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All 248 Miami Attractions »

Miami Sailboat Private Day Charters

4000 Crandon Boulevard, Miami, FL 33149
786-218-2454
Ranked #6 of 87 tours in Miami
5.0 of 5 stars 25 Reviews
Type: Tours
Owner description: Want to experience your best vacation day in Miami? Take a private sailing charter aboard the NEWEST and most elegant charter sailboat in Miami --...... more » Owner description: Want to experience your best vacation day in Miami? Take a private sailing charter aboard the NEWEST and most elegant charter sailboat in Miami -- award winning service and cuisine! Voted "Best Weekend Getaway" by Miami New Times newspaper. Aptly described as "equisite luxury and exceptional value." Snorkel, swim, or learn to sail. Be pampered by your captain and crew -- enjoy fine dining while you "sight sea" -- relaxing way to spend a day on Biscayne Bay!! « less
Useful Information: Activities for older children, Activities for young children, Stroller parking
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25 reviews from our community

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Date Rating
Hamburg, Germany
2 reviews
Reviews in 2 cities Reviews in 2 cities
5 of 5 stars Reviewed May 1, 2012

If you are looking for a very special and romantic moment or present, a sunset sailing trip with Captain Sir! Is the best choice! We spent a gorgeous evening on Captain Sir! Russell and Susan were perfect hosts and made it so special! I don’t know where to start…Russell even hoisted the German flag for us and Susan prepared “candles”... More

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Munich, Germany
1 review
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed March 17, 2012
1
person found this review helpful

You have just ONE DAY in Miami? And of course want to do the most unique thing the Magic City has to offer? --> Then: Just experience REAL MAGIC! This is how it works: Charter CAPTAIN SIR! and spend the most wonderful and unforgettable hours - or maybe even (a) day(s) - aboard this luxourius yacht, sailing on beautiful and... More

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Sewalls Point, Florida, United States
1 review
5 of 5 stars Reviewed January 10, 2012

When you board Captain Sir you leave your troubles at the Dock. Russell and Susan Boley (Capt., First Mate & Owners) do all that is possible to make your day truly YOUR DAY. To satisfy our love of sailing we had chosen Captain Sir many years ago for day charters and many times since have experienced the best that day... More

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USA
Reviewer
5 reviews 5 reviews
Reviews in 3 cities Reviews in 3 cities
8 helpful votes 8 helpful votes
5 of 5 stars Reviewed December 28, 2011
5
people found this review helpful

We just got back from a superb, all-day trip around Biscayne Bay with Captain Sir. We had three elderly people and two forty-year-old couples. Russel started with a short safety talk and tour of his impressive sailboat, one of the cleanest and best equipped boats I have ever seen (hot shower on swim platform, flushing toilets - first-class throughout, probably... More

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San Juan, Puerto Rico
1 review
7 helpful votes 7 helpful votes
5 of 5 stars Reviewed December 8, 2011
7
people found this review helpful

My family and I went on Captain Sir as a holiday family gift. From start to finish, we were consistently impressed with the ambiance and excursion they had designed for us. You have a peaceful journey combined with amazing views of miami, delicious homemade fresh food, under the stars, and friendly environment. I am begging my family to make this... More

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Coral Gables, Florida
1 review
6 helpful votes 6 helpful votes
5 of 5 stars Reviewed December 1, 2011
6
people found this review helpful

My husband and I took our adult children and their spouse and significant other on a sundown sail. When we first arrived we were greeted by the Captain's warm and inviting smile, which extended once aboard to his crew mate. The boat was beautiful, impeccably maintained and very comfortable. We were provided with a "tour" and guidance on what would... More

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humphreys@ala.net
Top Contributor
71 reviews 71 reviews
Reviews in 17 cities Reviews in 17 cities
66 helpful votes 66 helpful votes
5 of 5 stars Reviewed November 13, 2011
5
people found this review helpful

We just returned from an amazing harbor dinner cruise with Russell on the Captain Sir. This large 2 bedroom 2 bath sailboat is beautiful, new and spotless. Russell has thought of everything to make your trip comfortable and luxurious. Reclining cushions for stargazing on the bow, Sirius XM music of your choice in the background, romantic glowing pillar candles, wine... More

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Frankfurt, Hessen, Germany
1 review
5 helpful votes 5 helpful votes
5 of 5 stars Reviewed November 10, 2011
5
people found this review helpful

Hi guys, we spent a day on the boat with Captain Russell after our wedding at Miami Beach. We would like to thank Russell for that kind of experience we will never forget. The sailing was perfect, the food and drinks were delicious! Especially the award-winning and selfmade Key Lime Pie! No words can describe that taste... You must have... More

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Savannah, Georgia
1 review
5 helpful votes 5 helpful votes
4 of 5 stars Reviewed September 9, 2011
5
people found this review helpful

We chartered the " Captain Sir" for a four day cruise to the Florida Keys. Captain Russell & his wife Susan were wonderful. They are very accomodating & fun. The service was exceptional. We were completely spoiled from the moment we stepped on the dock. The sailboat is beautiful & very clean. Russell is a fabulous chef-his rack of lamb... More

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amjur613
Reviewer
3 reviews 3 reviews
Reviews in 3 cities Reviews in 3 cities
8 helpful votes 8 helpful votes
5 of 5 stars Reviewed September 7, 2011
5
people found this review helpful

If you want to have the most romantic evening of your life, this could be it. A fantasic dinner, great music, friendly but unobtrusive Captain Russ and crew (his delightful wife) make this an unforgettable experience. More

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