private boat trips



Welcome to Summerwind Adventures, your premier destination for exclusive private boat trips in St. Augustine, Florida. Our unparalleled yacht experience sets us apart from the standard tour boats, schooners, and excursions available in the area. If you seek a truly unique and luxurious journey on the open sea, look no further. Discover the epitome of pampering, relaxation, and adventure as you set sail with us aboard our elegant Jeanneau DS 50-foot sailing yacht. 

private boat trips

WHY CHOOSE Summerwind for private boat trips?

Luxurious Accommodations:

Indulge in the finest amenities aboard our exquisite sailing yacht. From electric flush bathrooms and private showers to a full kitchen, BBQ grill, televisions, diesel generator, and air conditioning, our vessel is equipped with everything you need for a comfortable and memorable journey. You and your guests will relax in plush robes, reminiscent of the most luxurious international hotels, as you enjoy the breathtaking ocean views.

Endless Activities and Unforgettable Moments:

Your private boat trip with Summerwind Adventures is more than just sailing; it's a gateway to unforgettable moments. Immerse yourself in the majestic beauty of St. Augustine's sunsets, engage in up-close encounters with fascinating sea life, and enjoy a variety of activities tailored to your preferences. Whether you're seeking adventure, relaxation, or a combination of both, our experienced crew will curate the perfect itinerary to make your journey truly extraordinary.

Pampering Experiences:

As part of our commitment to providing unparalleled experiences, we offer additional amenities to enhance your private boat trip. Unwind with a relaxing massage from our onboard masseuse, allowing you to truly immerse yourself in the tranquility of the ocean. Our talented chefs will cater to your specific dietary needs, ensuring gourmet dining experiences throughout your journey. Whether you're planning a romantic dinner, celebrating a special occasion, or even arranging a marriage proposal, our crew will go the extra mile to make your experience perfect.

Convenient Getaways and Advanced Bookings:

Escape the everyday and embark on an impromptu ocean adventure with Summerwind Adventures. With the possibility of advanced 48-hour bookings, the serene tranquility of sailing and the sights of beautiful St. Augustine are just a few clicks away. Experience the thrill of a private yacht experience and create cherished memories that will last a lifetime.


sailing st augustine

Your adventure awaits

Experience the ultimate luxury and privacy on our private boat trips in St. Augustine. Book your exclusive adventure now and set sail with Summerwind Adventures!

St Augustine Sailing Charters

The yacht

Welcome aboard Summerwind: An elegant Jeanneau, DS 50-foot sailing yacht, one of the largest private sailing yachts FOR CHARTER in St. Augustine.

You are welcome to sit back and allow our team to handle everything, or if interested we will provide instruction and helming, tacking, and gybing the boat as we sail out on the Atlantic. You and your guest will have the opportunity to fully understand ocean and inland sailing by
the end of your adventure.

Features & Amenities:

  • 75-hp Yanmar Turbo diesel engine
  • 2 electric flush bathroom facilities
  • Private showers
  • 3 staterooms, with spacious owner’s stateroom
  • 2 additional VIP staterooms
  • Salon is also spacious with room to accommodate 6 in total comfort
  • Fully equipped galley, refrigerator, freezer, coffee station and microwave
  • Cockpit can fit 10 guests, plenty of room for stretching-out under the stars
  • BBQ grill that can be utilized for hosting a wonderful cookout aboard.
  • YouTube TV for streaming and surround sounds stereo for 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 available

For safety, Summerwind carries an eight-man Winslow auto-inflate life-raft, two EPIRBS, two medical kits, four fire extinguishers, strobes, flares, and two-VHF radios for safety aboard.

St Augustine Sailing St Augustine Sailing Charters sailboat charter jacksonville fl


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.


St Augustine Sunset Cruise

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 Augustine sunset cruise is expertly taken care of. Onboard Summerwind, you're the commander of the schedule, creating a personalized journey tailored to your desires. 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 voyage, filled with endless customized experiences for you and your esteemed guests. Book now and elevate your sunset adventure to extraordinary heights!


Summerwind delivers the ultimate all-inclusive charter on the water aboard your own private yacht. Avoid the crowds with spacious accommodations and a premium, personalized St Augustine sunset 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. Book now and embark on a memorable journey like no other.

Bachelor & Bachelorette Outings & Engagements

Elevate your bachelor or bachelorette outing or engagement celebration with an exclusive private boat trip aboard Summerwind. Experience the epitome of privacy as you and your group have the entire yacht to yourselves. Cruise along the sparkling waters, indulge in swimming, relaxation, and sunbathing, all while immersing yourselves in the breathtaking sights of St. Augustine from your private boat trip. Create unforgettable moments in complete seclusion and luxury, making your special occasion truly extraordinary.

Families & group Adventures

Embark on a remarkable private boat trip with Summerwind, tailored for families and groups seeking unforgettable adventures on and off the water. Our private sailing charter offers the perfect blend of excitement and relaxation, ensuring an exceptional experience for everyone involved. Discover the joy of a private boat trip, where the wonders of the sea and quality time with loved ones come together to create cherished memories.

Corporate Events

Elevate your corporate event to new heights with a private boat trip on a luxurious yacht. Leave a lasting impression as you gather your team amidst unparalleled elegance, accompanied by an attentive crew, 5-star catering, and exceptional facilities. Create unforgettable memories during your exclusive private boat trip, where business and luxury seamlessly blend together for an extraordinary experience.

St Augustine Sunset Cruise

Embark on an enchanting private boat trip through the captivating beauty of St. Augustine. 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. Experience the all-inclusive indulgence of our private boat trips, from delectable meal options to personalized services, all against the backdrop of a breathtaking St. Augustine sunset. Book now and create cherished memories on your exclusive private boat trip.

St Augustine Sunset Cruise
get in touch

Contact Us

Looking to book a sailing charter on Summerwind?
Get in touch, either via the form below or calling us directly at (404) 229-0507. Someone from our team will address your needs and answer any questions you may have. We are happy to help and look forward to getting to know you!