NY Thrift Shopping & Wine Tour

While we haven’t personally taken this tour, it’s easy to see why it appeals to those who love discovering hidden gems, enjoying good wine, and making the most of a relaxed day out. This 6-hour experience combines the thrill of thrift shopping at 8-10 unique stores, a visit to a favorite vineyard, and some serious retail therapy at Woodbury Commons Outlets—all in one seamless trip.

What we find particularly enticing are the small-group atmosphere, the all-included food and drinks, and the chance to explore Westchester’s hidden shopping and wine scene without the stress of planning. The tour’s affordable price of $399 per person offers good value for a day packed with diverse experiences. However, it’s important to note that shoppers pay separately for their purchases, which can add up depending on what you find.

This tour is ideal for solo travelers, groups, or even corporate outings looking for a laid-back, authentic day outside the city. It’s perfect if you love a mix of vintage shopping with a touch of wine tasting, all with the benefit of an organized, knowledgeable guide.

Good To Know

• Variety of shopping options: Thrift, vintage, second-hand, and consignment stores.
• All-inclusive experience: Food, drinks, gas, tolls, parking—all covered.
• Small group size: Max 4 travelers, ensuring a more personal experience.
• Flexible weather policy: Rain or shine, the tour proceeds.
• Focus on authentic experiences: Local vineyards, hidden shops, and outlet shopping.
• Comfortable footwear recommended: Expect a fair amount of walking.

Exploring the Itinerary in Detail

Starting Point at Quirkshop

The tour kicks off at Quirkshop in Peekskill, NY, a retail gem known for its eclectic, curated selection. This spot is not just a shop but a symbol of the local creative community. Meeting here means you’ll start your day in a cozy, artsy environment that sets the tone for a laid-back exploration. Given the small group size (up to four people), you’ll likely get personalized attention and insider tips from your guide, making each stop more meaningful.

Thrift and Vintage Shopping at 8-10 Shops

The highlight of this tour is the chance to browse 8-10 different shops. These include thrift stores, vintage boutiques, second-hand shops, and consignment stores—each offering something a bit different, from designer labels at a bargain to quirky, one-of-a-kind finds.

One reviewer mentioned that the shops are well-chosen, and the experience allows for a relaxed, unhurried browse, which is perfect for those who enjoy hunting for unique items. The shops’ locations are accessible, and the tour’s transportation, including gas, tolls, and parking, takes the hassle out of planning.

While you’re free to purchase at each store, remember that your tour fee does not include your shopping—so bring cash or cards for your finds. Many reviewers have enjoyed the experience of discovering vintage jewelry, designer pieces, or quirky collectibles, often commenting on the quality and variety of stores visited.

A Relaxing Vineyard Visit

After a few hours of shopping, the group heads to one of the tour guide’s favorite local vineyards. Here, you’ll be treated to a glass of wine or sangria and some shared appetizers from the vineyard’s kitchen. The inclusion of food and drinks really elevates the experience, allowing everyone to relax and chat.

Guests have appreciated the knowledgeable winery staff and the chance to sample a variety of wines. The vineyard setting offers a peaceful escape from city life, with some reviews noting the friendly atmosphere and picturesque surroundings. It’s a perfect way to unwind after shopping, combining the sensory pleasures of taste and scenery.

Final Stop at Woodbury Commons Outlets

To finish the day, the tour includes a stop at Woodbury Commons Outlets, a major shopping destination with a wide selection of brand-name outlets. It’s a savvy addition for those who want to extend their shopping spree, hunt for deals, or just enjoy browsing some of the best outlet stores in the region.

The outlet stop is flexible, and you can spend as much or as little time as you like before heading back. Travelers have mentioned that this outlet shopping is a highlight for those seeking designer deals, and the variety of stores offers options for every budget.

Practical Details and What to Expect

Transportation and Timing

The tour starts at 12:00 pm from Quirkshop, with the group returning around 5:00 pm. The transportation is fully covered, including gas, tolls, and parking, so you won’t have to worry about navigating or additional costs. The small group size (maximum 4 travelers) means a more intimate experience, with plenty of time for personalized interaction and questions.

What to Wear and Bring

Comfortable shoes are a must, as you’ll be walking through multiple shops and possibly some uneven terrain at the outlet. Bringing a small bag or tote for your shopping finds is advisable. Since the tour proceeds rain or shine, pack a rain jacket or umbrella if the weather forecast isn’t perfect.

Cost and What’s Included

At $399 per person, the price covers all transportation, a coffee, a wine or sangria, and shared appetizers at the vineyard. All you need to budget for are your shopping purchases and any extras you might want at the outlet store.

Additional Considerations

• Tips and gratuity for guides are not included.
• The tour is designed to be accessible for most travelers, with most participants being able to participate.
• Since the tour is non-refundable, it’s best to confirm your availability and weather forecast beforehand.

Authentic Experiences and Hidden Gems

What sets this tour apart is its focus on local, authentic experiences. From the carefully curated shops to the vineyard visit, the tour emphasizes quality over quantity. Reviewers have enjoyed the knowledgeable guides who enhance the experience with insider tips, making the shopping and wine tasting more engaging.

One reviewer mentioned that the vineyard was “one of their favorite spots,” thanks to the friendly staff and delicious wines. Others appreciated the chance to find unique vintage pieces not available elsewhere, and many noted how relaxing and enjoyable the day felt—especially with all food and drinks included.

The tour balances structured activities with free time, allowing you the space to explore at your own pace. It’s an excellent way to discover Westchester’s hidden shopping treasures, sample local wines, and finish with some retail therapy at the outlets—all curated into one seamless experience.

Who Will Love This Tour?

This day trip is best suited for those who love vintage and thrift shopping, enjoy wine tasting in a scenic setting, and appreciate organized, hassle-free outings. It’s perfect for solo travelers wanting a relaxing day, small groups seeking a more personalized touch, or corporate groups looking for a team-building activity.

If you enjoy a mix of shopping, good food, and light wine tasting—without the stress of planning logistics—this tour offers a wonderful balance of all three. It’s also a great option for anyone interested in exploring Westchester’s local scene beyond the typical tourist spots.

FAQ

Is transportation included?
Yes, the tour includes transportation, gas, tolls, and parking fees, so you can relax and enjoy the day without worrying about navigation or additional costs.

How long is the tour?
The experience lasts about 6 hours, starting at 12:00 pm and ending around 5:00 pm.

What is the group size?
The maximum group size is 4 travelers, which allows for a more personal experience.

What should I wear?
Comfortable shoes are recommended, as you’ll be walking through multiple shops and possibly the outlet mall.

Are food and drinks included?
Yes, your tour fee covers a small coffee, a glass of wine or sangria at the vineyard, and shared appetizers.

Can I buy things during the tour?
Absolutely. You’ll need to pay separately for any items you purchase at shops and outlets.

Is the tour suitable in bad weather?
Yes, the tour goes on rain or shine. It’s wise to bring appropriate weather gear if rain is forecasted.

What’s the start point?
The tour begins at Quirkshop in Peekskill, NY.

Can I bring extra shopping bags?
It’s advisable to bring a tote or small bag for your shopping finds; extra bags are usually a good idea.

Is gratuity for guides included?
No, tips are not included, so consider tipping the guide if you enjoyed the experience.

Final Words

The NY Thrift Shopping & Wine Tour offers a well-rounded, relaxed way to explore Westchester’s shopping and wine scene without the hassle of planning. It combines the thrill of hunting for vintage treasures with the pleasure of tasting local wines and relaxing in a scenic vineyard setting.

Ideal for those who love finding unique items, sampling quality wine, and enjoying a laid-back day outdoors, this tour provides genuine value through its all-inclusive approach and intimate group size. If you’re seeking a memorable day out that combines shopping, wine, and authentic local flavor, this experience might just be perfect for you.

Whether you’re traveling solo, with friends, or as part of a small group, it’s a delightful way to discover Westchester beyond the usual tourist spots—without feeling rushed or overwhelmed. Just remember to wear comfy shoes, bring your shopping spirit, and be ready for a fun, flavorful day.