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About ChicaGo By Boat
2020 SAILING SEASON UPDATE: We feel it's time that we all get outside and enjoy ourselves and the 'Chicago' Summer. So, ChicaGo By Boat is excited to be able to introduce private sailboat charters in Chicago's North Shore. The S/V Nightswimming now departs multiple times daily from Waukegan Harbor and Marina. We invite private groups of up to six guests to book your boat charter so that we can host you on your own unique sailing experience. ChicaGo By Boat offers Chicago's premier affordable luxury boat charters. We invite private groups of up to six passengers aboard the S/V Nightswimming for two to three hours based on our guests' needs. Whether it's your first time, only time or just the next time; we want your sailing experience with us to be the BEST time you have this Summer.
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ChicaGo By Boat
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lacc wrote a review Jul 2020
2 contributions1 helpful vote
5/5 for Captain Conway and ChicaGO By Boat/SV Nightswimming! We were a group of 6 who took the Metra up to Waukegan from Evanston-- it could not have been easier or more fun! The Waukegan Harbor is a 3 minute walk from the Waukegan Metra stop. We quickly found Captain Conway and he was so terrific! So welcoming and clearly knew what he was doing aboard the boat. Made us all feel safe and at ease. We sailed for 2.5 hours and definitely did not want the fun to end. We all wish we had gone out for the full day! Could not recommend SV Nightswimming/Captain Conway more! We will DEFINITELY go again!
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Date of experience: July 2020
1 Helpful vote
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Response from svnightswimming, Owner at ChicaGo By Boat
Responded Jul 7, 2020
Thank you for sailing with us this holiday weekend. It helped finally make it feel like Summer! All of the points you made in your review are exactly the notes we are trying to hit so we appreciate you noticing. We look forward to our 'next time' sailing with you! Fair winds, Captain Conway
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Dave L wrote a review Jun 2020
Wilmington, Delaware, United States11 contributions3 helpful votes
Positive: Professionalism, Quality, Value Captain Conway was nice enough to open the COVID-19 delayed sailing season for me and my fiancée as we looked for a unique way to celebrate what would have been our wedding weekend. We sailed out of Waukegan harbor on a beautiful Sunday afternoon. Captain Conway hooked us up with a parking pass right next to the pier, had a bottle of champagne waiting on board for us, and took us out on a great cruise along the north shore. Not only was he a great and accommodating captain, he was a pleasure to just hang out and chat with for 3+ hours. We plan to do another cruise in the future with family and friends or just on another summer weekend date night. Highly recommend ChicaGO by Boat!
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Date of experience: June 2020
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Response from svnightswimming, Owner at ChicaGo By Boat
Responded Jul 7, 2020
To the future Lombardi family, Although the circumstances that lead to us meet one another were unfortunate, I appreciate that it gave us the opportunity to meet and host y'all. I am honored that you chose sailing with ChicaGo By Boat as a very solid plan b for what would have been one of the most significant days of your lives. As a Husband and Professional Mariner this is my wedding toast to you, in love and sailing it's better to be lucky than good. Congratulations to you both. We look forward to our 'next time' sailing with you!
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03040810 wrote a review Sep 2019
Naperville, Illinois36 contributions3 helpful votes
My husband received this as a Father's Day gift and we decided to make it the highlight of a getaway weekend in the city. It was perfect - such a unique way to see the city. Captain Conway was waiting for us at the gate and was a great host for the entire sail. We did the Sunset Sail and it was so beautiful and peaceful. There is something special about being on the water. Highly recommend as an experience and also as a gift. We wouldn't have thought to do it ourselves, but it was wonderful!
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Date of experience: September 2019
1 Helpful vote
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Response from svnightswimming, Owner at ChicaGo By Boat
Responded Dec 8, 2019
Thanks for the glowing review and I am sorry for the belated response. I'm not sure when TripAdvisor added the review response feature but I am glad they did. Now we can personally show our appreciation for our guests, and for time and care they spent in writing our review. Again, THANK YOU for joining us in 2019 and we look forward to our next time sailing with you! Fair winds & Happy Holidays, Captain Conway
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JDJ205 wrote a review Sep 2019
1 contribution1 helpful vote
Excellent experience and outstanding service. Great way to spend quality time with co-workers. Look forward to taking my family on a tour with Captain Conway.
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Date of experience: September 2019
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Response from svnightswimming, Owner at ChicaGo By Boat
Responded Dec 8, 2019
James, Sorry for the delayed response but thank you for the review and for giving us all five stars! It was an awesome experience but I credit you and you're team for that. If y'all are back next year I would love to host you again. We will make sure there's plenty of 'drinks' ready so we can maximize our time on the water and y'all's enjoyment. Fair winds & Happy Holidays, Captain Conway
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Sydney L wrote a review Jul 2019
1 contribution1 helpful vote
I bought this Groupon as a gift for my mom who was celebrating her 10 year anniversary. The booking for the charter was easy and even over a holiday weekend. The day of the sail, Captain Conway reached out asking to postpone the sail by an hour to ensure the best possible weather for the trip. Upon arriving to the harbor, Captain Conway was on time and friendly. He made us feel like he was personally hosting us on his boat and treated us like friends! He was engaging, joined conversation, and was a good sport with my little brother who was 8. The complimentary patagonias were a great touch! I have already booked my next trip with him!! Thanks for a great experience!
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Date of experience: May 2019
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Response from svnightswimming, Owner at ChicaGo By Boat
Responded Dec 8, 2019
Sydney, It was my pleasure to host y'all. This review means a lot but what is most meaningful is that her little brother, who is a great kid, went home and made a Lego Nightswimming complete with a Lego Captain Conway. To date, THAT is the highest praise we have received. I sincerely look forward to our 'next' time sailing with you and your family. Fair winds, Captain Conway
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