Start your first morning with a relaxed stroll and coffee at BrauHaus Coffee Co. before checking into your accommodation, then wander the historic brick streets to browse unique finds at The Old Bakery Emporium and artisanal shops on Market Street. Mid-morning, join a guided cellar tour and tasting at Stone Hill Winery to get an early introduction to the region's winemaking traditions and pick up a bottle or two for later in the trip.
After lunch, head to Hermannhöhle for a relaxed, informative underground cave tour that showcases local geology and cools you off on a warm afternoon. Follow this with a late-afternoon tasting flight and scenic patio time at Adam Puchta Winery, then wander the nearby Hermann Riverfront Park to watch the Missouri River light up as evening approaches.
As twilight falls, enjoy a relaxed dinner and local wine pairing at Boone's Wine Bar & Bistro, then take a short stroll to the riverfront for sunset views and live music if available at Hermann Riverfront Pavilion. Finish the night with a cozy nightcap and board games at Vintage Cellars Tasting Room, where the warm atmosphere and small-batch dessert wines make for a perfect first-night unwind.
Begin your morning with a leisurely tasting flight and vineyard stroll at OakGlenn Vineyards, where sun-dappled rows and sweeping valley views set a peaceful tone before the day's tastings. From there, stop for a behind-the-scenes tour and estate lunch pairing at Hermannhof Vineyards, sampling their signature Norton while learning about organic practices and the region's terroir.
After a leisurely estate lunch, drive the western loop to sip and savor at Stone Hill Winery's outdoor terrace for a tasting of their award-winning Norton and scenic vineyard views, then continue to Adam Puchta Winery for a guided barrel-room tour and a tasting of small-lot vintages paired with local cheeses. Finish the afternoon with a relaxed picnic on the lawn at Hermann Hill Vineyard & Inn, where sweeping river-valley panoramas set a tranquil mood before evening tastings back in town.
As the sun softens, settle in for a relaxed tasting and small-plates dinner on the terrace at Hermann Hill Inn & Vineyard Restaurant, where local cheese boards and a flight of estate rosés pair perfectly with sweeping valley views. After dinner, stroll over to Vintage Cellars Tasting Room for a cozy nightcap featuring limited-release dessert wines and a chance to chat with the winemaker, then enjoy live acoustic music or star-gazing on their patio to round out a day of western-loop discoveries.
Wake to a slow-start tasting at Stone Hill's Riverfront Tasting Pavilion with a sunrise flight focused on crisp Chardonnays and a view of the misty valley, then take a guided vineyard walk highlighting spring budbreak and pruning techniques. Continue across the eastern loop for a behind-the-scenes barrel sampling and luncheon pairing at Prairie Rose Winery, followed by a stroll through the sculpture garden and a tasting of their estate Norton on the sunlit patio.
Continue your eastern-loop discoveries with a relaxed midday visit to Hermannhof's Guest Terrace for a tasting of their lighter varietals paired with house-made charcuterie while you soak in vineyard vistas, then head to OakGlenn's Hilltop Pavilion for a guided tasting of their single-vineyard Norton and a brief walk through the estate's spring wildflower plots. Finish the afternoon at Hermann Hill Vineyard & Inn's Garden Patio for a sunset-focused rosé flight and a chef-led small-plate pairing, keeping the pace unhurried so you arrive back in town refreshed for evening plans.
Wind down with a relaxed dinner and curated wine pairing at Boetje's Riverside Bistro, where river-view seating complements an order of herb-roasted pork and a flight of Norton, Vidal, and late-harvest samplers. After dinner, take a short walk to Hermann Riverfront Pavilion for possible live music or sunset views, then finish with a nightcap and intimate port-style tasting at Vintage Cellars Tasting Room Annex, where small-batch dessert wines and cozy conversation close out an afternoon of eastern-loop discoveries.
Start the morning with a picturesque drive along River Road, pausing for a light breakfast and coffee on the patio at Market on the Square Café, then continue toward the bluff-top overlooks at Klondike Park for sweeping views of the Missouri River valley and spring wildflowers. After soaking in the scenery, stop at St. George Vineyard Overlook to stroll the short interpretive trail and gather local cheeses and fresh bread from Hermann Farmers Market for a riverside picnic near the shady banks of St. Alban's Landing.
After your riverside picnic, take the scenic drive south to Chesterfield Lookout for sweeping river-valley vistas, then pull over at Katy Trail Access at New Haven for a gentle 20-30 minute walk or bike ride along the river trail to stretch your legs. Finish the afternoon with a relaxed tasting and porch-side charcuterie at Hermann Hill Vineyard & Inn's nearby tasting patio, where valley views and late-afternoon light make for an easy, restorative pause before evening plans.
As dusk settles, head to Augusta Winery Tasting Room for a relaxed twilight flight on their rooftop terrace, sampling crisp Vidal and an aged Norton while watching the valley glow. Afterward, drive back toward town for a riverside dinner at The Riverbend Taproom & Grill, where locally sourced plates and a rotating selection of Missouri craft beers pair perfectly with a slow sunset, then finish with a digestif and stargazing at Hermann Ridge Overlook to cap a day of scenic drives and gentle exploration.
Begin with a guided tour of the finely preserved German-era exhibits at The Deutschheim State Historic Site, then stroll across to Hermann Museum to see local artifacts and learning about the town's 19th-century immigrant roots. Mid-morning, head to Revel Cellars Distillery for a hands-on craft spirits demonstration and tasting of small-batch eau-de-vie and gin, followed by a savory snack pairing on their sunlit patio to keep the pace relaxed before afternoon brewery stops.
After the museum and distillery morning, head to Big Chief Brewing Company for a relaxed brewery tour and tasting flight of small-batch ales paired with a hearty pretzel board on their shaded patio, then stroll over to Boettcher's Historic Tasting Loft for a sampling of craft ciders and seasonal brews in a restored 19th-century loft space. Finish the afternoon with a guided behind-the-scenes visit and tasting at Reinhardt Riverfront Distillers, where you can see the copper stills, sample a barrel-proof release, and buy a commemorative bottling to take home.
As twilight falls, enjoy a chef-driven dinner and seasonal wine-cocktail pairings on the patio at Boetje's Riverside Bistro before wandering to Hermann Riverfront Pavilion for possible live music or an outdoor performance. After the show, stop in at Vintage Cellars Annex for a late-night tasting flight of fortified wines and a behind-the-barrel chat with the winemaker, then finish with nightcaps and river views at The Riverbend Taproom & Grill's outdoor seating to round out an evening that bridges the town's history with its modern craft scene.
Ease into the day with a riverside breakfast picnic at Deutschheim Park, then rent bikes from Hermann Bike & Brew for a gentle pedal on the Katy Trail toward the scenic bluff viewpoints near Klondike Park-stop to photograph the valley and wildflowers. After your ride, unwind with a late-morning tasting and light brunch at Prairie Rose Winery's shaded patio featuring their estate Norton and house-made small plates before a lazy afternoon of choices.
Spend a leisurely afternoon exploring the shady trails and spring birdlife at St. George Vineyard Overlook, then pedal a gentle loop from Hermann Bike & Brew out to the Katy Trail Access at New Haven for a 30-45 minute riverside ride that stretches your legs without rushing the day. Afterward, unwind with a relaxed tasting and charcuterie on the porch at Hermann Hill Vineyard & Inn or choose a sunset-focused flight at Prairie Rose Winery's garden patio to keep the pace restorative and beautifully connected to earlier vineyard visits.
As dusk settles, enjoy a relaxed farm-to-table dinner at Boone Hill Farm Kitchen, savoring seasonal plates paired with local Missouri vintages on their candlelit patio, then wander next door for an after-dinner tasting of limited-release ports and late-harvest wines at Heritage Vault Tasting Room. Finish the night with a short drive to Hermann Ridge Overlook for stargazing and a quiet nightcap while the valley cools, keeping the tempo restorative after a day of gentle rides and scenic walks.
Begin the morning with an intimate barrel-to-bottle tour and private tasting at Hermannhof's Reserve Cellar, where the winemaker walks you through barrel selection and offers library pours paired with house-made local charcuterie. Follow with a boutique blending workshop at OakGlenn's Tasting Atelier, crafting your own mini-blend to bottle and label as a keepsake - a hands-on experience that builds on the earlier casual tastings and deepens your understanding of Hermann's winemaking craft.
Spend a relaxed afternoon at Prairie Rose Winery for a private, seated tasting of their limited-release Norton and a behind-the-vines tour that includes sampling directly from a recently emptied barrel; follow that with a curated cheese-and-preserve pairing on their sun-dappled patio. Later, head to Hermann Hill Vineyard & Inn for an intimate cellar-talk with the cellar master and a vertical tasting of vintages on the garden terrace, tying together what you learned in the morning blending workshop and deepening your appreciation of the region's older bottlings.
As dusk settles, enjoy a candlelit chef's tasting paired with library wines on the patio at Boetje's Riverside Bistro (reserve the chef's table for a guided pour-through of older vintages), then stroll to Hermann Riverfront Pavilion for seasonal live music or an outdoor performance to keep the evening lively. Finish with a late-night, docent-led fortification tasting and stories of barrel aging at Vintage Cellars Private Loft, where small-batch ports and a cozy leather sofa set the stage for relaxed conversation and a memorable final sip.
Ease into your final full day with a relaxed tasting flight and bottle-shopping at Boettcher's Historic Tasting Loft, where their curated gift-pack options and seasonal releases make finding souvenirs easy; follow with a cellar-sample experience and behind-the-counter chat at Vintage Cellars Tasting Room Annex to hunt for limited bottlings and personalized packing tips. Finish the morning with a stop at Market on the Square Café for a light lunch and to stock up on local jam, cheese, and crackers sold by regional vendors-perfect accompaniments for the wines you'll bring home.
Spend a relaxed afternoon hunting for final bottles and tasting small-production wines at Reinhardt Riverfront Distillers, where you can sample barrel-proof releases and pick up a commemorative spirit bottling, then stroll to The Old Bakery Emporium Annex for artisanal gift-wrapping and locally made crackers and jams to pair with your purchases. Finish with a leisurely seated tasting and custom packing advice at Hermann Hill Vineyard & Inn's Tasting Patio, sampling a reserve Norton or late-harvest rosé while staff prepare your carry-home cases so everything travels safely and stylishly.
For a relaxed final evening, enjoy a river-facing dinner flight and bottle-signing event at Boone's Wine Bar & Bistro, where the chef pairs small plates with select bottles you might want to take home. After dinner, browse curated, locally made gift selections and secure last-minute vintages with personalized packing at Hermann Wine & Gift Co., then finish with a twilight stroll and a nightcap on the bluff at Hermann Ridge Overlook, where valley views help you savor the trip's final moments.
For a gentle final morning, enjoy a leisurely riverside breakfast at Market on the Square Café Annex with freshly baked pastries and a last cup of Missouri-roasted coffee, then take a short walk to Deutschheim Park for one last view of the valley and a quiet moment by the historic gazebo. Before checkout, stop by Hermann Wine Locker to pick up any pre-ordered bottles and get expert packing tips so your favorites travel home safely.
Before you head out, linger over a relaxed late-afternoon light lunch and final tasting at Boettcher's Historic Tasting Loft, where staff can help consolidate any last-minute bottle purchases and offer travel-friendly packing tips. If time allows, take a gentle stroll through the nearby Hermann Riverfront Park to soak in one last river view and snap final photos, then collect your luggage and stop by Hermann Wine & Gift Co. for any wrap-up souvenirs and secure packaging before departure.
For a final, unhurried evening, enjoy a farewell dinner at Boetje's Riverside Bistro where the chef's seasonal tasting menu pairs beautifully with a glass from their reserve list, then stroll the nearby riverfront to watch the sunset over the Missouri. Afterward, stop by Hermann Ridge Overlook for one last panoramic view and a quiet nightcap from The Riverbend Taproom & Grill, letting the valley's glow close out your Hermann wine trail week.