Welcome Aboard

Our crew will treat you like royalty, while you cruise
comfortably from one destination to another.


Spacious and Elegant

The vessel is fully air conditioned,
and tastefully appointed throughout.


Explore the Virgin Islands

Visit white sandy Caribbean beaches.
Swim or Snorkel with colorful tropical fish.


A Yacht Charter For Every Vacationer...

Visit white sandy beaches and quaint Caribbean ports of call in the Virgin Islands. Swim or Snorkel with colorful tropical fish in warm crystal clear aquamarine waters of the Virgin Islands. Always wanted to try sport fishing? Now is the time aboard our crewed Caribbean yacht charter!

Snorkeling Fun

It’s time to explore the exclusive beaches of St. Thomas and snorkel the gorgeous surrounding reefs!

Caribbean Swim

Soak up the sun on the upper-deck or hop in the water for a refreshing swim in the warm Caribbean waters from your own private USVI sailing charter.

Sunset Cruises in US Virgin Islands
Sunset Cruise

Take in the beautiful St. Thomas sunset as we cruise heading into open water to catch the best view of the setting sun.

Sail the Caribbean with Second Wind Charters!

It’s Your Yacht for a Day – Time to Live!

Dedicated to Creating an Amazing Experience - 5 Star Reviews

The best way to spend a day in St ThomasA Gabriel - Columbus, Ohio

“We chartered a half day boating adventure with second wind during our stay in St Thomas during a Disney Cruise. It was a wonderful way to get some alone time during the busy schedule of a cruise. It was our daughter Ava‘s third birthday. We felt very special celebrating her birthday and truly enjoyed all of their hospitality. The food and drinks were amazing! We opted to do a snorkel day and it was perfect! I’d recommend them anytime you are in St Thomas. We will be back for more fun next time we are on the island. Thank you for a memorable day.”

Amazing!Mikey B

“I can't say enough good things about our charter. Wolfgang is hilarious and full of stories and information. Anna went out of her way to provide transportation for us. Alyssa prepared our lunch and everything was delicious, she even had a special birthday cake for us. Shane was very knowledgeable during our snorkeling adventure and even dove down to get a sea urchin and sea cucumber for us to hold. It was a once in a lifetime kind of day. Thank you all very much!!”

A Must Do if You're in St. ThomasJackson0211 - Newport Beach, CA

“We stopped for a day in St Thomas on a Disney cruise. We arrived to the boat to be greeted by a huge and delicious breakfast and mimosas by Alyssa. It was heaven. Our Captain, Wolfgang, took us to great spots for the kids to snorkel and swim with turtles. Shane, was very helpful in the water with our little boys. In the afternoon we were served a delicious and huge lunch made by chef Alyssa and the rum punch was flowing. All of our needs were catered to, Its a must, especially if you have kids. Perfect family day. Wolfgang also seems to know everything about the island, nothing you would ever read about in a travel book. We will definitely book again on our next trip to St. Thomas.”

Best. Day. Ever.Kimberly D

“Loved having a taste of St Thomas on board Second Wind. Alyssa is an excellent cook and catered to all my food needs, must appreciated! Captain Shane was our guide assisted by Captain Wolfgang. Such a fun duo! Shane led our snorkel adventures and was patience during mask adjustments. So much fun!”

Highlight of Our CruiseRudy D

“As many have said before this trip at St Thomas was one of the best from our cruise
Everything was well planned for us as our ship departed rather early in the day (5 PM) however Skipper Wolfgang took us out and showed us some fantastic spots. We had ample time to dine, snorkel, dine some more, snorkel some more and see some sights. Skipper Wolfgang had some great stories and we were wholeheartedly entertained.”

Let's Book Your Charter Today!

We Offer Non-Private and Private Charters!

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