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Explore Portland’s Old Port like never before on a two-hour happy hour tour that pairs unique cocktails with tales from the Prohibition era. Discover flavors and history in a lively, historic setting.
Explore Portland’s Old Port like never before on a two-hour happy hour tour that pairs unique cocktails with tales from the Prohibition era. Discover flavors and history in a lively, historic setting.
Book with Maine Foodie Tours
Verified experiences and guided adventures in the surrounding area.
Operated by Maine Foodie Tours · Portland, Maine
Portland, Maine's Old Port district offers more than just scenic waterfront views—it’s a lively hub of culinary creativity and rich history waiting to be discovered on the "It's Happy Hour Time" tour. This curated two-hour experience invites visitors aged 21 and over to engage with the city’s vibrant cocktail scene while walking through cobblestone streets steeped in stories from Portland's Prohibition era.
Beginning in the heart of Portland, the tour moves through iconic pubs and innovative restaurants, each stop offering light appetizers and signature cocktails crafted to reflect the local flavors and traditions. As you sip on uniquely balanced drinks, your guide will weave tales of the Old Port’s past—how this once-gritty waterfront district transformed from smuggling haunts and speakeasies into a celebrated culinary destination.
What makes this tour special is its perfect blend of food, beverage, and storytelling. Visitors don’t just taste the cocktails; they understand the cultural layers behind them, giving a deeper appreciation of Maine’s coastal charm and clandestine history. Beyond the drinks, the Old Port’s historic brick buildings and lively atmosphere provide an immersive backdrop that captures Portland’s evolution from maritime center to modern-day hotspot.
This experience stands out because it is both educational and indulgent, designed for travelers who want to explore a city’s spirit through its palate and past. Ideal for foodies, history buffs, and anyone looking for a curated urban adventure, "It's Happy Hour Time" delivers an engaging way to connect with Portland beyond the usual sightseeings.
Accessible via Portland’s central location, the tour is easy to integrate within broader explorations of Maine’s southern coast. It fits well within an evening itinerary and is a great social outing, pairing perfectly with the city’s welcoming nightlife.
Whether you're a visitor or a local looking for fresh insights, this happy hour tour offers a refreshing perspective on Portland. Taste handcrafted cocktails inspired by regional ingredients, discover the stories behind the spirited venues, and take in the lively streets of Old Port in an entertaining, approachable setting. It’s an invitation to sip, savor, and step back into one of New England’s most captivating urban landscapes.
easy.
2 hours.
Suitable for all fitness levels as walking is at a relaxed pace on urban terrain.
No, participants must be 21 or older to join this tour due to alcohol tastings.
Yes, please notify the tour operator in advance about any allergies or dietary preferences.
The tour includes walking approximately 1-2 miles at an easy, leisurely pace.
Contact the operator directly to inquire about private or customized group reservations.
Yes, the tour price includes all cocktails and light appetizers at each stop.
The tour begins and concludes at a central Old Port location provided upon booking confirmation.
Portland’s Old Port was a hub for smuggling and secret bars during Prohibition, shaping its resilient local culture.
The tour emphasizes support for local businesses and encourages environmentally friendly practices within the district.
Maine Foodie Tours is a culinary tour company based in Kennebunkport, Maine, offering guided food and beverage experiences across Southern Maine. The company organizes walking food tours, oyster cruises, and themed experiences in destinations such as Kennebunkport, Portland, Biddeford, and Casco Bay. Tours include ocean-based oyster cruises aboard the Brianna Marie, daytime and sunset cruises featuring freshly shucked Maine oysters and local sparkling wine or beer, as well as neighborhood walking tours that showcase lobster rolls, clam chowder, artisanal shops, and craft beverages. Local knowledge drives each itinerary: tours are led by experienced, locally based guides who connect guests with century-old bakeries, James Beard semi-finalist cafés, award-winning breweries, and family-run restaurants. Small-group formats focus on tasting authentic regional foods while sharing historical context about mills, maritime heritage, and culinary migration. Special offerings include a dog-friendly “Doggie and Me” Kennebunkport tour with limited spots and proceeds supporting the Animal Welfare Society. Maine Foodie Tours has been featured on The Adventure Collective and markets itself to both visitors and residents seeking authentic Maine flavors. Safety and quality are emphasized on boat cruises, which operate aboard a comfortable vessel, and on walking tours that move through historic downtowns and harborfronts. Booking information, schedules, and accessibility details are published on the company’s official listings and third-party partners. Guests can expect guided tasting portions, storytelling about local foodways, and curated stops designed to highlight Maine’s seafood, baked goods, and craft beverage scene. Tours accommodate many dietary preferences with advance notice from guests.
Book with Maine Foodie Tours