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Guests: 6
        Cabins: 3
        Crew: 1
Price from:            $10,000
Builder: Catana
          Length: 44.00 ft
Year: 2019


3 queen cabins with ensuite heads, shower and vanity.
4th cabin used by crew.
Boat is fully airconditioned.


Captain Only

CAPTAIN ONLY: $10,000 for up to 6 guests. Includes: Captain, yacht, paper products, basic condiments, propane, water, use of all water toys. Excludes: Food, beverages, bar, ice, fuel, mooring or dock fees, customs, port and immigration fees, cruising permits, airport transfers, shore excursions.


Salon Stereo: Yes
Salon Tv: Yes
Sat Tv: No
Multimedia System: Yes
Nude: Inq
Books: No
Crew Pets: No
Guest Pets: Yes
Camcorder: No
Number Dine In: 6
Water Maker: 180L per h
Water Capacity: 200
Ice Maker: Yes
Number Of Dvds: Apple TV
Number Of Cds: No
Board Games: No
Sun Awning: No
Bimini: Yes
Special Diets: No
Kosher: No
Bbq: Yes
Gay Charters: Inq
YachtNudeCharters: Inq
Hairdryers: No
Number Of Port Hatches: Yes, every
Smoking: Yes, aft deck
Crew Smokes: No
Children Ok: Yes
Minimum Child Age: None
Generator: 13.5KW
Inverter: 120VAC in all cabins and salon
Voltages: 120VAC
Hammock: No
Windscoops: No

Price Details

For 6 night charters, divide weekly rate by 7 nights X 6 nights. For 5 nights or less, divide weekly rate by 6 nights X number of nights.
If cruising area includes BVI, rates are PLUS permits, licenses and fees which are to be paid by client.


Sleep aboard the night before charter dates. Available for half of the daily rate. EXCLUDES: Christmas and New Year's weeks.

CHRISTMAS/NEW YEARS: 7 night minimum
Christmas 2023: $13,500 and must end by 12/27
New Years 2023: $15,000 and may not start prior to 12/28
HOLIDAY RATES ARE CAPTAIN ONLY: for up to 6 guests. Includes: Captain, yacht, paper products, basic condiments, propane, water, use of all water toys. Excludes: Food, beverages, bar, ice, fuel, mooring or dock fees, customs, port and immigration fees, cruising permits, airport transfers, shore excursions.


Copy link below & paste into browser to submit waiver:


Tube: 2
Guests: 6
Draft: 4
Helipad: No
Ac: Full
Ac Night: Yes
Built: 2019
Turnaround: 48 hrs, Inquire for 24
Cabins: 3
Queen: 3
Showers: 3
Basins: 3
Electric Heads: 3
Jacuzzi: No

BBQ: Yes
AC: Full
Generator: 13.5KW
Internet: Onboard WIFI


More Specifications

Flag: USA
Homeport: St. Thomas, USVI
Yacht Permit: 2
Yacht License: 2
Yacht Mca: 1
Yacht Insurance: GUARDIAN GROUP

Water Sports

Dinghy Size: Octenders OC350, Rigid carbon fiber
Kayaks 1 Pax: No
Kayaks 2 Pax: 1
Dinghy Hp: 15HP Suzuki
Floating Mats: No
Dinghy Pax: 5
Swim Platform: No
Water Skis Adult: No
Boarding Ladder: Horizontal transom with swim l
Water Skis Kids: No
Sailing Dinghy: No
Jet Skis: No
Beach Games: No
Wave Runners: No
Kneeboard: No
Windsurfer: No
Snorkel Gear: Yes
Underwater Camera: No
Scurfer: No
Underwater Video: No
Wake Board: No
Paddleboard: 1
Seabob: No
Sea Scooter: No


Captain: Sean O'Grady

Nationality: USA

I grew up sailing with my Dad and found the love for the ocean at an early age. After a few years off the water I got back into sailing a lot in SF Bay enjoying racing and charters both. I have worked with USA76 a former americas cup IACC yacht since 2018. I have done some commercial fishing in Alaska as well as some sport fish guiding this last summer 2022. I worked as the maintenance director and a captain on a pair of Santa Cruz 70’s in Monterey Bay for the last two years. I’m making my way to the Caribbean to get some sun and share my love of the ocean breeze with all the great people I get to take out on the water.


February 2023
Excellent week. Sailing, hiking, playing games, snorkeling and paddle boarding! Thanks so much for making every minute of our trip fun! Loved your motto “I want you all to be happy and have fun!” We did!
February 2023
We had an amazing week! Sean did a great job teaching us about sailing and making us feel welcome on his boat. Too many inside jokes with our group that shouldn't be put in writing. Thanks for a great trip!
January 2022
S - Super Great Guy
E - Excellent Navigator
A - An Operator of Registered Craft
N - Nice to hang with always

Sean O’Grady hit all the things we needed to do and sea, and really taught us a lot about sailing and life. 10/10 would do it again!
December 2022
We sailed with the Freestyle for a week! My fav part was swimming with the turtles.

Snorkeling was amazing (Full face mask) and Maho was fantastic. Lime out tacos, were the best tacoes Ive ever had. Thanks Sean for everything!

Thank you Captain Sean for everything! It was a trip of a lifetime and so grateful for all the places you took us to. My family thanks you for the Christmas popsicles.

Wow, what an awesome place! Everything this week was spectacular and I cant wait believe how much I missed the ocean. Diving off the roof was my favorite! Thanks for making cheese and I do the mommy shotgun lol

This place was sick! I love the turtles and reading on the deck. Thanks for a great trip and I hope you gave some good stories lol
December 2022
What an amazing 4 nights aboard the Freestyle with Capt. Sean! Our family enjoyed amazing shops in Caneel Bay, Cruz Bay, Maho Bay, Leinster Bay and Lameshur Bay. Each day was filled with fun activities including hiking, lots of snorkeling, paddleboarding, kayaking, and so much more. Each starry night was magical, and we really felt like Sean was part of the family playing fun family games and telling stories. Couldn't have asked for a better Christmas, Captain, or boat. Big thanks to Capt. Sean and the owner of the Freestyle. Until next time!
November 2022
We had the best 4 nights ever with Captain Sean on the sea! Some of our favorite activities were snorkeling, going to the Windmill Bar with an amazing view and the floating taco bar! Adam also caught 3 fish - the only crew member to catch anything! We saw several sea turtles and lots of cool fish at night. The view from the front deck at night was breathtaking. We saw many shooting stars. The mountainous landscape and deep blue waters were some of the most beautiful sights we've ever seen. We had so much fun and a relaxing time. We can't wait to come back some day - hopefully with captain Sean again too! Sincerely, Bethany & Adam Klein, Bethanie & Rish Derose, Jenny & John Amenhauser. (From New Jersey)
April 2022
Yacht & Captain
Please answer the following questions pertaining to the yacht you chartered and the crew.
Rating of Yacht & Crew:
(5 Being the Highest) 5
Was the yacht comfortable and clean?
Was the yacht well ventilated?
Was the yacht's cooking and cleaning equipment sufficient?
Was the captain friendly and accommodating?
Additional comments about the yacht and captain?
We sailed on the Freestyle in April 2022. Capt. Chris was a consummate professional, extraordinary captain and very easy to get along with. He was very accommodating to our schedule and laid back attitude made the pace of our trip our own. We felt as though we had our own private guide and local at every stop we made with excellent recommendations for shopping, restaurants and snorkeling.
Cruising Area
Did you like the area you chartered in?
March 2022
Rating of Yacht & Crew:
(5 Being the Highest) 5

Was the yacht comfortable and clean?
Very clean and organized

Was the yacht well ventilated?
Yes! Very comfortable climate. I loved being able to adjust my own cabin at night.

Was the yacht's cooking and cleaning equipment sufficient?
No complaints. We had everything we needed.

Was the captain friendly and accommodating?
We hands down could not have had a better Captain. captain Chris was the best captain ever!

He really made our trip fun and was able to lead us to the best locations for adventure.
Additional comments about the yacht and captain?
Thank you so much Captain for an amazing trip! We will definitely book with you in the future!

Cruising Area
Did you like the area you chartered in?
Yes. We had the best spots. Maho Bay and Honeymoon Beach were my favorites. Snorkeling in Water Lemon was the coolest thing ever. I felt like I was in an aquarium.
February 2022
We had such a relaxing and memorable holiday. It will stay with us for years to come…We’ll certainly be back -  just loved it.
February 2022
We had an amazing time, thank you for setting this up.
Chris was truly a pleasure to be around.
We will hang out with him next time he is in NY, that’s how much we liked him.
February 2022
It was a wonderful trip, complete with access to snorkeling spots and beaches we’d not
be able to get to otherwise. Living on the sea for a week was very special, the islands are so beautiful. In fact I still feel like I’m floating:) Will definitely do it again!
May 2021
This was an AMAZING adventure for our family and friends! Thank you, Captain Brian, for the hospitality, suggestions, advice, patience, teaching, and expert sailing! The boat was a dream! The bays, water sports & snorkeling will be memories we keep forever! This was the trip of a lifetime!

This week was definitely a trip of a lifetime, full of fun, adventure & trying new things. The boat is beautiful and we couldn’t ask for a better Captain!

This trip made me never want to go home and to permanently become an island girl! I absolutely loved going snorkeling and seeing the colorful fish, sting rays, and cute sea turtles! Thank you Capt. Brian for showing us the most beautiful bays, best snorkeling spots, and keeping seasick spirits high with your positivity and humor! I will never forget this incredible trip (or the sunburn that came with it!!!)
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April 2021
Didn’t think it was possible to completely forget about Covid but thanks to Brian’s hospitality, knowledge and desire to please, we enjoyed 4 incredible days on Freestyle.

We packed in sailing, fishing, snorkeling in Salt Pond, Waterlemon Cay and Congo Cay. Topped it off with kayaking, learning to SUP, and celebrating our daughter’s 18th birthday in style. Through it all, Capt. Brian was there with a helpful hand and genuine smile.

This was our first ‘captain-only’ charter – definitely the way to go! We are returning home today feeling revived and looking forward to a return trip!

With much appreciation for the treasured memories,

“Joanna” & “Emilily”
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April 2021
Thank you Captain Brian for the trip of a lifetime. You provided memories my son and I will cherish forever. Finding the new reef, catching the shark, and don't forget discovering the old scoop anchor. Priceless memories! The boat was well maintained. In closing, Brian, please know that we greatly appreciate all you did for us. Please don't tell the other guests about how this old guy can cook!

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March 2021
We had an amazing trip with Captain Brian. The seas were calm except for the 1st full day. Brian put us in the best possible spots each day they allowed us to do a number of activities such as diving off the boat, fishing (caught a large Spanish marcel which was an excellent lunch) hiking visiting ruins, snorkeling (saw a res shark, sea turtle feeding, several sting rays. make sure to watch out for the black sea urchins. Not fun when you step on one.

Brian was great cleaning up constantly after us and ready to help out with a beer or cocktail so we never had to get out of the floating chairs. The kids and us will remember this trip the rest of our lives
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March 2021
We has the most amazing time exploring St Thomas and St John on the Freestyle :) It was our first time spending an extended amount of time aboard at sea on a boat and it could not have been a more pleasant experience.
Brian was an amazing captain! he was so attentive to our needs and made sure to guide us so we had the best trip possible. Brian took the time to engage with us on the trip teaching us basic sailing terms/skills as well as the best places to explore dinning our trip.
Some of our favorite parts of me trip were kayaking in the Megan's bay, snorkeling in salt panel, sleeping on the deck under the stars, lounging in the water and the beautiful sunrises and sunsets.
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Price from $10,000 /week
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