exploring the Blue Ridge Mountains within a short drive from town. We recommend Humpback Rocks outside the park and Blackrock Gap inside SNP for under-an-hour hikes with great panoramic views!
• Breweries, Wineries, Cideries and Distilleries – If sampling local beverages is in the cards for your proposal weekend, it’s hard to even know where to start. We’re pretty sure that there are over 100 combined breweries, wineries, cideries and distilleries just within a 30-mile radius of town! Although not a complete list, the Brew Ridge Trail and Monticello Wine Trail are great places to start.
• Orchards – The three Chiles Family pick-your-own-fruit Orchards around town are also a great (non-alcoholic) way to spend an afternoon, just check what’s in season before you plan your trip!
• Historical Tours – Thomas Jefferson’s Monticello, James Monroe’s Highland and The University of Virginia’s Academical Village all offer historical tours and other experiences for those who are interested in learning about Charlottesville’s long and fascinating history.
• Shopping – the Barracks Road Shopping Center and it’s higher-end cousin the Shops at Stonefield are places where you could easily spend an afternoon if you (or your special someone) are into shopping, or if you want to knock some Holiday shopping off your list! Dress appropriately as they’re both outdoor malls.

 

 

Well, That’s All, Folks!

We hope that this list has given you some great ideas for how to spend a weekend in Charlottesville! Like you read about in Part 3, the proposal itself is only a small part of what could be an incredible day, and now that day will just be part of an unforgettable weekend!

 

We also hope that this entire series, “A Guy’s Guide to Proposing Well”, has given you some extra confidence and some great ideas when it comes to asking the biggest question you’ll ever ask! We sincerely hope that the proposal goes smoothly, and that we’ve helped you create incredible memories that last a lifetime. As always, if you have any questions about anything, think we missed something, or want help planning your own proposal, please drop us a line at any time!

 

With love,
Hunter + Sarah

 

 

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Check out the rest of the series at the links below!

• A Guy’s Guide to Proposing Well Part 1: Four Questions to Ask Yourself Before You Get Engaged
• A Guy’s Guide to Proposing Well Part 2: How to Pick the Right (Sized) Engagement Ring
• A Guy’s Guide to Proposing Well Part 3: Planning the Big Day
• A Guy’s Guide to Proposing Well Part 4: When is My Boyfriend Going to Propose Already??
• A Guy’s Guide to Proposing Well Part 5: Where to Propose
• A Guy’s Guide to Proposing Well Part 6: How to Propose to Your Girlfriend

 

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If you’re interested in planning your own surprise proposal, click here to get in contact with us!