Charlottesville trip planning services are here! I moved to Charlottesville in 2007 and fell in love. While my career took me various places over the past decade, Charlottesville always remained a home base for me> So much so that I moved back 3 more times and now it appears I am here to stay. After successfully hosting groups via AirBnB in the area since 2014, I learned all of the questions that people have when they are looking to book and plan a trip to the area.

Like many cities, it's tough to conceptualize where different areas are and then figure out where you want to stay and what you want to do once you're there. Could we stay a few blocks out of downtown to save some money but still be in a good area? That's a very common questions, and we have you covered. We see this restaurant listed with good ratings on websites, but are there other gems that all the locals know about that we should hit? Well, we are locals and love good food and drinks so we can point you in the right direction! Let us know what type of experience you want to have and we will help you book your travel accordingly. Here are some common examples of what we hear. Do you fall into one of these categories?:

Downtown Fun: "I want to be downtown, in the center of the action! So that we can safely walk home from bars late at night and enjoy the Farmer's Market and coffee on Saturday morning."

Bachelor/Bachelorette/Friend Getaway: "We are a group of girlfriends celebrating a bachelorette. We plan to cook at the house one night and go on a wine tour Saturday and head out Saturday night. We are more concerned with space for everyone and staying in the same house together where we can relax and have a nice home base that is within a reasonable Uber distance to downtown."

Breath of Fresh Air: "We are coming to Charlottesville to stretch out and enjoy the history and wine country. We want sweeping mountain views and a deck to sit out and enjoy some local wine and beer. A comfortable place with modern amenities."

Romantic Getaway: "I am planning a romantic getaway. I want to know what restaurants would be great for an intimate yet trendy dinner and a great place for sophisticated cocktails. And if we were to go to one vineyard with the ambiance we are looking for, what would it be?" (And we are happy to help coordinate a proposal, too, if that is in the cards!)

Kid-Friendly Fun: "We have kids that we have to keep entertained but we also want the adults in the group to have some fun. What restaurants and activities would be good for our group? Where can we stay where the kids won't be bored?"

And last but not least...

Live Like A Local: "I want to live like a local for the weekend! Tell me about all the cool stuff that goes on in Charlottesville and what you and your friends would do. I want all the secret spots and great food and drinks!"

No matter what type of experience you are looking for, we can tailor an experience that fits your needs. We can consult about:

  • Lodging options (private home rentals, Inns/B&Bs, hotels)
  • Vineyard tours (booking the tour, tailoring the itinerary)
  • Bachelorette parties
  • Restaurants & bars
  • Hikes & historical excursions
  • Local gems
  • Local events, weekly and special events
  • Shopping & antiques/vintage
  • And more!

Fees assessed for consultation will be on a case-by-case basis. After we chat about what you're looking for, we will let you know the fee to come up with a custom itinerary, starting at only $35 for simple but tailored recommendations. Email

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