Captain Sir! Charters

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!!!

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.

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!

We booked Captain Sir for a relaxing half-​day (4 hour) event for my best friend’s bachelorette party this past weekend for a group of 6 girls. Ad let me tell you, this boating experience was THE highlight of our trip. Everything absolutely exceeded our expectations, from the generous service we received from Captain Russ, the ease of communication with him prior to the event, the perfect weather while we laid out, the delicious food and dessert, and the pristine condition of his sailboat! It was well worth what we paid.
Captain Russ was always quick to respond to emails and phone calls, making it a pleasure to book his sailboat and customize our lunches/​dessert/​alcohol to fit our needs. On the boat, he had pristine service and catered to us the entire time when he wasn’t maneuvering the wheel — he poured us glasses of champagne that I bought online and he picked up for us, brought us fresh cut fruit and cheese served on a silver platter, brought us fresh watermelon after we all jumped into the bay and got all wet, and served us lunch with such nice presentation. and we can’t forget his famous key-​lime pie that was to die for!!!
I would recommend Captain Sir and captain Russ to anyone that wants to have the best boating experience of their life in Miami without breaking the bank! I want to go back already and do it all over again. Thank you so much Captain Russ!!! You are the best!

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.

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!

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.

Captain Russ truly made our trip fantastic. We chartered his beautiful sailboat for the day/​night out on Key Biscayne for my mother’s 60^th 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.

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.

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.

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!