Simplicity Charters
Simplicity Charters
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Simplicity Charters Custom Day Charters Exploring The Best Of The Virgin Islands. Established in 2006, Simplicity Charters knows the best areas without the crowds. Amazing reefs and beaches await. Sailing in the Caribbean with an open bar, island tunes, and some of the warmest and clearest water in the world. Snorkel with turtles, stingrays, a variety of colorful fish, and of course the amazing coral of all shapes sizes and colors. The choice is Simple, book your day in paradise with Simplicity Charters and let us handle the rest. No better way to unwind, relax, and let your stress disappear. LookingforwRdtpour day of sailing, sun, and fun!
Red Hook, U.S. Virgin Islands
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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.
5.0
535 reviews
Excellent
528
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AandJ7237
Naperville, IL7 contributions
Jan 2015 • Couples
I am so disappointed that it took me three trips to St. Thomas to find the Simplicity in St Thomas. We booked a six hour day on the water on the Simplicity Charter about two months in advance. Charlie was quick to respond and gave detailed instructions on where to meet as we were coming in on a cruise. The lunch was advertised as a BBQ chicken and my wife does not eat meat so Charlie advised he would accommodate. We walked off the cruise ship at 8am and immediately found a cab. Be sure to let them know you want to go to fish tales restaurant and not just 'red hook.' It takes about 20-25 minutes to get there. The taxi dispatcher will wait until they fill one of their dump trucks to take everyone over to go over to St. John. We arrived at Fish Tales and Charlie met us at the pier.
We arrived on the Simplicity and went through an introduction. Charlie and Josh treated us like royalty the entire time. They are very easy to get along with. We went out sailing before stopping at a location to snorkel. They provided all the gear and told us where to go. We both went out on our own and found several sea turtles. There were some good views in where we stopped. We came back aboard and Charlie had prepared lunch for us. It was absolutely delicious! My wife loved her Portobello burger and the bottomless beverages.
We continued on and stopped at another location to snorkel. More good views under water. Back onto the boat for some sun and pure relaxation. We came back into the marina and Charlie had a cab waiting for us to get back to the ship. This trip was an absolute blast and would do it again in a second.
Some questions that may come up. How long should I go for? Don't waste your time on a 2-1/2 trip. Do their 6 hour trip. It flew by so fast and it was so much fun. But then someone may say, well what if I miss my cruise ship? I don't think Charlie and Josh are going to let anyone miss their cruise ship. That wouldn't be good for business and there's forums like tripadvisor that would let others know they missed the ship. We didn't even come close to missing ours and wouldn't hesitate one bit if you are a cruise traveler.
Simplicity will only take a maximum of 6 people so its very peaceful and relaxing. The cruises typical get 50-100 sheeple at a crack and pack them onto a cattlemaran. If you like being elbow to elbow with dozens of other people coughing and sneezing all over you then this charter isn't for you. If you like relaxation, excellent service, and a fun time in St. Thomas, I would highly encourage you to book a six hour trip.
Oh I almost forgot Hinckley. She slept for awhile but when it was time to go to work, she popped right up. A+ all around!
We arrived on the Simplicity and went through an introduction. Charlie and Josh treated us like royalty the entire time. They are very easy to get along with. We went out sailing before stopping at a location to snorkel. They provided all the gear and told us where to go. We both went out on our own and found several sea turtles. There were some good views in where we stopped. We came back aboard and Charlie had prepared lunch for us. It was absolutely delicious! My wife loved her Portobello burger and the bottomless beverages.
We continued on and stopped at another location to snorkel. More good views under water. Back onto the boat for some sun and pure relaxation. We came back into the marina and Charlie had a cab waiting for us to get back to the ship. This trip was an absolute blast and would do it again in a second.
Some questions that may come up. How long should I go for? Don't waste your time on a 2-1/2 trip. Do their 6 hour trip. It flew by so fast and it was so much fun. But then someone may say, well what if I miss my cruise ship? I don't think Charlie and Josh are going to let anyone miss their cruise ship. That wouldn't be good for business and there's forums like tripadvisor that would let others know they missed the ship. We didn't even come close to missing ours and wouldn't hesitate one bit if you are a cruise traveler.
Simplicity will only take a maximum of 6 people so its very peaceful and relaxing. The cruises typical get 50-100 sheeple at a crack and pack them onto a cattlemaran. If you like being elbow to elbow with dozens of other people coughing and sneezing all over you then this charter isn't for you. If you like relaxation, excellent service, and a fun time in St. Thomas, I would highly encourage you to book a six hour trip.
Oh I almost forgot Hinckley. She slept for awhile but when it was time to go to work, she popped right up. A+ all around!
Written January 18, 2015
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.
Kelly L
3 contributions
Mar 2018 • Couples
Just spent another great day on the water with Charlie Whitmore! Since Charlie unfortunately lost Simplicity to the storm, we mixed it up and had a great time on the Mojo Deux with Capt. Scott Schroeder (Aqua Blue Charters). As always, Charlie is great company on the island. He always knows what’s going on in the USVI so it’s always great to catch up while we make our way to snorkel stops. This time, we cruised up the north side and snorkeled Maho. We told Charlie and Capt. Scotty we wanted to see some turtles and they delivered! Then it was off to Leinster before heading to Pizza Pi for lunch. We had to insist that Charlie and Scotty grab some pizza. Eventually they caved! (Who can resist delicious Pizza Pi!?). After lunch we snorkeled the area nearby Christmas cove which was great! Then, always trying to make sure we are doing what we want, Charlie gave us the option of a beach or another snorkel. We opted for beach and again it was great to discuss the islands with Charlie and Scotty while the beach goers had their fun. The reefs are active, the water is beautiful, we only wished we had more time to spend in the USVI before moving on. There were turtles, rays, hundreds of fish and all kinds of other beautiful wildlife to see (all of which Charlie can fill you in on). We always look forward to sailing with Charlie because he is such a great and knowledgeable host! We’ve lost count how many charters we have done with him, which speaks for itself. Every time I bring someone new along with Charlie, they go on and on about what an amazing day it was! You are guaranteed to have a great time if you book with him!
Written March 27, 2018
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.
Lovetotravel3816
Pensacola101 contributions
May 2013 • Friends
When we ported in St. Thomas on May 30th, my friend and I, along with a group of friends I had met on Cruise Critic, opted to do the full day sail with Simplicity Charters instead of doing an over booked cruise excursion, and we are so glad we did!! From the moment we showed up at the dock, Charlie and Josh were there to make sure we had a wonderful day! We sailed for a while surrounded by the most beautiful back-drop of St. Thomas and St. John. When we anchored, Josh took 5 of the group snorkeling. Due to sinus issues, I opted to stay on the boat, but Charlie and Hinkley were there to keep me company! I just lounged and relaxed. The same week, my friend and I had just snorkeled the reef wall in Grand Turk, and she commented that this snorkeling was so much better! I hate I missed it but hopefully next time! For lunch, Charlie and Josh served us a delicious meal of chicken, salad, rice, bread, and to top it off, mangos from Charlie's yard. They were yummy!! Well, all of it was yummy!! After lunch, we sailed to another spot and anchored. I took the raft to the beach with Charlie and Hinkley and swam for a while. We then headed back to the boat, floated on the noodles for a while and then made our way back to the dock. During our sail, Charlie called and arranged for their usual taxi driver to be waiting on us when we got back to the dock. She was wonderful...no waiting around to pick up other riders!! On a side note, I would like to say that Charlie and Josh take their jobs very seriously. All safety measures were followed, from the number of people allowed on the boat, to the number of life jackets needed, to the raft,.....etc. This was one of the highlights of our entire trip!! Take this sail!! You won't regret it!!!
Written June 6, 2013
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.
jthompfam
Lake Stevens, WA17 contributions
We recently booked a day sail with Simplicity Charters for a family of 4 (kids ages 9 and 12). Getting to the marina was seamless but if you are traveling from the cruise ship terminal it will cost you $10 per person, each way. The seas were pretty rough during our sail but Charlie navigated us to areas around St. John that were calm and would enable us to do a bit of snorkling. This day sail was very relaxing and we thoroughly enjoyed the company of Josh. He was very informative and genuinely cared about making our time in St. Thomas memorable. We felt as though Charlie on the other hand was all business. We were told that "it was not part of the deal to leave our kids on board" while we snorkled. Our nine year old son does not swim well and had had his fill of snorkling but we wanted to go one more time. When we booked the day sail he had no hesitation of hanging out on the beach if our son did not want to snorkel. I do want to say that Charlie finally decided to take our son to shore to walk the dog but we could have done without the additional commentary. Charlie has a beautiful boat and will be very successful at what he does as long as he realizes that families choose his smaller boat to avoid some of the party boats in St. Thomas and enjoy the flexibility (we were the only group on the boat). I would throughly recommend this day sail to anyone who does not have children. Charlie will also let you know that a substantial tip for Josh should be paid in addtition to the day sail fee. I'm all for Josh getting paid, I just hope he gets a larger peice of the pie than just tips. Josh was great and seems to enjoy children or at least comes across as enjoying children. If he ever decides to captain his own boat we will definitely look him up the next time we are in St. Thomas.
Written September 9, 2008
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.
ChefTIO
Arizona151 contributions
Oct 2012 • Couples
Had a great sail with Admiral Hinckley and Crew. Perfect waters and great spots for snorkeling. Indeed one of our highlights of our trip to St Thomas and St John’s in October. Very casual and engaging in conversion the whole time. No more than 6 people at a time, so there is no worry about getting lost in the crowd like some of those other larger boat companies. Thanks again for the trip.
Written February 8, 2013
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.
Christine F
Scottsdale, AZ62 contributions
Oct 2011
My parents have charted with Captain Charlie and First Mate Josh before and they couldn't stop raving about the great, one of a kind experience they had. So when we planned a family cruise to the Caribbean my Dad arranged a trip with Simplicity Charters. I wish I had enough room to detail our great time but I'm afraid I don't have the vocabulary to do these two gentlemen the justice they deserve. Well, I'll try: They take care of everything! They even arranged for an air conditioned, private cab to take us back to our cruise ship so we wouldn't have to ride back on the public bus. We had a great place to snorkel and they provided all the gear. All we had to bring was the sunscreen! Rum punch.. ( I need not say more) and a delicious lunch, prepared on the sailboat by our Captain and his first mate, was a welcome treat after snorkeling in the most beautiful water I've ever seen. It is easy to get distracted while enjoying all there is to see and I swam pretty far off. They keep track of all the snorkelers and when they didn't see me they came looking for me! It is vey safe. First Mate, Josh took my seven year old niece to the beach of a small island to look for shells and hermit crabs. He was WONDERFUL with her and she had a great time. The vessel is a beauty and so well taken care of. It is very comfortable, clean and there is a bathroom (head) on board, so ladies, don't worry! Our only disappointment was their Admiral, Hinkley, (a dog they rescued and is an integral part of the crew) was recovering from surgery and unable to join us in the fun...Oh well, next time!! As far as we are concerned the charter adventure with Simplicity Charters was THE highlight of our entire Caribbean vacation. Captain Charlie, First Mate Josh and Admiral Hinckely (once recovered) will make your vacation. I promise!
Christine
Scottsdale, Arizona
Christine
Scottsdale, Arizona
Written October 24, 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.
Pioneer297307
1 contribution
Feb 2016 • Family
I wasn't able to experience what I'm sure is a fantastic day on the Caribbean. Charlie was kind of a jerk about my reservation. I explained that we were looking around and didn't completely confirm our reservation. He proceeded to cancel our reservation in a way that seemed like he was irritated by me. Needless to say he made our decision quite easy by displaying less than stellar character. I have no doubt our day with Simplicity Charters would have been beautiful but nothing can compare to genuine understanding. I'll take my love of the water and sunshine somewhere else. Happy Sailing Everyone!!
Written February 13, 2016
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.
soxfan1975
Needham, MA233 contributions
Dec 2015 • Family
This full day sailing experience was clearly the best day of our seven day cruise. Our family of four (two adults and 18 and 15 year olds) were the only passengers on the Simplicity for a sail in the crystal clear water between Red Hook and St. John recently. It was a warm, sunny and breezy day, and we felt good to be able to get away from the large groups in cruise tours.
Charlie promptly met us at the pier and brought us in the dinghy to the immaculate and comfortable sailboat, which was quickly under way. Both Charlie and Josh clearly love what they do, were informative guides, and provided an ongoing commentary. We went to Christmas Cove, where we snorkelled and saw eagle rays and turtles. The snorkelling equipment was clean and in good condition. After that we enjoyed a tasty lunch featuring Spanish rice and marinated, grilled chicken breast. Special vegetarian options were available for the vegetarians in our group.
After lunch, we went in the dinghy to a secluded beach that we had entirely to ourselves. After about half an hour there we were brought back to the boat in the dinghy, and we sailed with a group of dolphins accompanying us back to Red Hook. Hinckley was excited and barked at the dolphins much like many dogs would bark at squirrels, and Josh captured the activity (both the dolphins and the barking) in a video that he sent us by email.
One of us was recovering from a broken ankle and wearing a removable air cast on his leg, but this did not impair his enjoyment of the day, since Charlie and Josh were very attentive and helped him safely climb in and out of the boat. Charlie, Josh and Hinckley went out of their way to make the day enjoyable. We felt that we were safe and that Charlie and Josh were expert sailors. Communication with Charlie prior to the trip was easy, and he responded to all emails promptly and clearly. It was easy to find him at the pier and we did not have to wait any time at all.
Bring sunglasses, a bathing suit, towel and a camera. A waterproof camera is a good idea for the snorkelling. Dramamine might be helpful for some people, but we did not need it, and Charlie is good at finding sheltered areas for snorkelling and beach visits.
Charlie promptly met us at the pier and brought us in the dinghy to the immaculate and comfortable sailboat, which was quickly under way. Both Charlie and Josh clearly love what they do, were informative guides, and provided an ongoing commentary. We went to Christmas Cove, where we snorkelled and saw eagle rays and turtles. The snorkelling equipment was clean and in good condition. After that we enjoyed a tasty lunch featuring Spanish rice and marinated, grilled chicken breast. Special vegetarian options were available for the vegetarians in our group.
After lunch, we went in the dinghy to a secluded beach that we had entirely to ourselves. After about half an hour there we were brought back to the boat in the dinghy, and we sailed with a group of dolphins accompanying us back to Red Hook. Hinckley was excited and barked at the dolphins much like many dogs would bark at squirrels, and Josh captured the activity (both the dolphins and the barking) in a video that he sent us by email.
One of us was recovering from a broken ankle and wearing a removable air cast on his leg, but this did not impair his enjoyment of the day, since Charlie and Josh were very attentive and helped him safely climb in and out of the boat. Charlie, Josh and Hinckley went out of their way to make the day enjoyable. We felt that we were safe and that Charlie and Josh were expert sailors. Communication with Charlie prior to the trip was easy, and he responded to all emails promptly and clearly. It was easy to find him at the pier and we did not have to wait any time at all.
Bring sunglasses, a bathing suit, towel and a camera. A waterproof camera is a good idea for the snorkelling. Dramamine might be helpful for some people, but we did not need it, and Charlie is good at finding sheltered areas for snorkelling and beach visits.
Written January 4, 2016
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.
DavidDiversified
Jasper, IN6 contributions
Aug 2015 • Solo
Crew was fun, food excellent, snorkling amazing, sailing exciting, and stories and history great, and of course Hinkley! Also, a lot of good information about the area. Thank you again Charlie and Josh for a great time!
Written August 12, 2015
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.
MELODIE1994
16 contributions
Jul 2015 • Family
After visiting the Simplicity Charters website followed up by Trip Advisor reviews, I knew this was the sail for our family of 3. My daughter loves the ocean, so having Josh the Marine biology expert on board ( and boy was he knowledgeable and full of energy!) was the icing on the cake. Hinkley, oh Hinkley! She is totally on island time. She makes you want to curl up with her and take it slow. (Give that girl her own private suite on deck!) Charlie was meant to live on an island. He is so in-sync with everything happening on the island and he IS a TRUE native. To Charlie: Your grafted mangos win our seal of approval!
My travel advice: If you want to take a sail but not feel like cattle being herded nor feel the need to cover your children's ears from dozens of guests with "loose lips" who drank way too much, add Simplicity to your list now. We are vegetarians and those guys hooked us up with more food options, flavor and textures than we could ever imagine! We were stuffed! My 11 year old daughter ate every bite! Half way into the trip she said we need to come back and sail with Charlie and Josh again...she was THAT comfortable! To Josh: Dude, my mask stayed fog-free for the duration of my 10 day trip! Thanks! See you guys soon!
My travel advice: If you want to take a sail but not feel like cattle being herded nor feel the need to cover your children's ears from dozens of guests with "loose lips" who drank way too much, add Simplicity to your list now. We are vegetarians and those guys hooked us up with more food options, flavor and textures than we could ever imagine! We were stuffed! My 11 year old daughter ate every bite! Half way into the trip she said we need to come back and sail with Charlie and Josh again...she was THAT comfortable! To Josh: Dude, my mask stayed fog-free for the duration of my 10 day trip! Thanks! See you guys soon!
Written July 24, 2015
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.
Hi Kelly,
Do you happen to have contact info for Capt Charlie? We are heading there this saturday.
Written June 5, 2019
Hello
This is Captain Charlie with Simplicity Charters. I am still without a boat since the hurricanes but plan on being back in business with a boat by November of this year. Sorry I won’t be around to take you for a sail. Next time! Enjoy your vacation!
Written June 6, 2019
Hi Charlie our family sailed with you about three years ago! It still is our favorite excursion we have ever done! It is still my Facebook front page picture of the simplicity. I am so sorry to hear she was lost during the hurricane.We will be back in May of 2019 with a large group of 32 people. Do you have a boat to take us out on? If not can you recommend anyone? We will be coming in on the Harmony of the Seas The week of May 12,2019.
Thank you for your help,
Patty Wilcox
Written January 6, 2019
rconaty917
Bayville, New Jersey
hi, I'm cruising the end of February on Norwegian. Do you guys work with any cruise lines as an excursion or work with your costumers to make sure they are back to the ship on time?
And what is your cancellation policy in case weather isn't okay
Written June 15, 2018
We do not work directly with any cruise lines. We work with cruise passengers regularly and know their schedules in order to take the worry away from missing your ship. If your ship doesn’t come to port due to bad weather there is no charge. All weather related cancellations are made by the captain at their discretion if weather looks unsafe for boating. Hope that answered your questions. Enjoy your cruise.
Written June 16, 2018
We are staying in Maeghans Bay this June 14-June 18. Do you have any availability for a charter Friday Saturday or Sunday? It would be for 2 people. Thank you!
Written June 13, 2018
Thanks for your inquiry. I am currently off island searching for a new sailboat and will not be available during your visit. Sorry I couldn’t help. Enjoy your vacation.
Written June 13, 2018
We will be cruising with Royal Caribbean and will be in St. Thomas on Wednesday, May 17, 2017. We have sailed with you probably 5 years ago and had a wonderful time. Therefore, we would love the opportunity to book with you again! We are a family of four....ages 21, 22 and up! Do you have room for us on that day?
Thanks!!
Pat & Todd
Written March 30, 2017
I am available for a full day sail on May 17th, 2017. Our full day sail is six hours and we could sail from 9:15AM-3:30PM local Atlantic Standard Time. We are a small company and only take a maximum of six guests. You will need to taxi to Red Hook where we will depart for our sail. Taxis are a flat rate of $10-12 each way per person and takes around 20-30 minutes from most parts of the island. I can arrange your return taxi. The boat is a 42' Pearson aft cockpit sloop with a full shade/bimini over the cockpit. There is also a restroom/head on the boat.
For lunch, I serve BBQ chicken, Seasoned rice, and ceasar salad. There is an open bar for the duration of the sail. In addition, I have all of the snorkel gear and flotation if needed. We do not do any BVI trips as we stay in US waters. We can fit two stops in the day to snorkel, beach, or just relax on deck. We select the calmest and most secluded reefs without the crowds.
The full day rate is $150 per person or $900 for a private sail. We are a cash only charter and do not accept credit cards. With that said, payment is made in cash the day of the sail. I also have a very friendly dog, "Hinckley," that goes on all sails. To confirm your trip simply email the okay and I will reply with all final details (where to meet, what to bring, etc). Please include a cell number should I need to contact you on island. For any additional info or photos please visit my website linked below.
Thanks
Written March 30, 2017
How easy was it to get on and off the boat- I am 69 and find it diffiult if there isnt an easy ladder!
Written March 1, 2016
Our boarding ladder goes three steps into the water. Although I will say it is basically her vertical so some find it harder than others. We dour best to offer help and try to make it as easy as possible.
Written March 1, 2016
Hi guys, I was wondering if you offer afternoon sail only trips. We are just looking for that incredible sailing experience. If so what is your cost. Thank you
Written January 20, 2016
they will do a full or half day sail
Written January 21, 2016
Is there a minimum age for kids? What are the maximum number of passengers if we book a private charter?
Written November 24, 2015
We can take six passengers max as it is a coast guard regulation. As for children, we prefer kids ages 5 and up who can swim. Anything younger becomes a safety concern and too much sun for the little ones. Hope that answers your questions. Please email me directly of you would
Like to book a sail. You can find my email on my website
Written November 30, 2015
Hi, will be at cruise dock in St. Thomas consecutive Mondays in January 2016. Looking for morning sail, snorkeling not necessary, possibly more than one date. Transportation a concern. Two adults. Any availability?
Written August 22, 2015
What would a day out for a sail cost for two in Feb around the 7 or 8 we are flexible with days we arrive the 6 an leave 13
Written July 26, 2015
Wendy,
I am available for a full day sail on February 8th, 2016. Our full day sail is six hours and we sail from 9:15AM-3:30PM. We are a very small charter and limit our number of guests to a maximum of six. You will need to taxi to Red Hook where we will depart for our sail. Taxis are a flat rate of $10-12 each way per person and takes around 20-30 minutes from most parts of the island. I can arrange your return taxi. The boat is a 42' Pearson aft cockpit sloop with a full shade/bimini over the cockpit. There is also a restroom/head on the boat.
For lunch, I serve BBQ chicken, seasoned rice, and ceasar salad. There is an open bar for the duration of the sail. In addition, I have all of the snorkel gear and flotation if needed.
The full day rate is $150 per person or $900 to have the boat private. We are a cash only charter and do not accept credit cards. I also have a very friendly dog, "Hinckley," that goes on all sails. To confirm your trip simply email the okay and I will reply with all final details (where to meet, what to bring, etc). Please include a cell number should I need to contact you on island. For any additional info or photos please visit my website linked below.
Thanks
Simplicity Charters
Captain Charlie Whittemore
simplicitycharters
caribcharlie@yahoo
Office: 340-774-9348
Cell: 340-998-9129
6501 Red Hook Plaza Ste 201
St Thomas VI, 00802
Written July 27, 2015
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