After arriving and settling into your lodging, start the day with a leisurely breakfast at Cafe am Rhein before stretching your legs along the scenic Hermann Riverfront Park for views of the Missouri River and historic stone bluffs. Mid-morning, visit Stone Hill Winery for a guided cellar tour and tasting of their signature Norton and Vignoles-pair a sample flight with a light cheese plate on the patio to ease into the week of wine exploration.
Stroll the shady lanes to OakGlenn Vineyards & Winery for an intimate tasting of estate Rieslings and a behind-the-vineyard walk, then linger on their terrace with a glass paired to a rustic charcuterie board. Later, head to Hermann Hill Vineyards for a late-afternoon tasting flight and panoramic bluff views - time your visit to catch golden-hour light over the vines before an easy walk back to town for dinner.
As twilight settles, wander to Tin Mill Brewing Company for a relaxed glass or craft beer and outdoor seating that often features live acoustic music-perfect after a day of tastings. Afterward, enjoy a leisurely riverside walk before heading to Stone Hill Winery's Garden Pavilion for a nightcap-style tasting of dessert wines or port-style offerings beneath string lights, rounding out your first day with gentle conversation and vineyard views.
Begin your morning with a flaky pastry and coffee at Anvil Restaurant & Cidery (their patio is perfect for people-watching), then wander the brick streets to explore the charming shops and historic architecture along Schiller Street. Mid-morning, join a guided tasting and behind-the-scenes tour at Hermannhof Winery, where you'll sample their estate wines and learn about traditional German winemaking techniques while taking in vineyard views that build naturally on yesterday's first-cellar experiences.
Head uphill to Hermann Hill Vineyard & Inn for a leisurely tasting on the terrace, sampling their dry whites and estate reds while enjoying sweeping bluff views that continue the riverfront perspective from this morning. Later, meander to OakGlenn Vineyards & Winery's tasting room for a comparative flight of Rieslings and dry rosé, then settle on their lawn with a locally sourced charcuterie board as the afternoon light softens and conversation drifts to tomorrow's deeper vineyard explorations.
As dusk falls, enjoy a cozy dinner at The Tin Kitchen where farm-to-table entrees pair beautifully with their curated Missouri wine list, then stroll the lantern-lit sidewalks to browse handcrafted gifts and local art at Hermann Tasting Company's evening pop-up events. Afterward, settle in for a relaxed tasting of small-batch dessert wines and port-style pours on the rooftop patio at Adam Puchta Winery, letting the soft glow of the river bluffs and mellow live music carry forward the week's unhurried pace.
Start with a relaxed breakfast on the shaded patio at Hermann Coffee Company, then stroll the scenic loop through Deutschheim State Historic Site to admire preserved German immigrant homes and riverside gardens that deepen your sense of local history. Mid-morning, head to Hermannhof Vineyards' Riverfront Tasting Room for a crisp flight featuring local Chardonnays and Grüner Veltliner, followed by a short drive to Adam Puchta Winery's Hilltop Lot for a vineyard walk and open-air tasting overlooking the Missouri River bluffs.
Spend the afternoon exploring the hillside terroir with a tasting and panoramic views at Stonehaus Cellars, where you can sample their estate Norton and enjoy a guided barrel-room talk that builds on your morning riverfront perspective. Later, picnic on the bluff overlooking the Missouri at Deutschheim Overlook Park (grab provisions from Hermann Mercantile) before a late-afternoon visit to Bacchus Ridge Winery for a relaxed comparative flight of dry rosés and small-batch reds as the light warms the vineyards.
As the sun dips, enjoy a relaxed dinner and wine pairing at Otto's on the Hill, where seasonal small plates highlight local produce alongside a curated selection of Missouri reds; linger on their porch to watch the bluffs turn gold. Later, head to Hermann Riverfront Amphitheater for an evening concert or community event when available, or settle into a cozy tasting of fortified wines and late-harvest selections at LaChance Vineyards' Tasting Room under soft string lights to carry forward the week's unhurried, riverside rhythm.
Ease into the day with a sunrise stroll and a hearty breakfast at Hermann Mercantile before driving to Bacchus Ridge Winery for a guided tasting of their small-batch reds and a brief tour of the barrel room that builds on the prior days' cellar visits. Mid-morning, head to Stonehaus Cellars for a hilltop tasting flight paired with a chef-prepared picnic basket you can take to Deutschheim Overlook Park, where a shaded spot and river bluff views set the scene for a leisurely al fresco pause before the afternoon's winery hop continues.
After your picnic at Deutschheim Overlook Park, continue the vineyard thread with an easy drive to Hermannhof's Scenic Tasting Pavilion for a comparative flight of dry whites and a narrated tasting that connects vineyard practices to the flavors you're noticing; linger on their lawn with a glass and local cheese. Later, weave uphill to Hermann Hill Vineyard & Inn's south-facing terrace for a late-afternoon tasting of estate reds and a short vineyard walk to catch warm light on the vines before returning to town for dinner.
As dusk settles, savor a relaxed dinner at The Millstream Brewing Company with river-view seating and a Missouri-sourced menu that pairs well with their seasonal cask ales or a bottle from the local list, continuing the day's tasting thread with a more casual, hearty meal. Afterwards, stroll to Deutschheim State Historic Site for an evening ranger talk or moonlit walk when available, then finish with a nightcap on the patio at Hermann Tasting Company-sample small-batch dessert wines or a late-harvest pour while the bluff lights and gentle river sounds bring the day's vineyard rhythms to a peaceful close.
Kick off the morning with a hearty lakeside breakfast and paddle at Katy Trail State Park - Riverview Trailhead, renting a kayak from Hermann Outfitters to glide along a peaceful bend of the Missouri River while watching songbirds and bluffside vineyards wake up. After your paddle, stretch your legs on a guided nature walk through Montgomery County Conservation Area, where a local naturalist points out native wildflowers and scenic overlooks that deepen your sense of the landscape you've been touring all week.
Spend a sunlit afternoon mountain-biking or hiking the rolling vineyards and limestone bluffs on well-marked trails at Strehly Farm & Trails, then cool off with an easy swim or riverside lounge at the shaded beach area of Hermann Riverside Park-perfect for a picnic of local cheeses and crusty bread. Later, head to Tin Mill Brewing Company's Biergarten for a brewery tour and tasting flight of seasonal ales paired with wood-fired pretzels and live local music, continuing the week's shift from vineyard-focused tours to more casual, outdoors-forward conviviality.
As twilight falls, enjoy a hearty riverside dinner at Otto's on the River-their terrace seating and locally sourced menu pair perfectly with a cold draft from the nearby Boone County Brewing Taproom for a relaxed, post-adventure meal. After dinner, take a lantern-lit stroll along the bluff at Deutschheim Overlook Park to watch the valley glow, then finish the night with board games and a rotating tap flight back at Tin Mill Brewing Company's Biergarten Annex, where low lights and live acoustic music keep the evening easy and communal.
Begin your last full day with a relaxed tasting flight and behind-the-vines tour at LaChance Vineyards, sampling their late-harvest and fortified selections that build on earlier cellar experiences while enjoying vineyard views. Mid-morning, wander the artisan stalls at Hermann Farmers & Artisans Market to pick up regional souvenirs-hand-poured beeswax candles, locally made jams, and handcrafted glassware-then stop by Hermann Chocolate & Confections for a pairing of truffles with a crisp white to round out the morning before an easy midday pause.
Spend a relaxed afternoon sampling small-batch pours at Stone Hill Winery's Riverfront Tasting Room, then take a short drive to Adam Puchta Winery's Barrel Room for a guided tasting of their reserve reds and a peek at current cooperage work. Finish with a leisurely stroll through Hermann Mercantile to pick up local jams, artisanal crackers, and a bottle or two from the day's favorites-perfect souvenirs that connect back to the week's vineyard discoveries.
For a celebratory final evening, enjoy a riverside dinner and flight of small-batch blends at Tin Mill Cellars & Kitchen-their chef's seasonal tasting menu pairs beautifully with limited-release bottles you won't find elsewhere. After dinner, browse hand-crafted keepsakes and gourmet treats at Hermann Trading Post (perfect for last-minute gifts), then finish the night with a cozy tasting of port-style wines and vintage reserve pours on the candlelit patio at Bacchus Cellar Room, letting the week's vineyard stories settle as you savor one last glass.
Before you pack, treat yourself to a relaxed final morning with a savory breakfast and espresso at Hermann Java & Bakery, then take a short stroll to Riverfront Park Gazebo for last views of the Missouri and a few final photos of the bluffs. If time allows, pop into Hermann Mercantile Annex to pick up any forgotten souvenirs-local honey or a favorite bottle from the week-before checking out and heading home, carrying the gentle vineyard rhythms of your trip with you.
Before you depart, enjoy a relaxed late-afternoon stop at Otto's on the Hill for a light plate and a final glass while taking in one last panorama of the bluffs; their terrace is perfect for savoring lingering vineyard views. If time allows, wander through Hermann Tasting Company's shop to pick up a specially curated bottle and talk with staff about cellar-storage tips for travel, then take a final riverside stroll at Hermann Landing Park to breathe in the river air and say goodbye to the valley before heading home.
For a calm final evening, settle into a riverside table at The Millstream Taproom for a last plate of locally sourced comfort food paired with a small-batch Missouri wine or seasonal brew, reflecting on the week's tastings. Afterwards, take a gentle twilight stroll to Deutschheim Gardens to soak in the illuminated historic landscaping, then finish with a nightcap and final souvenir pour at Hermann Wine Company's Tasting Room, selecting one last bottle to travel home with you.