Private Drunk History Tour

A Unique Way to Explore San Antonio’s Historic Heart

If you’re after a different kind of city tour — one that marries history, local haunts, and a splash of fun — the Private Drunk History Tour might just be your perfect fit. Priced at $250 per person, it lasts about two and a half hours and takes you through downtown San Antonio, focusing on key landmarks like the Alamo and historic hotels, with a lively guide leading the way. What makes this experience particularly appealing is its private setting—so it’s tailored to your group—and its relaxed, conversational tone.

Two aspects stand out: First, the personalized attention you get from your guide, Emzy, who is praised for his vast knowledge and engaging storytelling. Second, the combination of historic sites with local bars where you can enjoy a drink, making history feel approachable and fun. On the flip side, a consideration is that alcoholic beverages are not included, so you’ll need to budget for drinks separately. This tour is ideal for history buffs, social travelers, or if you simply want a lively, personalized way to see San Antonio while enjoying some cocktails.

If you enjoy a small, intimate tour with a knowledgeable guide who can tailor the experience to your interests, you’ll find this tour very worthwhile. It’s also perfect if you’re curious about hidden stories behind San Antonio’s landmarks or prefer an experience that feels more like a private evening out with friends rather than a large group activity.

Key Points

Private and personalized: Only your group participates, with flexible departure times.
Rich storytelling: Your guide, Emzy, shares detailed insights and historical photos, making history come alive.
Historic and social blend: Visit iconic landmarks and enjoy drinks at historic bars.
Cost clarity: Price is $250 per person; drinks are not included but can be purchased at stops.
Flexible scheduling: Meets at Alamo Plaza with a seamless start.
Highly rated: Consistently scored 5.0/5 from 50 reviews, with 98% recommending it.

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Exploring Downtown San Antonio with a Twist

We loved the way this tour balances history and fun — a rare combo that makes exploring the city both educational and lively. The two and a half hours fly by as your guide, Emzy, guides you through key spots like the Alamo Plaza and the Menger Hotel, giving you insider stories and historical context you won’t find in a guidebook. The personal touch of a private tour means you can ask questions and tailor the experience to match your interests.

The tour begins at 204 Alamo Plaza, the heart of San Antonio’s historic district. From the start, you can expect a friendly, engaging atmosphere as Emzy sets the scene, sharing stories about the famous battle of the Alamo. This stop is free of charge but packed with significance, giving you a solid foundation of San Antonio’s pivotal moments.

Next, the focus shifts to the Menger Bar, a historic spot where Teddy Roosevelt recruited his Rough Riders. Here, you get to purchase a drink in a place that exudes history — the walls tell stories of past patrons and legendary battles. Reviewers rave about Emzy’s knowledge and storytelling, often mentioning how he shows photos and shares secrets that bring the place to life. One reviewer called it “soooo much more fun than I ever expected,” which speaks to how this tour transforms history from dry facts into a lively narrative.

The third stop takes you inside the St. Anthony Hotel, another historic building from 1909. You’ll enjoy a private tour of this elegant hotel, then relax with a cocktail while absorbing more stories about the city’s development. The architecture and timeless elegance of the hotel make it a standout, and the fact that it’s still a functioning hotel adds authenticity to the experience. Reviews mention that Emzy’s depth of knowledge and enthusiasm make this segment particularly engaging.

What to Expect at Each Stop

Alamo Plaza

Your tour kicks off here, with a 15-minute discussion about the famous battle and the surrounding area. It’s a great way to set the scene and understand why this site remains a symbol of Texas independence. Since it’s admission-free, you’ll have ample time to absorb the historic significance and snap some photos of the iconic mission.

Menger Hotel & Bar

At the Menger Bar, you’ll spend about 45 minutes enjoying a drink and hearing stories about Teddy Roosevelt and the haunted reputation of the hotel. The connection to Roosevelt’s Rough Riders adds a romantic adventure aspect, and the historic ambiance makes it a memorable spot. The walls and photos Emzy shares make the history feel personal. Many reviews highlight how knowledgeable and engaging Emzy is, often adding hidden stories that you won’t find elsewhere.

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The St. Anthony Hotel

The final stop involves another 45-minute visit, where you get a private tour of this luxury hotel. Then, it’s time to unwind with a cocktail in hand, soaking in the timeless charm. The hotel’s architecture and the stories behind its founding add a sense of grandeur and history to your evening. Reviewers consistently mention the depth of Emzy’s historical knowledge and his ability to tailor the experience, making it both fun and informative.

The Experience Beyond the Landmarks

A highlight for many is the personalized approach. Emzy’s extensive knowledge — often described as encyclopedic — means you’ll learn more than just the surface stories. He leverages photos, documents, and personal anecdotes to make the history tangible. Guests frequently mention how fun and enthusiastic he is, making the evening feel like hanging out with a knowledgeable friend.

Another aspect worth noting is the value for money. At $250, the price might seem steep for two and a half hours, but considering the private setting, the access to historic locations, and the personal storytelling, many find it to be well worth the cost. Plus, the small group format means you get more attention and customization.

While drinks are not included, the tour visits established historic bars where you can purchase quality cocktails. Many reviewers praise the selection and atmosphere of these venues, making it a culinary as well as a cultural experience.

Who Will Love This Tour?

This tour is perfect if you want to combine history, local culture, and social fun in a relaxed, private setting. It appeals to history enthusiasts who enjoy stories and photos, as well as those looking for a night out that feels both educational and entertaining. Since the tour is private, it works well for couples, small groups of friends, or families wanting a tailored experience.

If you’re interested in learning about San Antonio’s landmarks in a way that feels more like sharing stories with a friend, this tour is an excellent choice. It’s especially suitable if you appreciate dynamic guides who can bring the past to life with enthusiasm and depth.

FAQs About the Private Drunk History Tour

Is this tour suitable for all ages?
While the tour focuses on historic sites and includes alcohol stops, it’s primarily aimed at adults. Minors may not find it as engaging and should consider age restrictions or preferences.

Are alcoholic beverages included in the price?
No, drinks are purchased separately at the stops. The tour provides the historic venues where you can enjoy a cocktail, but the beverages themselves are not included in the $250 fee.

How long does the tour last?
It is approximately 2 hours and 30 minutes, giving enough time to enjoy each stop and absorb the stories without feeling rushed.

What is the group size?
Since it is a private tour, only your group participates, which allows for a more personalized experience.

Can I choose a different departure time?
Yes, the tour offers flexible departure times to accommodate your schedule, making it easier to fit into your plans.

Where does the tour start and end?
The tour begins at 204 Alamo Plaza and concludes at The Rose of San Antonio, 420 E Houston St.

Is the tour physically demanding?
The tour involves walking between sites, but it’s generally manageable for most travelers. It’s a good idea to wear comfortable shoes.

Do I need to book in advance?
Yes, most travelers book around 11 days in advance to secure their preferred date and time.

What if the weather is bad?
The tour is weather-dependent. If canceled due to poor weather, you’ll be offered an alternative date or a full refund.

Can I bring service animals?
Yes, service animals are allowed to accompany guests, ensuring accessibility for all.

Final Thoughts

The Private Drunk History Tour in San Antonio offers a memorable blend of historic insight and social fun. Emzy’s reputation as a knowledgeable and engaging guide shines through in every review, and the tour’s intimate setting ensures you get a personalized experience. The stops at iconic landmarks like the Alamo, the Menger Hotel, and the St. Anthony Hotel give you a taste of San Antonio’s storied past, all wrapped in a lively, conversational style that many travelers find irresistible.

While the cost may seem high, the value lies in the depth of storytelling, the private setting, and the chance to enjoy local bars with a knowledgeable host. It’s especially suited for history buffs, couples, or small groups looking for a fun, relaxed way to explore the city after dark.

If you want a personalized, engaging, and somewhat spirited way to learn about San Antonio, this tour could be the highlight of your visit. Just remember to budget for your drinks and prepare for a memorable evening of stories, laughter, and local flavor.