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Captain Sir Charters - Private Day Tours

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Captain Sir Charters - Private Day Tours
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Travelers talk about
“key biscayne”(16 reviews)
“sunset sail”(7 reviews)
Go sailing on the NEWEST Charter Sailboat in Miami for a day of sailing/sightseeing OR a Romantic Sunset and City Lights Tour of Miami.We specialize in Romantic Sunset and Night Evening Tours. Also available: Romantic Dinner Trips, Overnight...more
401 Biscayne Blvd, Miami, FL 33132
+1 786-218-2454
Reviews (130)
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All reviews key biscayne sunset sail sailing experience perfect afternoon maryland crab cakes award winning key lime pie gracious hospitality highlight of our trip perfect trip hour cruise beautiful miami susan sailboat sailed homes sails outing
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1 - 10 of 125 reviews
Reviewed June 14, 2018 via mobile

What an amazing way to celebrate 40 years of this beautiful life. My husband booked this sunset 4 hour cruise with my little 4yr old. It was a beyond perfect trip. Captain Russell was so kind and honest. He put together the most delicious fruit...More

Thank Terri-Ann B
Reviewed May 17, 2018

An April 2018 getaway….. What a great cruise my husband, daughter, son-in-law and myself experienced with Russ & Susan on their sailboat “Captain Sir”. The sailboat is sleek, beautiful and spotless. We chartered her for a ½ day sail around Key Biscayne and received the...More

Thank lindylu2018
goodfoodguy747, Owner at Captain Sir Charters - Private Day Tours, responded to this reviewResponded May 18, 2018

Thanks so much for sharing your experience and we look forward to hosting you aboard again in the future. We have so many interesting side trips around Biscayne Bay that offer lots of fascinating sights for our guests -- look forward to sharing more with...More

Reviewed April 1, 2018 via mobile

Russ and Susan have a spectacular philosophy and sailboat. I love being on the water and really just wanted to chill and relax and listen to the water and watch the sails. It was a 10 out of 10 perfect experience can't wait to return...More

Thank bleph
captainsir, Owner at Captain Sir Charters - Private Day Tours, responded to this reviewResponded April 7, 2018

I'm so glad we had the opportunity to show you the beautiful side of Miami and have you relax for a bit with us. That's really what most people don't know until they experience it -- but the getaway, the quiet, the sound of the...More

Reviewed March 30, 2018

My wife and I recently booked a 2 night sailing charter with Captain Sir out of Miami and let me tell you, Captain Sir Charters sure knows how to cater to your every need. Captain Russ and Susan were the connsumate hosts and pampered us...More

2  Thank sangercruise
goodfoodguy747, Owner at Captain Sir Charters - Private Day Tours, responded to this reviewResponded April 2, 2018

Thanks for taking the time to share your experience on Trip Advisor. After doing this for 29 years, we have gotten pretty good at the planning process and that ensures our guests have exactly what they like and have a fabulous experience on their trip....More

Reviewed March 12, 2018

Given to me as a Christmas present, we enjoyed a fantastic weekend of sailing with Captain Russ and his First Mate, Susan. Our travels took us to Elliott Key, Sand Key, Boca Chita Key, and through Stiltsville. Equally amazing was the menu of food –...More

1  Thank Tom S
Reviewed December 4, 2017

Last week we had a relaxed sail with Captain Russ and Susan for "personal business"... to scatter my parents ashes in the ocean. As you've read many times before in other reviews, Captain Sir is a beautiful vessel and the team did a great job...More

1  Thank RalphOinTX
goodfoodguy747, Owner at Captain Sir Charters - Private Day Tours, responded to this reviewResponded December 6, 2017

We always are flexible with our guests when it comes to weather -- that's something neither of us can control and consequently, neither of us should be penalized for inclement weather. We have the most liberal weather policy of any charter boat in Miami --...More

Reviewed October 7, 2017 via mobile

I surprised an out-of-town guest with a sailing charter for four of us friends. Captain Russ was a very amiable and knowledgeable guide who even gave little sailing lessons to us and allowed my friend with sailing experience to have her turn at captaining the...More

2  Thank Christine D
Reviewed September 24, 2017 via mobile

My family and I had an amazing experince with Captain Sir Charters. Captain Boley and first mate, Mrs. Boley took us for an early morning trip to watch the sunrise and it was just beautiful. We had our small children 4 yo and 1 yo...More

1  Thank Expedition535054
goodfoodguy747, Owner at Captain Sir Charters - Private Day Tours, responded to this reviewResponded September 26, 2017

I'm so happy you and your family enjoyed your sunrise sail on Biscayne Bay. That was a perfect way to cap off your vacation in Miami! Not too many guests get up that early to see the sunrise and so glad you got some great...More

Reviewed August 8, 2017

Captain Russ and his lovely wife gave us a memorable sailing trip around Key Biscayne on the Captain Sir. The boat is simply fantastic, and very comfortable. Our sunset cruise was one of the highlights of our holiday and I would recommend to anyone visiting...More

1  Thank Paul B
goodfoodguy747, Owner at Captain Sir Charters - Private Day Tours, responded to this reviewResponded August 12, 2017

Hi Paul, It was our pleasure to have you and your family aboard to enjoy the sunset on Monday. We always enjoy showing the best take on Miami to our guests. It just is so magical from the water and we often hear those words...More

Reviewed July 26, 2017

This review is way over due... Captain Russ and his wife and crew made our mother's day weekend 2017 a dream come true. It was paradise! We chartered two sailboats for our family get together. Everything about our trip was a breeze. Captain Communication, punctuality,...More

2  Thank YohamaMichelle
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Questions & Answers
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Ian P
November 30, 2016|
Response from captainsir | Property representative |
CAPTAIN SIR! Is a 46 foot Island Packet sailboat. It sleeps 7 in 3 cabins and has 2 heads and showers plus another hot/cold shower on the stern for showering after swimming. Check out the website for more information.
August 18, 2016|
AnswerShow all 4 answers
Response from goodfoodguy747 | Property representative |
Coast Guard regulations limit the # of paying passengers to 6.