I know NOTHING about sailing so this review won't have a shred of technical sailing terms/words. I am one of those people that gets seasick at the SIGHT of a boat so let's just say I was not too eager to board. My BF is a sailing enthusiast so I made a serious compromise. First let me say that Cap'n Russ is awesome. The boat was beautiful and clean. Russ keeps it in tip-top shape. He gave us a quick little tour and off we went! I learned about jibs and masts (oh baby) and it was a beautiful day. Cap'n Russ gave us privacy but was perfectly attentive and accommodating. He made the best little appetizers! So thoughtful. He took us through the little waterways to see the huge/gaudy homes that are everywhere in SoFla -- he showed us Andy Garcia's house and we saw him outside. Cool! Don't have enough nice things to say about Russ and the boat. The experience was fantastic. I didn't get seasick either which was quite a relief for all of us! read more

Captain Sir! Charters - Rob and I on the sailboat! - Boating Near Me

My wife and I spent San Valentines Day with Russel and Susan and their sailboat Captain Sirs. It was a delightful experience. From the moment we set foot on their 46 feet long sailboat we know we had made a great choice. We were attended to our needs in every aspect imaginable. The head (restroom) and galley (kitchen) were immaculate. The inside of the boat had accommodating and comfortable leather seats. We sailed across the Miami Bay area and witnessed a beautiful sunset while sipping on some wine and nibbling on crackers, cheese and fruits. As the night fell, they brought some LED candles that accentuated the mood and prepared a delicious meal consisting of three courses: Coconut Shrimp with dipping sauce, Salmon over spinach and wild rice, and carrot cake for dessert. We sailed right past the intercontinental and under the Biscayne bridge and were astonished at the sight of downtown from a different perspective. Russell and Susan were great companions in our short trip. We wouldn't hesitate in recommending them to our close friends and family if they were looking for a romantic night out in the beautiful bay of Miami. read more

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Thanks to Russel and Susan for an outstanding service, they are such an amazing sail boat power couple! They were so attentive to our needs the whole trip. We left the dock approximately at 14:30 and were able to enjoy the incomparable Miami sunset to one side and on the other side the Miami skyline. On the boat they have all the amenities to control music from bluetooth to SiriusXM. Make sure to try they're crab cakes, so delicious! And Russell surprised my group with mouthwatering (award-winning) key lime pie, which we enjoyed on our way back to the dock. We didn't want the unforgettable evening to end, I highly recommend Sir Charters to celebrate any occasion. Thanks again, Russel and Susan! You'll be hearing form me in April 2020! All the best. read more

Captain Sir! Charters - Boating Near Me

Captain Russ and Susan are awesome! A fantastic evening off Key Biscayne and downtown Miami. Above and beyond in all aspects! read more

Captain Sir! Charters - Boating Near Me

Couldn't think of a more perfect way to celebrate our 20 year wedding anniversary thanks to my husband!! A wonderful sail on the beautiful Captain Sir~ Captain Russ & Susan we're lovely and our sunset sail couldn't have been more perfect~ seeing the beautiful Miami skyline at night & relaxing under the stars while enjoying wine, cheese & fruit and the BEST key lime pie!!! read more

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My husband loves for us to visit Miami at least once a year so when he requested we visit for his birthday last month I wanted to try to make it a special trip. I began my yelp search to find private boat rides around Miami to surprise my husband and I was happy to come around Captain Sir Charters. I sent an email through yelp with my quote inquiry and received a prompt response. Captain Russ was very thorough, responsive and warm. He was very attentive to all of my requests and assured me he would do his best to make it an awesome experience. I texted Captain Russ when we landed in Miami to confirm our arrival wasn't delayed. The weather was gloomy but he was optimistic the weather would be great the next day which was the date we had planned to sail. As we'd hoped the next day was PERFECT clear blue skies! Captain Russ and I were secretly texting back and forth that morning to ensure I had all the details for the day. My hubby and I went to an early breakfast and then I told him we had lunch reservations which was actually the surprise boat ride. Our uber arrived and drove us to the dock where Captain Russ and his lovely wife were waiting for us. It was perfect! My hubby was so surprised. There were a dozen long stem red roses on deck per my request for hubby. We had an amazing sail and the lovely couple was so attentive and warm. Captain Russ gave us the history of the Keys as we sailed and he even explained the sailing process throughout. His gorgeous wife was the cutest server as she delivered our delicious cheese and fruit platter on a silver platter. They went out of their way to find us Crystal Geyser bottled water as well. Lunch was fabulous! They were happy to take as many pictures as we liked from as many angles as we wanted to capture the experience. We ended the 4-hour ride with the best homemade key lime pie I have ever tasted!!!! It was DELICIOUS!!!!! My husband was so surprised and thankful it really was a treat. I paid in cash which was very reasonable for the experience we had. Captain Russ made our trip the best trip we've taken together to date. I'd highly recommend this service. I can't wait to have this experience again! read more

Captain Sir! Charters - Boating Near Me

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Incredible sailing tour - a must if you are in Miami!! We had a great day sailing around the bay, learning about sailing, and eating wonderful food. Russel is a knowledgeable, well-organized, and kind person--as well as a terrific cook. I enthusiastically recommend this trip - what a great value. The boat is fantastic, too. Super clean, up-to-date, and comfortable - not your ordinary charter boat. read more

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My third time going out with Captain Sir and it just keeps getting better and better. Russell and his wife Sue are by far the most courteous, professional and just a pleasure to be with. We couldn't stop laughing for the four hours we were with them, and what else can you ask for..... Except for Russell buying the best stone crabs I have ever had. He cracked them open for us and was the perfect host. What a perfect day!!!!!! read more

Sailed twice last week on Captain Sir and I must say that it was a great experience! The sailing was great and the only thing better was the food, wine and hospitality! Thank you Captain Russ! read more

We had such an amazing experience sailing with Captain Russ and Susan. We went out for half a day, and everyone agreed it was the highlight of our Florida trip. We had 3 adults and 3 teenage girls in our group, and everyone had a blast. The girls had so much fun jumping off the back of the boat into the bay and Russ did a great job capturing their jumps on his phone. He even taught the girls (and us) a thing or two about sailing. The boat itself is beautiful - the girls loved hanging out downstairs! Since we have picky eaters, we opted to bring our own food, but I was pleasantly surprised that once we got onto the boat, Susan took over putting out all the food and snacks, and I got to relax! All in all a wonderful trip, and we look forward to when we can do it again! read more

During our visit to Key Biscayne, we had a magical girls day on the Bay with Russ and Susan. Russ was a delight to work with in terms of planning and the sail exceeded all of our expectations. Drinks, music, swimming and lunch were great, but didn't compare to the kindness and hospitality that Russ and Susan provided. We can't wait to go back! read more

Captain Sir! Charters - At the helm! - Boating Near Me

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Captain Boley and his First (and only) Mate, Susan, were amazingly accommodating to our girls group of six. I can't imagine having a better experience than we did on a sunny, Saturday afternoon in August. Communication with the Captain was easy and direct; he called less than 3 hours following our initial email inquiry and from that initial call, I knew that we would be sailing the Captain Sir. Captain offered suggestions on how to get the best out our experience such as ordering alcohol ahead of time from a local store where he would pick up and have everything waiting on us when we arrived to sail. On the day of the sail, Captain also texted to make sure we were running on time; because of a late night out, we were running behind, but the Captain was patient and accommodating and did not force us to lose any time off our cruise. We chose an afternoon cruise and selected a lunch menu that was tailored for our group (not just sandwiches and chips like most of the competitors). The perk here is that the Captain is also a chef, and the food was carefully prepared to satisfy our palettes; from the international fruit and cheese platter, to the delicious shrimp salad and homemade garlic toast, to our final course, triple Ghirardelli chocolate brownies served with vanilla ice cream, we were in foodie heaven. Thanks again Captain Boley and Ms. Susan! We had a great time spending Saturday afternoon with you and we will be sailing the Captain Sir next time we're in Miami. read more

This was one of the most romantic dates I've ever planned and Captain Russ and his sweet wife made sure of it. The food was excellent. The crab cakes are a must and to top it off... his famous key lime pie.it took so much planning because we all know how the weather can get in Florida but Captain Russ was very accommodating and made sure everything was going to be PERFECT. I couldn't of celebrated my anniversary no better way that this sail ride. We didn't only have an awesome time but we also made a great connection with Captain and his wife and now have friends for life! Can't wait to do this again in a few months when we return to Florida! Thank you both again so much!!!!! read more

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Amazing experience with the most AMAZING individuals I've ever met! Mr. & Mrs. Boley (or Captain Sir!) greeted us as if they've known us for years! My 3 daughters (10,11 & 15) my husband and myself had such a wonderful experience. Captain Sir and his beautiful wife assured us with their experience and safeness of their sailboat once we arrived. Then as we became familiar with the sailboat we decided to sit on these portable most comfortable seating front row of the sailboat. Then as we are gliding through the bay we were asked if we needed a drink or if we were hungry! I mean talk about VIP treatment!! As the sunset began to set we just could not believe the front row spectacular view of the sunset! Once the sun went down we noticed candles all around us as my daughter played our wedding song in the background! This wonderful experience definitely didn't end there but all I can say is that it is an experience WE will never forget! I wish I had a MILLION + more followers to experience this because it definitely should be in everyone's Bucket List! Thank you Captain Sir!! I added you to my contacts... I will definitely be back! Xo read more

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AMAZING!!! The ride was soooo relaxing, beautiful views, informative and just all around AMAZING!!! The food and service was on the money. Speaking of food, I want that shrimp salad and pizza bread ( - my friends nickname 4 it - Ask for it and you'll understand) right now. Btw, the service was NON-STOP.....which is why I give the crew & this experience 10 stars!!! Cant wait to do this again!!! Thx Capt & Wife...Texas Loves YOU!!! read more

Captain Sir! Charters - Shrimp Salad with house vinaigrette..... AMAZING - Boating Near Me

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While I was skeptical about Captain Sir based on the other reviews appearing to be fake, Russ truly was the ideal host. The boat was gorgeous and so quiet as we cruised up to the Yacht Club and down to Brickell before returning to the dock. We wanted to keep it intimate so there were only three of us, but we could have brought three more. We left at 6pm and got back at 10pm for $600. I believe the full day costs $900, but since we didn't have time, the sunset cruise was well worth it. read more

Big thank you to Captain Russ for making our wedding day sailing excursion extra special! We were married in the morning and out on Captain Sir! by 1:00. Captain Russ was great, the boat is immaculately clean, organized and well appointed. Everything that we could have needed was on board. Read the other reviews, and know what we agree with all of them. Great afternoon! read more

Captain Russ is the best! His boat is so clean and nice. My husband and I had the most romantic dinner sunset cruise and then got to see the Miami skyline after dark it was just breathtaking. I highly recommend captain Russ to anyone in the area we will definitely do this again every time we come back! read more

Captain Russ truly made our trip fantastic. We chartered his beautiful sailboat for the day/night out on Key Biscayne for my mother's 60th birthday and Russ ensured that everything was taken care of. He was punctual, personable and took the extra step to ensure that the day would be perfect. I highly recommend this trip for its fair price, beautiful boat, and great guide. read more

If you are coming to South Florida and looking for something to do - check our captainsir.com The 45' CaptainSir is helmed by Russ Boley, a licensed captain for who has been sailing since he was 5. Both he and his wife, Susan, who often is the "first mate," make guests feel welcome immediately. A host of four-hour, day, weekend or weekly charters are available in and around Miami. Seeing the city from the water -- aboard a sleek and inviting sailboat -- is the perfect way to "sightsea" while in the area. Whether you are a visitor at a hotel or a local looking for something in the way of entertainment (they do sails for all special occasions as well as no special occasion) -- couldn't find a more relaxing and enjoyable activity. Expert at both manning the helm and manning the galley, Captain Russ whips up some delectible offerings for those who prefer not to bring their own snacks or meals aboard. Whether it's a lazy brunch anchored in No Name Harbor on Key Biscaye, a tasty lunch or a tantalizing dinner while feeling the breeze and watching the lights of downtown Miami brighten the skyline -- the CaptainSir is a perfect interlude. Step aboard and leave the shore. By the time you slip into the slip, you will not only have made new friends (Russ and Susan) but discovered an inviting retreat from the hectic Miami pace. Check out the website captainsir.com read more

Capt Russ and Susan were very hospitable during our 2 hour sailing excursion. It was more than a plain outing: it was a lesson about the history of Key Biscayne and the surrounding areas of Miami. We thoroughly enjoyed the sailing around the homes and the lighthouse, while nibbling on the great fruit/cheese platter that Susan prepared for us. Thanks for the wonderful time! We will surely recommend you to our friends. A great family activity! read more

I planned a (relatively) last minute birthday trip for my boyfriend. Captain Russ made the whole process incredibly easy... making suggestions as to the type of cruise and the menu served. The sunset cruise was really great...the boat itself was incredible & well-maintained, and Russ & his wife took care of everything and made it a really nice night for us. read more