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Sailing Winsome Charters

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Address: 501 S. Beach St, Daytona Beach, FL 32114
Phone Number:
+1 904-631-7074
07:00 - 22:00
Closed now
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Sun - Sat 07:00 - 22:00

Winsome, a classic 36.5 foot Pearson Sloop, is available for full-day or...

Winsome, a classic 36.5 foot Pearson Sloop, is available for full-day or half-day sailing charters on the scenic Intracoastal Waterway (Halifax River in the Daytona area), or the Atlantic ocean through Ponce Inlet. Evening sunset-cruise charters, sailing lessons, marriages at sea, and memorial ash scattering services are offered. Refreshments are provided. $70 per hour includes six passengers.

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TripAdvisor Reviewer Highlights

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Sunset sailing

We are wanting to learn to sail to hopefully charter and or own our own sailboat some day in the future and Captain Rick was very informative in all aspects from what type of... read more

Reviewed 3 weeks ago
DeBary, Florida
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25 Reviews from our TripAdvisor Community

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Showing 25: English reviews
DeBary, Florida
1 review
Reviewed 3 weeks ago

We are wanting to learn to sail to hopefully charter and or own our own sailboat some day in the future and Captain Rick was very informative in all aspects from what type of sailboat to purchase to how to sail one. Going through the Inlet was exhilarating and a blast! Thank you for an amazing Sunday afternoon / evening.... More 

Thank cwhite279
P365Sailor, Owner at Sailing Winsome Charters, responded to this review

Sincerely appreciate your comments. Look forward to being of assistance on the future!!!! More 

Level Contributor
27 reviews
9 attraction reviews
common_n_attraction_reviews_1bd8 5 helpful votes
Reviewed 23 July 2016 via mobile

This is just a guy who is retired and taking people out on his sailboat for fun. It wasn't super windy when we went and we didn't see any dolphins unfortunately but we still had tons of fun. He has great stories if you just ask him questions and he likes to read as well if you want to have... More 

1 Thank KayDawn97
Level Contributor
26 reviews
10 attraction reviews
common_n_attraction_reviews_1bd8 7 helpful votes
Reviewed 15 July 2016 via mobile

We had a great experience. It was relaxing and beautiful and Captain was very friendly. It was great to be out on the water, see a few dolphins and just enjoy the sounds of the sea.

Thank travelingparty5
Deltona, Florida
1 review
common_n_attraction_reviews_1bd8 6 helpful votes
Reviewed 23 May 2016

From the moment I met Captain Rick and went aboard his beautiful sailboat, Winsome, I knew I was going to be okay despite what I had come there to do that day . . . . to scatter my dear brother's ashes. But, it actually began sooner than that. It began with my initial phone call when I was searching... More 

6 Thank jackiecandler3
1 review
Reviewed 4 May 2016 via mobile

Rick responded to my call immediately and started to help me plan an appropriate cruise to celebrate a death in our family. He was flexible with our schedule and made special arrangements to meet our needs. He even brought flowers for us to drop in the ocean. Capt. Rick's skills at sailing, put us all at ease. Thank you for... More 

Thank Eva S
Danielson, CT
Level Contributor
52 reviews
21 attraction reviews
common_n_attraction_reviews_1bd8 35 helpful votes
Reviewed 23 April 2016 via mobile

Have to agree with all the other reviews! Captain Rick is amazing. He brought us out for a Sunset Cruise on the inter-coastal in Daytona Beach down to Ponces Inlet. It was a wonderful experience. We had our teenage daughter and her bestfriend with us who are not easily impressed. They loved the boat right, and had smiles the entire... More 

1 Thank CMminera
Orlando, Florida
Level Contributor
19 reviews
5 attraction reviews
common_n_attraction_reviews_1bd8 18 helpful votes
Reviewed 11 August 2015

Wow, my husband and I can't say enough about what a great Captain and teacher Captain Rick was for us this past weekend. We are wanting to learn how to sail and his easy demeanor and plethora of knowledge was all we could have asked for. We now have a great friend and we will definitely be going back for... More 

1 Thank Lostlo45
Washington DC, District of Columbia
Level Contributor
25 reviews
6 attraction reviews
common_n_attraction_reviews_1bd8 12 helpful votes
Reviewed 5 May 2015

If you are looking for an unforgettable experience, just trust me and book it! From my first phone call to check on availability, a very last minute idea (full moon fever!), Rick made me and my family feel welcome and at ease with our customized venture - a bit of sailing, a Florida sunset and a full moon cruise. Several... More 

3 Thank Jillda50
Durham, North Carolina
Level Contributor
24 reviews
5 attraction reviews
common_n_attraction_reviews_1bd8 8 helpful votes
Reviewed 14 January 2015

Rick was a great teacher. He was patient and very good at explaining the concepts. We had a great time and will do it again next time we are in the area.

1 Thank allergicToDairy
Level Contributor
2 reviews
common_n_attraction_reviews_1bd8 2 helpful votes
Reviewed 29 November 2014

This was the most magical travel experience I have had. Our family chartered a half-day trip, and had a hard time coming in after 8 hours. Our boys (19, 16, 10) all thoroughly enjoyed themselves. Captain Rick was a fantastic teacher and accommodating beyond measure.

2 Thank Keri_Rae

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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?