We love to Sail Chicago!

Google Rating

5.0

Based on 84 reviews

The Salty Dog Sailing Co.

5.0

Claire Forrest

15:05 20 Oct 23

LOVED our sail with Salty Dog- the boat was so beautiful and Woody was the absolute best first mate buddy. We loved the views and the time was perfect. Would absolutely recommend.

Amy Kathryn Reddoch

15:45 13 Sep 23

The couples sunset sailing cruise was my favorite thing I've done in Chicago! Captain Kirk was wonderful and Woody was the best co-captain. The views were beautiful. We celebrated my boyfriend's 30th birthday and it is something we'll remember forever!

Marla Johnson

12:47 04 Sep 23

Great time with Captain Kirk and Woody! We booked an afternoon sail aboard Salty, with Captain Kirk expertly sailing his boat for two hours. According to the Captain, the conditions were perfect for a great time. We brought snacks and drinks which were quickly forgotten as we instead enjoyed the sail, and learned a bit about sailing.If I had to make a recommendation, I’d say leave the canned wine and snacks for after the sail and take in the excitement and fun of sailing a smooth, sturdy and FUN boat for your short two hour sail. It goes by way too fast. Captain Kirk is knowledgeable, fun, interesting and loves what he does. His First Mate Woody, a sweet little Golden doodle, was curled up on his little perch and was fun to have aboard.I highly recommend The Salty Dog. If you’re concerned about safety, know that Captain Kirk puts safety first and is incredibly experienced. If you want to have thrills, have him take Salty; however, in the Captain’s words-if you want the charcuterie board choose the Peony: Equally as fun but better for those not looking for quite a thrilling ride.Thank you to Captain Kirk for providing us with a really fun adventure on our trip to Chicago.

Joe B

22:36 02 Sep 23

We had the best time with Captain Kirk and Woody! He was great to hang out with and talk to. The sail was phenomenal! We will be going back for sure and will be recommending him to everyone!

John Bender

17:56 02 Sep 23

Super nice. Chill ride and Woody the dog is the best co captain

Jon S

03:03 02 Sep 23

Had a wonderful time sailing with Salty Dog Sailing Co. Captain Kirk and his trusty dog, Woody, made it a unique experience. Highly recommended!

maribeth dirksen

19:00 29 Aug 23

We had a great time and the pup was the icing on the cake! Highly recommend

Dawn 92

18:19 29 Aug 23

We had an absolutely wonderful experience on the Salty Dog sailboat charter with Captain Kirk and his first mate Woody. The attention to detail, friendly demeanor, and expert navigation skills of Captain Kirk ensured a smooth and enjoyable voyage. Woody's presence and overall charm added to the trip. The beautiful views, wonderful weather and the overall ambiance made for a truly unforgettable adventure. I highly recommend this charter to anyone seeking a fantastic sailing experience.

Paul Adams

17:39 29 Aug 23

Just the best afternoon and evening of the summer, that's all it was! Wonderful to share this evening sail with Woody the Doodle, Captain Kirk and my family. Captain Kirk was most accommodating throughout the afternoon, and answered my lubber-ish questions with grace and deep knowledge gained from his experience as a sailor and long-time successful business owner. He even gave me a turn at the wheel of the Salty, which was an unexpected and highly enjoyable privilege. Everyone loved the sailing, and the tour of the anchorage just off the beaches. My highest recommendation for a perfectly enjoyable afternoon. Thanks Kirk and Woody!

David Wilson

22:39 23 Aug 23

Just back from a fabulous day out with Captain Kirk and Woody ,one of the best days we had in chicago highly recommended

Tommy Feldman

13:54 22 Aug 23

Kirk Bennett

19:11 21 Aug 23

Incredible time on Lake Michigan with Captain Kirk. As much as his tastefully curated (and optional) playlist added to our experience, his dog Woody stole the show. Will definitely go again.

Matt Valentini

02:18 21 Aug 23

Great charter trip, highly recommend!

Jay Gerak

14:49 20 Aug 23

Chartered Salty Dog Sailing for 2 couples on a Wednesday night. Captain Kirk was awesome. Knowledgeable, a great skipper, and generous with his time. He made our evening (our wedding anniversary) a night to remember. He stayed out extra time so we could take in the lakefront fireworks. His first mate, Woody (his mini golden doodle), was a wonderful addition to the crew. When we want another sunset cruise it will definitely be with Salty Dog Sailing. Unqualifiedly recommended.We had our second wonderful experience with Captain Kirk (and First Mate, Woody, the Doodle) last night (08/19/23). We chartered Salty for the fireworks time-slot, and were not disappointed. Kirk is VERY professional, no-nonsense, makes all of his passengers comfortable - regardless as to the amount of time they've spent aboard a boat. His pre-journey communication is excellent - letting first-timers know exactly how and when to get the dock, find him, what to bring (and NOT to bring), and prepare for the experience. Captain Kirk is extremely friendly and personable, and Woody is a devoted crew-member. HIs music selection for fireworks viewing demonstrates canny understanding of what his clients/passengers might appreciate, and he made our time wonderful. Expertly navigating through a myriad of other boats we were parked almost under the fireworks display (which were uncommonly good last night). We've sailed with other captains before, but when we have a choice of who to skipper our Chicago Lakeside cruises, we'll go with Captain Kirk (and Woody) and Salty Dog Cruises EVERY time.

Ann Murtlow

00:37 13 Aug 23

We had a great sail on Lake Michigan with Captain Kirk (yes, really) today. Great weather, nice wind and terrific views of a large regatta and the spectacular Chicago skyline.

Adrienne Burgos

17:44 11 Aug 23

Booked a sailing ride for our anniversary and it was such a relaxing and beautiful evening out on the water. Captain Kirk taught us so much about sailing and even Chicago history. And woody, the poodle, gave us the best snuggles ever. Really great experience.

Jill Bender

01:21 08 Aug 23

We had an amazing time out on lake Michigan with Salty Dog Sailing Company! Captain Kirk was great, so informative about sailing and Chicago. Very nice to unplug and enjoy the afternoon, especially with his dog Woody! We ended up being able to extend our adventure and go out on his second boat, each one was a different experience! If looking to do something special in Chicago, definitely worth checking out! :)

Stephen Blaskey

02:03 02 Aug 23

My group had a great time on the Salty Dog. The weather was perfect and Captain Kirk was terrific! And he can sing!!!

perrie h

22:30 26 Jul 23

Our family had a wonderful time aboard the Salty Dog. Captain Kirk made sure every passenger was comfortable and enjoying the trip. Our kids were thrilled to have, Woody (the most adorable dog!), join us for our sailing trip. We had the most enjoyable time and made memories to last a lifetime!

Gary Shimomura

20:27 22 Jul 23

We had a really enjoyable sail with Capt Kirk and Woody. We opted for an exciting type of trip rather than a slow cruise. We were hiked over much of the time yet we all felt very secure with Capt Kirk. We learned about sailing, types of boats, and had a good time just talking. We would definitely recommend the Salty Dog and would like to book future excursions.

Ted Carey

01:18 15 Jul 23

My wife and I had the best experience! Captain is very knowledgeable and fun. Also his dog Woody is super cute.

Tom Perkins

14:54 10 Jul 23

The slaty Dog was the best experience out of all boat charters in Chicago! Affordable and reasonable. We had Captain Kirk and he was the best, had fun with us out on the water and recommended a lot of great stuff to do in the city! We went out in a great day weather wise and was fun to sail on the water. He loves what he does and makes it a fun time.

Savanna Redd

22:55 20 Jun 23

Had the best time with Captain Kirk and Woody. Truly this experience cannot be beat! We choose to do the 2 hour couple trip from 7-9 pm to watch the sunset and it was so relaxing, fun, beautiful - an all around incredible experience. A must do if you have a group of 6 or less! Caption Kirk was such a pleasure, he talked with us about safety, what to expect, why not to be nervous or afraid, everything you need to know about enjoying your trip! He made sure to keep us comfortable always offering us a blanket, a cushion, candy, etc! And Woody the pup is so cute and fun to hangout with. 10/10 would highly recommend.

Kenneth Barnett

18:04 31 May 23

Had an anniversary outing and it was a great time! Captain Kirk was great and knowledgeable about everything involved, with nice conversation.

John Bialorucki

17:04 29 May 23

It was super fun! The captain definitely knows what he’s doing and was more prepared than we were, accommodating to what we needed.

MaryBeth Dryer

15:48 25 May 23

I have been on Salty Dog with Captain Kirk and his Co-Captain Woody a few times. Every experience has been wonderful. Last summer, my fiancé surprised me (hard to do) with an engagement on the summer solstice. My fiancé asked me to share my life with him at sunset, with beautiful chicago in the backdrop while we were sailing on Lake Michigan. I will cherish that evening, that precious memory for eternity. Capt. Kirk captured the moment with pictures and truly made this beautiful moment extra special. We are looking forward to doing a couple of sailings this summer. We love sailing with Capt Kirk and Woody. Kirk truly delivers an exceptional experience!!!! We LOVE sailing on the Salty Dog and sailing with Kirk at the helm. This has become one of our summer must do’s….a summer in chicago ritual….makes our summer complete. 😁 I love how relaxed I feel while sailing. And, Kirk is a great Captain who makes me feel safe. #EXCEPTIONAL #BESTEXPERIENCE #SALTYDOGSAILING

Eric Pace

17:49 17 Apr 23

Had a great experience on this classic sailboat. The captain (Kirk) was very knowledgeable, very friendly and we all felt safe. He had a very friendly dog (Woody) that my daughters fell in love with. Lookin forward to the next time I can go again.

Caitlin Carducci (Caitlin C)

16:40 16 Oct 22

We had a great day with Captain Kirk and Woody! Salty is a perfect sailboat for Lake Michigan, and Kirk did a wonderful job explaining the safety rules and features, as well as letting us know about upcoming wind and waves so we (but mostly me) wasn't surprised or startled. We will happily be repeat customers!

Michael Hawker

22:35 08 Oct 22

Definitely have to book this!!! Kirk is an awesome captain!! You will actually get to experience what real sailboating is all about!! Amazing experience!!

Charles Drummond

15:08 04 Oct 22

I would recommend Salty Dog to anyone visiting Chicago, captain Kirk and his side kick Woody made sure everything was perfect. The boat itself is great fun and with Kirk at the helm you get to do some proper sailing.

Sean Varney

15:57 28 Sep 22

Had the most amazing adventure sailing with Kirk! I booked this as a birthday gift for my significant other and it couldn't have gone any better, it was definitely an experience worth remembering.

Tony Karlovich

23:42 24 Sep 22

Great time on with Capt Kirk and 1st Mate Woody out sailing today. Very enjoyable time and great for the value. Made our trip! Thanks again for the great afternoon sailing.

Katie Hearn

18:20 26 Aug 22

We enjoyed a lovely weeknight sail with Captain Kirk and his trusty first mate, Woody the goldendoodle. Kirk was proactive and communicative before our sail, making sure we had all of the details ahead of time. We felt safe and so relaxed the whole time, and even got a 5 minute lesson in aerodynamics (aka, sailing for beginners)! The absolute highlight was our front-row seat for the Navy Pier fireworks, during which Kirk queued up some epic classical music to accompany the pyrotechnic show. There is no better birthday gift / date night option for this price in Chicago - we are so excited to come back next season!

Bailey Johnson

20:58 18 Aug 22

We booked a last minute sunset sail with Captain Kirk and had an absolutely lovely night. Kirk was warm, attentive, and extremely safety-conscious. We learned some basics about sailing (and got a ton of amazing recommendations for the rest of our trip), enjoyed some choppy adventurous waves and also nice calm water near the harbor. And Woody the dog was the sweetest boy. Highly recommend, best value of our whole trip and one of my favorite nights I’ve ever had!

Hojin Kim

04:24 11 Aug 22

Extremely happy with the experience! I recommend saturday night time with the fireworks. His music selection was superb as well :)

Jen Bradburn

16:35 06 Aug 22

We did a morning sail with Captain Kirk and had a blast! I got some snuggles from his trusty salty dog sidekick Woody, and the views were fantastic. We highly recommend this experience to visitors and locals - it’s a great way to take in the city!

SaltyBoi

18:22 31 Jul 22

Our 2nd time sailing with Capt Kirk and Woody, and it was just as awesome as the first time! Gorgeous night, beautiful sunset and a very relaxing evening! Great conversation and sailing lesson with Capt Kirk, and some sweet cuddling with Woody; he's the best! Booking online was extremely easy, and Capt Kirk stayed in touch via texts leading right up to our sailing time. Getting there and parking was a breeze, even during Lollapalooza! Highly recommend Salty Dog for a lovely charter sailing

Emily Case Lazzaro

04:00 25 Jul 22

Captain Kirk is one of the best sailors around. My sister, 4-yo son, and I joined him for a mid-day sail. He was extremely knowledgeable…great with my son (with the help of Woody :) …very communicative leading up to the day as well as on the day and was very safe and very confident in the high winds we had. We can’t wait to go again! Thank you!

Nicole Mize

18:40 24 Jul 22

We are so happy we found Salty Dog Sailing! This was our second time sailing with Captain Kirk and Woody and it was another beautiful sail. The Captain is a very knowledgeable and skilled sailor and makes your safety his main priority. He also has great taste in music, is very generous with time on the water, and it’s impossible not to fall in love with Woody. We will be lifelong customers!

Cal Ehrke

19:56 17 Jul 22

Captain Kirk was so great and helped make our experience so enjoyable. He was extremely accommodating to our wishes on where we wanted to sail. Would highly recommend!

Maggie Lamb

15:56 14 Jul 22

Wonderful sail! Went out on a Monday night with my fiancé for his birthday. Kirk met us with the parking pass, and his directions on the website are super clear. He is friendly, confident, and safe. Plus, he has Woody the pup! Overall, absolutely amazing. Recommending to all my family and friends!

Jason Dunkerley

18:02 12 Jul 22

We had a great morning out on the lake with Kirk and Woody! Great little side adventure for our trip to Chicago.

Sean Kennedy

18:15 11 Jul 22

Had an amazing experience with Kirk and his dog Woody. I am going to recommend a trip with him to all my friends and family visiting Chicago.

Angie McManus

02:26 10 Jul 22

My family had a great adventure sailing with Kirk and Woody! Kirk was serious about safety and I noticed he watched other boats nearby very carefully, too. Kirk made sure we were all comfortable. We had a chilly night (even though it was the first week of July) and the waves were 2-4 feet. So, real sailing. My only complaint is it went by too fast!

Vestspire Group

01:40 05 Jul 22

Captain Kirk was the best on the water hands down! For first timers or anyone who has been on the water before, Kirk is a great time and is very experienced when it comes to sailing!

Mike Burcker

01:37 05 Jul 22

Robert Wietecki

14:47 29 Jun 22

Absolutely amazing evening on Lake Michigan with Captain Kirk and Woody. Kirk is clearly a tremendously skilled and experienced sailor and even gave us a quick crash course in sailing. He was great to chat with and the cherry on top was his Goldendoodle, Woody, who accompanied us on the boat. I would recommend Kirk and Salty Dog to anyone looking to sail Lake Michigan and I don't think this was our last charter either.

Amy Bartleman

03:43 18 Jun 22

This was our first sailing experience and it won’t be our last. Captain Kirk was outstanding! He was very knowledgeable and down to earth. His little ship dog, Woody, was an added bonus. He was such a laid back little cuddler. Needless to say, the views of the Chicago skyline were breathtaking!

Mollie Taylor

19:40 31 May 22

Fantastic morning for my family and I (6 people). Capt Kirk and Woody were professional, timely, and a ton of fun! Thank you for a great start to Memorial Day weekend!

Vincent Migeotte

13:37 30 May 22

Chicago the Windy City! Great time with Captain Kirk! It was a windy day in front of Navy Pier and had a blast. Strongly recommend The Salty Dog Sailing.

Amy Benson

14:39 11 Oct 21

We had an AMAZING afternoon with Captain Kirk and Woody. Everything ran extremely smoothly from the on line reservation, to the perfect winds on the lake, and everything in between. It was the perfect way to celebrate our wedding anniversary with the beautiful city as the backdrop. Can't wait to book again in the spring!

David Halbur

21:29 25 Sep 21

Captain Kirk was phenomenal! He worked with me on planning my proposal too!! I highly recommend him

Jessica Maxey

19:34 25 Sep 21

Kirk was phenomenal! An absolute joy to talk to. Full of information, gave lots of detail about sailing and physics. Made it super easy for my now fiancé to propose on the front of the boat! I couldn’t have asked for a better moment and Kirk helped make it happen 😊

Nicole Green

01:06 18 Sep 21

An absolute 10/10 experience - we shot our engagement photos on our sail at sunset, such a beautiful, unbelievable view and an awesome sailboat. Captain Kirk was so helpful and kind - taking us to the best spots for sunlight and calm waters. We will be back again for sure!

Rita Kogan

12:03 09 Sep 21

It was a true sailing experience, with a great performance boat and super professional and super cool Captain Kirk. I would be happy to sail with him again. Woody is the sweetest dog and Chicago skyline from the Lake is unforgettable. Anyhow who loves sailing should do it.

Emily Yates

13:10 07 Sep 21

We had an AMAZING experience aboard the Salty with Capt Kirk and his sidekick, Woody.Book it. You won’t regret it. We had to reschedule a few times due to weather but Capt Kirk wanted us to have the best experience possible and was really flexible. The boat is a piece of art. The views are incredible. No picture will do it justice. It’s super easy to get to and you park right next to the dock. Capt Kirk is an absolute joy to be around, Woody is the star of the show second only to the scenery. It’s an unforgettable experience.

Apoor Gami

02:25 07 Sep 21

Awesome time on the Lake with Capt Kirk! Gorgeous and powerful sailboat. Can make it whatever you want with Kirk’s easy going and super helpful manner. Wouldn’t hesitate to book if you’re looking for a private charter.

Mike Rish

21:15 31 Jul 21

Gf surprised me with a sailing date and I had a blast . Captain Kirk was fun to talk to and very knowledgeable about sailing and the city’s history (all history actually). Woody his dog is amazing too. 10/10 would recommend. We will be back in September , skipper 😉

Ryann Parker

18:13 30 Jul 21

What a wonderful evening on the water. Captain Kirk and his trusty deckhand (Woody) treated us to beautiful views, great conversation, and topped it off with fireworks at the end of the night. It was a very memorable evening we won't forget and was a big highlight of our trip.

Chase Parker

21:47 24 Jul 21

Great time on the water at a great price! When I make it back to Chicago, this will be on my to-do list every time. The boat, the captain, and his deckhand (dog) Woody would have made the trip alone. Add to it, sunset and fireworks and it was an evening we won't soon forget. A few simple guidelines on the site to follow that made us well prepared when it got a little chilly.

Dr. Christina Brown O.D.

13:47 12 Jun 21

My husband and I had a very relaxing sail with an amazing sunset view of the city after a hectic travel day. It was amazing to see the skyline from the water. Captain Kirk was very friendly and knowledgeable about the city’s history, but the real star of the show is Woody the sailing pup who greeted us at the dock and climbed on my lap when we got on board. Would definitely recommend.

Jared Johnson

17:48 19 Sep 20

This was an amazing time. Kirk went above and beyond to ensure that everything went smoothly. He’s a very kind guy with a great taste in music. Woody the dog is an incredibly gentle and well behaved. I would highly recommend sailing with the Salty Dog.

Mike Fenech

19:58 17 Sep 20

Captain Kirk was great. No frills or hassle when booking like I experienced with other private sailing companies and he was also the best price. The sail was gorgeous and a neat perspective of the city, especially at night. Kirk is down to earth and a laid back, nice guy who’s happy to share his knowledge and make sure your time on the water is enjoyable. Good music and and amazing dog made it that much better.

Austin Bourdages

19:29 16 Aug 20

Captain Kirk did a great job getting us out to the inland sea with a level we were comfortable sailing. He really knows what he’s doing and we were very pleased with the overall experience.

Matt

14:37 08 Aug 20

Had a great time sailing with Captain Kirk! Great customer service and we loved learning about sailing. Highly recommended!

darlene kober

15:56 03 Aug 20

Captain Kirk gave us a great sail to celebrate my daughter's 24th birthday. He made it easy to sign up, communicate with prior to the sail, and meet up with him at the harbor during the day of sail. We had a great couple of hours before some rain came in. Kirk was prepared with jackets and vests and made us all feel very comfortable. I would recommend it!

Erika Barber

13:00 01 Sep 19

What a fantastic experience yesterday on The Salty Dog cruising around Lake Michigan! Captain Kirk made sure everyone was safe, comfortable and enjoying the ride. From booking to communicating and coordinating the logistics of the day to the charter itself- everything was handled professionally. We’ll definitely book again...especially if Woody dog is on board again!

Melissa Chism

16:11 31 Aug 19

It was a really great experience. Kirk was very informative and Woody was the cutest.

Sarah Kamer

19:28 18 Jul 19

My fiance and I went on a 2 hour sail on a Saturday afternoon with Captain Kirk. We both enjoyed his stories and education about sailing. It was a great way to get out on Lake Michigan and see the activities but also be more secluded. We would definitely recommend this to others. And we'd love to go out, again. Thank you!

Jillian Lemery

19:19 14 Jul 19

I originally had booked a charter with a different company who had cancelled. With just less than 24 hours notice, Captain Kirk was able to book us in his busy schedule.We had a cousin in from overseas, so we did a night sail and watched the Navy Pier fireworks. Captain Kirk was a great conversationalist and Woody was such a good boy. Sailing with these two is going to be our "go-to" activity for when guests come in from out of town.

Marie Holmdahl

13:29 06 Jul 19

Thank you so much, Captain Kirk, for a great time sailing on Lake Michigan. My dad and I had a lovely time and I greatly recommend this experience to others who are looking for a fun activity to do in Chicago.

Kristin O'Callaghan

17:13 29 May 19

We had a fantastic evening sailing with Captain Kirk. We booked a very last minute cruise and Captain Kirk was very responsive to our calls and texts with questions. We will be recommending The Salty Dog Sailing Co. to our family and friends when they visit Chicago; it is a beautiful way to experience the city!

Thomas Bohac

17:22 26 May 19

What a great experience sailing on Lake Michigan. Captain Kirk and Woody were awesome hosts. We had southwest winds at 20+ knots so the sailing was super fun. We will definitely be booking again and recommending this experience to our friends. Thanks again for a great time!

Michael Holmes

17:07 26 May 19

Salty Dog Sailing Co. is the real deal for all those who are experienced with sailing or beginning. Whatever your comfort level is Captain Kirk will provide you with the best experience while you are visiting or local here in Chicago. His experience is above the rest! I’ve learned so much from him about Sailing I keep going back for another charter!Best Sailing charter in Chicago. NO DOUBT! Book with him now and see Chicago for the water. What an experience!Enjoy!

Daniel O'Callaghan

04:19 26 May 19

I would highly recommend sailing with Kirk and his dog. We had a great time!

Mike S.

21:20 24 May 19

Captain Kirk and First Mate Woody were a fantastic host and crew on an unbelievably romantic sail around Chicago! Captain was a true pro sailor. We felt safe and had a lot of fun watching the sun set over the city. Higly recommend booking sooner than later!Mike and Jackie from CO.

Roy Wagner

04:49 27 Aug 18

My wife and I did a night sail and loved it. It was fun to see the city from a unique view. Kirk is a great guy and his dog is a nice addition. You can tell he really loves what he does and is very knowledgeable. Would highly recommend!

Bryon Jones

14:18 20 Aug 18

Wonderful experience. Captain Kirk allowed us to reschedule due to pending rain for our originally scheduled time. Very knowledgeable and showed us a great time on the lake. Highly recommend! Woody, the dog, was a fantastic first mate too.

Hershel Caywood

15:38 05 Aug 18

Enjoyed sailing about Lake Michigan with Capt. Kirk. He provided a sailing experience that was thrilling and fun while making our group of six feel comfortable and safe. I enjoyed the experience and would recommend to anyone who enjoys being on the water, seeing the fantastic Chicago Skyline, and having an adorable golden doodle (Woody) along for the ride.

Janie McDonald

15:45 18 Jul 18

Aubrey Weaver

22:45 18 Jun 18

Captain Kirk did a great job! We really enjoyed our time sailing with him and his pup Woody. We did a sunset cruise, and the views of the Chicago skyline were incredible. Kirk is on the ball and super accommodating with reservations. We’d highly recommend booking a tour with Kirk!

Anay Amin

14:32 23 Jul 16

Skyline Treasurer

21:50 28 May 15

Capt. Kirk and his 1st Mate "Woody", such an adorable lil' pup, were a pleasure to go sailing with. Our group had an awesome time and the views of the Chicago skyline were truly amazing! The group got some really cool pictures. Kirk was an extremely nice Captain and fortunately was willing to share his knowledge of sailing with our inquisitive group. I highly recommend Salty Do Sailing and be prepared for a memorable time out on the water!

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