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For groups larger than 5, we recommend booking a private tour so we can better accommodate your group size and preferences. Larger groups may require additional planning time, so please reach out in advance to confirm availability. We’ll do our best to arrange comfortable transportation and a seamless experience for everyone.
Pricing varies depending on the tour type, number of guests, and pickup location. You can view our most up-to-date pricing on our booking page or contact us directly for a custom quote. A 20% gratuity for the driver is included, as well as all applicable taxes. Tasting fees are already included in our Wine Tour options, with options to upgrade, but tastings are not included in our Hourly Rental Service. Please review details carefully before booking.
Vehicle type depends on the size of your group and availability on the day of your tour. Smaller groups typically enjoy luxury SUVs or vans, while larger groups may be placed in a private shuttle or sprinter. All vehicles are air-conditioned, clean, and driven by professional, licensed chauffeurs.
Our Join-In Tours do not include food. We recommend eating a big breakfast or brunch! The wineries typically have charcuterie or other wine snacks that you can purchase while you are at the winery. Be sure to order first thing, as delays are possible. Texas Tipsy Tours will not delay the tour due to delays at the wineries for food.
We recommend booking your wine tour at least 2-4 weeks in advance, especially if you’re planning to visit during peak season (March-May and September-November) or on weekends. For bachelorette parties, large groups, or holiday weekends, booking 2-3 months ahead is ideal to ensure availability. Our most popular tours, like the “Let’s Go Girls” bachelorette buses and Saturday VIP experiences, often sell out weeks in advance. However, we do our best to accommodate last-minute requests when possible, so don’t hesitate to reach out even if your trip is coming up soon!
Our tour packages include round-trip luxury transportation from your pickup location, a professional and knowledgeable chauffeur/guide, reserved appointments at premium venues, bottled water and light snacks throughout the tour, and all coordination and planning. The specific inclusions vary by tour type—some packages include tasting fees while others do not. A 20% gratuity for your driver is included in both our tour and hourly rental pricing, as well as all applicable taxes. When you book, we’ll provide a detailed breakdown of exactly what’s included in your specific tour package so there are no surprises. We believe in transparent pricing and want you to know exactly what you’re paying for upfront.
Absolutely! We want everyone in your group to have an amazing experience. When you book your wine tour, let us know about any dietary restrictions, food allergies, mobility concerns, or other special needs. We can recommend wineries with appropriate food options, ensure wheelchair accessibility if needed, and work with you to customize your tour. Many Hill Country wineries offer gluten-free, vegetarian, and vegan food options, and we’re happy to help you plan accordingly. For guests who don’t drink alcohol, wineries typically offer non-alcoholic beverages, and we can include brewery or distillery stops that might have more variety.
Dress comfortably and appropriately for the weather! Most guests opt for “casual chic” – think sundresses, nice jeans with blouses, or stylish casual wear. You’ll be walking around wineries and standing during tastings, so comfortable shoes are essential (save the stilettos for photos only!). Texas weather can be unpredictable, so we recommend layers: bring a light jacket or sweater even in summer, as some tasting rooms can be quite cold. Don’t forget sunglasses and sunscreen – the Hill Country sun is strong! In winter, dress warmly as you’ll be going in and out of vehicles. Our top tip: wear something you feel great in for photos, but prioritize comfort since you’ll be on your feet for several hours.
Most of our standard wine tours visit 3 wineries over a 4–6 hour period, which we’ve found is the perfect balance for an enjoyable experience without feeling rushed or exhausted. You’ll typically spend 60–90 minutes at each winery, allowing time for 4–5 tastings, exploring the grounds, taking photos, and purchasing wine if you’d like. Some tours include lunch stops or additional destinations like breweries or distilleries. Your tour time includes transportation to and from your pickup location, so the total time away from your accommodation is typically 4–6 hours.
Yes! While we have carefully curated wine tour routes featuring our favorite wineries, we’re happy to work with you to create a custom itinerary for private tours. Want to visit a specific winery that’s special to you? Prefer to include a brewery or distillery stop? Need to accommodate a lunch reservation you’ve already made? We can make it happen. Just let us know your preferences when booking. Keep in mind that some wineries require advance reservations and may have minimum group sizes or fees, so the earlier you let us know about customization requests, the better we can accommodate them. Our team knows the Hill Country intimately and can make excellent recommendations based on your group’s preferences – whether you want big, bustling wineries or intimate, boutique experiences.
Canceling outside of 30 days of your planned tour date: Your deposit will be refunded, and no charges will be made. Canceling within 30 days (and five days before your tour): A $100 cancellation fee will be charged if it is canceled within 30 days of your tour to cover administration time to plan the event and help mitigate loss due to other groups being turned away. Canceling within 5 days: There will be no refunds; the tour will still be charged at 100%.
Thanks to our recent expansion and acquisition of Texas Tipsy Tours and Paradigm Limo, we now offer comprehensive service throughout the entire Texas Hill Country region! We provide pickup and drop-off in Fredericksburg and surrounding areas, as well as extended coverage throughout the Hill Country including Dripping Springs, Johnson City, Stonewall, and Hye. For guests staying outside our primary service area, we can often arrange transportation with advance notice and may apply a distance fee depending on the location. Many of our guests find that staying in Fredericksburg for the weekend provides the best experience, as you’re right in the heart of wine country. However, we understand that everyone’s situation is different, so we’re happy to discuss pickup options from your specific location when you book. Contact us to confirm that we service your area!
You’re welcome to bring snacks and non-alcoholic beverages on board – in fact, we encourage it! We provide bottled water and light snacks, but if you have specific preferences or want heartier snacks for the ride between wineries, feel free to bring them along. We have coolers available on our vehicles. However, outside alcohol is not permitted on our wine tour vehicles per our licensing and insurance requirements. You’ll have plenty of opportunities to enjoy wine at the wineries we visit! Many of our wine tour routes include a lunch stop at a winery with food service or a location where you can enjoy picnics, and we’re happy to help you plan accordingly. If you purchase wine at the wineries during your tour, we’ll safely store it in the vehicle for you until the end of your tour. Some groups like to bring a celebratory bottle of champagne to enjoy back at their accommodation – we can help you keep it chilled!
We offer both options! Our “Cowboy Booze Cruise” is our public tour where you’ll join other wine lovers for a fun, social experience – it’s a great budget-friendly option and perfect for couples or small groups who don’t mind meeting new people. However, most of our tours are private experiences where you’ll have the entire vehicle and guide exclusively for your group. This includes our VIP Hummer Limo Experience, VIP Excursion Limo Experience, and both “Let’s Go Girls” bachelorette party buses. Private tours offer more flexibility with timing, itinerary, and the overall experience – you control the music, the pace, and the vibe. They’re ideal for bachelorette parties, corporate groups, family celebrations, or anyone who wants a more personalized experience. Private tours typically require a minimum group size or minimum spend, but the per-person cost becomes very reasonable with larger groups. When you book, we’ll help you determine which option best fits your group size, budget, and preferences.
Still have questions? We’re here to help! Contact us at 830-333-9426 or visit cowboy-tours.com to chat with our team. We’re happy to answer any questions and help you plan the perfect Texas Hill Country wine tour experience.