Set Sail on the Ultimate Sailing Adventure: Easy as 1-2-3!

No!  If you want to learn, Captain Wendy is a certified instructor and is happy to teach you as much as you want to know, but she is very capable of taking novices aboard for a sailing vacation.

We sail in stunning destinations across the Caribbean and beyond, including favorites such as Tahiti, Australia and Thailand.  Have a particular destination in mind? Contact us and we'll customize a trip just for you.  From hidden coves to iconic beaches, your itinerary can include the spots that excite you most. 

 We recommend booking at least 3–6 months in advance to secure your preferred dates and vessel. For peak seasons or special occasions, early booking ensures you get the experience you dream of.

The first step is to contact us at captain@sailthevineyard.com and let us know your preferred destination and how many days you'd like to spend aboard your sailboat.  

Charters range from 5 nights to 2 weeks or more, depending on your schedule and destination preferences. Longer voyages allow for deeper exploration or visits to more remote islands. 

Sailing vacations can be booked between December 1-April 30.  For dates outside this range, email us for case-by-case consideration.

You'll need to have an idea of how many nights you'd like to be aboard the sailboat, how many guests total you want to accommodate, and a date range for your preferred sailing dates.  You'll also want to have an idea about whether you want to prepare your own breakfasts and lunches or prefer to include a chef to prepare and serve all of your meals aboard.

Using the information you've shared during the first call, we will create a list of a few available boats for your dates and send you a precise cost per person and dates for your sail. After you review the information, you'll select your preferred sailboat and proceed with reserving your vacation.

We will need each guest's personal contact details, passport information, sailing or boating experience, and food and drink preferences.  Our online forms make this process simple and easy.  We'll send a link via email to each guest in your group.

A minimum of 90 days notice is required to cancel or reschedule your vacation date.  This is industry standard for charter boat rentals.  Less than 90 days notice will results in a 50%-100% cancellation fee.

After you select your sailboat and dates, a deposit payment is due immediately to secure the dates and the boat.  Depending upon how far in advance you have booked, this typically ranges from 30-50% of the trip cost. 

Your charter price covers the vessel, professional Captain (and crew if you opt for a fully crewed trip), onboard amenities (including linens), taxes, cruising permits, mooring ball fees, National Park Fees, boat fuel, a smaller tender vessel to transport you from the boat to shore at each island, and custom itinerary planning.  Any additional excursions or special requests are arranged separately.  

The final payment for your trip is due 60 days prior to departure. 

Tipping is customary in the yachting industry and is a way to show appreciation for your Captain and Crew. They do far more than navigate the boat —they serve as your hosts, chefs, bartenders, instructors, entertainers, engineers, plumbers, and most importantly, ensure your safety at sea. With extensive training and years of experience necessary to achieve professional licensing, they handle every detail to keep your voyage smooth and enjoyable. A gratuity of 15–20% is customary and is customarily given directly to the captain, who distributes it among the crew.  Cash gratuity is preferred.

Sailing catamarans can accommodate 6-8 guests.

All of the boats we offer typically have 3 or 4 bedrooms (cabins) for guests and have air conditioning with individual cabin controls. Most boats also have private bathrooms (called "heads") for each cabin; some have one shared bathroom for every 2 cabins.   Most boats have a WiFi option for an additional fee.  Water toys, SUPs, kayaks, and snorkel gear are also available as rentals for an additional fee.  Bath towels, beach towels, bed linens, and pillows are included for each guest.

Whether you choose to prepare your own meals aboard the boat or include a chef in your vacation plans, we'll need to collect information about what each guest prefers to eat, as well as any food sensitivities, allergies or dislikes.  We have easy-to-complete online forms for gathering this information.  We'll send the link to each guest and use the information collected to generate meal plans and shopping lists.  This service is included as part of your vacation planning package for charters including a chef; it's available as a fee-for-service for self-catered trips..

We'll collect your preferences for any alcoholic or non-alcoholic beverages you'd like to have aboard.  We will send a link to each guest to complete information about their preferences.  These beverages will be aboard the boat upon your arrival.

In your food and beverage preference forms, we'll ask you to let us know how much water you typically drink each day.  The boat will be stocked with drinking water prior to your arrival.

If you choose our chef-included trip, or include our provisioning service as a purchase add-on, we include the shopping and stowage of all food and beverage items aboard the boat.  With this service, we'll provide you with a printed list of your food and beverages aboard and organized stowage information on board so you can find your items easily.

It is customary for the Captain and Chef's meals to be included with the charter.  If you're enjoying meals on the boat, allow for enough to share those meals with the Captain and crew (if chef/crew was included in your trip.)  If your meal plan includes breakfasts & lunches onboard but dinners ashore, it is customary for guests to cover the costs of the Captain & Crew's dinner as well.  

One of the joys of a sailing vacation is that every day brings its own unique adventures. Wake to breathtaking views of crystal-clear waters framed by vibrant Caribbean peaks and pristine white-sand beaches. Savor your morning coffee or juice on the back deck in the shade, or bask in the warm sun at the bow, feeling the wind in your hair and the sea around you.

After breakfast, we’ll weigh anchor and set sail for our next stunning anchorage. Depending on the day’s route, expect 2–5 hours of leisurely sailing to reach your next secluded cove. Once there, dive in for a swim or snorkel, explore the shore, paddle a kayak or SUP, or simply relax and soak up the sun.

Arrive in time for sunset cocktails, giving you a moment to freshen up before dinner. Depending on your chosen package, enjoy a memorable meal ashore or a gourmet dinner prepared on board. As night falls, experience the magic of a Caribbean midnight, marvel at the stars above, and drift off to sleep, ready to do it all again tomorrow.

We know the inside scoop on land excursions, snorkeling sites and other fun things to do on the islands.  We can arrange as much of this ahead of your trip as you'd like, or we can take a more relaxed approach and offer you an array of choices as we move to each anchorage.  The Captain & crew need not go with you for land-based excursions unless you specifically request it.  If you do, it is customary to cover the Captain's cost of any entrance fees, taxi fares or other costs associated with the excursion.  

Absolutely!  You may bring your own mask, fins and snorkel or rent them from the dive shop located close to the charter base.  Your Captain will direct you to some of the best snorkel spots at each anchorage.

We can also arrange "rendezvous diving" to have a local dive shop pick you up from our boat and take you for a SCUBA excursion.

Several anchorages we will visit offer windsurfing, kayak, and SUP rentals.  We are also able to rent a SUP, kayak or other water toys to keep aboard our boat during the trip.  Additional fees will apply.

Whenever the itinerary allows, guests are welcome to explore on their own. Your crew ensures safe docking and offers guidance on local highlights.  We will also make recommendations and help arrange some don't-miss land-based excursions on various islands.

Yes! Several of the islands and anchorages we will visit have these services available close to the dock.  Your crew is happy to help coordinate these services and arrange appointments for you.

If you need assistance, we'll talk with you about recommended routing options for getting to the charter base and departure port. We can discuss flights, ferries, taxis and any other modes of transportation that a might be recommended to get you there. 

We'll arrange taxi service to get you from the airport or ferry terminal to the boat.  You'll need to pay the taxi driver directly for the trip, but we'll arrange it for you and have a driver waiting for you on your arrival. 

Yes, tipping your taxi driver in the islands is customary.  Standard tipping is 15-20%. 

The boat typically leaves the dock at noon on Day 1 of your vacation.  Flights arriving into the islands typically arrive in the afternoon, so you'll need to arrive the day before your charter begins. We can make recommendations about where to stay upon arrival. 

Your yacht is crewed by a licensed, experienced professional Captain trained in navigation, safety, and hospitality.  Your Captain is also a certified sailing instructor.  If you opt for a Captain-only trip, the Captain will teach someone in your group to assist with some activities as needed during the trip.

Your Captain (and crew if applicable) are trained in first aid, emergency procedures, and onboard safety protocols. The boat is stocked with all required safety equipment, including but not limited to life jackets, fire extinguishers, and flares.

Sailing vacations are generally planned for periods of settled, peak season weather.  However,  your crew monitors conditions closely and adjusts the itinerary as needed to ensure safety while maintaining as much of your planned experience as possible.  

People who are prone to sea sickness usually know it before their arrival for a sailing vacation.  If this is a concern for you. there are several options for preventing sea sickness, both medication-based and natural remedies.  Natural options include bands worn on the wrist that utilize a pressure point and ginger products.  

There are inexpensive pressure-point bands and more expensive ReliefBands that emit a small electrical pulse.  Feedback from our previous guests indicates that the ReliefBands work the best, if your budget allows.  Ginger, in the form of chews, lozenges or gum can be helpful as well.  Ginger snaps or cookies are typically not helpful as they contain more sugar than ginger. 

Medication options, which you should discuss with your doctor, include prescription scopolamine patches and over-the-counter medications such as Dramamine.

Rolling suitcases are not ideal for liveaboard sailing vacations.  Space aboard is limited and it's typically difficult to find a place to stow an empty rolling suitcase.  Duffle bags that can fold up are much easier to stow and are easier on the boat's deck and floor surfaces. 

Though it may be less expensive at home, we recommend purchasing sunscreen on arrival in the islands.  This saves both space and potential messes in your suitcase.  Spray sunscreen is never a good idea on a boat - lotion is best! Overspray makes decks slippery and can discolor cushions and fabrics on the boat.

You'll want a hat and sunglasses as well.  We recommend considering a croakie to keep your sunglasses from going overboard and a hat keeper to prevent your hat from blowing away.  (Click on the links for where to purchase recommended products.)

We recommend a dry bag for transporting your wallet, towel, sunscreen and other important items ashore with you.  If you plan to do alot of sailing and water sports going forward, K3 is our favorite brand.  For a more economical option, consider the iDryBag brand.  If you are traveling as a family or group, you really don't need one bag per person - the group can share one or two dry bags.

As little as possible!  On a sailing vacation, you'll spend most of every day in a bathing suit, sometimes with a cover up and sometimes without.  Plan to pack 2-3 bathing suits so you don't have to wiggle into a wet bathing suit in the morning. You'll quickly learn the sailing lifestyle - hanging your swimsuits and towels with clothes pins on the sides of the boat to dry in the warm tropical breeze! You'll need 2 pair of shorts and shirts to go with them at the most.  If you wear them at all, it will be just long enough to go to dinner. You'll find that sailors don't usually use a new outfit for each day.  Ladies will likely want 2-3 sundresses to wear ashore or for dinner.  Men may want 2-3 collared shirts for dinner.  Shorts and sundresses are always appropriate for every restaurant on every island.

You will need a pair of flip flops that can get wet.  Trust us - they WILL get wet! You can consider a second pair of shoes to change into for walking excursions ashore.  For this, we recommend something like a women's or men's Teva shoe with a supportive sole but is still good in a wet marine environment.  Flip flops are always appropriate for every restaurant on every island.