Introduction

If you’re someone who loves exploring a city’s flavors and stories through its wines, this Portland Old Port Wine Tasting Walking Tour might just be a perfect fit. Promising a relaxed two-and-a-half hours wandering Portland’s charming streets, it offers a delightful way to taste local and international wines while learning about their origins.
What we especially appreciate about this experience is how it balances informative guidance with genuine leisure — you don’t just sip wines, you also get a taste of Portland’s vibrant atmosphere. Plus, the small-group setting makes it feel intimate and personal, which can often lead to engaging conversations with both guides and fellow wine lovers.
One potential consideration is the price — at $99 per person, it’s not the cheapest outing, but the quality of tastings and the expertise involved can make it well worth the investment. This tour suits travelers who crave an authentic, laid-back experience that combines good stories, great wines, and a bit of Portland’s local charm.
Key Points

- Expert-guided experience combines education and casual tasting.
- Three handpicked stops highlight local favorites and international options.
- Leisurely pace allows for meaningful conversations and exploration.
- Small groups ensure personalized attention and a friendly atmosphere.
- Includes tastings and water at every location, with no pressure to buy.
- Perfect for wine enthusiasts and curious explorers alike.
You can also read our reviews of more walking tours in Portland
Exploring Portland’s Old Port Wine Scene
Portland’s Old Port is known for its historic brick buildings, lively waterfront, and now, a burgeoning wine scene that offers a refreshing twist on the city’s culinary reputation. This tour offers a structured yet relaxed way to sample its best offerings without the hassle of figuring out where to start.
Why this tour stands out
One of the most appealing aspects of this walking tour is the attention to detail—from the choice of stops to the knowledgeable guides who share captivating stories about each wine’s background. It’s clear that the focus is on quality and meaningful experiences rather than just ticking off tasting samples.
The Tour’s Three Stops
Let’s break down each stop to understand what makes them unique and how they contribute to a well-rounded tasting experience.
Stop 1: Portland Beer Hub

The tour begins at Portland Beer Hub, where your guide will introduce the group to a draft Prosecco and curated wine tastings. This initial stop sets a relaxed tone, blending casual beer and wine experiences that immediately make you feel at ease.
What you can expect:
This spot is ideal for warming up your palate and loosening up the group with some light conversation. The inclusion of a sparkling Prosecco is a thoughtful touch, offering a taste of Italy’s popular bubbly in a casual setting. The warm welcome from staff and the lively atmosphere often earn praise, making this a great way to kick off your tasting adventure.
Traveler insight:
Many reviewers appreciate how the guide’s storytelling makes each wine or sparkling option more meaningful. One said, “We loved the way they shared stories about each wine’s origin, making the tasting more engaging.”
You can also read our reviews of more food & drink experiences in Portland
Stop 2: Cellardoor Winery Portland

Next, you’ll visit the Cellardoor Winery, renowned for its small-batch craftsmanship and expressive style. The guided flight here focuses on Maine-made wines, allowing you to taste the local flavor at its best.
What makes it special?
The sleek tasting room provides a refined setting to appreciate Made-in-Maine wines made with care and attention. The guided flight offers a chance to compare different styles, from crisp whites to deeper reds, all crafted with passion.
Duration:
This stop lasts approximately 50 minutes, giving you plenty of time to savor each pour and ask questions about winemaking in Maine.
Feedback:
Guests frequently mention the knowledgeable guides and the quality of the wines. One reviewer noted, “The wines were small-batch and expressive, and the guide’s explanations helped me understand what makes Maine wines unique.”
Stop 3: Angoor Wine Bar

The final stop is the Angoor Wine Bar in Portland’s East End. This self-pour bar offers over 50 wines on tap, allowing you to explore at your own pace.
Experience:
Sampling from a rotating selection, you might find crisp whites, bold reds, or sparkling options—all available without the pressure of traditional tastings. It’s a relaxed way to wind down your journey, with the freedom to choose what intrigues you most.
Duration:
This segment lasts around 50 minutes, giving ample opportunity to chat with other participants or revisit a favorite pour.
Traveler tip:
Many enjoy the self-pour setup, as it encourages a more personal tasting experience. One reviewer said, “It felt like I was in a wine shop with friends, exploring different options at my own pace.”
Practical Details and What They Mean

Price:
At $99 per person, this includes all tastings, water, and guided insights. Considering the quality of wines and the expertise involved, this offers solid value—especially when you factor in the small-group setting and the convenience of a curated experience.
Tour Length:
The 2.5-hour duration is perfect for a relaxed but engaging outing. It’s long enough to enjoy multiple tastes without feeling rushed, making it suitable for both casual wine lovers and more serious enthusiasts.
Group Size:
Limited to 15 travelers, the small-group format ensures personalized attention and the opportunity for genuine conversations. It also helps create a friendly, intimate atmosphere, which many travelers appreciate.
Location & Meeting Point:
Starting at 320 Fore St, the tour is centrally located and near public transportation, making it easy to access from various parts of Portland.
Weather & Cancellation:
Since the tour is outdoors and involves walking, good weather is important. The policy allows free cancellation up to 24 hours in advance, providing flexibility if plans change.
Why It Works for Travelers

This tour is particularly well-suited for those who enjoy a relaxed pace and want to combine sightseeing with tastings. It’s perfect for couples, small groups, or solo travelers eager to learn about Portland’s wine scene without the fuss of formal wine tastings or large, impersonal tours.
If you’re looking for a way to explore the city’s streets while savoring some excellent wines, this experience hits the right note. Its focus on local Maine wines, engaging storytelling, and casual atmosphere makes it a memorable way to spend an afternoon.
Final Thoughts

The Portland Old Port Wine Tasting Walking Tour offers a charming, well-organized introduction to Portland’s burgeoning wine scene. The knowledgeable guides and curated stops ensure that you learn something new with every sip, all within a relaxed setting that feels more like visiting friends than a formal tasting.
While the price might seem on the higher side, the quality of wines, the personalized experience, and the chance to explore Portland’s streets make it a worthwhile investment. Whether you’re a wine novice or a seasoned enthusiast, you’ll enjoy the blend of education, local flavor, and Portland’s vibrant vibe.
This tour is best for those who value authentic experiences, enjoy good conversations, and want a taste of Portland’s local culture alongside its wines. Its small-group setup guarantees a friendly, engaging atmosphere where you can truly connect with your guides and fellow explorers.
FAQ
Is the tour suitable for all ages?
Yes, most travelers can participate, but since it involves alcohol tastings, it’s primarily for adults.
How long does the tour last?
The experience runs approximately 2 hours and 30 minutes, including walking and tastings.
What’s included in the price?
The fee covers visits to three wine-centric shops, guided insights, water, and wine tastings at each stop.
Can I buy additional wine?
Purchases of extra wine or bottles are not included in the tour price.
Is this tour wheelchair accessible?
The tour involves some walking and outdoor segments, so accessibility might be limited; it’s best to check with the provider directly.
What if the weather is poor?
Since good weather is needed, if canceled due to rain or storm, you’ll be offered a different date or a full refund.
What should I wear?
Comfortable walking shoes and weather-appropriate clothing are recommended, especially since the tour involves outdoor walking.
How far in advance should I book?
Most travelers book about 20 days ahead, so plan early to secure your spot, especially in peak seasons.
In the end, the Portland Old Port Wine Tasting Walking Tour offers a fantastic blend of local culture, expert guidance, and delicious wines—all within the charming streets of Portland. It’s a chance to see the city from a new perspective while enjoying some of its finest flavors.
More Walking Tours in Portland
More Tours in Portland
More Tour Reviews in Portland
Not for you? Here's more nearby things to do in Portland we have reviewed
- Sunset Windjammer Cruise Along the Coast of Portland Maine
- Portland Tea Party Outdoor Tea Ceremony Experience
- New Hampshire White Mountains Day Tour
- Portland Oregon Art Walk
- Afternoon Windjammer Cruise Along the Coast of Portland Maine
- Portland Old Port Wine Tasting Walking Tour
- Keep Portland Weird Neighborhood Culture Tour
- Alberta Arts District Food Tour
- Portlands Downtown Scavenger Hunt Adventure
- Portland, Maine East End Bakery Crawl – Ladies only!
- Private Oregon Wine Tour – Bring Up To 10 People – Three Wineries
- Portland’s Best Barbecue, Brewery, and Distillery Van Tour
