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Florida Keys Sailing

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Address: Turn onto 35th Street, 3502 Gulfview Ave, MM49, Marathon, FL 33050
Phone Number:
+1 305-619-0140

Tartan 34C, ready to sail in the keys.

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The Jolly Rover

While in Key West take the sailing schooner The Jolly Rover. It's a two hour trip complete with occasional cannon fire. Rio, our Captain will not disappoint you and you'll even... read more

Reviewed 26 January 2015
Cathy W
Ruckersville, Virginia
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47 Reviews from our TripAdvisor Community

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Showing 47: English reviews
Ruckersville, Virginia
Level Contributor
46 reviews
16 attraction reviews
common_n_attraction_reviews_1bd8 14 helpful votes
Reviewed 26 January 2015

While in Key West take the sailing schooner The Jolly Rover. It's a two hour trip complete with occasional cannon fire. Rio, our Captain will not disappoint you and you'll even learn a bit about sailing.

3 Thank Cathy W
Centerville, Ohio
Level Contributor
2,595 reviews
780 attraction reviews
common_n_attraction_reviews_1bd8 3,913 helpful votes
Reviewed 16 March 2014

We like nearly all of the Marathon sail companies. We like the absence of sea sickness. We like NOT planning ahead.

4 Thank SavantIII_11
Knoxville, Tennessee
Level Contributor
72 reviews
29 attraction reviews
common_n_attraction_reviews_1bd8 41 helpful votes
Reviewed 26 January 2014

We visited on our own sailboat from Baltimore, MD...it took several months to arrive, and we spent 2 months in the Keys before heading North again. People are friendly, there are great bus and taxi services at affordable prices, and we found plenty of interesting things to do ranging from bird sanctuaries to tiki bars to little out of the... More 

4 Thank 4knots
Cary, North Carolina
Level Contributor
166 reviews
63 attraction reviews
common_n_attraction_reviews_1bd8 70 helpful votes
Reviewed 16 October 2013

We went on the sunset cruise, thinking that we would sail around the area a bit before the sunset, and be able to watch the sun set over the water. First we were a half hour delayed while we waited for a late couple. Captain Dale and Lynn were both friendly and pleasant, but all we did was circle the... More 

17 Thank luvin2go
Shelby Township, Michigan
Level Contributor
31 reviews
10 attraction reviews
common_n_attraction_reviews_1bd8 16 helpful votes
Reviewed 3 August 2013

We spent the week in Marathon and rented bikes and kayaks and it was wonderful. A manatee swam right under us and we saw dolphins and flying fish. This is a beautiful place to vacation and would love to retire here and remain barefoot at all times. Great trip and much to do including sailing.

2 Thank CarrieMI2013
Level Contributor
56 reviews
15 attraction reviews
common_n_attraction_reviews_1bd8 31 helpful votes
Reviewed 24 July 2013

Living in the Keys for 15 years but visiting for an additional 30 years prior, I have seen many changes - many are not good. But I am still in awe of the beautiful and unbelieveable color of the waters here. Sailing you must be careful as many areas are very shallow, and our environment is very fragile. Please abide... More 

5 Thank keywestbeachgirl
Level Contributor
71 reviews
40 attraction reviews
common_n_attraction_reviews_1bd8 42 helpful votes
Reviewed 21 April 2013

We did this and scuba diving , one of those things in life you never forget, really loved it! try the key hopper its great

1 Thank scott l
Syracuse, New York
Level Contributor
5 reviews
3 attraction reviews
common_n_attraction_reviews_1bd8 10 helpful votes
Reviewed 7 April 2013

We had a very pleasant sail with Captain Dale on the Sirius Catamaran. He was very nice and informative. The weather was beautiful. We even saw dolphins.

2 Thank JGak
Ottawa, Canada
Level Contributor
33 reviews
common_n_attraction_reviews_1bd8 20 helpful votes
Reviewed 11 March 2013

We sailed on "Danger" with Danger Cruises. Excellent value with the wine and snacks provided to view the world famous sunset in Key west.

3 Thank Patricia S
Ames, Iowa
1 review
common_n_attraction_reviews_1bd8 3 helpful votes
Reviewed 18 July 2012

Well, I've had the full experience. In 2010 I took the basic keel boat and basic cruisng with my wife on the Catalina 30 (Salina), J24 (Chaquita), and C&C 36 (Sea Wings). Over Christmas of 2011, we bareboated his Irwin 34 Serendipity for a week with my parents and three little daughters. We're just planning our adventure for 2012.... Bruce... More 

3 Thank Gary L

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Lake Orion, Michigan
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  • How should I dress for this tour?