Raymond

Captain Dawn and Ted were amazing! We spent two hours touring around Lake Michigan at sunset and it was beautiful. Dawn and Ted are fun, laid back and easy to talk to! We would sail with them again in a heartbeat!

Our trip on Siren of the Sea was wonderful. Captain Ray and crew were very kind and made sure we were comfortable the whole time. Would book again!

We were in great hands with Dawn and her husband, feeling safe while having lots of fun on the water. We did a Sunday afternoon ride, out to see the skyline and Blue Angels wrap up the air show. It was quite a delight. We then stopped to swim and chill on the boat. Lovely time would highly recommend!

Thank you captain ray and Cassidy for a wonderful sunset sail. On time, friendly, helpful and fun! Boat was great and just what we were looking for. Appreciate the communication and all the info provided beforehand. Will be recommending to friends. Thank you!!!

Such a spectacular day. Ted and Dawn are such knowledgeable sailors and just downright delightful to sail with. Despite a bit of drizzle in the forecast, we made the most of our excursion and they showed us an excellent time. Could not recommend them enough. Can't wait for our next sail!

Very nice time on the water with captain Ted, highly recommend.

They were so kind and knowledgeable! I would definitely want to go again!

Ted and Morgain were our captain and first mate and made an excellent team
We all felt safe and comfortable and the sail was perfect. They framed our sail around our request. We sailed for approximately half the time and then anchored and swam near the Shedd Aquarium. We loved every minute of our four hour booking. Ted and Morgain can’t thank you enough

Spectacular boat charter experience. Could not be more happy. Captain Dawn and crew Ted were very professional, interactive, safety, conscious, and terrific sailers. They answer all our questions and the boat was ship-shape and ready to go when we arrived. I cannot wait to book the “Siren Song“ again when I return to Chi-Town. Thank Dawn and Ted on behalf of all of us!

It was awesome, thank you so much Dawn! We enjoyed a lot!

I loved the company it was only me and my husband but the captain and his wife were such a vibe I felt like I was with my friends I love it and I will definitely booked again

Amazing captains. Loved our time!!

Always a great experience with this crew. Highly recommend!

Booked Captain Ray and his other hand, Doug for our engagement shoot. We couldn’t stop smiling. They helped make our dream a reality! Doug, a local photographer, also supported our photographer for the best shots! Captain Ray made sure we had the best views of the Chicago skyline.

This was great! And Captain Ted was awesome!

We had a wonderful time on the water for a sunset cruise. Our party was 3 adults, plus the captain and a crew member. It was a lovely experience- we sailed for 2 hours and then ended with a swim in the harbor. I would definitely book again and recommend for a nice time on the water!

What a special evening we had!! Couldn’t recommend this charter more. Best way to take in the Windy City and with such great hosts. 10/10.

We had the best time! Thank you to Captain Ray and crew for being so patient and great with our boys and helping to ensure they loved their first sailing experience. They’re still talking about it at home and with friends! We will definitely be booking again in the future.

Had an amazing time on this rental!! Amazing and relatable crew ensured a perfect trip, including being flexible in time to ensure perfect conditions. Can’t recommend enough!

Perfect weather for sailing! It was so fun to clip along the lake. Dawn and Ted were fantastic captains and so fun to get to know! Can’t wait to do it again! Highly recommend!!!

Such an amazing day!! We took my mom out for her birthday and she loved it. Dawn was such a great host, I can’t wait to sail with them again!

We had the most amazing time with Dawn and Ted! It was my friend’s bachelorette and they made sure we had a great time with amazing views of the city. Can’t wait to book my next sail with them!

Flawless experience and great crew!

Dawn and Ted were an absolute joy. They were able to accommodate our last minute request which was greatly appreciated. If you’re considering a sailing experience do not look any further. The boat was clean and Dawn and Ted made sure we had everything we needed during our excursion. Thanks for an amazing afternoon! We came as strangers , left as friends.

Simply incredible day with captain Ted / Tim.. everything from communicating / to the day was absolutely seamless

The wind was great , so we actually dared to sail, and it was arguably one of the best moments on water for me. Smooth , smooth , smooth sailing; like butter

Can’t recommend these guys enough

- h

We had the best time SAILING, yes really sailing, with Dawn and Ted! Exciting and fun! They are wonderful to be with and it was a beautiful setting too!

We had an exceptional experience with our boat charter! As someone who had never booked a boat before, I didn't know what to expect, but Ray made the process seamless. He was incredibly communicative and provided clear instructions on what to expect and where to be. The boat itself was in excellent condition, and the crew was both highly professional and a lot of fun. I can’t recommend this charter enough and we’ll definitely be coming back in the future!

Had an amazing experience. The crew were very experienced and helpful in assisting us throughout the ride.

Ted, Morgan, and Madison were amazing.
We went out for a fairly long charter and they made sure we had a great time!
Thank you again.

Siren Song was EXACTLY what we needed for our girls weekend. Ray & crew made the booking process exceptionally easy. We needed room for 3, be mindful the cap on this boat is 6. Day of Communication was fantastic! The team sent me a map, I still got lost but Ray was so patient and helpful. Ray navigated the waters well, keeping our seasickness at bay. We were able to swim in the lake though it seemed dangerous with boats still driving by. Overall, it was an amazing experience with my girls!

Dawn and husband were great. Our family loved it!

Fantastic experience! We loved the attention to detail and extra effort in building is the best itinerary for our visit.

Dawn and her husband were professional, fun and friendly. Our group had a great time!

My time on the water was great & smooth sailing. My captain Dawn was very informative and let us know from booking onto boarding where to go and what to do. Would definitely book again with them! They even let us play our own music, drink, etc.

Absolutely loved it!
Dawn and her husband are truly amazing skippers and great to hang out with!

Ted and Dawn were such lovely hosts. My friend and I had a wonderful time with them. They were engaging and very friendly. We will definitely book with them again.

We absolutely loved our time out on the lake. Great experience & I would highly recommend

I would highly recommend! We had a lovely time and we felt very well taken care of. 10/10!

The ride was phenomenal the crew was awesome and really made the experience unforgettable! I highly recommend this for a romantic date night or an outing with friends on the water it was relaxing and an overall awesome experience.

We had a great 3 hours of sailing on Lake Michigan for Sunday's Air & Water Show. Our captains Dawn and Ted were friendly, fun to chat with and love to sail. Thank you very much!!

Raymond was amazing! We had so much fun on the boat. I would definitely recommend using him for any sailboat activities you need! Can't wait to go again :)

Captain Ray showed us an amazing time! The boat was perfect for our group of 6. Do it, you won’t be sorry!

You’ll never be able to predict the weather in Chicago, so make sure you’re sailing with Ted and Dawn for a warm experience :) They captained a trip for us on the Fourth of July and were generous in adjusting the times to accommodate for the rain. They are both certified and wonderful teachers whose passion for sailing shines through even on the gloomy days - book and book again!!

Had a great multi-generational family trip on Siren Song with Captain Ted and first mate Parker. The communication was good and they made sure we had all details needed to have a good day on the water. They were great. The boat was great size for the 5 of us. We enjoyed sailing around and seeing the skyline and then dropped anchor in Monroe harbor and jumped in with the big floating mat and noodles. I would recommend this boat if you are looking for a family friendly activity.

Ted & his daughter were so sweet. We went with 6 people & had an amazing time watching the sunset from the boat!(: would 100% do it again.

Ted was communicative and a pleasure to work with. He and Ryan went above and beyond to make our experience amazing, and help me pull off the ultimate marriage proposal. My girlfriend and I were blown away. The views were amazing, and I highly recommend this experience.

Our captains Dawn and Ted made our trip a wonderful experience. They were very attentive in ensuring our safety and making sure we were happy with our views of the city from the lake. We definitely would sail with them again.

Ray was very communicative leading up to our experience. He was informative and helpful in utilizing our time in an efficient manner. We will definitely be booking in the future. Thanks Ray!

Fantastic experience with Ray and Cassidy to make my dream proposal go off without a hitch. They accommodated everything I had asked for to make it incredibly scenic, special, and fun. Thank you so much for an afternoon we will never forget!

Amazing experience! Great views & great Captain & team. Thanks Dawn & Ted.

Ray and Eric made a great experience for our group enjoying the weather and Chicago skyline. Booking and communication were detailed and timely. I highly recommend their service.

We had an awesome time out with Dawn and her husband for a sunset cruise during the week. We got lucky with a perfect night but had a blast seeing the city from the lake and they even showed us the ropes (literally). 100% recommend booking!!