Wayward Sailor
Wayward Sailor
5
About
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.
St. John, U.S. Virgin Islands

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(102 reviews)
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Most Recent: Reviews ordered by most recent publish date in descending order.

Detailed Reviews: Reviews ordered by recency and descriptiveness of user-identified themes such as wait time, length of visit, general tips, and location information.

Popular mentions

5.0
5.0 of 5 bubbles151 reviews
Excellent
137
Very good
8
Average
4
Poor
1
Terrible
1

sljones
St. Thomas69 contributions
5.0 of 5 bubbles
Aug 2011 • Family
We sailed with Captain Phil in the summer of 2011 and enjoyed the whole experience. He's very knowledgeable about STJ,the VI, and marine ecology. I wasn't concerned that he carefully handled a few marine creatures, and I didn't ask them how they liked it. Then again, I didn't ask the seafood I ate on STJ how they liked, either. Maybe I should have? But then, I'm an insensitive Republican so only so much can be expected of me. That said, as greedy as I am (being a Republican and all), I'm more than happy to tip someone who does a good job, as is expected in the tourism business, even in Colorado (last time I was there), and my family and I are still enjoying the tasteful hats and t-shirts Cap Phil sold us at the end of the day. The Wayward Sailor cap is now my favorite to wear when I "captain" our family speed boat! ;-)
Written July 1, 2012
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Bugsylover
Boulder, CO57 contributions
3.0 of 5 bubbles
Feb 2012 • Couples
Captain Phil claims to be a naturalist but he chose to use his motor instead of his sails while taking us to Lavongo Cay from Cruz Bay on St. John for a snorkel trip. There was plenty of wind, but there was no negotiating this. He is very dictatorial. To boot, I had to listen to a political Republican rant on the way over. On the plus side, he was very knowledgeable about the coral reefs and shared some of his knowledge with all of the people on the tour. His boat is very clean and orderly. Handling some of the sea life so snorkelers could enjoy it might have pleased some of them, but I wonder how the sea life felt about that? Cost was $70 but he outwardly asks for a tip and tries to sell you his hats and shirts after the trip. Captain Phil does not seem to like what he does for a living... comes across as rather bitter. But the reefs on the south side of Lavongo were worth seeing for an approximately 45 minute snorkel and thus it was worth putting up with him for the 3 plus hours of the tour.
Written April 2, 2012
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

jcontre1
Phoenix, AZ93 contributions
4.0 of 5 bubbles
Sep 2011 • Couples
We recently returned from a great day sail adventure with Capt Phil and Tarn on the Wayward Sailor. We opted for the all day BVI excursion to Jost Van Dyke. Capt Phil met us near the ferry wharf in Cruz Bay on time at 8am and we quickly tendered out to the Wayward Sailor which he keeps moored in the harbor.

Phil immediately gave us a safety briefing on the boat including locations of life jackets and other equipment as soon as we were on board. The Wayward Sailor was Phil's home for over 20 years and she has been lovingly maintained. As a sailor myself, I appreciate the effort it takes to keep a boat in tip top condition. She is sturdy, comfortable and safe.

We set out for snorkel stop before heading to Jost where Phil and I got in the water. We saw a very rare black and white reef shark and some very interesting coral formations. Then we sailed across the channel to Jost where we cleared customs at the shack next to Foxy's. Normally Phil likes to have lunch at Foxy's but as it was the off season, we motored over to White Bay (10 mins away) and anchored for lunch at the famous Soggy Dollar Bar. We bought Painkillers and tee shirts and I successfully hooked the ring (go there are you'll see what I mean).

We had time for a quick swim after lunch and then we sailed back across to St John. Captain Phil is an interesting character with hundreds of stories--one or two of which might be true (he is a sailor afterall...). Tarn is warm, friendly and inviting and together they make a fine team.

One thing to note: Phil likes thing done his way, particularly on the boat and in the water. If you are very independent or not prone to following directions, this may not be the charter boat for you.

That having been said, we had a nice day with Phil and Tarn and we highly recommend then to anyone looking for a nice sail from St John.
Written September 20, 2011
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Stephen s
New England33 contributions
5.0 of 5 bubbles
My wife and I are advanced snorkelers, and we went out with Captain Phil last week. Without question, it was the highlight of our vacation. Earlier in the week we went on a catamaran snorkel trip, and while it was okay, the 30 or so on the boat was overwhelming... and kids that disrespected the Captain made it worse.
Wayward sailor takes no more than six on a personalized trip, with an amazing man named Captain Phil. He does not sit by and wait for you to come back to the boat... he comes with you and tells you all about the marine life you are seeing. So for advanced it is great, and for beginners too... an all-around wonderful trip. we would highly recommend and we'll be going next time.
Thanks Captain Phil!!!
Written March 30, 2010
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Hunter2312
Nutley, NJ2 contributions
5.0 of 5 bubbles
Sep 2022
Several years ago. we had the great pleasure of sailing on the "Wayward Sailor" and wanted to rebook. Regrettably Captain Phil has passed on, and I wish him calm seas and following winds. His legacy lives on in Captain Daniel Benson! Dan is a second generation sailor, a capable and worthy successor to say the least. Our primary goal for the day was to scatter my wifes ashes between STJ and the BVIs. This emotional task was handled exceptionally well, and with respect. Afterwards we had a great day sailing and snorkeling with Dan and his Mate Mitch. Both were quite knowledgeable about the islands and aquatic wildlife. Can't wait for our next trip!
Written September 20, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

MaryAWhite
Erie,PA56 contributions
5.0 of 5 bubbles
Jan 2021 • Family
Our group - grandparents, parents and teens - enjoyed our 1/2 day sail and snorkel adventure. Captain Phil is extremely experienced and explains everything clearly. Highly recommend!
Written January 1, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Jbonander
Atlanta, GA101 contributions
5.0 of 5 bubbles
Dec 2019 • Family
We’ve done a number of day sails through the Caribbean and I can’t say we’ve met many like Captain Phil. The experience and stories are worth the charter alone. We brought our 13 yr old for his first snorkel trip and Phil took *a lot* of care and time to instruct him on snorkeling basics - couldn’t have asked for more. Memorable beyond words - if you can, charter with Phil and Tarn, you won’t regret it.
Written December 25, 2019
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

larissas05
1 contribution
5.0 of 5 bubbles
Aug 2019 • Family
Phil and Tarn made sure to add a great experience to our annual family vacation! Both are extremely welcoming and knowledgeable and should be on everyone's list when staying in St John. Thank you for an unforgettable experience!!!
Written August 17, 2019
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

GAViatoribus
2 contributions
5.0 of 5 bubbles
Aug 2019
Highlight: This experience was worth every penny.

My wife and I booked a day sail (8AM - 4PM) from St. John to Jost Van Dyke via the Wayward Sailor website. The user interface on the website was easy to use.

We met Captain Phil right on time at the Cruz Bay, from there on out it was smooth sailing. My wife suffers from motion sickness, both Captain Phil and Mate Tarn were sympathetic and helpful (Captain Phil had some special bracelets).

The day started with some brief snorkeling off Lovango, where we saw some truly beautiful aquatic life, including a Sea Biscuit that Captain Phil let us hold. From there it was off to Jost Van Dyke.

The sailing itself was interesting (beautiful waters and general interest of sailing on a yacht for the first time), but Captain Phil was very entertaining (he has been sailing in the Caribbean for long enough to collect a host of interesting stories).

Once we got to Jost, the Captain took care of BVI customs (remember to bring your passport) on our behalf while we took in the sights. After that it was lunch at Foxy's Bar (would recommend the Fish & Chips) and a short visit with Foxy himself (highly recommend if he is there). Next was a short sail up the coast where the Captain put us ashore by ourselves for some relaxation and a Painkiller at the Soggy Dollar.

On most of the journey to and the return sail we sat upfront (would recommend for the motion sick) with Tarn (the only Tarn we've ever met) who was wonderful and very knowledgeable about local history and myths and an array of other topics. She helped us pass the time in good fashion and kept us supplied with whatever we needed.

Overall this was one of the highlights of our honeymoon. For those looking for something different and adventurous, we would wholeheartedly recommend. You'll meet some truly amazing people all while enjoying a sail with incredible views to some cool places.

P.S. The brownies and pineapple were also good.
Written August 15, 2019
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Teresa's Adventure Club
Chicago, IL2 contributions
5.0 of 5 bubbles
Jul 2019 • Family
Best sail and snorkel tour of all on St John. Don't let looks deceive you! Yes, there are "sexier" boats but none can compare with the rich history and authentic sailing experience aboard Wayward! Captain Phil is a big fish who led the way on our snorkeling-- taking us through structures we never would seen or explored on our own like underwater passages and canyons- snorkeling felt like an adventurous sport following his lead. Our family of 4 including my 15 year old very athletic son and 13 year old daughter, received more than expected sailing with legendary Captain Phil and First Mate, Tarn. The time and care taken to suit each of us personally with snorkel gear as well as the care he took getting to know a bit about my teens meant we connected with this salty, big-hearted sailor. My kids walked away knowing something about character, endurance and living meaningfully in their day to day. And very happy to have brownies after their wraps! Yum. Thank you for sharing stories, Captain Phil! We would follow Captain Phil through any underwater canyon!
Written July 29, 2019
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

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Wayward Sailor - All You Need to Know BEFORE You Go (2024)