My boyfriend and I had the most wonderful evening aboard Alpha Puppy last night. Probably the best views of Chicago you can get, great weather, a relaxed cruise that wasn't commercialized and stiff. We felt like a bunch of friends just out for a sail, which was exactly what I was looking for! We will definitely book future sails and can't recommend it enough. Kevin was also so understanding when we went to the wrong place and were running late. Thanks for a perfect end to summer!!! read more

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HORRIBLE EXPERIENCE. From the rude responses of the captain to strict cancellation policies, this has to be the worst booking experience. I'm sure a representative is going to try to justify their actions with some bs excuse as I've seen them do on other reviews here. I asked if at the very least they can issue credit for what I've paid for and he rudely responded. I can see why most people chose other sailboat rentals over this one which I should've done. Also, the Groupon says it FITS up to 6 people, never does it say it's shared! Smart and tricky usage of words. read more

I purchased a private charter with Captain Rick and my husband and I took off to celebrate our anniversary. My husband used to sail many years ago and I know how much he misses it and I asked in advance if could help out a bit as he loves that stuff. Captain Rick was more than accommodating, having my husband help most of the time, husband was SO happy! We had a very enjoyable cruise and Rick was a pleasure to sail with, so much so that I booked a repeat cruise already for my husband to take some sailing lessons. Nice job Offshore and Rick! Very happy with your services. read more

We tend to use Groupons to try things out, and often it's a "that was nice, but probably wouldn't do it again" experience. Not at Offshore Adventures - definitely looking forward to doing this again! Capt. Rick is extremely personable and professional. On the evening we went out for a weekday fireworks cruise around Navy Pier, the wind had picked up unexpectedly. Neither the other two couples nor us had ever really been sailing on the big Lake, so after about 15 minutes or so, Capt. Rick could tell that the experience might be getting a bit dicey, so he trimmed the sails and turned on the motor. Would love to go back when the wind wasn't so strong, but really appreciate his reading of the weather AND his guests. Just learned that he does sailing lessons as well, so that might be next on the agenda. Initially his appointment confirmation went into my SPAM email, but he sent it right away, so make sure you look for it. Also, a few days before our scheduled outing, he sent another email with all parking and directions details. Highly, highly recommend Capt. Rick and Offshore Adventures! read more

I've been meaning to write this review for a few weeks. I bought a Groupon for the two hour BYOB sailboat cruises. I went with a friend and we had a blast! Captain Bill is an amazing captain. He is full of a ton of sailing knowledge and has some pretty amazing sailing stories, all you have to do is ask! Bill was super nice and welcoming, he made sure we knew that we felt comfortable on the boat and told us that for the next two hours the boat was our boat. After mentioning I've done some sailing before Captain Bill even let me take control of the tiller and steer for a bit! It was so amazing!! It's nice to get away from the hustle and bustle of the city and just enjoy the beautiful skyline from the Lake. I went at night and loved seeing the city all lit up at night, I would highly recommend a sunset or night time boat cruise. Happy Sailing! read more

Looks like I didnt finish this review last year so here it goes. Once again Offshore Adventures out does themselves! We had one of the best nights ever on Saturday for the fireworks. Captain Andy is awesome! Our lovely 'booking' Captain Anne, is always so accommodating. I have read some of the negative comments and will says this, its sailing people! This is not like seeing a movie. Good and safe sailing is dependent on several factors and if it looks like rain, lightning, high winds/waves... it might not be safe to go out. You might have to reschedule. Just get over it and realize that its not OA's fault! I have booked ~3 sails a year for 5 years now and Offshore Adventures is always the best. See you guys in a few months!! read more

My voucher of expired sometime ago. I spoke to Capt. Rick and he was very accommodating about rescheduling. Unfortunately, since being assured that he would honor the voucher I have called and emailed him and his staff at least 4 times and have not had the courtesy of a reply. Very disappointed! read more

My family and I scheduled a private sailboat ride last Saturday. I purchased the Groupon deal as a Father's Day gift that my family could enjoy as well. Definitely be proactive and schedule a date as soon as possible, as they book quickly, especially on weekends. Initially I was a little hesitant in purchasing this deal, but I'm very glad that I did-both myself and my family had a great time! We were fortunate in that the weather was beautiful and trip ran very smoothly. Word of advice: Do plan ahead and leave early, as the location is a little tricky to find and the parking garages are a decent walking distance from the shore. Captain Rick did an amazing job! He was very friendly, knowledgeable and made an effort to make the trip as comfortable and enjoyable as possible. My family and I really enjoyed talking with him. The views are also absolutely gorgeous! This is money well spent-I would definitely purchase again. Thanks again to Captain Rick and Offshore Adventures! read more

A group of friends and I have been taking 2 trips with Offshore each summer for 3 years now and absolutely LOVE it!! We have a great time out on the boat and wish we could spend all day out there. The captains are all super accommodating, fun, knowledgeable and professional - shout out to Captain Ann, our fav!! We've never had a single bad experience and thoroughly look forward to our trips each year. We've even discussed doing a third trip in the fall. Highly recommend Offshore if you're looking for something fun to do in the summer in Chicago. read more

Absolutely awful customer service. I purchased a trip through groupon and booked a cruise to celebrate my boyfriend's 30thi birthday. his birthday was in june, but i booked in august due to our schedules. so, five days before the cruise, my grandmother unexpectedly passed away. death is not something that can be planned (in case that wasn't obvious). so, the day that my grandmother passed away, i emailed and called to let them know. never got a response. so, i hoped that they would've been understanding, but the day of my grandmother's wake, i received a call from the company asking if i was on my way and needed directions. i was totally appalled that my email was totally ignored and that i never received any response. when i finally did speak to someone weeks later, i was told that they never received any. calls or emails from me. totally unacceptable and ridiculous. read more

Finding this place by foot is a bit hard but once you do it's so worth it! Captain Rick was lovely- informative but not too chatty and let us relax and enjoy the night. We took the sunset cruise from 8-10pm and it was really beautiful. I would definitely go again. What a perfect date night. Captain Rick played soft like chill music and we had a great night. There was another couple on the boat and they were lovely too. Large boat with tons of moving space. Beautiful city views!! read more

We had an unforeseen circumstance that happened to us the first time we booked with Offshore Adventures, but we were able to re-schedule and had an AMAZING experience cruising with them. Ann was our captain and went above and beyond to make sure we were having a good time. She made sure everyone was happy, answered all of our questions, even offered if any of us wanted to try and learn how to sail when we were far enough from all the other boats, which was definitely a plus. She made sure to check on us if we were too quiet to find out if we were feeling ok or getting sea sick. She had a smile on her face the whole time and a positive attitude that made the whole difference! I definitely recommend Offshore Adventures and will not hesitate to cruise with them again in the future! PS: Make sure you leave a nice tip to your captain if they are like Ann and go above and beyond to make sure you are having a great time! ;) read more

Purchased a Groupon and scheduled a 2-person sail. Got a text the day off saying that it's canceled because of weather - no problem. Was told that I would receive instructions for rebooking. 3 follow up texts and 2 follow up emails later (not to mention the phone number goes immediately to a full voicemail), we never got any follow ups or ways to rebook. read more

Had a scheduled trip and invited 5 clients (who all took the afternoon off from work). Confirmed the trip the day before. NO ONE FROM OFFSHORE ADVENTURES SHOWED UP, CALLED OR EMAILED TO SAY THEY CANCELLED THE DAY. Tried calling them but all I got was a "this mailbox is full" recording. This is a poor excuse for a business - buyer beware. read more

Bill is awesome. He's smart, funny and knows Chicago. His love for the water is infectious.

I was expecting that sailing around Chicago would be a blast and Captain Rick didn't let me down. Boat was great, ride was super smooth and enjoyable. Rick is a cool guy, I'm glad I found him, I'd go have a beer with him anyday and hear his great stories. I would and will recommend his company fully. Can't wait till the next cruise! read more

My group used a Groupon voucher to do a private 2-hour Skyline cruise on a small sailboat. We were very happy with the experience. Reserving - Reserving online was very straightforward, including using the Groupon. Our boat left right on time and arrived back at the dock in 2 hours as scheduled. The boat - Contrary to some of the reviews, our boat had a cushioned seat so that it was quite comfortable. It would be a bit tight with six passengers, though I doubt that would ruin the experience unless you were expecting a really roomy boat. We reserved for six though we were just 3 people, since we had a big discount with the Groupon, and it was a good choice. There was a bathroom, though I don't know what it was like because I didn't use it. Also contrary to some reviews, it was quite easy to get on the boat. No one got wet and overall the ride was very pleasant - not rocky except for a few brief moments. We went on a calm, sunny day. You can play music using your iPod or phone. The captain - Captain Rob was very personable and professional. We made good conversation and I learned some things about sailing and Chicago. He clearly knew what he was doing and he said that Offshore Adventures only hires crew who are licensed by the coast guard, which not all companies do. We felt like we were in very good hands. read more

Captain Matt was great! He taught us some sailing lingo and some basics about the sail boat! We had a great and relaxing day!

My good friend bought me this cruise for my birthday so I took my husband. There was one other couple present and it was such a peaceful cruise. Because it was last minute for us, we didn't BYOB and were 10 mins late, but the others were very understanding. Captain Dan(?) was great and even gave us a lesson in sailing. I will definitely do this again with a cooler, some smooth Jazz music and my sunglasses. Thank you for a wonderful birthday! read more

Giving a one star because I have to give a star rating to give a review. We waited for almost 45 minutes for Captain Rick to show up for our private 6 person off shore adventure. It was a very cold day and we made the trip to the city just for the boat tour. We parked in the recommended parking ramp (which cost $50 for around two hours) and proceeded to take an Uber to the dock (an additional $10). We called multiple times and were sent to voicemail which told us to send an email. Multiple emails were sent and finally after waiting 45 minutes we decided that we should give up and head back to the car. It is now almost 6pm (our off shore adventure was scheduled for 3pm) and we finally heard back from "Captain Rick". He claimed that because of the weather he had to cancel the tour. He let us know of this three full hours after the scheduled departure time. He was not remorseful about having to cancel the tour and didn't even try to make it right. We booked this tour through Groupon, and he informed us that the only way to get our $200 back is to go through Groupon. He ended the phone call with "alright". Absolutely zero professionalism. I would NOT recommend booking with this company. read more

My fiance and I had purchased a groupon a few months ago with offshore adventures after a friend telling us about it. We bought it in the early summer but it was very difficult to find a weekend or time that wasn't booked so we didn't get to go until a chilly September night. However, its byob which was very cool and captain Bill was incredibly knowledgable. He has a lot of fascinating stories that kept us entertained. The sail was very beautiful. Definitely recommend read more

We just got back from the most perfect sail today! We had Captain Amy since Captain Rick was racing to Mackinac this weekend. She was amazing and so was Christian. We got lucky with great weather but they provided a great atmosphere and were personable and friendly. The sail offered great views of the city and a very laid back and relaxing time. We were able to bring aboard snacks and drinks and Christian did a fantastic job at getting us everything we needed. No need for cups or ice, they had it all. I would recommend this sail to anyone in a heartbeat! It was great! read more

Although I cannot rate the actual sailing lesson experience, I can rate this business. Offshore Adventure and Captin Rick are very unprofessional. If you want to learn, use another service. It's the same lake and same views. Don't waste your time or money. First, I bought 2 voucher through Insiderzedge and when I asked Rick about it, as I was having a problem with his website, he denied I had a reservation. I rescheduled and on the date planned we got to the dock, there were no directions to find him and when I called him, he ignored the call. Someone here posted they were 10 minutes late, well I was not but Rick said he waited 20 minutes for me. When I inquired about what happened, he just lied and refused refunding me. Thank goodness there were some nice boaters at the dock, who can attest to my time and one said they were shocked he had already taken off but another boater said it has happened before. Never trust someone who does business this way. read more

Captain Rick was awesome. We truly enjoyed our day on the water. It was the perfect day and the "TMI" cruise was a blast. We will do it again in the future. read more

We bought a groupon for this last year, and due to some health issues, were not able to use it. Rick was perfectly willing to extend the offer to this year, and we booked a morning cruise for mid-May. Well, it turned out to be that freak weekend that was in the low 40's, and Rick was more than willing to extend us again to a time where the weather was more suitable. This past weekend was great weather, and a great time. We were on the boat with two other couples, so it was not too crowded. The boat is a basic 35' sailboat, not a lot of frills, but you don't need them. The skipper was knowledgeable and pleasant, explained the basics of it, and was extremely pleasant. The reservation process was really straightforward, but as the other folks said, look for the email about a week prior to your sail. I would recommend this trip to anyone. read more

Had an amazing experience with Captain Bill. He was phenomenal and very informative about Chicago and sailing. Buy the groupon, worth the experience!!!! We want to go again!!!! Highly recommended!!! read more

As Captain Rick stated, he did immediately reimburse me, but we were in contact via email, so I could not have hung up on him. He did apologize and refund me, so all is well. read more

All in all great cast of guys. Just the right amount of professionally and fun. Definitely would and will use this company again. Threw a surprise birthday shindig and when I arrived with the birthday girl the captain was wearing a surprise birthday hat too! He even put up with my one too many babbling. We had a great time. I'd recommend this company highly. We took a sunset cruise it was gorgeous. Thanks! Thanks! Thanks! read more

Great day out on the water! Rick took a group of 5 of us out on a 11:30 cruise. Rick was very personable and a class act. Don't look anywhere else book here and have a blast! read more

Offshore Adventures - Boating Near Me - Chicago, Illinois

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Awesome afternoon on the lake. Could not have been any easier to book and find. Three boats went out at our time. We had six guests plus our captain Bill. The captain was very knowledgeable about anything water related from Chicago's water sanitation supply to bird life to boat racing ! Fun fun afternoon would highly recommend. read more

We booked a 6 person sailing trip for 2 hours and we had a blast! The directions were clear, the cruise started on time and our captain was hilarious. We enjoyed hooking up our phone to the built in speakers and they even had a cooler full of ice waiting. Highly recommend! read more

I was really hoping for a better experience. I can't review the sailing experience precisely because there wasn't one! The Captain (Rick) cancelled our first attempt to do a 2 hr sail for 6 in early July, 1 hour before we were to meet him. Ok, that's understandable - if the coast guard said no sailing, that's fine. I rescheduled, and regrouped with the 5 other passengers to see what day we could all find (like herding cats). Mid-Sept was all that was now available on Rick's schedule. So I grabbed a day. Sure enough, that day came, and while it was barely foggy out and no rain, i got a text, this time, from Rick cancelling the sail again! This time 2 hours before the sail. I responded by asking him a question about the weather, and never heard back from him. The weather was NOT cancellation weather. The wind was decent, no rain, and the fog had burned off by the time we would have been meeting. This guy just doesn't want to work when he doesn't feel like it, apparently. Don't waste your precious time or money on this guy. He seriously inconvenienced 6 people TWICE with no remorse or remedy. I'm out the money and won't be rescheduling a 3rd time now that its practically OCT! read more

Reserved a 6-person boat for 530pm yesterday using Groupon. We waited for more than an hour and NO ONE from the company showed up, no calls, no emails, no explanations. When I tried to call them, also no one answered except voice recordings. Very disappointed. read more

I used a Groupon for a 2 hour cruise yesterday evening and it was a blast! The 2 other couples on board were great company and Captain Bill made the ride fun and educational. Overall we really enjoyed the cruise and would love to do it again next year when it's warm again. Also, we ran into some traffic and did not arrive 15 minutes early, as advised. As we pulled into the parking garage Capt. Rick called me to make sure we weren't lost. We felt really bad about being a couple of minutes late and sprinted down the bike path. We weren't the last to arrive and I appreciated that Offshore Adventures called to see if we needed help and waited until everyone arrived. I felt this was great customer care. read more

Great trip today. Captain Bill was sociable and very informed on city history and sailing

Scheduled cruise for July 17th. Policy states, there is a 1 week cancellation policy. Called 1 week prior to find, all of office was on vacation for the entire week. Sent an email as well. Heard back day prior to cruise via email. I said I would need to reschedule. On the day of the cruise our cruise vouchers (from Groupon) were marked as redeemed. Because they were marked as redeemed, Groupon needs to go through different process to credit. (which we did not even originally want, just wanted to reschedule). Not a great way to do business. read more

We love Offshore Adventures and we love Captain Anne! We are a group of 6 and originally found out about OA through Groupon. Now we have made this an annual tradition! With the Groupon the 6 person cruise is also very affordable. The weather plays a huge part, but even on a foggy year we still had a great time on the boat. We bring lots of wine, cheese, crackers, etc. and plug in our playlist and are ready to go. We always have a lot of fun, and get great views of the city (aka Instagram worthy photos) as a bonus. We have done daytime and nighttime cruises and I would suggest trying both! Obviously there are times when the cruise has to be cancelled due to weather.. this happened to us this past May and we had to reschedule. However we have had an easy enough time rescheduling both times this has happened and one can't expect Offshore Adventures, or even the amazing Captain Anne, to control the weather. Something to keep in mind if you're just visiting Chicago. read more

Anne is amazing!!!!! Great charter. Wonderful sailing experience. Captain felt like she was one of our best friends for years. read more

Offshore Adventures - Boating Near Me - Chicago, Illinois

Had a blast sailing with Bill and Offshore Adventures! Learned lots, shared laughs and snapped great pictures. Looking forward to doing the same next summer. I recommend booking with the company. Whether it's your first time sailing or 20th, you'll have a blast. read more

Omg! Captain Rick is amazing! He was very professional and extremely friendly! We had an absolutely perfect evening! Thanks again Captain Rick! Amazing!!! read more