set sail for the adventure of a lifetime aboard

Sailing Summerwind

SUMMERWIND

Sail for a few hours or an entire week in the U.S. Virgin Islands aboard a luxurious 50ft private sailing yacht: Summerwind

SUMMERWIND

SERVING ST. AUGUSTNE & THE VIRGIN ISLANDS

Unforgettable Adventures in the Virgin Islands & St. Augustine, FL

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SUMMERWIND

WHY CHOOSE Summerwind?

Endless Activities

Our adventures offer majestic sunset views, up-close encounters with sea life, and so much more! Whether you want to share a romantic dinner, surf the waves or enjoy a relaxing massage, Summerwind adventures offer a unique experience like no other.

Advanced Technology

Summerwind is an elegant Jeanneau, DS 50-foot sailing yacht. She is fully equipped with amenities like electric flush bathrooms, private shower, full kitchen, BBQ grill, televisions, diesel generator, air conditioning and more to ensure an amazing experience for any length of time you choose to stay.

Luxury Accomodations

We offer only the best to those aboard Summerwind! Our catering, dedication to cleanliness, and attention to detail is bound to impress. Our crew will always go the extra mile to make any special occasion perfect, including marriage proposals.

Convenient Getaway

Got the sudden urge to escape the everyday for the thrill of the ocean and a private yacht experience? Summerwind has the answer. With the possibility of 48-hour advanced bookings available, the sights of beautiful St. Thomas & St. Augustine and the peaceful tranquility of sailing is just a few clicks (or a phone call) away.

ADVENTURES

summerwind

Your adventure awaits

SUMMERWIND
Onboard Activities Aboard Summerwind

Sailing Summerwind

sailing st augustine Luxury Sailing St. Augustine
Stand Up Paddleboard
Ocean Swimming Platform
Rare green sea turtle (Chelonia Mydas), swimming in open ocean, Moalboal, Cebu, Philippines
Sail & Snorkel with Sea Turtles
Excursions for Cruise Ship Passengers & Resort Guests
Birthdays
Corporate events
Anniversaries
Anniversaries
Bachelor / Bachelorette Parties
Bachelor / Bachelorette Parties
Company parties
Weekend Outings
SUMMERWIND
Frequently Asked Questions

FAQs

WHY THE NAME SUMMERWIND?

The name Summerwind comes from the wonderful song, "Summer Wind", which has been sung by dozens of top artists, but made legendary by Frank Sinatra.

 

Following are the lyrics:


"The summer wind came blowin' in from across the sea. It lingered there so warm and fair to walk with me. All summer long, we sang a song and then we strolled on golden sand, two sweethearts and the summer wind. Like painted kites those days and nights, they went flyin' by. The world was new beneath a bright blue umbrella sky. Then softer than a piper man one day, it called to you, and I lost you, I lost you to the summer wind.

 

The autumn wind and the winter winds they have come, and they have gone. And still the days, those lonely days they go on and on. And guess who sighs his lullabies through nights that never end?

 

My fickle friend, the summer wind. The summer wind, the summer wind. The summer winds."

(Summer Wind is available on Apple Music).

WHO ARE TYPICAL SAILING ADVENTURES CUSTOMERS ON SUMMERWIND?

Summerwind Adventures are experienced by:

  • Romantic Couples Weekends
  • Families and Group Adventures
  • Bachelor and Bachelorette Outings
  • Engagements and Weddings
  • Memorials
  • Executive Team Meetings and Team Building Adventures
  • Guest Speakers Adventures
  • Women’s and Men’s Groups or Annual Trips
  • Customized Adventures (please contact us to discuss)

WHAT IS THERE TO DO ON BOARD?

On board, we have many activities for you and your guests to enjoy such as a circular swimming platform that is deployed in the water and is attached to the yacht. This makes ocean swimming more enjoyable. Aboard you will have the use of a tandem kayak, boogie boards, windsurfer, a stand-up paddle board, surf boards and electric bicycles available throughout St. Augustine for exploring on land at any extended adventures. We offer unique adventures that aren't available elsewhere. Our adventures offer majestic sunset views and up-close encounters with sea life, which is sure to please even the most discriminating guests.

Can I charter the Summerwind sailing yacht for a specific occasion?

Yes, absolutely! Whether you're celebrating a special anniversary, hosting a family reunion, or planning a unique executive team-building event, Summerwind Sailing Adventures caters to all occasions with tailored experiences. You have the freedom to personalize your journey and choose to stay for a few hours or an entire week.

When and where do Summerwind Sailing Adventures operate?arter the Summerwind sailing yacht for a specific occasion?

Summerwind offers year-round sailing adventures in two locations.  

  1. Thomas (U.S. Virgin Islands) is available from November through April.

St. Augustine (Florida) is available from May through October

What amenities are included in the charter?

Our charter includes access to a range of amenities designed to enhance your sailing experience, including a circular swimming platform for ocean swimming. We also have other options such as tandem kayaks, stand-up paddleboards, boogie boards, electric bicycles and snorkel gear, perfect for adding extra fun to your sailing tour.

How far in advance do I need to book a charter with Summerwind Sailing Adventures?

Advanced 48-hour bookings are available for our charters, ensuring flexibility and convenience for our guests. We recommend booking as far in advance as possible, especially during peak seasons.

Are there any restrictions on who can charter the Summerwind yacht?

There are no strict restrictions on who can charter the Summerwind yacht. Whether you're a couple, a family, a group of friends, or hosting a corporate event, we welcome guests of all ages and group sizes to experience the luxury and adventure of sailing with us.

Can I choose my sailing destination, or are there specific routes available?

While our experienced captains can recommend routes and destinations based on your preferences, you have the flexibility to choose your sailing route within the designated areas of St. Thomas and St. Augustine. Whether you prefer to explore secluded coves, snorkel among vibrant coral reefs, or simply enjoy breathtaking sunset views, we'll work with you to create an unforgettable sailing experience tailored to your desires.

EXPLORE OUR DIFFERENT SUMMERWIND EXPEDITIONS

CHOOSE YOUR OWN ADVENTURE

We offer an array of adventures than span from a few hours to multiple overnights. We offer flexibility for your timeline and budget. We can even create a customized adventure to meet your every need.

PRIVATE 2 HOUR SAILING ADVENTURE ABOARD SUMMERWIND

From

 

$495

Plus $60 per hour for captain and crew

PRIVATE 1 NIGHT SAILING ADVENTURE ABOARD SUMMERWIND

From

$2500

Plus $60 per hour for captain and crew

PRIVATE 2 NIGHT SAILING ADVENTURE ABOARD SUMMERWIND

From

$3500

Plus $60 per hour for captain and crew

PRIVATE 3 NIGHT SAILING ADVENTURE ABOARD SUMMERWIND

From

$4500

Plus $60 per hour for captain and crew

testimonials

WHAT OUR CUSTOMERS SAY ABOUT US

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.

BRENT T / CUMMING, GA

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.

ELLEN M / DUNWOODY, GA

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!

Hugh B / MARIETTA, GA

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!

Jim D / ATLANTA, GA

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

ALLISAN M / DULUTH, GA

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.

FRANK T / ATLANTA, GA