Begin with breakfast at Miss Shirley's Cafe on Main Street, enjoying their crab cakes benedict and locally roasted coffee to fuel a day of tastings.
Take a leisurely stroll through the Annapolis Historic District, stopping at Maryland State House for photos and a quick orientation to the waterfront neighborhoods.
Board a short scenic harbor cruise with Chesapeake Heritage Conservancy (or a similar local operator) to see Annapolis from the water and learn about the city's maritime history.
Return to shore for a light pre-lunch tasting at Vin 909 Winecafe, sampling Maryland and East Coast selections paired with a small cheese plate.
Lunch at Carpaccio Tuscan Kitchen for wood-fired pizzas and a glass of Maryland rosé while watching Main Street activity along the waterfront.
Stop by Stone House Distillery for a short tasting of locally crafted spirits and an explanation of their farm-to-bottle process.
Drive to Quiet Waters Park for a gentle walk along the scenic trails and a chance to relax lakeside before evening tastings.
Head to The Chart House or its nearby wine-friendly bar for an early evening wine flight that highlights East Coast and Maryland producers.
Return to downtown Annapolis for a tasting-focused happy hour at Rye or a cozy wine bar offering small plates and regional wines.
Walk to Chart House's waterfront bar for sunset views and a curated glass of East Coast Chardonnay while you watch the harbor lights come alive.
Dinner at Osteria 177 (or nearby Vin 909 if you prefer lighter fare), pairing house-made pasta with a bottle from Maryland vineyards recommended by the sommelier.
Head to Rye for a relaxed post-dinner tasting of regional wines and craft cocktails in a cozy, dimly lit setting with small sharable plates.
Finish the evening with a moonlit stroll along the Annapolis City Dock, stopping for a nightcap at Reynolds Tavern or a nearby late-night bar if open.
Start the morning with breakfast and a coffee at Miss Shirley's Cafe on Main Street, enjoying a Maryland-inspired omelet before your day of strolls and pairings.
Join a guided walking tour of the Annapolis Historic District, learning about colonial architecture and stopping for photos at the Maryland State House.
Pop into Chesapeake Bay Wine Company (or a local wine shop) for a short orientation tasting of Maryland varietals and expert recommendations for the afternoon pairings.
Visit Bacon & Rye for a mid-morning nibble and sample a suggested aperitif or Maryland cider while soaking up the café's historic ambience.
Lunch at Carpaccio Tuscan Kitchen for wood-fired pizza or pasta paired with a recommended Maryland rosé; enjoy people-watching along Main Street by the waterfront.
Take a short drive to Quiet Waters Park and stroll the waterfront trails, stopping at a scenic bench to sample a picnic wine from Chesapeake Bay Wine Company if you picked one up earlier.
Head to Vin 909 Winecafe for a relaxed tasting flight focused on regional producers and a light cheese board to compare styles side by side.
Pop into Stone House Distillery for a quick tour and tasting of their farm-to-bottle spirits, learning about how local ingredients shape their profiles.
Return downtown for an early evening wine-focused happy hour at Rye, sampling small plates paired with East Coast wines in a cozy setting before dinner.
Begin the evening with a curated wine flight at Rye, sampling East Coast varietals alongside small plates while the room fills with mellow Sunday energy.
Walk to Osteria 177 (or Vin 909 for lighter fare) for a leisurely dinner pairing house-made pastas or seasonal mains with a recommended Maryland red or Italian selection from their list.
Take a short stroll down to the Annapolis City Dock to savor harbor views and stop for a nightcap at Reynolds Tavern, enjoying historic atmosphere and a final regional pour.
If you're up for one last low-key spot, drop by Rye's lounge area (or a nearby cozy bar) for a digestif or late glass while reflecting on the day's tastings before returning to your accommodation.
Begin with breakfast at The Village Café in downtown Poolesville for fresh pastries and locally roasted coffee to fuel a day of vineyard visits.
Drive to Sugarloaf Mountain Vineyard for a relaxed morning tasting on their terrace, sampling estate chardonnays and learning about their cool-climate approach.
Head to Avenel Farm Winery for a guided tasting and a short tour of the barrel room; enjoy conversation with the winemaker about their small-lot reds.
Stop at Rocklands Farm Winery (or their tasting room) for a late-morning flight paired with a light charcuterie plate while you take in pastoral views.
Enjoy a leisurely lunch at The Barns of Gaithersburg's café (or nearby Kingfisher Farm Café) with a seasonal salad and a glass of local white before the afternoon tastings.
Drive to Black Ankle Vineyards for an afternoon tasting of estate rosés and reserve reds, followed by a stroll through their vineyard trails to see terroir up close.
Head to Olney Winery for a seated tasting and a short talk with the winemaker about their small-batch techniques, paired with a sampling of locally made cheeses.
Stop at Great Country Farms Market (farm stand) for a quick browse of local produce and to pick up a bottle or two of Maryland wine to take home.
Finish the afternoon with a relaxed tasting flight on the patio at Rocklands Farm Winery's tasting room (if you prefer a second, deeper tasting) while watching the sunset over the rolling fields.
Drive to The Red Bear Brewing Co. (nearby in Poolesville) for a relaxed drink if you want a break from wine - they often have guest Maryland wines and small bites to pair with your evening.
Return toward downtown Poolesville and enjoy dinner at Kingfisher Farm Café or Blue Door Café & Bakery, savoring farm-forward dishes paired with a bottle of the Maryland wine you purchased earlier.
Stop by The Black Ankle Vineyards tasting room (if open for special evening events) or a local wine bar such as The Wine Room in Gaithersburg for a final, seated tasting flight focused on reserve selections.
If you prefer a low-key end to the night, drive to Sugarloaf Mountain's base area for a short sunset or moonlit walk, or return to your accommodation for a nightcap with a bottle from Black Ankle while relaxing and reflecting on the day.
Breakfast at The Grille at Federal House with a farm-fresh omelet and locally roasted coffee to fuel a day of vineyard touring.
Drive to Linganore Winecellars' Prince George's tasting room (or a nearby satellite tasting) for a seated flight that introduces you to Maryland's early-season whites and sparkling options.
Arrive at Anaia Cellars for a guided vineyard tour and tasting; stroll the vines while the host explains soil, microclimate, and how they craft food-friendly wines.
Visit Twin Oaks Winery (or a nearby estate tasting room) for a light pre-lunch tasting paired with a house charcuterie board and conversation about local pairing suggestions.
Lunch at CafÈ Mezzanotte (or The Grille at Federal House if you prefer to stay local) featuring a seasonal salad or panini paired with a recommended Maryland white to keep the palate bright for afternoon tastings.
Drive to Shady Grove Vineyards (or a nearby small estate) for a seated tasting of their reserve whites and a guided talk on how their food-pairing program complements local Chesapeake fare.
Visit Mt. Airy Cellars tasting room (satellite) for a flight focused on medium-bodied reds and an artisan cheese plate that illustrates pairing contrasts and balance.
Stop by Prince George's Farmers Market (if open seasonally) or a local farmstand to sample regional preserves and pick up a tranche of local charcuterie to pair with a later bottle.
Return to a scenic spot at Anaia Cellars (brief revisit for a different tasting style) or settle on their patio for a pre-dinner tasting of a food-focused flight and notes from the winemaker on pairing techniques.
Drive into Upper Marlboro for dinner at Black Market Kitchen (or Hard Times Cafe for a casual bite) and order a bottle from a Maryland producer to practice the afternoon's pairing lessons with heartier evening fare.
Enjoy a relaxed dinner at Black Market Kitchen, ordering a Maryland-friendly dish and a bottle from a local vineyard to practice pairing lessons from the afternoon.
Walk to The Cellar Door (if open) or a nearby wine bar for a curated nightcap flight focused on reserve selections and dessert-friendly wines.
Stop by Shoreline Bistro & Wine Bar (or a cozy Upper Marlboro lounge) for a final digestif or late glass while comparing tasting notes and jotting down favorite bottles to buy before departure.
Return to your accommodation for a quiet end to the evening - uncork a bottle from Anaia Cellars or Twin Oaks Winery and enjoy a small plate of charcuterie while reflecting on the day's pairings.
Enjoy a waterfront breakfast at Carpenter Street Saloon & Bistro, savoring crab-and-egg specials with locally roasted coffee while watching the harbor come to life.
Stroll the quaint streets and boutiques of St. Michaels Historic District, popping into galleries and specialty shops to pick up local artisan treats and maritime souvenirs.
Visit St. Michaels Winery (or their tasting room) for a seated flight of boutique Maryland wines and a short chat with the host about local grape varieties and production methods.
Take a short drive to Tilghman Island Vineyard (or a nearby Talbot County tasting room) for a tasting on their porch and a chance to sample a crisp estate white while overlooking pastoral waterways.
Grab a light pre-lunch bite at The St. Michaels Crab & Steak Company or a café on Talbot Street and pair it with a glass from a local vineyard to prepare for the afternoon's boutique tastings.
Drive a few minutes to The Crab Claw and enjoy a relaxed waterfront lunch pairing a seasonal seafood special with a recommended Maryland white from their wine list.
Head to Inn at Perry Cabin's bar for an elegant tasting of East Coast wines or a curated glass, taking in the estate grounds and maritime views while the host explains local producers.
Visit St. Michaels Winery's nearby retail shop (if you didn't linger earlier) or stop at Waterside Marketplace to sample boutique bottles and pick up a souvenir bottle from a Talbot County producer.
Take a short drive to Tilghman Island Vineyard's scenic tasting porch for a seated tasting of their estate rosé and white, enjoying breezy views of the marshlands as the afternoon light softens.
Return toward downtown St. Michaels and pop into Ava's Pizzeria & Wine Bar (or Bistro St. Michaels) for a casual late-afternoon tasting flight paired with small plates and locally sourced cheeses.
Walk along the waterfront to St. Michaels Market or a nearby café to sample artisan chocolates or preserves paired with a dessert-friendly Maryland wine, preparing for dinner.
Dine at The Lighthouse Bar & Grill (or Bistro St. Michaels if you prefer a more intimate setting), ordering a bottle from a Maryland producer to continue your waterfront tasting while the harbor lights come on.
Enjoy a relaxed nightcap at Inn at Perry Cabin's lounge or bar-ask the bartender for a chef-selected dessert wine or an East Coast red while taking in the estate's evening ambiance.
Take a moonlit stroll along the St. Michaels City Dock, pausing for a final glass at a late-night spot such as The Tasting Room (if open) or to savor a bottle you picked up from St. Michaels Winery back at your accommodation.
Return to your lodging for a quiet tasting of any new purchases-spread out a small cheese plate from St. Michaels Farmers Market and compare notes on favorite bottles from the day.
Start with coffee and a pastry at Sagamore Spirit Distillery's Café or a nearby Baltimore café, pairing a light breakfast with a tour of the distillery shop for last-minute local spirits souvenirs.
Visit Lexington Market to wander stalls selling Maryland specialties-sample fresh crab spread, local cheeses, and pick up artisanal jams to pair with any wines you plan to bring home.
Head to Broadway Market (if open) or Fells Point Farmers' Market for seasonal produce, boutique baked goods, and a chance to chat with vendors about regional pairings and recommendations for picnic-friendly bottles.
Drive to Loch Raven or Patapsco Wine Shop (local bottle shop) for a final tasting or to have staff recommend and pack a travel-safe bottle from Maryland producers for your trip home.
Stop by Clavel Restaurant & Taqueria (or another favored neighborhood eatery) for an early lunch and to enjoy a final glass from a Maryland winery on their list while reflecting on the week's favorite bottles.
If time allows before departure, make a quick visit to Baltimore's Harborplace to pick up any last-minute gifts or boutique wines at the specialty shops and enjoy a waterfront moment before heading to your next destination.
Walk to The Food Market in Hampden for a modern American lunch plate paired with a glass from a Maryland producer; enjoy the neighborhood's quirky shops afterward.
Head to Union Craft Brewing (Remington) for a palate-break with a tasting flight and to browse any guest Maryland wines or cider they may be pouring alongside small pub-style snacks.
Visit The Wine Source in Roland Park for a short consult with staff and to have a prized bottle from a Maryland vineyard gift-wrapped or packed for travel.
Drive to Sotterley Winery's Baltimore tasting partner (or a nearby satellite tasting room such as Vino Garage) for a seated comparative tasting of two regional reds and a light cheese pairing.
Take a scenic stroll along the Inner Harbor promenade toward Federal Hill, stopping at Top of the World Observation Level for panoramic views and a final photo moment before evening travel.
Enjoy an early farewell drink and small plates at Muse by Wyndham's lobby bar (or LP Steamers rooftop if open), ordering one last Maryland bottle to savor as you pack up purchases and prepare for departure.
Walk across to Federal Hill Park for a short sunset viewpoint and enjoy a relaxed pour from a bottle you picked up earlier while watching the city lights emerge over the Inner Harbor.
Dine at The Local Fry (Federal Hill) or Pierpoint Restaurant for a waterfront dinner pairing a Maryland-friendly red or white with a seasonal seafood entrée.
Head to R. House in Remington for a lively, late-evening atmosphere-sample a by-the-glass selection from local Maryland wineries at their wine-focused vendors or grab a craft cocktail if you want a break from wine.
Stop by The Wine Source (if still open for special evening hours) or Vino Garage for one last curated tasting and to confirm travel-safe packing for any bottles you're bringing home.
Enjoy a nightcap at The Owl Bar (Belvedere Square area) or the cozy lounge at The Ivy Hotel-ask the bartender for a Maryland dessert wine or an East Coast red to close out the trip.
Return to your accommodation for final packing; spread out any purchases and enjoy a quiet final tasting of a favorite bottle with a small cheese plate from Lexington Market while reflecting on highlights from the getaway.