Trek & Trail

We had such a great time taking a whole day kayaking tour with Trek & Trail while visiting Wisconsin. Our tour guide was Emily and our group size was 6. We originally were supposed to go to Sand Island, but due to the weather we ended up just going to kayaking to a shipwreck, having lunch and taking a hike on Basswood Island. Emily was a great and very informative tour guide giving us a lot of history about the islands and answering any questions we had. The kayaks were in great condition and the overall tour was fun! We were lucky the other 4 people in our group were very entertaining people. I would definitely do trek & trail again, and might even try an overnight backpacking trip. Highly recommended!

Chad and Emily were very competent guides. We had a deluxe tour and the sights/​caves were stunning. The incredible weather and lake conditions didn’t hurt either. We had a wonderful time and wouldn’t hesitate to recommend the trip.

We just got back from the ‘Paddle Through Time’ 2 night/​3 days kayaking and camping excursion led by Bill, and had an amazing time. Most of the credit for the success is due to our guide’s proficiency and great personality, although we definitely also lucked out with beautiful weather and good kayaking conditions.
I really can’t say enough great things about our guide and highly recommend trying to schedule your next camping/​kayaking adventure with him. Most importantly, he has the critical survival expertise (weather, navigation, nautical) to lead a group safely, all without being bossy or overbearing. His calm demeanor, even during times of slight angst, put the group at ease and reconfirmed that we were in good hands. Bill has 18+ years of experience leading sea kayaking trips in the area and it shows. In addition to knowing the lake and the Apostles like the back of his hand, he also has an immense wealth of knowledge including geology, natural history, and local history.
Even though I’m comfortable backpacking on my own and with novice hikers in black bear country, I wouldn’t even think of attempting this type of trip until learning from a professional. The lake is a beast and acts like an ocean, sans the tide. Huge swells can come out of nowhere, it’s much harder to get back into a kayak than you’d think (you have to do it twice to get through the safety course), and it only takes 15 minutes in that bad boy to get hypothermia. It’s nothing to mess around with.
As a novice kayaker, I completely underestimated what it meant to paddle 32 miles in 2.5 days. It was beautiful, and I’d love to go back, but if you want more leisure time and less open water paddling, then go for a trip with a base camp and lots of built-​in hiking/​relaxation time. We launched from Little Sand Bay, spent the first night on Sand Island after paddling through the sea caves, spent the next day stopping off at York and Raspberry Islands before spending the second night on Oak Island. From there we made our way back to Bayfield.
In addition to our fantastic trip guide, the front desk staff were great to work with for scheduling, the gear seemed in top shape, and the catered food was very tasty. The shop is also stocked with a nice selection of gear.

Had a wonderful trip to the sea caves with a family of 6. Full day trip. Porter and Joe were our guides. Very knowledgable about the area — sharing a great narrative about the lakeshore. Friendly and talkative all day. Had a weather change on the return trip with some 3 foot swells– Porter helped out our younger kids and a managed the situation so we all felt comfortable. He knows what he is doing! Great lunch I believe from the Fat Radish topped it off!

Very friendly and knowledgeable staff made our cave adventure very fun! Our group had kayakers of all levels and both guides were accommodating to all by having one with those at the front of the group and one with those in the back. They also shared fun facts about the area!

We had such a great time on the 4 pm ½ day cave tour. Stephanie and Abbie (? We’re all arguing about her name, Sorry Ally/​Abby/​something that starts with a different letter) were wonderful! Patient and fun! View was beautiful. 3 hours was perfect for us newbies. Thank you!!!

Lynn with Trek & Trail did a wonderful job arranging a trip for our crew of 8. We had extremely complicated logistics, but she handled them with ease. She also arranged great meals for our crew, and things went off without a hitch. I would highly recommend Trek & Trail!

Earlier this month my friend and I kayaked and camped in the Apostle Islands with Trek and Trail outfitter in Bayfield, WI. This was the first time I had spent any time exploring the Apostle Islands. Last summer my friend paddled with Trek and Trail on a similar length and distance trip and had an amazing time. Her experience was so incredible for many reasons; most notable was their guide, Jon Flynn. In preparation for our trip, I called Trek and Trail and asked if Jon could guide our 3-​day 2-​night Paddle Through Time trip. The office staff was so friendly and accommodating and despite our proposed dates being scheduled back-​to-​back with another trip Jon was guiding, he graciously accommodated our request. Our experience was unbelievable. The gear supplied by Trek and Trail was great and the meals, catered by the Fat Radish were fantastic and Mother Nature certainly took care of the scenery and wildlife. While it would be hard to elevate our experience any further, Jon made an already memorable experience even more memorable. Jon is a very experienced guide who made us feel safe and secure on a very unpredictable lake, as the weather can quickly shift without warning. His depth of knowledge on the history and natural ecology of the region comes only from someone with a true passion and natural curiosity. In addition to everything else, Jon managed to surprise me with a birthday cake, candles and all, on our second night (I have no idea how he managed to hide the cake in the kayak); he photo-​documented every detail of our 2.5 day experience and surprised us with LED toys that made three adults giddy as kids playing with light against the night sky. I have been on a number of guided expeditions before but have never experience such an amazing combination of perfection. Everything about our experience with Trek and Trail and Jon, in particular, has me wanting to book my trip again for next summer. Thank you so much! A+++

Under new ownership as of the 2015 season. We did a half day sea caves tour with Chad and Porter and it was great. My boyfriend had never kayaked and it had been quite a while (10ish years) since my last paddling adventure. They were great at showing everyone the basics and keeping everyone together. The caves were great too. Be warned that the drive out to Myers Beach is further than you think. If you get to Cornucopia you’ve gone too far. If I am in the Apostle Islands again I’d definitely do another trip with T&T.

Margaret, who was on the phone, is super friendly and cuztomer-​oriented.
Porter, who was our tour guide, is funny, knowledgable, and knows what he’s doing.
We had a full day kayaking (9 – 4), which is super exhausting for beginners like ourselves, but we enjoyed it. Now it’s time for that 5-​hour nap! We recommend if you just want to see the sea caves, then do a half-​day, that might be easier.
Please check the weather before you come because even at the end of June, it is still around 50°F.

They went above and beyond! My boyfriend and I did a 6 day sea kayaking trip, camping at different Apostle Islands and went thru trek and trail. We had a great instructor for the safety course. We rented a tandem kayak and the fixings from them, it was a great boat. We also had them shuttle us to little sand bay.
The staff was super friendly and helpful— they really went above and beyond in our case. My car was parked in their small day parking lot, right before we were to hop in the shuttle, we went to move it to the municipal lot a couple blocks away for overnight parking. And then my car battery wouldn’t start. Our shuttle driver came over and popped his hood and tried to jump it, and let it charge up for a while. Unfortunately it was a bigger issue (starter). They recommended a reliable, quality mechanic in town. Since it was sunday, he was closed. Trek and Trail let us leave the car in their lot and followed up with the mechanic on our behalf, since we wouldn’t have cell service out on the water. We came back and the car was fixed, all ready to go in their lot. Trek and Trail had even fronted the mechanic the money to fix my car since my credit card wasn’t going through. They were super super helpful and friendly, and flexible to our situation. We had a great experience going through them. Also, their location is super convenient, they have their own little beach right in Bayfield, we paddled back there from Oak island and pulled our boats right up to their shop.

I am in agreement with most of the other reviews here. Four of us went to Bayfield on a «guys weekend» to paddle the Apostle’s. Unfortunately it was before Living Adventure’s season had started so we went with Trek and Trail. We had no problems making our reservations with Trek and Trail. To T&T’s credit, the safety course we were required to take before setting off on our trip was helpful and well run.
Being mid-​May it was still cold and the week we were on the water was very stormy. We weathered the storm for most of the week but on our last day we had very bad thunderstorms. We decided to paddle off the islands and get back to mainland in hopes that T&T would pick us up one night early. We spent 8 grueling and wet hours waiting out storms and choosing safe routes and times getting back to Little Sand Bay. We were going to pitch our tents and stay the night until the weather took a turn for the worse and we discovered there was a tornado warning. We thought it was best to get back to Bayfield to be safe. We called T&T from the campground near Little Sand Bay and the person at T&T was positively horrible. We had difficulties with reception and the lady was actually getting annoyed that we would call her. Despite being able to communicate to her that we were hoping to get an early shuttle because of the dangerous weather, she was simply not interested in helping us. She mentioned several times that they closed at 5 o’clock and getting punching out at exactly this time was of upmost importance, even more so than the safety of our group. We ended up spending the night on the floor of the campground bathroom waiting out the tornado warnings. They were able to pick us up in the morning — when it was totally convenient for them — and still charged us the $ 50 fee.
The kicker for me — and the reason for this negative review — is that they stole my cooler. We left a cooler in the shuttle van that dropped us off at the beginning of our trip with the intention of getting it when we returned. After a chaotic trip (see above), however, we forgot to grab it. I phoned T&T shortly after and told them that I had forgotten it and that I would likely be back that way or have family/​friends that would swing through Bayfield, WI and could pick it up. Now just this week when I phoned T&T to see about the cooler, they had no idea what I was talking about. I called them three times with exact details of where and who I left the cooler with. They told me they would return my call three times and have not returned a call once. Again, they are just ignoring me and hoping that their «problems» go away.
I hope that you will consider another outfitter when visiting Bayfield and the Apostle’s.

Got a groupon as a gift for one of their weekend adventures. Called in May to find out the schedule for the summer, and EVERY SINGLE DATE for the entire summer is already booked. This groupon cannot be used! I can go on a standby list in case someone else gets sick at the last minute (which doesn’t do me any good as I’m 8 hours away). Why would you sell so many deals if you know you can’t book them!!! Terrible company and the woman that answered the phone for the company was super rude!

Their training course and the guys who get you prepped for the trip were great. There was a lot of useful information, and we felt better about our trip after.
The owner is very difficult to work with and seems intent on handling all of the customer service, unfortunately. They have a very tricky cancellation policy. Make sure to ask to know these policies before you book. The policies are written on their invoices but not stated outright. I lost $ 175 to them, and the owner was not budging an inch despite some difficult circumstances that I could not control. You’ll want to make sure everybody in your group books separately so that you’re not responsible for their fee in case they cancel.

We ended up using that partial credit (still lost ²⁄₃ of our original payment) and got a smaller group to go kayaking a few weeks later. Porter ran the training course and did a great job. We all felt much safer having learned how to rescue each other and ourselves, plus we learned some strokes and techniques.
And then when we went out on our own, the staff helped us load the kayaks onto our car. Everyone but the owner seems to be great to work with.

Had an awesome time with these guys. Scott and Chris took our group out to the sea caves and we had so much fun. I would have been very disappointing if I ended up going with the group that left before us which went with a different company. They were far to cautious and turned back with the little bit of wind. Scott asked us what we liked to do and we all voted to go ahead and it was such amazing fun. Most of us were not experienced kayakers and it was not a difficult paddle.
We will be back next year.