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Sail Florida Adventures

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Travelers talk about
“captain james”(35 reviews)
Sunset sailing trips in Key West should be romantic with friends and or family. That's why we only offer private Sunset sails. Our beautiful sail boat is not rented to anyone else during your sail. As matter of fact in most cases its cheaper than...more
Suggested duration: 2-3 hours
951 Caroline St, Conch Harbor Marina Slip# 3, Key West, FL 33040-6720
+1 305-587-9158
Ways to Experience Sail Florida Adventures
from $350.00
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from $255.38
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Reviews (78)
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All reviewscaptain jamesprivate sunsetloggerhead keycrackersprivate chartervisit key westboatmateblastknowledgekeyskayaking
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1 - 10 of 77 reviews
Reviewed 4 weeks ago

Capt. James was great. His sailboat, Talisman is a very nice 41' sailboat. We were lucky that we hit good weather, although the day was a bit windy and we had 3' - 4' seas, Capt. James took us into more protected waters and we...More

Thank Luis V
Reviewed July 8, 2018

Captain James and His 1st mate Emilia made sure our sail was all that we could ask for. The service was excellent, they were very receptive to our wants and needs, the snorkeling equipment was in good condition (my son got a brand new set)....More

1  Thank TamiR137
Reviewed June 12, 2018

Our family spend a wonderful evening on the private sunset sail with Captain James last week. Our children, ages 8-15, all said it was their favorite thing all week! James took the time to show them the hows and why of sailing and let them...More

Thank rcg0ld
Reviewed June 5, 2018 via mobile

Captain James deserves the utmost respect and highest praise for his commitment to pleasing his clients. We had high hopes for our adventure, but we're uneasy booking relying only on internet reviews. The reality is that all of our expectations were exceeded!! He was very...More

Thank Chad W
Reviewed May 29, 2018

We had a great afternoon sail with Capt. James. He was very flexible and accommodating with our plans. We scheduled a snorkeling/sunset cruise for 4 hours. When it became apparent that clouds were going to ruin the sunset, he gladly rescheduled us for earlier in...More

Thank danfalke2018
Reviewed May 21, 2018

Sail #1 ... You know the road - the one paved with good intentions? Yep, that one. We signed up for a sunset cruise. At the appointed time we met our intrepid caption, Dano, and headed to the boat through raindrops. (Ah, Key West, you...More

2  Thank LisaMalmar
Reviewed May 2, 2018

Be prepared for last minute changes( we had a couple of them). On our trip the motor ran most of the trip and the other boats did not seem to have problems with the wind. I think the trip could have been better.

Thank Randy S
Reviewed April 29, 2018

I learned to pilot a sailboat! Capt Dan was a very experienced sailor and more than willing to share his knowledge and experiences - he even put limes in the beer! He let me pilot the boat for over 2 hours of the 4 hour...More

Thank Rosemary S
Reviewed April 26, 2018

This was the true highlight of our trip to Key West. Capitan James was so knowledgeable and a perfect host for our sunset sail. Our two teenaged boys were really interested in the boat and he took the time to explain and teach them about...More

Thank laurakreitz
Reviewed April 25, 2018

We had a great time on our private sunset sail! The weather was perfect. Just the right amount of wind and beautiful sunset. It was my husbands 80th BD and it meant a lot to him that he was allowed to sail the boat. Can't...More

Thank liptakl
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Questions & Answers
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September 10, 2016|
AnswerShow all 2 answers
Response from James B | Property representative |
For a 4 day trip that includes Captain and mate. $4200 for 2 with an additional $25 per person per day beyond two. Three meals a day cooked to order. kayaking, snorkeling at loggerhead key (little Africa)and dry tortugas... More
April 19, 2016|
Response from James B | Property representative |
Hello, Yes we do hold a permit to charter to Fort Jefferson. We only charter 4-5 day charters due to the remote location its up to a 12 hour sail. If you have more than one day you may try grande Nellie out of stock... More