Travel Tips

Your Guide To A Small Business Saturday Getaway

Get tips on where to shop, where to stay and more

The Vacationeer
Couple strolling, storefront-lined main street, Charleston, South Carolina.

While mapping out your travel adventures for the year, consider adding something different to the list like visiting a big city for Small Business Saturday. This not only offers a new perspective on familiar destinations but also allows you to engage with and contribute to local communities while discovering distinctive gifts for your loved ones.

We’ve highlighted a few of our favorite shops around the country below. Learn how to discover others and start planning your Small Business Saturday stops today.

New York

Where to Shop:

  • Fine & Raw Chocolate Factory is a perfect spot to grab goodies for your sweet tooth friends. This small business in Brooklyn boasts tasty treats like hazelnut butter spreads, truffles, chocolate bars and beyond. Plus, they curate creative gift sets that are sure to satisfy.
  • From new and used books to author-signed copies and quarterly subscription boxes, Strand Bookstore is well-stocked. Shop for a bookworm buddy or treat yourself to a good read.
  • Find something unique for your trendy loved ones at Miansai. Founded in 2008, this jewelry and accessory shop features fashion-forward statement pieces for the everyday, modern minimalist. 

Where to Stay: Experience the treasures of city life with the comforts of home at The Hilton Club — New York, a unique, private retreat in the heart of Manhattan.  


Where to Shop:

  • Penny Post in Old Town Alexandria, Virginia is a perfect place to shop for the writers, sketchers and stationery lovers in your life. Plus, if you’re in need of unique holiday greeting cards and wrapping paper, this is where to find those seasonal essentials.
  • If you’ve got a lot of people to shop for, Urban Dwell is a great go-to for gifts for all ages. This veteran-owned boutique boasts carefully curated merchandise following the latest trends in accessories, books, kitchen items, home décor and more.
  • Family owned Honeybunny Boutique is a must-stop shop for all-natural soaps, scrubs, body butters and beyond. Each item is handmade with care and superior ingredients — many of which are food-based items you’ll find in your own kitchen. 

Where to Stay: Elevate your Washington, D.C. timeshare experience by staying at The District, a Hilton Club. Nestled on the upper levels of the Embassy Suites by Hilton Washington, D.C. Georgetown, our array of finely furnished Suites boasts kitchenettes, stylish décor and contemporary touches, along with exclusive access to a variety of premium amenities.


Where to Shop:

  • Well-stocked with modern home goods, gifts and artwork that are handmade, fair trade and eco-friendly, Neighborly makes for some of the best shopping in Chicago. You could easily spend an hour or two browsing through unique items you won’t find at big-box stores.
  • Located in Bronzeville, Black-owned Absolutely Anything Essential Gift Shop literally has anything you’re looking for, from mugs, candles and keepsakes to body scrubs and beard care. It’s also known to host free events on Small Business Saturday each year.
  • For a more personalized play on holiday shopping, check out Versatile Images. Family owned, this full service printing shop offers premium customization services for all sorts of items — from apparel and accessories to drinkware, keychains, buttons and beyond.

Where to Stay: Developed within the DoubleTree by Hilton Hotel Chicago — Magnificent Mile, Chicago Magnificent Mile, a Hilton Grand Vacations Club is a model of urban imagination just steps from the city’s premier attractions.


Where to Shop:

  • Just a quick drive outside of Orlando, is the wonderful Winter Garden, Florida. From apparel, jewelry and home décor to gourmet goodies, bakery treats, pet supplies and beyond, this charming town is a must-visit for holiday shopping.
  • Featuring footwear, sports apparel and accessories, Tri and Run of West Orange is where to shop for your fitness-fanatic friends and family members. While there, take advantage of their complimentary 5-step personal and custom fit process to find yourself some comfortable walking or running shoes.
  • The Ancient Olive of Winter Garden features 55+ premium single varietal and flavored extra virgin olive oils and balsamic vinegars. You’ll also find a selection of Spanish olives, French mustards, award-winning preserves, dry-cured sausages, nuts, hand-crafted pastas, cocktail mixers and more. Get a taste of what you’re gifting with free samples.
  • Shoo Shoo Baby Boutique is one of the many fashion boutiques in the area. Stock up on some new pieces for yourself or find something trendy for a friend.
  • While in the area, check out the Winter Garden Farmers Market for freshly harvested fall produce, artisan creations, seasonal décor and more.

Where to Stay: Close to top Orlando attractions and less than 30 miles away from Winter Garden, lies Tuscany Village, a Hilton Grand Vacations Club. Stay here and enjoy spacious accommodations, well-appointed amenities and family-friendly on-site activities.


Where to Shop:

  • Zoolikins is a baby boutique with a mission to inspire the next generation by offering toys that promote curiosity, books that motivate and teach empathy and activities that encourage creative expression. Shop their carefully curated selection of items for loved ones or your own littles.
  • Explore various local talent under one roof at The Merchantile of Scottsdale — Old Town Scottsdale shopping at its finest. With the wide assortment of goods, you’re sure to find unique gifts for everyone on your list.
  • urbAna is a great go-to for the hostesses with the most in your life. Shop awe-inspiring artisan décor items, party goods, entertaining decorations and much more.

Where to Stay: Unwind after a long day of shopping at Scottsdale Villa Mirage, a Hilton Vacation Club. This resort features spacious accommodations and great amenities including an outdoor pool and hot tub, children’s pool and fitness center.

With resorts ranging near and far, you can plan more unique getaways like this one with Hilton Grand Vacations. Check out “3 Family-Friendly Destinations To Discover.

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The Vacationeer

The Vacationeer is a collective of Hilton Grand Vacations storytellers whose goal is to inspire travelers to go further. We're always on the lookout for new destinations to explore, useful travel tips, and unique ideas to help you plan the most memorable vacations possible.

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