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Captain Sir Charters - Private Day Tours

4000 Crandon Blvd, Miami, FL 33149-1102
+1 786-218-2454
Review Highlights
World class sailing charter

I surprised an out-of-town guest with a sailing charter for four of us friends. Captain Russ was a... read more

Reviewed 2 weeks ago
Christine D
via mobile
Sunrise on the bay

My family and I had an amazing experince with Captain Sir Charters. Captain Boley and first mate... read more

Reviewed 3 weeks ago
A TripAdvisor Member
via mobile
Read all 124 reviews
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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 Charters to the Florida Keys, and Week Long trips to the Bahamas. Step aboard the Best and the Newest Sailboat in Miami -- it's truly sailing FIRST CLASS! Check out the website and photos of the boat. CAPTAIN SIR! is in a class by itself but no more expensive than sailing in coach class!
  • Excellent99%
  • Very good1%
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Travellers talk about
4000 Crandon Blvd, Miami, FL 33149-1102
+1 786-218-2454

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Reviews (124)
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1 - 10 of 119 reviews

Reviewed 2 weeks ago 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

Thank Christine D
A TripAdvisor Member
Reviewed 3 weeks ago 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

Thank A TripAdvisor Member
goodfoodguy747, Owner at Captain Sir Charters - Private Day Tours, responded to this reviewResponded 3 weeks ago

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 8 August 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

Thank Paul B
goodfoodguy747, Owner at Captain Sir Charters - Private Day Tours, responded to this reviewResponded 12 August 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 26 July 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

Thank YohamaMichelle
Reviewed 29 June 2017 via mobile

I could fill the page with accolades about the boat, the couple that operates it and the perfect weather but that would not do the experience we had, justice. Stop reading the reviews, reach out to Russ or his wife, get on the water and...More

Thank Joshua K
Reviewed 18 June 2017

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...More

Thank Deepa I
Reviewed 14 June 2017

My husband and I chartered a private sail with Captain Russ for a full day at the recommendation of the Ritz Carlton. It was the highlight of our trip. I have been on several private charters in the past and this one was the best....More

2  Thank MerrylJones
goodfoodguy747, Owner at Captain Sir Charters - Private Day Tours, responded to this reviewResponded 17 June 2017

Thanks so much for sharing your experience with other on Trip Advisor. We had one of those PERFECT days for you -- so glad you enjoyed the food. That's why I custom prepare a menu to suit the tastes of my guests -- and we...More

Reviewed 26 March 2017 via mobile

My girlfriend and I had such an amazing time while sailing on a romantic sunset cruise with Russ and Susan. Captain Sir was very spacious and clean. I would highly recommend booking this lovely experience and making it a memory you'll never forget!

Thank Meyer92
Reviewed 25 March 2017

Captain Russell's kind manner and incredible knowledge of the Key Biscayne/Miami area let us know we were in good hands. The sailboat, Captain Sir!, was immaculate. Captain Russ and his wife, Susan, made us feel as if were family all while delivering top notch service...More

Thank AnnualGirlsTrip
Reviewed 24 March 2017

What a perfect, wonderful 2 hour sunset cruise with Russ and Captain Sir! Our young boys loved the experience, the food, and what great relaxation on a beautiful evening with a fantastic view of Miami's skyline. The boat was perfect for our family of four,...More

Thank shcypes
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Ask a question
Questions & Answers
Ian P
30 November 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.
19 August 2016|
AnswerShow all 4 answers
Response from goodfoodguy747 | Property representative |
Coast Guard regulations limit the # of paying passengers to 6.
17 January 2016|
AnswerShow all 2 answers
Response from captainsir | Property representative |
The half-day rate is $650; the full day rate is $900 All the rates are on the website. Lunches are custom prepared and cost $20 per person; dinners are customized to suit the taste of our guests and cost $50 per person