We have sailed with Captain Rick several times - once with 2 other couples we did not know and once with a full boat of 6 friends. Both experiences were great! Would highly recommend and we always check his schedule early on in the summer as dates can book up! read more

My friends and I sailed with Rick S. A couple of times so far this summer. We had a fantastic time both times, in very different conditions. Rick is an accomplished sailor, great sense of humor and has lots of fun facts about the city, sailing, and music. We will definitely do it again! read more

I have been wanting to go sailing on Lake Michigan since I moved to Chicago six years ago. I don't think we could have chosen a better company to make it happen! We met Captain Tim at the designated picnic tables and he was there waiting for us. He was very patient and understanding when we told him that a couple people in our party were running about a half hour late. He let us stow all our food and drinks and hang out on the boat while we waited for them to arrive. The vessel was nothing special, just a small little sailboat that reeked of the '80s with wood paneling lining the entire interior. When we finally got out onto the lake, Tim answered all of our questions and told us stories about some of the crazy passengers he's had. He danced along with our music and made us feel very welcome. Out on the lake, the views of the city are incredible. We made it almost all the way out to the Four Mile Water Crib before turning back. On the way back in, Captain Tim took us right by the Chicago Harbor Lighthouse, which was a great photo op. Once back in the harbor, he docked like a pro, helped us offload our supplies, and we went on our way! I hope we will be able to book another cruise with Captain Tim is this summer! read more

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Captain Tim gets 5 stars! He was fun, informative, and wanted us to have a great time. He's an easygoing guy who makes the whole adventure one for the books. We went out with friends for a birthday cruise on a gorgeous spring night! We brought drinks, snacks, and tunes to make the most of our time. Be sure to be there about 15 minutes early as it's easy to get lost and takes a few minutes to get to the right meeting point (all clearly laid out in the website info section). I believe our group leader used a Groupon, so we got a great deal. Keeping that in mind, it explains the 1980s decor in the cabin. You're not meant to spend much time down there, so don't expect much from it. There is a bathroom onboard, but it's basically a port-a-potty situation. Plenty of room to store coolers, jackets, purses, etc. Don't forget your camera as you'll be able to see some stellar skyline views! Ask to go by the lighthouse and get close up views of a late 1800s structure. It's pretty cool. There is parking nearby, I believe it was $20 for the duration of our cruise. We opted for Uber/Lyft to keep it simple. Bon voyage!! read more

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We got this as a Groupon and very happy with our purchase. We had Rich as our tour guide and he was great at showing us the city. We were socially distanced, a group in the front and our group in the back. This was the first time me and my boyfriend had sailed. He was a little scared but it was a beautiful site! (We had the sunset cruise). I do regret not bringing my own bottle (it was BYOB) but It's an excuse to go again in the future! Thanks again! We loved it! Very romantic! read more

This was our 3rd time and it's always a great time! Our whole family loves it. Highly recommend!

I have been contacting the business because I have some questions about an upcoming sail. No one returns my messages or calls. Very frustrating. read more

Went on a private sailboat ride on a Tuesday night in September because that was all that's available. I bought a Living Social deal in April and procrastinated in picking a date. Find a date you like and book it 5-8 week in advance because they're booked quick. (Maybe it's because I had to find a boat that was completely free?) anyway Cpt Bill drove is around (wasn't windy enough to sail) and we had a wonderful time. The sailboat is a bit dirty and the bathroom could use some cleaning, but otherwise I have absolutely no complaints. My girlfriends and I ate cheese and drank wine. Also, the sailboat we were on had an aux cord that doesn't work so play it safe and bring your own auxiliary cord if you want to play music. Also, I had to add this after seeing people complain about customer service-- I had to change my sail date and I only gave OA a few days notice. The woman I spoke with was kind and said if she could find someone to fill the date I originally booked, I could reschedule, even though I was passed the allowed time frame. I was very pleased with the outcome and didn't even expect I was going to be able to do this. read more

Offshore Adventures - Tuesday night sail. Wasn't windy enough to actually sail so we were driven around. - Boating Near Me - Chicago, Illinois

Bought the groupon deal for semi-private for 2, which is an amazing deal. We went on the sunset tour with 2 more couples, and it was really fun. The ocean (aka lake) is a very calming place, I can see the appeal in it for certain fictitious serial killers... We weren't able to sail because of the weather conditions we had, but we got to go out with a motor and see the city as the sun was going down. Captain Rick is a very personable guy who will make your trip a really fun experience regardless, and it's actually great to have him there especially if your group of 6 is made up of 3 pairs of strangers. I wish we got some sailing action, but it was still a great way to relax and see the city from a new perspective. It was just a very chill time, washes away the stress from the week for sure. LOOK OUT FOR AN EMAIL from him that explains all the details the week before. Mine ended up in the spam since it came from a really generic email address from an electronic system, so I didn't get any information beforehand and were confused and like 15 min late :( But thankfully everyone was super understanding, and we were greeted with a warm welcome when we finally got to the right dock. Check spam folder! Try not to let that person be you, hah.... A solid 4 star time for us, but a bump to 5 for the great "service," so to speak. And I don't doubt that the captain would've provided an expert sailing experience had we gotten the chance. read more

Great way to spend a Saturday morning/afternoon. I bought a YouSwoop voucher back in June and emailed Richard to set up a time. I got one of his last available slots at 9am on a Saturday, which initially I was a little bummed about since it was BYOB and that seemed a little early for my tastes. I quickly got over that after the 100 degree weather streak we had, and figured 9am would be a refreshing sail time. We arrived a little before our sail time at 9am and Richard pulled up in the "Alpha Puppy" slightly after 9am and we were promptly boarded and given the low down on the specifics of the ship. Richard was a great host/captain and was great company for the 2+ hours that we sailed around in Lake Michigan. He has a 36 foot sailboat that's perfect for the max group size of six people per each YouSwoop deal. The ride was incredibly smooth (obviously weather permitting) and he allows you to BYOB for the entire ride and offers up some cooler space. I can't really say much more than that my boyfriend and I had a great time, and I'd highly recommend this to anyone. You get a great view of the city in a more memorable and less touristy setting. I'd do this again anytime, and I hope to go back next summer! read more

Offshore Adventures - Captain Richard! - Boating Near Me - Chicago, Illinois

This sailing cruise was a gift for my boyfriend. We both had a fantastic time. Captain Rick was extremely personable, helpful and on time. We brought some snacks to eat and wine to drink, the boat had all the utensils you'd need. It was a small group, only us and another couple which added to the experience. Overall, the sunset cruise was GORGEOUS, the captain was great, and we had a great time. Definitely will be back. Tips: bring layers, mittens and wear socks! It gets quite chilly when the sun goes down. read more

Offshore Adventures - Gorgeous sunset cruise - Boating Near Me - Chicago, Illinois

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My husband and I bought the Groupon for the two-hour BYOB tour and it was so worth it. The owner took us out with one other couple and he was a great guy - super friendly and we learned about sailing while drinking champagne. Would definitely recommend this to a friend. It was a great way to see the city. read more

Offshore Adventures - Perfect views. - Boating Near Me - Chicago, Illinois

This is a scam!!! And it will be very difficult for you to get your money back! I bought this on Groupon. First, they have you to redeem the code when making an appointment, then they would only send you a text saying the trip is cancel due to the weather but they never send you an email for rescheduling or any update!! You have no way to get your money back because the code was redeemed in advance, I complained to Groupon about this business and they stood for the business!! And I got a new phone, so I didn't have the old text. So I never got my money back !!!! It was about $ 150. read more

This was a birthday gift I received. We booked our tour three months in advance because they were so busy and had no openings. When we arrived to the dock, a person with a clipboard let us know that the engine had just broken and that they were canceling our boat ride. It seems standard that we should've received a phone call from the company, especially considering what we paid for the trip. (If only so that we could tell the cab we paid for to turn around and take us back home.) They also told us they could reschedule our tour but also said they're full until the end of the season so we'd have to set one up for next season or go during the week if we wanted to go this season. Two weeks passed, and we still heard nothing from this company. No one contacted us after the tour to get a refund or to reschedule or even to communicate what had happened in the first place. (Were they hoping we'd forget about the money we paid so they could pocket our money?) And when we did, Captain Rick's response was "I'm sorry you were inconvenienced, but we couldn't have called you." They've delivered sub-par customer service from start to finish. Not sure how many cancellations they issue, but I know we won't be going back for another try. read more

*****CONSUMER ALERT****** If you're a Groupon customer and you're buying a private tour make sure when you book online you book it for 6 people even if it's 2 or 3 or 4 or 5 in your group. You must book it for 6 people otherwise your private sailing trip will become a semi-private. I purchased the $200 Groupon for a private trip for my family and myself. When I booked online it prompts you how many in your group. I put 4, When we arrived at the meeting space there was another couple who was just as surprised as we were that their romantic private sailing trip was now a semi private with a family of 4. I overheard her saying "I thought this was supposed to be private", So if I paid $200 for private and they paid $200 for private, That means offshore got paid $400 for one trip. Very sneaky Offshore! Of course they do not tell you in the fine print that if you want private you need to book 6 even though your party is less than 6. So this is my public service announcement. As for the trip, our captain was very polite and we had a decent time it's just not what we paid for. I've seen semi-private for less money. read more

My wife and I enjoyed a great couple of hours out on Lake Michigan with Captain Bill, who was a vast encyclopedia of nautical knowledge. Not only did we have a fabulous and relaxing time, we also learned a great deal. Highly recommended! read more

We had an incredible time on the lake with Captain Bill! Pre-cruise, Offshore Adventures was organized and made sure we had directions as well as instructions about what to do if the weather didn't cooperate. Thankfully, the weather was perfect! We rented a two-hour cruise for six -- with the deal on Yelp, it was a steal! Captain Bill was the perfect host. He was so personable, knowledgeable and safe. It felt like we were on a friend's boat the whole time! From mini sailing lessons, to stories at sea, or just kicking back with a glass of wine and taking in the skyline, you couldn't ask for a better experience. This is seriously one of the best ways to enjoy Chicago. Thank you, Captain Bill, for giving us such an incredible memory!! We plan to come back to Offshore Adventures and Captain Bill throughout the whole summer! read more

Offshore Adventures - Beautiful view of the harbor while sailing with Offshore Adventures, Chicago - Boating Near Me - Chicago, Illinois

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Even though I had a bit of a rough start trying to get the cruise schedule originally, overall I give it 5 stars. We had to reschedule once due to the weather. We sailed (not really, not windy enough, so couldn't sail, oh well) this past Saturday with Cpt. Bill and he was funny and very knowledgeable. We picked the 7pm time (golden hour!) and it was beautiful. Highly recommend. read more

This was a great Friday afternoon - good company, the captain was very easy-going and set a relaxing tone, and the views were great! We loved hanging out at the front of the boat! Thanks for a great alternative to drinking wine at home! read more

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CAPTAIN BILL! This experience was nothing like what we expected in the absolute best way. We opted to get the 6 person private sailing cruise for 2 hours, but there were only 4 of us, and honestly that was probably best. The sailboat is pretty small (I think? I've never sailed but it felt smaller than I thought it would be), so you all just sit up front with your captain. If your captain isn't cool, you could seriously have a strange 2 hours. But Captain Bill had our hearts immediately, and we aren't the easiest crowd to win over! It was every single second an absolute pleasure to be on this boat, get to know Bill, share stories about life, and just take a time out from the city for a few hours and reflect! Wind in our hair, wine in our bellies, and great conversation was a perfect end to a beautiful Chicago summer. Cannot WAITTTT to come back in the spring! read more

Offshore Adventures - Seeing Chicago from the Sundog sailboat was unlike anything we've ever experienced. The time flew by and we loved every second of it! - Boating Near Me - Chicago, Illinois

I wish I could give this more stars! Our captain Bill was amazing! He was very knowledgeable about the city and all the building, very enthusiastic. The boat was a good size, very clean. Water today was absolutely perfect, small smooth waves. Cannot wait to return! read more

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I do not often write negative reviews but my experience with this company has been AWFUL! My boyfriend had booked a sailboat for 6 people back in May, and the day of the outing, we received a phone call saying that due to weather, our trip was being cancelled. It DID NOT rain a single drop that day, however it was during a Blackhhawks playoff game, so we were weary... Anyways, upon asking to reschedule, we were told there were no available dates until September and we could not be refunded.... We rescheduled for today, September 21st. This morning we received a phone call, again, saying that due to thunderstorms, our trip had been cancelled for a second time. Once again, it DID NOT rain!! When we called and asked for a refund they said they do not refund based on weather cancellations and we explained how the weather has been fine both times and they still said no. Now the only date they gave us was for a Tuesday in October... we cannot do this as I am in class. They said if not, we can reschedule for NEXT YEAR! This is by far, the most god awful costumer service we have ever experienced... honestly HORRIBLE! They are refusing to refund us, despite the fact that both times, they have cancelled, not us! I know that they will just continue to claim it was the weather but at this point, any company with morals and decency would offer us a refund. read more

I originally scheduled this cruise last year (2014). By the time I scheduled the cruise, I was looking at a September date to sail. The day of, I received a call indicating there were rip tides in Lake Michigan. We were advised to select a different date. Due to how late in the season it was and our group's scheduling constraints, we were advised to push the cruise off until 2015. We then chose a July date in 2015. The day of, we experienced torrential downpours, so I called Offshore's main number to see if we were still on. They have a very long voicemail message, which is probably helpful if you are finding out info, but trying to contact them directly is a fool's errand. I left two voicemails after listening to the same 5 minute outgoing message. I wrote 2 emails to their main email address and happened to notice I missed a call from a 773 number. I listened to the voicemail and it was Rick, our captain. I called the number back and it went to voicemail. The voicemail said "Michael" versus Rick. Additionally, after I didn't hear back, I called the number again. Some woman answered and seemed upset I was looking for a Rick. Meanwhile, the rain kept coming. Chicago was in a flash flood warning and a tornado watch, yet I couldn't figure out what was happening with my cruise. When the rain wouldn't let up, I called it. I said it's not worth our safety to go out on Lake Michigan. My friends agreed. I was going to try for a refund. Well at about 4:31 or so, Rick called again from the same number I had been calling, to see where we were. I told him I had a ridiculous time contacting Offshore. We decided to call it because he didn't answer the phone number he called from when I called. He seemed agitated: "Well I called you an hour ago..." to which I responded that when I tried him back, I didn't get a number that seemed to be associated with him. I asked for a refund for the cruise. We had tried twice, very unsuccessfully. He said I had to take it up with Groupon directly. The best part? Somehow Offshore marked my Groupon from last year as "Redeemed." How I am supposed to get a refund is beyond me. It's a good business model you have there. Buyer beware is right. read more

Our group of 6 purchased the two hour cruise for Saturday, August 9, 2014. We arrived and met Captain Rick. Such a gorgeous day, 80 degrees with a mild wind and sunny. We boarded the boat and were told that the water was too choppy to exit the harbor and we wouldn't even be able to actually sail! For two hour we motored around the harbor. What a waste. read more

Offshore Adventures - Boating Near Me - Chicago, Illinois

Booked through Groupon in January, recieved an email in March stating that they overbooked and were canceling us. We had people traveling in from out of town and there were no options to accommodate us that would work. Extremely frustrated as if this were caught earlier we could have found something that worked but instead just had to cancel since all the weekend dates are now full. Very disappointed and won't be able to trust them in the future to keep bookings. The Groupon page has endless reviews regarding cancellations that never got rescheduled. read more

Went on a sunset sail on Oct 2 and I have to say we had a great time. Captain Rick is a superb sailor and did everything possible to show us a great time on his boat the "Alpha Puppy" ( ask to see a picture of his dog Popeye. he gave us a quick overview of the J35 we'd be sailing on and off we went. The views of the city at sunset were AMAZING and our group was able to enjoy the snacks and drinks we brought as we wished. One of the great things a bout Captain Rick is he is a very accomplished and capable sailor. Because of that he can give you as much a sailing adventure as you like ( wind/weather provided). If you want a quiet sail on smooth waters he can stay withing the break-wall and still give you a really fun sail. I had spent plenty of time on a J35 in high school, Had a small er sailboat with my brothers and sailed on and off since then. As a result we went out into the lake and really sailed in 4 to 6 foot swells doing between 6 and 7 knots . LOTS OF FUN! Even the people with us who had not sailed before had a great time. We did spend the last hour back in the break-wall and still had fun but my experience out on the lake was worth twice the price ! ( Just don't tell Captain Rick that!) If you want a great sailing experience and to see this beautiful city from a perspective very few people get to see, go sailing with Captain Rick. He is personable, funny, knowledgeable and a great sailor. You;'l be super glad you booked with him. read more

I used an Amazon coupon and got a reallly good deal for a 2 hour "private"cruise for 2. The weather was crazy all day with rain falling off and on. It finally stopped raining at the the time we went out for the cruise. We had Captain Bill and he was great. Told us a lot of great stories and facts. We booked an 8:00 PM cruise and had a beautiful view of the Chicago skyline. We even stayed out a bit longer than the 2 hours. A perfect night. Now the only reason I am giving 4 stars instead of 5 is the misleading "private" that was on my voucher. We wound up sharing the boat with 4 others. No big deal as they were nice people. But when I see the word "private" it means just that. Private. So make sure you understand this if you do book with them. Would I recommend them or use them again? Yes I would. But I would get a verification of what I am getting next time. read more

RUDEST CUSTOMER SERVICE REP EVER! Made reservations for 4 & we were in jeopardy of being late because we could not find out how to get there. So I call & I let the reservations rep know, but instead of being helpful and giving us some type of direction, the rep replies "we sent directions to your email". Mind you, I'm not the one who booked the reservations so how would I know that? Seems like the rep was too busy being negative Nancy to be helpful. She told us that the captain can not hold the boat for us because there were 2 others waiting. Ok, so in my mind I figure with her lack of assistance, we're not going to make it, so I ended the call with ok, I understand, thanks for your help (if you can call it that). At the time of our reservations, she calls back and my mom answers the phone. She tells my mom "everyone else was able to find it", and continues to be rude and disrespectful to my mom. Never have I ever had a customer service rep CALL ME to be rude. We were genuinely lost and we may have been able to make it with a little positively and guidance seeing how Google maps kept telling us we where 5 minutes away. We would rather forfeit our reservations anyways than to have to tolerate a Debbie Downer anyways. read more

ASK FOR BILL! We lucked out with the weather and the captain. We booked our sailing for early Sunday morning, we almost didn't make it out of bed; so glad we did. Bill was great; he made conversation, sprinkled some nautical knowledge and made us feel comfortable. Planning on booking a sunset sail before it gets to cold read more

I love groupon deals, and this one worked out perfectly! Did the 6 person private sailing, and after working out which day would work for us, booking it was a breeze! The hardest part about this whole experience was just finding the correct spot. I was worried we were taking the wrong way by going along the lake past the Chicago yacht club, but that was the correct way to go! Captain Rick greeted my group and then showed us down the pier to our sailboat and our awesome Captain Brad! After our safety talk we were on our way out to an amazing time on the lake. We all had a great time enjoying some wine, booze and snacks while taking in the skyline and letting the sails down and chilling. It was so relaxing and peaceful out on the lake and we never wanted to go back in. Captain Brad was very friendly and we would go back to hang out with him on the lake any time!! read more

We loved our time with Bill and Offshore adventures. I bought a groupon and booked a7pm cruise for 6. The booking was smooth as was the pick up at DuSable Harbor. The directions on their website are very specific. Follow them and you'll get right where you need to be. Bill was a delight - very friendly and informative. The weather was great (though offshore can't guarantee that!) and I thoroughly enjoyed my first time on a sailboat! Would definitely book through them again. read more

Offshore Adventures - Bill, the city, and Dan. Great trip! - Boating Near Me - Chicago, Illinois

We rented one of the sailboats for a private sail, and were fortunate to get Captain Bill as our navigator. Not only was he very knowledgable about all things sailing, but he made us very comfortable and really gave us the opportunity to enjoy the entire trip. Best money ever spent - and we're talking about making this an annual event. Thanks again for a great sail! read more

Don't buy a groupon for Offshore Adventures if you're a tourist with limited availability. The group is not flexible and is unwilling to accommodate individual needs (even when they have the ability to do so). For a small operation, the staff is rigid and almost seems to DELIGHT in their professed "inability" to reschedule your trip. I have no doubt that the trip is amazing (I was thrilled to book it!), but due tot he rigidity and downright nastiness of the Offshore Adventure team, I am unable to report on it first hand, as I was unable to go on the trip. Mother Nature is of course to blame, but the customer service is the worst I've ever experiences outside of the local cable company. Hands down. And scratch that! It wasn't even raining the day that they cancelled my trip and there harbor was FILLED with other cruise and civil sail boats and I was just left perplexed. Save yourself the energy (and the money!) and just take the river cruise and call it a day. Seriously, these people just suck. read more

We used the Groupon for this as many of the reviewers mentioned they had done, and it was absolutely worth it. The weather was a little ominous before our cruise started, but it cleared up very nicely about 30 minutes before we set sail. Our captain Bill was very knowledgeable about the boat and all things sailing. He took us out to a great spot where we caught some wind and we were really able to get some great shots of the skyline at night. I can honestly say that I really enjoyed myself and learned some things in the process. We were able to bring our own alcohol (bonus) and food, and there was good music on the boat. Overall a great experience, I would recommend it to anyone (as long as the weather cooperates). read more

The weather was absolutely perfect when we went so that was a nice bonus, the prettiest view I've seen of this city so far. however it wasn't very windy and our captain kept apologizing every few minutes that we had to use the motor, even though we were having a great time. We plan on going again with friends and drinks, and hoping for wind read more

Offshore Adventures - Boating Near Me - Chicago, Illinois

We had an excellent night with Captain Rick. The meeting location instructions were clear, and Rick met and greeted us timely prior to departure. There was plenty of room to move around the boat which included cockpit seating as well as an option to sit/lay up front. Rick had cups and ice available when we boarded, and the boat included a bathroom. The captain demonstrated expertise in navigation and enthusiastically answered our many questions. We sailed out approx. 4 miles and then made our way back. The evening was very relaxing and enjoyable. Pricing was more than reasonable. We enjoyed conversation with Rick as well as the other passengers. I would not hesitate to rebook or refer friends and family to Offshore Adventures. Thanks for a perfect sailing experience. read more

Captain Brad was awesome! He made sure everyone knew all the safety rules and made us feel at ease and at home. I have never been on a sailing boat and it was a great experience I would definitely do it again in a Heart beat. My friends and I had a great time sailing with captain Brad. The Chicago skyline at night on the lake is extraordinary it's something you have to experience for yourself. read more

Offshore Adventures - Boating Near Me - Chicago, Illinois

We had the pleasure of enjoying one of the most perfect summer nights out on the water with captain Matt. He was so nice and was willing to answer all our questions and even tell some great stories. We had a groupon for the private 8 pm cruise. Please know that for it to be "private" you should bring 6 people. If you bring any less you might be sharing a boat with someone else. Overall everyone we dealt with at Offshore was pleasant. We would definitely do this again and recommend this company to friends and family. Thank you for a great evening. read more

Offshore Adventures - Night sailing with captain Matt beautiful skyline - Boating Near Me - Chicago, Illinois

If I could give negative stars I would!!! I had a bought a voucher thru living social - booked a cruise for 5/21. Then I got injured a few days before the cruise date, Messed up my knee, looking like I'll need surgery to fix it. Contacted them via email to let them know. Was told they have a 7 day cancellation policy. Which is understandable, but life happens and they should be flexible. I contacted the and just didn't show up so they could have resold the seats. I wasn't able to go because of an Medical issue, not that I just wanted to reschedule. Then they marked my living social used and called me the day on the cruise. The same lady, Ann that answered my email earlier, well the first one, she didn't bother to reply to my second one. I think this is poor customer service and will be telling everyone I know about how they treat customers with emergencies!! They need to understand that things happen and work with people. I will be disputing this through living social to get my money back! Dina Chamblee read more

Great experience! I've been on many large boats for the Fireworks, but really enjoyed the private 6 person fireworks boat cruise. We were able to get fairly close for a front row view of the fireworks and enjoy the company of our friends. Kudos, had a great time! read more