Frequently Asked Questions

Why are the sailing charter rates so different between sailing charter companies?

When comparing rates among charter companies there are several important factors to consider.

1) Will you be chartering aboard a sailing yacht like Summerwind, a 50-foot yacht or on a smaller sailboat? Will you be sailing for a few hours or a few nights?

2) Are you choosing a private charter adventure for you and your guests or will you be sharing a boat with a few strangers or a few dozen strangers? 100% of Summerwind Adventures are private.

3) Will you be chartering during a weekday, a sunset charter, or a weekend or holiday?

4) What amenities are offered on the yacht? Do they offer kayaking, stand-up paddleboards, ocean swimming, catered meals, extensive safety equipment aboard such as an auto-inflate life raft, dual chart plotters, safety jacklines, additional auto-inflate life jackets with harnesses for the on watch team, back-up EPIRBS, etc.?

What if the forecast calls for rain during my adventure? What happens then?

Because we are based in St. Thomas (U.S. Virgin Islands) & St. Augustine (Florida)., during some parts of the day, forecasts may call for some rain. For most weeks, forecasts call for short showers during a period of time, but it is no problem for our sailing adventure. The cockpit is fully covered by a dodger and Bimini to repel the rain. We also have a large salon down below to remain fully dry during any showers. Also, remember if it is a 30% chance of rain, there is a 70% chance that it won’t rain. In addition, in the summer a little rain can cool off the weather and can be a treat. When requested, we also go swimming and enjoy whatever the weather offers. Thunderstorms will pop up on occasion, but we only have to cancel less than 1% of our sailing adventures. If you are thinking about booking a charter, but see the forecast shows some or chance of rain, book anyway, as it will most likely rain for a short period and can be a great day. Some people wait until the last minute to book only when they see 100% dry weather and many times miss the opportunity to sail finding that the yacht is already booked. In the rare instance you are the 1% of our adventures where we must cancel because of safety issues, we will try to reschedule when possible or provide a full refund.

Does each guest need to register?

No, only the primary guest who is paying for the sailing adventure is required to register. During the online registration process you will be asked how many guests will be joining you, and you will need to provide the names of your guests at that time. You may add additional guests at boarding time as long as you don’t exceed the maximum of 10 in your party for day adventures and four maximum guests for overnight charters. The maximum number of guests allowed aboard (not including the captain and crew) can increase from six guests to 12 guests upon being granted a COI from the U.S. Coastguard in advance.

What should I bring with me for the sailing adventure?

If you and your group are not spending the night aboard Summerwind, bring bathing suits, sunscreen, a towel, sunglasses and don’t forget a camera. You might also want to bring binoculars, a hat, and towels if you plan on ocean swimming at anchor or at a mooring. We provide chilled water, soft drinks and a snack during hourly sailing adventures. You are welcome to bring additional beverages and snacks on the boat including alcoholic beverages. Guests who will be spending overnights aboard Summerwind will be provided breakfast and lunch aboard. Special meals can be arranged with a private chef when requested. Your group will be provided water transportation (without charge) to and from shore on our center-console tender to explore hotels, quaint shops or the local eateries and watering holes.

What should I wear aboard Summerwind?

In warmer weather, bring sun cover-ups as you would when going to the beach.  Wearing long sleeves to keep the sun off you, hats and sunglasses are advisable. In the winter months, we suggest dressing in layers so you can remove layers as needed. Be sure to bring a jacket so you can adjust for the cold as well. All passengers should wear soft-soled shoes such as topsiders or other boat shoe brands. Tennis shoes work as well. Please don’t wear black heeled shoes or boots because you could slip or could cause damage to the yacht’s decks. 

Can I bring additional guests?

The maximum number of guests allowed aboard (not including the captain and crew) is up to 12 guests upon being granted a COI from the U.S. Coastguard.  This law is taken very seriously, and no exceptions can be made.

Will I or my guests get seasick?

It is not unusual that in a group of 10 passengers that someone begins to feel a little seasickness, so don’t be alarmed or embarrassed. We have had a rugby player and marathoner onboard who each got seasick, so it can happen to anyone. If you or your guests feels sea sickness, we suggest to remain on deck and stand looking forward while holding one of the helm stations, keeping your eyes looking forward to begin feeling better. You are also welcome to go below and lay down until feeling better. Also, at your request, we can leave the ocean and sail in the Tolomato River where it is mostly smoother. We also can pick up a mooring downtown and still the boat on the mooring until everyone is feeling stronger. Although the great majority of our guests don't get seasick, concerned passengers could bring products that contain ginger, such as ginger cookies or Ginger Ale, because they have been known to help calm an upset stomach.


This is your adventure, and we will do as you request, but we typically do not go back to the dock when someone feels seasick. So, be prepared for us to encourage those feeling sea sickness to rest, to take a drink or to go down below until they feel better or can do their best to tough it out so that everyone else can still enjoy the outing. With time, everyone gets over sea sickness - even though it can feel miserable during an episode.

How do you insure the Cleanliness of the yacht?

The yacht is cleaned between each outing and our overnight guests enjoy freshly laundered linens as well as luxurious towels and robes.

Can we fish on board?

Yes, if you have a necessary fishing license. We do not provide poles or bait, but feel free to bring your fishing gear on board if you have a valid fishing license.

Can we swim off the yacht in the ocean?

Yes, we are glad to make time for swimming on any adventure. We can deploy our ocean swimming platform when on the ocean if the seas are relatively calm. This device is secured to the yacht when deployed.

Are pets allowed?

Unfortunately, we do not allow pets of any kind onboard, regardless of size or training of the animal. We try to provide an exceptionally clean yacht for guests, some of whom might have allergies, so we won’t permit pets onboard.

Does the Yacht have AC and a generator?

Yes, Summerwind is a luxury yacht that has supplemental air conditioning and heat supported by an onboard generator that we will operate as requested.

Are crew members provided on the Summerwind yacht for charter in St Augustine FL?

Yes, crew members, including a Captain and attentive staff, are provided on the Summerwind yacht to ensure a safe and enjoyable sailing experience for guests.

When is Summerwind in St. Thomas & When Is it in St. Augustine?

It is beautiful in St. Augustine year round, however it does tend to get a little cold during the winter months. We want to make Summerwind Adventures available year-round to the greatest number of people looking for a memorable sailing adventure. As a result, we have chosen to locate Summerwind in the Virgin Islands during the months of November - April. 

Can you snorkel in St. Augustine like you can in St. Thomas?

We maintain snorkel gear on board and would have the ability to snorkel while Summerwind is in St. Augustine. However, the waters in St. Augustine are not particularly suited for snorkeling or scuba diving because of the water's lack of clarity. Also there aren't any reefs located nearby beautiful St. Augustine. We have our swimming platform that can be attached to Summerwind at either location so travelers can enjoy swimming from the yacht. St. Thomas is breathtakingly beautiful, with sparkling waters and many reefs located in the area with the potential to view rare sea turtles and other amazing sea life.

What is the cancellation policy?

If you need to cancel or reschedule your adventure, we require that you notify us a minimum of 7 days prior to your adventure start date. If a cancellation request is received between 7 days and 48 hours prior to your sailing date, a 50% credit will be provided for a future date. For cancellation requests received within 48 hours of the sailing date, no refunds will be available.

What is your tipping policy for the captain or crew?

In the charter industry a gratuity or tipping is expected for a job well done. The typical charter industry industry gratuity is 20%. Gratuities for your Captain and crew are not included in the fees paid for your adventure and are discretionary. Our team will work hard to make your adventure a special time for you and your guests.

What if there is inclement weather causing a safety issue?

Cancellations because of foul weather or unsafe sea conditions will be made by the Captain at his/her discretion. If we must cancel your adventure because of unfavorable or unsafe weather or ocean conditions, you'll be given the option of to reschedule or receive a full refund.

Do I need to make an advanced reservation?

It is advisable to make your reservation in advance to assure a favorable adventure time. On occasion we can accommodate last minute reservations, but we strongly recommend that you call to see if there are any cancellations or reservations available. Crew is scheduled on an as needed basis, so having the yacht available and crew available is a gamble. As a result, we highly recommend that you call and make a reservation in advance. During high-travel dates, vacation periods or holiday weekends, we recommend calling weeks or months in advance.

Do you provide food or refreshments on the boat?

For sailing adventures where our guests spend the night aboard Summerwind, we provide breakfasts and lunches daily except for the final day, where we will provide breakfast only. Dinners will be on your own at one of the many wonderful restaurants onshore. For overnight guests, we provide free dingy service to and from shore for dinner outings. For guests not spending the night aboard, we provide chilled water, soft drinks and a light snack while aboard. Feel free to bring along additional snacks and alcoholic beverages, but glass bottles are not permitted onboard for safety. However, you are welcome to bring aboard your own snacks and drinks to supplement what we provide.

Do young children count as a full guest on board?

Coast Guard regulations considers every person on board (except for the Captain and crew) as a passenger. In addition, children under the age of 13 must wear a USCG approved Type 1 PFD (life jacket) provided for you during your adventure. Children require supervision by parent or guardian at all times and must be capable of remaining calmly in the cockpit or down below for several hours. We do not recommend bringing children under 7 on charters longer than a few hours or when planning on ocean sailing.

What safety equipment do you maintain onboard Summerwind?

Summerwind is equipped with more safety systems than any other private St. Augustine sailing experience. She is a true 50-foot luxury yacht that is well maintained and fully insured for charter. She is the largest and nicest yacht available for charter in St. Augustine. Summerwind exceeds safety requirements by the United States Coast Guard with on board equipment. 

  • There is a coast guard approved lifejacket for each person onboard. If you are a strong swimmer and over 13 years of age, you can listen closely to the safety briefing and note where the life jackets are stowed (under the navigation station below) and be prepared to put on a lifejacket should an emergency be declared by the captain.

  • There are four fire extinguishers on board, one in each cabin and one in the salon. We also maintain all the necessary coast guard required devices including throw rings, life slings, audible signals devices and VHF communications.  Should you see or smell a fire, immediately shout "fire" and get the crew who will use the closest fire extinguisher to fight the fire.

  • Although it is not required by the coast guard, we keep an auto-inflate Winslow rescue life raft onboard in case of an emergency. It is stored in the salon. We are one of the few private sailings yachts with so many safety systems aboard.

  • Also not required, but we keep (two) EPIRBs (electronic rescue beacons) onboard that are registered with the coast guard. The EPIRBs have never been used in my 15 years of ocean sailing, but they can provide critical notification to the coast guard if ever required. If an EPIRB was activated, it would transmit a mayday warning with our location by sending our latitude and longitude to the coast guard so they could locate us within an approximate 50-foot radius.

  • The boat has both Ray Marine and Garmin Chart plotters for navigating and displaying the yacht’s system functions. Summerwind also has (two) iPads onboard with backup navigation software in case the yacht’s internal navigation system fails.

  • The boat has a VHF radio for communicating with the local marina, other boats or the coast guard if necessary.

  • Cell phones will work as well during our trip, being typically reliable within 8 miles of shore.

  • We will keep a close eye on the wind and weather, so we know when to shorten the sails (reefing the sails) so the boat does not get overpowered by the wind.

  • The boat is equipped with a dodger and Bimini covering the cockpit and shielding it from the sun if you are sun sensitive.
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).

What about smoking or vaping?

We do not permit smoking, cigarettes, cigars, vaping or the use of tobacco of any kind while aboard Summerwind, including in the cockpit or on the decks.  Please respect this restriction.

How is the experience of the crew?

Each of our captains are coast guard licensed captains and our crew are experienced boaters. Our founder has sailed more than 25,000 ocean miles around the world, as you can read in founder’s story.

Can I apply for a job with Summerwind?

We are always looking for licensed master captains with a focus on safety and strong customer service skills. We also choose deck hands with experience. Please contact us via the form on this website.

Can you always see shore?

Typically we will be in site of land, but there could be times that we sail further than you can see. If requested, please let our crew know, and we can be sure to stay in range for visibility of shore. We want to make sure that all of our guests are completely comfortable and satisfied. 

Can we cook on board?

For safety, cooking on board is available when a crew member is on board. The crew will assist in cooking food brought on board as well as the meals provided during our overnight adventures. For safety reasons, we can only permit cooking if a crew member is on board.

What is there to do on board?

On board, we have many activities for you and your guests to enjoy such as a a swimming pool device which is attached to the yacht on the ocean. When requested, you will have the use of a tandem kayak, boogie boards, a stand-up paddle board, surf boards. We offer unique adventures that aren't available elsewhere. Our adventures offer majestic sunset views and up-close encounters with ocean sea-life, which is sure to please even the most discriminating guests.

These water devices can be requested for a fee when the sailing adventure is at least for hours in duration.

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
  • Burials
  • 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)
Do you offer a sailing in St. Croix?

Because St. Croix is located 45 miles from St. Thomas and much of the day is spent sailing to and from St. Croix, we only offer St. Croix as part of a multi-day adventure.

Are there reasons you should choose a sailing adventure on Summerwind rather than the dozens of other charter yachts available?

We think there are many reasons to choose a sailing adventure aboard Summerwind. We offer one of the few 50-foot, monohull sailing yachts in the market for a true ocean sailing
adventure. Our yacht is larger, wider, and newer with an open cockpit, twin helm design for a better experience aboard that others in the market. We offer air-conditioning as an option below deck, high-speed internet, ice maker, water maker, Brio chilled water dispenser, a washer and dryer, and other luxurious amenities. Our crews are US Coast Guard certified and Red Cross CPR/AED certificated. In addition, our onboard team members are Red Cross certificated lifeguards and have significate other ocean water experience (See the About Us) section of the website for additional crew member ocean experience.