Sailing Southern Charm

22/08/2023

DOUBLE TAP IF YOU WOULD LIKE TO OPEN YOUR BLINDS TO THIS IN THE MORNING. 🌊☀️🏝️

The time is now!
DON’T WAIT. Book the trip!
Now booking 2024.

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17/06/2023

The BUBBLY POOL was rocking for our guests! What a blast we had with this group! Looking forward to seeing them again next season!

23/04/2023

21/04/2023

Sailing, Hiking, eating tacos while floating. Just another day here in the USVI. ⛵️🥾🌮

612 likes, 7 comments - A S H L E Y • W E S T ☀️ () on Instagram: "Having the worst time…cant you tell?! 🤣 "

20/04/2023

Day ✌🏻

176 likes, 3 comments - A S H L E Y • W E S T ☀️ () on Instagram: "How could one NOT live, laugh, love in these conditions?! On ☁️ 9 atm… "

19/04/2023

Southern Charm meets Southern West. It is going to be a great week! 🌞⛵️👙

948 likes, 13 comments - A S H L E Y • W E S T ☀️ () on Instagram: "Southern Charm 🤝 Southern West DAY 1 "

10/02/2023

Pretty Girls Walk Like This!

Now chartering in the BVI!

The time is now!
DON'T WAIT. Book the trip!
Still soom room in 2023. Now booking for 2024.

Follow our charter adventures at
Sailing Southern Charm or DM us for more information on chartering!

08/02/2023

Get in my belly…

… new to the Southern Charm breakfast menu, mouthwatering mini Shakshuka’s!

Now chartering in the BVI!

The time is now!
DON’T WAIT. Book the trip!
Still some room in 2023. Now booking 2024.

Follow our charter adventures at or DM us for more info on chartering!

19/01/2023

I would rather live a life full of more moments where I say "I cant believe I did that" rather than "I wish I would have done it."

16/01/2023

Postcard from Paradise!


Can you name this famous bay?

The time is now!
DON’T WAIT. Book the trip!
Still some room in 2023. Now booking 2024.

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12/01/2023

We sailed into our 3rd season of chartering…

…and first BVI charter, with this fun family from Denver! We rang in the new year island style, celebrated a BIG birthday, and saw some amazing sunsets! Until next time friends!

The time is now!
DON’T WAIT. Book the trip!
Still some room in 2023. Now booking 2024.

Follow our charter adventures at or DM us for more info on chartering!

04/08/2022

Work. Save. Travel. Repeat.

The time is now!
DON’T WAIT. Book the trip!
NOW booking for 2023.

Follow our charter adventures at or DM us for more info on chartering!

30/07/2022

HOME SWEET HOME! We still have a few weeks available for our 2023 charter season. If you have never experienced the USVI from a boat, now is your chance!

St. Thomas is both the gateway to the U.S. Virgin Islands of St. John and St. Croix and a beloved Caribbean vacation destination in its own right.

12/07/2022

And I think to myself, what a wonderful world! After living in the USVI for 2 years, we are STILL finding new bays and beaches! Using our time off to explore and research to bring you a totally new experience next season!

Whose ready to book a week aboard???

The time is now!
DON’T WAIT. Book the trip!
NOW booking for 2023.

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05/07/2022

Hey Did you say, BUCKET LIST TRIP…

… we KNEW you would ❤️ it! Take a cue from these WORLD TRAVELERS and BOOK THE TRIP! Now get back here Rachel! 😘

The time is now!
DON’T WAIT. Book the trip!
NOW booking for 2023.

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04/07/2022

Our goal is…

… to keep fresh, beautiful, and healthy (mostly 😉) food in front of you during your week aboard Southern Charm. This is one of our favorite salads, the LUAU! It is a Cheesecake Factory copycat, and a pretty good one at that! While we have a general standard menu, we always do our best to accommodate to preferences and ALWAYS for allergies.

The time is now!
DON’T WAIT. Book the trip!
NOW booking for 2023.

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03/07/2022

Are you CURIOUS…

how a sailboat works? We all understand the general idea. Wind moves boat. But what we don’t all understand is the details. The foil and angle of the sail, trimming the sail to maximize speed, and all the technology we use to move this big girl around. Captain Kevin loves nothing more than to teach! Especially SAILING! You can count on him answering all your questions and letting you get in on the fun in the helm if you want to learn.

The time is now!
DON’T WAIT. Book the trip!
NOW booking for 2023.

Follow our charter adventures at or DM us for more info on chartering!

26/06/2022

Fish you were here…

… no, REELY. With 2 trolling rods and several light weight tackle rods, we have your fishing needs covered. FYI, no fishing license required in the USVI!

The time is now!
DON’T WAIT. Book the trip!
NOW booking for 2023.

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17/06/2022

So many MUST SEE spots on St. john! What’s your favorite??? 🥽🐠🏝

The time is now!
DON’T WAIT. Book the trip!
NOW booking for 2023.

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08/06/2022

We love repeat guests especially when they are hometown friends. 🍾🍾🍾

🍾🍾🍾 Can’t wait to host you again next season

The time is now!
DON’T WAIT. Book the trip!
NOW booking for 2023.

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06/06/2022

Some food for thought…

… you have never had crab cakes like this. And that’s a PROMISE. Thanks to our good friends on for sharing this recipe. It is the Captains favorite meal aboard! 🦀

The time is now!
DON’T WAIT. Book the trip!
NOW booking for 2023.

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05/06/2022

The forward lounge has quickly become…

… one of our guests favorite spots aboard. This spot is perfect for everything from a little quiet time, reading or napping to spending quality time with friends and family.

The time is now!
DON’T WAIT. Book the trip!
NOW booking for 2023.

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26/05/2022

If your idea of vacation is…

…adventure, we have some ideas! Have you ever wanted to learn to e-foil? Jeff and Jane at .foils are the experts in the USVI. From lessons to weekly board rental, they are our go to. All of our guests who have tried it have loved it!

The time is now!
DON’T WAIT. Book the trip!
NOW booking for 2023.

Follow our charter adventures at or DM us for more info on chartering!

26/05/2022

Thankfully, we are seeing the end of Covid requirements to enter the USVI!

USVI Travel Portal to be Discontinued June 1, Governor Bryan Confirms

20/05/2022

Well, that doesn’t happen very often…

… the only boat to overnight in Leinster Bay. Easily one of the most popular bays in the USVI. Our season is quickly coming to an end. It is becoming more obvious that boats are beginning their journey to safer waters for a few months. But, we will be back in November. If you are interested in spending a week with us in the USVI, we still have room in our calendar!

The time is now!
DON’T WAIT. Book the trip!
NOW booking for 2023.

Follow our charter adventures at or DM us for more info on chartering!

19/05/2022

BUCKET List Trip!…

…Our last charter of our first season (2021)
“this trip would not be the same with any other crew!” What a blast we had with this sweet family! While we love the larger groups with all the energy, we equally enjoy the quieter and more intimate groups. So fun to get to know charter groups on a deeper level.

The time is now!
DON’T WAIT. Book the trip!
NOW booking for 2023.

Follow our charter adventures at or DM us for more info on chartering!

19/05/2022

Now THAT’S a sandwich…

Naturally, Southern Charm’s take on a reuben would include some fish. I give you the Mahi Reuben. Truly an delicious lunch!

The time is now!
DON’T WAIT. Book the trip!
NOW booking for 2023.

Follow our charter adventures at or DM us for more info on chartering!