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Captain Sir Charters - Private Day Tours

4000 Crandon Blvd, Miami, FL 33149-1102
+1 786-218-2454
Review Highlights
Sunrise on the bay

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

Reviewed yesterday
A TripAdvisor Member
via mobile
Fabulous family cruise

Captain Russ and his lovely wife gave us a memorable sailing trip around Key Biscayne on the... read more

Reviewed August 8, 2017
Paul B
Dubai, United Arab Emirates
Read all 123 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!
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4000 Crandon Blvd, Miami, FL 33149-1102
+1 786-218-2454

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Reviews (123)
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1 - 10 of 118 reviews

A TripAdvisor Member
Reviewed yesterday 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
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

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

Thank YohamaMichelle
Reviewed June 29, 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 June 18, 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 June 14, 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 June 16, 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 March 26, 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 March 24, 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 March 24, 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
Reviewed March 20, 2017

I have sailed on Captain Sir three times now and can say that every experience has been superb. Frankly, I cannot say one negative thing about the charters. In fact, the boat is pristine, their hospitality is top-notch, and each of my trips have been...More

Thank suzanne1007
RussellSusan, Owner at Captain Sir Charters - Private Day Tours, responded to this reviewResponded March 23, 2017

We love having repeat guests and so glad you chose to celebrate your Dad's 70th birthday on a sailing trip on CAPTAIN SIR! this year. We are the perfect venue for these kinds of family celebrations -- it's intimate, peaceful and quiet -- relaxing for...More

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Questions & Answers
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.
January 16, 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