Visit our rates page to choose the Summerwind package that's right for you.



Use our online booking form to choose the perfect time, and let us know any additional details for your charter.



Use our online booking form to choose the perfect time, and let us know any additional details for your charter.



Once we've received your details and the payment is confirmed, we'll be in touch!



Let our crew take care of the rest and leave you with memories you'll cherish forever.



Let our crew take care of the rest and leave you with memories you'll cherish forever.

Romantic Weekends

Imagine yourself silently gliding through the waves in the lap of 5–star luxury on your own private 50ft. yacht. With a dedicated captain and attentive crew, every detail of your St. Thomas or St. Augustine sunset cruise is expertly taken care of. Onboard Summerwind, you're the commander of the schedule. We create a personalized journey tailored to your desires and delight your taste buds with a range of delectable meal options, from home-style Southern cooking to exquisite offerings like oysters, caviar, and champagne. Embark on an unforgettable luxury sailing trip filled with endless customized experiences for you and your esteemed guests. Book now and elevate your sailing adventure in St. Thomas to extraordinary heights!


Summerwind delivers the ultimate all-inclusive private yacht charter on the water aboard your own private yacht. Avoid the crowds with spacious accommodations and a premium, personalized St. Thomas or St. Augustine private dinner cruise experience. Whether it's a 2-hour tour or a whole weekend, immerse yourself in luxury and serenity while witnessing the breathtaking beauty of the sunset.

Bachelor & Bachelorette Outings & Engagements

Chartering with Summerwind is a great choice for the ultimate privacy. You get the entire yacht to yourselves. You can cruise, swim, relax, suntan and take in the wonderful sights of St. Thomas or St. Augustine from your private yacht charter.

Families & group Adventures

A sailing charter from Summerwind is perfect for families and groups looking for fun on and off the water.


Experience the captivating beauty of St. Thomas (November - April) while aboard Summerwind on a Sail and Snorkel adventure. Jump into the beautiful, clear waters of the U.S. Virgin Islands and swim with the sea life. We offer semi-private and private charters and snorkel gear is provided for those who need it.

Sunset Cruise

Experience the captivating beauty of St. Thomas or St. Augustine on our unforgettable sunset cruise. Step aboard the luxurious yacht, Summerwind, and let our dedicated Captain and crew pamper you as you sail through gentle waves, surrounded by vibrant colors painting the sky. Indulge in the all-inclusive experience, from delicious meal options to personalized services, and embrace the tranquility of your own private yacht. Book now and create cherished memories against the backdrop of a breathtaking St. Thomas or St. Augustine sunset.

St Augustine Sunset Cruise

Corporate Events

Nothing is more memorable than an event held on a private luxury yacht, complete with an attentive crew, 5-star catering and outstanding facilities.

A Summerwind Adventure is ideal for corporate team building activities, board meetings and leadership events.

The Enchantment Awaits!

As the sun dips below the horizon, casting golden hues upon the shimmering water, your own exclusive sanctuary aboard Summerwind awaits. We offer a unique blend of tranquility and elegance that few can dream of. By offering an exquisite private yacht charter in St. Thomas, we help you enjoy life in a different, better, and unforgettable way. Every moment aboard the yacht promises a journey that transcends ordinary excursions, and every wish of yours is merely a whisper away from reality. Let's whisk you away! Book now and embark on a memorable journey like no other. We'll make sure everything is taken care of.



Your adventure awaits

St Augustine Sunset Cruise

St. Thomas & St Augustine Sailing Charters

The yacht

Welcome aboard Summerwind, your gateway to an unforgettable sailing adventure. Whether you’re seeking relaxation or excitement on the open seas, our experienced team is here to cater to your every need. As one of the largest private sailing yachts available for charter in St. Thomas or St. Augustine, this elegant Jeanneau DS 50-foot sailing yacht offers an unforgettable sailing experience like no other.

Unwind like never before on our sunset cruise aboard Summerwind. Glide through gentle waves as the sun dips below the horizon, painting the sky with breathtaking hues. Let our dedicated captain and crew treat you with exceptional service and attention to detail. From delicious meal options to personalized services, every aspect of your journey is tailored to exceed your expectations. Relax and embrace the serenity of your own private charter yacht as you create unforgettable memories with your loved ones.

Whether you prefer to sit back and relax or get hands-on with sailing, the choice is yours aboard Summerwind. Allow our experienced team to handle everything, or if you’re interested, we’re happy to provide instructions on helming, tacking, and gybing the boat as we sail out on the Atlantic. By the end of your adventure, you and your guests will have gained a deeper understanding of ocean and inland sailing, creating memories to last a lifetime.

St Augustine Sailing St Augustine Sailing Charters sailboat charter jacksonville fl

Features and Amenities:

  • 75-hp Yanmar Turbo diesel engine
  • 3 staterooms, with spacious owner’s stateroom
  • 2 additional VIP staterooms
  • Private showers
  • 2 electric flush bathroom facilities
  • A salon which can accommodate up to six persons comfortably
  • A fully equipped galley with refrigerator, freezer, coffee station, and microwave
  • A cockpit which can easily fit up to 10 guests with plenty of room for stretching out under the stars
  • A BBQ grill for hosting memorable cookouts aboard
  • YouTube TV for streaming and surround sounds stereo system providing music throughout the yacht.
  • All Garmin navigation and electronics, including two chart plotters, AIS, Radar, Autopilot, and stereo, installed in 2022
  • Private chef and masseuse options are also available.


Sailing with Marty was my first experience as an adult sailing off the coast. We had a wonderful trip starting in St Augustine. First, we were given some basic information about the boat and safety, the other crew members and our destination. Then we were off. We sailed up to Amelia Island for most of the day and then docked at Fernandina Beach marina. We had a short walk into downtown and had a wonderful meal. It was also a great way to really get to know the other members of the crew. The next morning we set off and sailed north to Cumberland Island. Once on the island, we explored the ruins, had a nice hike and enjoyed dinner on the boat. The next step was amazing. We headed off into the sunset on the boat and sailed all night. It was truly exhilarating sailing through the night. At all times, I felt safe but the excitement got me hooked on sailing. Marty is honest, helpful, and always cheerful; exactly what you want in a captain.


This past summer my husband and I had an awesome time on Summerwind. The weather was warm so it was a great time sailing to downtown St Augustine and simply grabbing a mooring ball eating a yummy lunch with our family and diving off the back for a refreshing dip. The following day we took the boat several miles out in the ocean with all the sails up, music on in the cabin; a complete escape from work etc. At day’s end we sailed right up to Caps On The Water restaurant for my birthday where we enjoyed a seafood dinner and drinks. We can’t wait to plan another visit aboard Summerwind, It was a complete vacation over only a single weekend. Many thanks.


Sailing with Marty is truly a treat... He and his trusty Yacht are one with the mighty ocean. Years at sea and behind the helm show, and pay off in high seas or calm. But don't get too comfortable because he is always game to teach you the ropes and be sure you are part of the adventure. There is nothing more peaceful and fulfilling than a day at sea with Marty. Thanks for the memories!


We had such a peaceful experience taking in the joys of the sea while sailing with Marty. He was willing to let us take on roles to help sail the boat (and willing to let us fail, too!) We brought along our two little children (2.5 years and 10 months) and they enjoyed playing below deck and seeing the beautiful scenery sailing by. We were grateful for Marty’s expertise, generosity and passion for sailing!

Claire L / DAPHNE, AL

I've sailed with Captain Marty several times and it was a joy. One of the trips was a longer sail from Puerto Rico to Saint Augustine, Florida in May, 2013. We had a great time and I felt totally comfortable with Marty as our Captain. His sailing and navigating experience made me feel very at ease while on the water - he is a safety conscious sailor. I would give the trip 5 stars!


Being a novice on boats, this was a very exciting time for me. Marty and the crew made me feel very comfortable aboard the Yacht. We sailed down the Cooper River, under the incredible Arthur Ravenel Jr. Bridge and into Charleston Harbor. I enjoyed seeing the USS Yorktown and the submarines. The view of the city of Charleston and the historic homes was amazing! Marty is very knowledgeable about historic sites. Seeing Fort Sumter from the water was also a memorable experience. I would rate this sail as 5 stars


My family and I have sailed many times over the last ten years with Marty and his crews including wonderful afternoons off the coast of St. Augustine. We have had many fabulous overnight trips to places like Fernandina Beach and Cumberland Island. Summerwind is a beautiful Yacht and she sails like a dream. Some our family’s greatest moments have been sailing on Summerwind with the sails up on a beautiful day with gentle breezes moving along the ocean effortlessly. We strive to create lifelong memories with our family by having experiences together and a day on Summerwind is an unforgettable experience. We give Summerwind and the amazing crew 5 stars and can’t wait for our next sailing Adventure.