If you’re looking for a way to see Portland that’s both active and relaxed, the Around The Peninsula Bike Tour might be just what you need. This guided experience takes you along some of the most scenic spots around Portland’s harbor and old town — all at a pace that balances sightseeing with a bit of exercise. While I haven’t personally pedaled through it, I’ve gathered enough info to give you a clear picture of what this tour offers.
One thing we really love about this experience is how accessible it is — loaner bikes and helmets are included, making it easy to jump in without extra fuss. Plus, the knowledgeable guides don’t just lead you around; they share stories about Portland’s history, food, and culture, which adds layers to the ride beyond just the sights. On the flip side, a potential consideration is that parts of the route involve road riding, which might not suit everyone’s comfort level, especially if you’re not used to city biking.
This tour is a solid pick for anyone wanting to see Portland’s highlights without committing to a full day of exploring. It’s especially good for those who enjoy a bit of outdoor activity but also want some local insights and snacks. If you’re traveling with friends, family, or even on your own and love a relaxed, guided bike ride, this experience could fit right into your trip.
Key Points

- Accessible adventure with free loaner bikes and helmets
- Beautiful waterfront trails and scenic views of Portland’s harbor and Back Cove
- Informative guides who share local stories and culture
- Includes snacks to keep you fueled during the ride
- Short duration of around 3 hours makes it manageable for most
- Small group size (max 10 travelers) for a personalized experience
What the Tour Offers

The Around The Peninsula Bike Tour is designed to give you a taste of Portland’s waterfront, historic districts, and natural scenery, all within a few hours. From the start point at the Portland Encyclepedia on Commercial Street, you’ll hop on a bike and begin your journey along some of the city’s most picturesque paths. The tour lasts about three hours, which is perfect if you want a substantial snapshot of Portland without it taking up your entire day.
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The Itinerary in Detail
Stop 1: Eastern Promenade Trail
Your adventure kicks off at the Eastern Promenade Trail, a stretch renowned for its spectacular waterfront views. As you pedal along the bike path, you’ll get a feel for Portland’s scenic harbor and enjoy some fresh sea air. This stretch is about 30 minutes, and the path is flat and wide, making it suitable for most riders. The reviews highlight the beauty of this area; one traveler mentioned “great views of the bay,” which is exactly what you’ll see here.
Stop 2: Back Cove Trail
Next, the tour moves to the Back Cove Trail, a loop around the cove that offers a peaceful escape from the city bustle. The trail is also about 30 minutes long, and it’s a favorite for its calm waters and views of the Portland skyline. The route is well-maintained and offers a gentle ride, which makes it accessible for most participants. Reviewers have raved about how “beautiful the trail around Back Cove was,” noting it as a highlight.
Stop 3: Old Port
The final section takes you into Portland’s Old Port, famous for its charming brick buildings and historic waterfront. This part is about 20 minutes, giving you a chance to explore on foot if you wish or just soak in the architecture from your bike. The area buzzes with local cafes, shops, and lively energy, making it an ideal spot to end your ride. One reviewer summed it up as “beautiful brick buildings along the waterfront,” emphasizing the visual appeal.
The Experience and Logistics

Starting at The Portland Encyclepedia, the meeting point is conveniently located near public transportation, which makes the whole process smoother. The tour is limited to 10 travelers, ensuring a friendly, relaxed atmosphere and plenty of personalized attention from guides like Chuck, Steve, Michelle, and Rick, all of whom reviewers mention positively.
Snacks are included, which is a nice touch, especially if you’re riding mid-morning or early afternoon. The bikes are prepped and cleaned before each ride, adding a layer of safety and comfort. Helmets are provided free of charge — a small but important detail that many travelers appreciate.
Pricing at $85 per person might seem a tad steep at first glance, but considering the inclusion of bikes, helmets, snacks, and the guidance, it offers fairly good value. The tour’s popularity, with an average booking time of 40 days in advance, suggests it’s well-loved and worth planning ahead for.
What We Heard from Riders
Many reviews praise the guides — calling them knowledgeable, friendly, and responsive. One comment from a recent rider said, “Great guide! Knowledgeable and responsive,” which shows you’re in good hands. Others mentioned how much they appreciated the local insights, especially the stories about Portland’s history and culture.
Not everyone found the ride perfectly suited to their comfort level. For instance, one reviewer noted that the ride around Back Cove was “assume,” but also acknowledged that hills or road riding might be unavoidable in some parts. If you’re not an avid cyclist or a little wary of city streets, it’s worth considering this.
Bonus: The Social Distancing & Safety Measures
Given ongoing health considerations, the tour providers practice social distancing, and bikes are prepped for safety. This attention to detail helps ensure a relaxed experience, even if you’re cautious about crowds or hygiene.
Who Should Consider This Tour?
This bike tour is best suited for travelers who enjoy gentle outdoor activities and want a guided look at Portland’s waterfront and historic areas. It works well for those who are comfortable biking for a few hours and want a local’s perspective without the hassle of navigating on their own.
While not specifically marketed as family-friendly, older children who are comfortable on bikes might enjoy this experience. It’s also ideal for solo travelers or couples wanting to combine sightseeing and activity in a manageable, fun way.
Final Thoughts

The Around The Peninsula Bike Tour offers a balanced mix of scenery, history, and activity. It’s a good choice if you want to see Portland’s waterfront, learn about its past, and enjoy some fresh air — all without spending an entire day on the go.
The small group size and knowledgeable guides make it feel personal, and the included snacks and rental bikes simplify the logistics. While parts of the ride involve city streets, most of the tour focuses on scenic trails, making it accessible for many.
If you’re up for a relaxed, engaging way to explore Portland, this tour can give you a meaningful glimpse of the city’s charm. Just remember to book in advance, especially in peak season, and be comfortable with a bit of cycling.
Around The Peninsula Bike Tour
“It was a pleasure and so much fun riding around with Chuck as well as getting the history of Portland, ME. My husband and I didnt even realize we w…”
FAQ
Is the tour suitable for beginners?
Most travelers find the route manageable, especially since bikes and helmets are provided. However, if you’re not comfortable biking on roads or in traffic, you might want to consider your comfort level.
How long does the tour last?
It’s approximately 3 hours, including stops, which makes it a great afternoon activity without feeling rushed.
Are bikes included?
Yes, loaner bikes are available at no extra charge, along with helmets.
What should I bring?
Bring comfortable clothes suitable for biking, sunscreen, and maybe a camera to capture the views. Snacks are provided, so no need to pack extra unless you want specific refreshments.
Can I cancel if my plans change?
Yes, the tour offers free cancellation if you cancel at least 24 hours in advance. Less than that, and you won’t be eligible for a refund.
Is there a minimum or maximum number of participants?
Yes, the tour has a maximum of 10 travelers, ensuring a friendly environment and personalized attention.
Where does the tour start and end?
It begins and ends at The Portland Encyclepedia, located at 6 Commercial St, Portland.
Is the tour available year-round?
It’s weather-dependent, but if canceled due to poor weather, you’ll be offered a different date or a full refund.
Can I bring children?
The tour is most suitable for those comfortable biking for a few hours, but it isn’t specifically marketed as family-friendly. Older children who can bike comfortably should be fine.
Exploring Portland via bike offers a blend of fresh air, scenic beauty, and local stories. Whether you’re a casual cyclist or a history buff, the Around The Peninsula Bike Tour could be a highlight of your visit — a way to see the city from a different, more personal angle.
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- Forest Park Carbon Gravel Bike and E-Bike Tour
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