Well, well, well, here we are! The final post in our “How to Propose” series! Last week, we talked about the most important part of the entire process, the proposal itself! This week we’re finishing our series with our thoughts on how to plan a proposal weekend, specifically here in Charlottesville! It’s no secret that getting engaged is a thing worth celebrating. And since most of our surprise proposal clients are coming from out of town, they often ask us for advice on how else to spend this monumental weekend! So this blog could just as easily be called, “Best Charlottesville Restaurants and Activities”!

 

 

Make Your Proposal a Weekend-Long Event!

Although the day you propose will be a one-of-a-kind memory no matter what, we’ve had many of our 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! So rather than just a day, plan a proposal weekend instead!

 

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!

 

This is especially easy for couples who will be coming from out of town to get engaged in Charlottesville. But even if you’re local and have go-to spots, use this as an excuse to branch out, and try something new!

 

 

How to Plan a Proposal Weekend: Best of C’ville, As Judged By Us

We certainly don’t claim to be experts on all things Charlottesville. However, here are just a few of our favorites in each category as you plan a proposal 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 in the comments!

 

If you aren’t planning a proposal weekend in Charlottesville, but have been reading this blog for 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 5-Bedroom AirBnB – No joke! Want us to be your photographers AND your AirBnB hosts? Sarah and I spent four months and more than $100,000 transforming this house into the perfect spot for wedding guests, families, or anyone looking to enjoy C’ville! This is perfect if your entire family or friend group will be (secretly) celebrating the proposal together.
• The Oakhurst Inn – If you miss the days when AirBnBs were just… BnBs, the Oakhurst Inn is your best bet. This true bed-and-breakfast is located a block away from UVA, and they have a wonderful little café that’s open to guests and the public alike.
• The Doyle (Formerly Quirk) Hotel – The Doyle (you may know it as Quirk) is an absolutely gorgeous, modern hotel just a short walk from Charlottesville’s Downtown Mall. Their rooms and furnishings are modern, their lobby is filled with artwork, and their rooftop bar is the stuff of legends.
• Kimpton the Forum Hotel – Especially if you have any connection to UVA or UVA Law, the Kimpton is an amazing place to stay. But even if you have no connection at all, you’ll be blown away by the beauty of Charlottesville’s newest hotel. Let us know if you plan to stay here — we have a connection with their event team, and might be able to hook you up with some freebies!

 

A Few of Our Favorite Charlottesville Places for Dinner + Drinks

• Ten – If sushi and Japanese food is your thing, this is the place to be! Their modern aesthetic and large bar make this the perfect place for a sake cocktail or a multi-course sushi meal.
• 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, so authentic Italian Pizza is an understatement. Before they started offering take-out at a satellite location, the restaurant often boasted 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! It’s one of our go-to restaurants for a great date night.
• Alley Light – This is another one of our favorite date-night spots in Charlottesville. Whether you’re after a “dealer’s choice” cocktail or some delicious french cuisine, make sure to get a reservation well in advance! Alley light only has a few dozen seats, and used to be a 1-bedroom apartment!

 

The All-Important Breakfast Stop

• 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.
• 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.
• Marie Bette – Another amazing cafe, with two locations in Charlottesville. But where Marie Bette shines most is in their breakfast sandwiches and bowls! Try a breakfast sandwich on an everything-“prezzant” (pretzel-croissant) and thank us later.
• Cou Cou Rachou – Cou Cou Rachou has the best french pastries in Charlottesville. Maybe anywhere in Central Virginia! And we will fight anyone who says otherwise. The pastry chef and owner Rachel De Jong was trained at Le Cordon Bleu in Paris. Find us here often, sipping an oat milk latte and devouring an almond croissant.

 

 

For the Sweet Tooth (Or Teeth)

• • La Flor Michocana – An 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!
  • Chap’s Ice Cream – You can’t go wrong with this classic 50s-themed ice cream parlor on the Downtown Mall. Stop in for a waffle-cone or a milkshake, and be sure to try some locally-inspired flavors! As an added bonus, we’ve done several photoshoots inside Chap’s before!
  • 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.)
  • Cake Bloom – If you haven’t tried eating cake while sipping champagne, you’re missing out! Cake Bloom offers two things: cake and bubbles. What more do we need to say?! Just be sure to check their hours, as you’ll need to plan your visit before dinnertime.

 

 

Charlottesville-Unique Activities

• Hiking – The southern entrance of Shenandoah National Park only 30 miles from Charlottesville! In addition, there are 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.

 

 

Thanks for Reading our How to Propose Series!

We hope that this list has given you some great ideas for how to plan a proposal 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, “How to Propose”, 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!

• How to Propose Part 1: “Should I get engaged?”
• How to Propose Part 2: How to pick the right engagement ring
• How to Propose Part 3: “When should I propose?”
• How to Propose Part 4: “When will he propose?”
• How to Propose Part 5: Where to propose (in Charlottesville)
• How to Propose Part 6: How to Propose to Your Girlfriend/Partner
• How to Propose Part 7: How to Plan a Proposal Weekend in Charlottesville

 

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If you want to learn more about our full-service proposal planning and photography services, click here!