We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
Want the lowest hotel prices? You're in the right place. We check 200+ sites for you.

Breezin Sailing Charters

Certificate of Excellence
Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Get directions
Address: 201 William St, Dock E Slip #7, Key West, FL 33040-6679
Phone Number:
+1 305-797-1561
Website
Description:

Breezin the Keys with Captain Dees - Private sailing charters, sailing...

Breezin the Keys with Captain Dees - Private sailing charters, sailing lessons, snorkeling, weddings and memorials. Learn the fundamentals of sailing! Or just sit back, relax and enjoy a beautiful Catalina 42 foot sailboat.

read more

TripAdvisor Reviewer Highlights

Read all 170 reviews
Visitor rating
  • 168
    Excellent
  • 0
    Very good
  • 0
    Average
  • 0
    Poor
  • 0
    Terrible
Just Amazing

I am SO thrilled we booked this. It's been nearly two weeks now and I'd give anything to be going back and do it all again. The experience was just perfect in every way. Dennis is... read more

5 of 5 bubblesReviewed 4 days ago
lucycharles86
,
London, United Kingdom

Similar Things to Do in Key West

Add Photo Write a Review

170 Reviews from our TripAdvisor Community

Traveller rating
Traveller type
Time of year
Language
Showing 168: English reviews
London, United Kingdom
Level Contributor
3 reviews
5 of 5 bubbles Reviewed 4 days ago NEW

I am SO thrilled we booked this. It's been nearly two weeks now and I'd give anything to be going back and do it all again. The experience was just perfect in every way. Dennis is a charming host and Susan, who was also sailing with us on the day, was just lovely. Everything about the sail was brilliant and... More 

Helpful?
Thank lucycharles86
Plymouth Ma
Level Contributor
3 reviews
common_n_attraction_reviews_1bd8 1 helpful vote
5 of 5 bubbles Reviewed 5 days ago NEW

We also happened on Dennis and the Breezin by accident. We had booked a 3 hour dolphin trip thru our hotel which brought us to the dock. The original boat was in dry dock so there was a replacement boat, which honestly was in disgraceful shape. After listening to the captain's explanation and was told there would be no bathroom... More 

Helpful?
Thank waitressindistress
Saint Louis, Missouri
Level Contributor
53 reviews
19 attraction reviews
common_n_attraction_reviews_1bd8 11 helpful votes
5 of 5 bubbles Reviewed 4 weeks ago

My wife and I were in town for a babymoon last summer and were booked on a sunset cruise with a different vessel, but do to scheduling conflicts they set us up with Dennis to take care of us. What a fortunate surprise for us. Dennis was absolutely amazing and we had such a great time. We plan on coming... More 

Helpful?
Thank Brian L
Level Contributor
11 reviews
8 attraction reviews
common_n_attraction_reviews_1bd8 1 helpful vote
5 of 5 bubbles Reviewed 25 December 2016 via mobile

Amazing time, extremely personable April and Dennis, had an absolute blast and am jealous that they get to do that every day. Snacks were quality and drinks came as much as you wanted. Tipped 100$. Worth every penny. Got to pilot for as long as I wanted as well. Spent most of time on front of boat enjoying the beautiful... More 

Helpful?
Thank 328ijunkie
Sewell, New Jersey
Level Contributor
116 reviews
9 attraction reviews
common_n_attraction_reviews_1bd8 45 helpful votes
5 of 5 bubbles Reviewed 14 November 2016

There is no better way to see Key West than on the water at sunset. Captain Dennis and April were more than accommodating even letting a power boat captain like me take the wheel for a while. This is by far the best bang for your buck water activity on the island. We will return.

Helpful?
Thank Jemurf
Level Contributor
2 reviews
5 of 5 bubbles Reviewed 25 October 2016

Visited Key West from the UK mid September. Planned a few months before to book a sunset cruise to propose to my now Fiancé, Was not disappointed. Captain Dennis and April were amazing. They made us feel very welcome and supplied us with fresh fruit and drinks. the sunset itself was perfect. then on the way back in they sailed... More 

Helpful?
Thank Matt C
Sugar Land, Texas
Level Contributor
29 reviews
15 attraction reviews
common_n_attraction_reviews_1bd8 6 helpful votes
5 of 5 bubbles Reviewed 17 October 2016

This was without a doubt the best snorkeling trip I have taken. We chartered the sailboat for 4 hours. Because of the weather Dennis pushed our trip for 3 hours so we would have the calm water at the Coral Reef. He had water, soft drinks, beer and wine waiting for our trip to the Coral Reef. It was beautiful... More 

Helpful?
Thank Steffany S
Atlanta, Georgia
Level Contributor
1 review
5 of 5 bubbles Reviewed 11 August 2016

Fantastic option if you want a more private sunset sail as opposed to a booze cruise. Captain Dennis and his first mate April were the friendliest people. We loved every minute of our experience aboard Breezin. We each got to take our turns sailing and learning the ropes. Enjoyed a sunset view from the front of the boat .You can't... More 

Helpful?
Thank Laur928
Level Contributor
11 reviews
4 attraction reviews
common_n_attraction_reviews_1bd8 1 helpful vote
5 of 5 bubbles Reviewed 2 August 2016 via mobile

This was the perfect way to end our trip. A private sunset cruise w a captain who loves what he does. So much nicer than being on a boat with 30+ strangers and not having personalized attention. We were served fresh fruit, cheese and crackers, wine and beer. We were able to play the music of our choice and both... More 

Helpful?
Thank Michelle B
Baltimore, Maryland
Level Contributor
8 reviews
4 attraction reviews
common_n_attraction_reviews_1bd8 10 helpful votes
5 of 5 bubbles Reviewed 19 July 2016

Captain Dennis has impressed us so much over the years we've sailed with him repeatedly and even had him marry is several years ago. We sailed with him on Breezin' recently and enjoyed snorkeling near Sand Key Light. His charters are customized for his passengers. You can learn to sail, swim, talk books, relax, and simply enjoy life aboard Breezin'.... More 

Helpful?
Thank leekinginc

Travellers who viewed Breezin Sailing Charters also viewed

 

Been to Breezin Sailing Charters? Share your experiences!

Write a Review Add Photos & Videos

Is This Your TripAdvisor Listing?

Own or manage this property? Claim your listing for free to respond to reviews, update your profile and much more.

Claim Your Listing

Questions & Answers

Questions? Get answers from Breezin Sailing Charters staff and past visitors.
Posting guidelines
Typical questions asked:
  • Will you pick up and drop off at my hotel?
  • I have a family of 7. Can your tour accommodate all of us together?
  • How should I dress for this tour?