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“Captain Chalker is the Best!”
Review of Wayward Sailor

Wayward Sailor
Certificate of Excellence
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Attraction details
Owner description: St. John, VI Day sail charters, voted Best Day Sail Charter boat on St. John for the past five years, specialize in guided snorkeling, eco-tour with marine naturalist, personal service, family oriented; full day sails,half day, sunset sails, Jost van Dyke, BVI; snorkel reefs accessible only by boat, all inclusive, discounted price, fresh Caribbean lunches, homemade brownies, maximum of six guests, safe, comfortable classic 30' sloop, Coast Guard approved, beginner snorkelers welcome.
Reviewed March 24, 2014

We had a great time on the Wayward Sailor, and Captain Chalker was very friendly and knowledgable about the islands. The snorkeling area he took us too was great and close by beautiful coral reefs. We recommend taking a sailing tour with him if you want a more intimate and relaxing experience.

Thank pennykim
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
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49 - 53 of 88 reviews

Reviewed February 6, 2014

I grew up on the Gulf Coast of Florida and thought I was a know it all. I was wrong. I have learned so much from Captain Phil on my three snorkeling trips. This has become a family tradition for us to sail with him when we visit the island. We always have a great day and lots of laughs and a new adventure. And as a Mom, what a treat it is for me to just step on the boat and have everything taken care of. The drinks, lunch, snorkel gear, and activities are already taken care of. My husband and I just returned a couple of days ago and are already planning our next trip with the Wayward Sailor . If you travel to the island it is a must to get in the water and snorkel and see for yourself the beauty of the reef and the alien water world of the octopi and fish. Don't worry if you have never snorkeled before or feel that you are not a "great" swimmer . You are in good hands with Captain Phil and his first mate Tarn . They will take good care of you and your family.

Thank Tbadali
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed January 4, 2014

We arrived at the planned meeting spot; the gazebo in the village square. Capt. Phil met us. My boyfriend was signed up for snorkeling, I was going along for the boat ride, I have advanced multiple sclrosis. I was using my walker/rollator. Capt. Phil didnt seem bothered by the fact I had challenges. I've been on other sailing adventures where I was discouraged by some boat hands to not even go!! I'm just a size 6, so that didnt have anything to do with it!! Capt. Phil made me feel welcome!! We took a small dingey to the awaiting sailboat anchored a bit off shore. Capt. Phil was very patient with me, and helping me, as I manouvered my body into, and out of both the boats. The weather was perfect!! Capt. Phil detailed the snorkeling procedures to my boyfriend. He's snorkled many times before, but, you can never hear correct techniques of snorkeling enough!! Humans are not perfect, we do make mistakes. (I'm just a retired college instructor) Thats why airlines go over procedures before "every" flight. I didnt realize Capt. Phil was an ordained minister, too, when we were with him, and Tarn, but I'm not suprised!! He has a very big, and bright aura!! I really enjoyed the discussion he shared with us about octopi. And other sea creatures native to the area. We had a very enjoyable afternoon with Tarn, and Capt. Phil. I'm looking forward to returning to St. John!! and meeting up with Capt. Phil and Tarn, again!!

Thank Mariette B
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed November 15, 2013

There's good and there's not so good. First the not so good.... My husband and I mentioned multiple times that we had rented dinghys and sailed several times. We also told Capt Phil and Tarn we've snorkeled 3 times this week. We are also responsible thirtysomethings. We felt like Capt Phil ignored all of this and provided over the top instructions on everything. We felt very much like the day was all his agenda. From the time we met him, we felt very uncomfortable having drinks on the boat. In fact, it is stated on the website that they provide beer and soft drinks. Clearly, when the selection is lukewarm Budweiser and Miller Light, they don't want you to have a drink. I respect that Capt Phil is a recovered alcoholic; however, we are not. We wanted to relax and enjoy our $300+ sail, but we felt more like we were in Navy Seals training. We felt it was awkward, sort of like Big Brother watching us, when they insisted that we put everything on the same tab. Honestly, I think they were counting our painkillers at the Soggy Dollar Bar. Agree with reviewers that said he's dictatorial, and if you are the slightest bit independent or knowledgable of a boat, the ridgedness can be too much.

We've chartered a private sailboat in the past and were able to have a lot of fun. We feel that the Wayward Sailor should market toward families or specifically those looking to have an educational, instructional day at sea.

On a positive note, Capt Phil and Tarn ensured we were safe and sound the entire trip. He is extremely knowledgable, and had the conditions been better for snorkeling I'm sure we would have seen and learned a great deal.

3  Thank sbc1209
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed November 1, 2013

Although he was on time and nice enough, website says sunset cruise is an hour and a half. Cut it off at less than an hour. For 280.00 plus tip not worth it. His wife kept calling. Hope you will have better luck.

2  Thank David B
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.

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