Having a professional crew take care of all of the details allows you to relax and fully immerse yourself in your vacation from the moment you step on board.

A crewed yacht charter is a luxurious, yet affordable way to explore the Caribbean. For the duration of your charter, the crew will manage every aspect of your vacation to bring you a private and personalized experience.

All of the work of running the boat and prepping the yacht for your vacation is handled by the crew. Benefits of having a professional crew include:

• Customized menu planning and food preparation
• Provisioning the yacht with necessary items for charter
• Cleaning – the crew takes care of all the cleaning
• Yacht handling – no need to worry about the details
• Local knowledge so you can visit out-of-the-way places
• Cruising itinerary planning

Simply fly into the islands and meet the yacht and crew. Once you’re aboard you’re on vacation!

A vacation of a lifetime with family and friends in the beautiful Caribbean!

Charters begin at noon on the first day of the charter period, and end at noon on the final day.  Upon arrival at the marina, you will be met by the crew who will help you aboard and settle into your guest cabins.  After a safety briefing and tour of the vessel, snacks or lunch will be served and cold drinks will be on hand as you cruise out of the marina and set sail into the Caribbean waters.

Each day you will set sail and make stops along the way to your overnight destination.  These stops will allow you to visit picturesque swimming bays and famous snorkel spots, explore ashore, or use the water sports equipment.  Every afternoon the crew will anchor the yacht in a different bay so you can enjoy the water and an evening beneath the Caribbean stars.

Starting early in the morning and throughout the day, your chef will prepare customized meals and snacks for your party. Meals can be served to your group al fresco in the cockpit, overhead on the fly-bridge, or inside in the salon.  Beverages are always on hand with an open ships bar which includes standard wine, beer, cocktails, and mixers along with assorted non-alcoholic options.

An all-inclusive crewed yacht charter is a great way to vacation completely stress-free as the crew are there to handle the yacht and all preparations. If you would like to get involved with the sailing, you might have the opportunity to pull some lines.  Many crews are happy to teach the basics of sailing to guests.

Along with the yacht, the crew is a very important aspect of a yacht charter vacation.  Many groups say that the crew is an integral aspect to the charter yacht experience.

Most crews are industry professionals hired by the yacht’s owners, but some crews are owner-operators which means they own and crew their own vessel.

A crew typically contacts you a week or so before your charter to introduce themselves and arrange for a time to talk further about meal, preference and itinerary planning. The crew helps to bring your vacation together and provides everything you need in a floating resort, allowing you to simply relax and have exploring the Caribbean.

Read more about the role of the crew on your yacht charter vacation.

There are three main types of yachts available for crewed charters: Sailing Catamarans, Monohull sailboats, and Power/motor yachts.

Considering a few factors on what you are looking for in your charter vacation will determine which of the yacht types will be the best fit for your group. Here is a brief guide:

Sailing Catamarans

Catamarans are the most popular style yacht to charter for crewed charters. The majority of our catamaran charters are on sailing catamarans, but there is also a power catamaran option. Catamarans have two hulls which offer a broad and stable platform. This means there is plenty of deck, cabin, and dining space for your group to spread out and find your own space in the sun or shade. Most catamaran guest cabins have double size or larger beds with en-suite bathroom and vanity, and have some closet space.

There is a wide selection of crewed catamarans available for most budgets and party sizes. Economy catamarans are usually smaller (starting at 44ft in length) accommodating up to 6 guests, and offering great value for an all-inclusive yacht charter experience.

High end luxury catamarans range up to 80ft in length accommodating up to 12 guests in 6 en-suite cabins plus crew. A sailing catamaran is the best choice for great value and comfort.

 View some of our favorite crewed Catamarans

Monohull Sailing Yachts

Monohull sailing yachts offer a classic sailing vacation experience. Monohulls tend to have less space than similar length catamarans although the trade off is great sailing performance, especially up wind.

There are crewed monohull sailboats for a wide range of budgets starting at 45ft Caribbean-style economy vacations to well over 150ft sophisticated luxury charters.

 View some of our favorite Monohulls

Power Yachts

Luxury power yachts are at the top end of the price scale and offer a high crew-to-guest ratio which allows for excellent service. Power yachts are able to get you about the islands swiftly and in style. They also have space for the every water toy and offer discerning guests the comfort of a high end condo catered by top chefs with the flexibility to cruise to any point in the Virgin Islands.

 View some of our favorite crewed Power yachts

View feedback from our customers here.

After each charter, we reach out to the guests to ask for feedback on their crewed yacht charter vacation and, with approval, we publish the reviews. Here are some recent reviews:

“John at Sailing Directions was a great help in planning this trip. He always answered my emails in a timely and helpful manner.”
– Priscilla F, aboard Catamaran Anastasia, sailing the British Virgin Islands

“We were very happy with the service from Sailing Directions. I appreciated the updates you provided following the storms and the very helpful reminders along the way. The website is extremely helpful. Especially the charter preparation information. It really set us up for success. Our charter was an experience of a lifetime. We will always cherish the memories we made.”
– Diane B, aboard Catamaran Xenia 74, sailing the British Virgin Islands

“Sailing Directions and John Lane were extremely professional and very attentive to accommodate us in sorting through the complications the hurricanes presented, Well done! I like your website the best as far as crewed charter sites go because you post real pictures of boats the you took, not promotional stuff that could be out of date. I would refer you anytime and will use you in the future.”
– Ray L, aboard Catamaran White House, sailing the British Virgin Islands

When you charter a crewed yacht in the Caribbean there are a large range of activities available. One of the main activities is being able to explore locations that are only accessible by boat.

Water based activities include snorkeling, SCUBA diving, sailing, kayaking, stand up paddle boarding, stargazing, swimming, water skiing or tubing behind the yacht’s tender, sunbathing, board games, movie nights and more!

See the ‘Specs’ page for each yacht to find a complete list of water toys and amenities available.

There are also plenty of activities to do ashore which include hiking unique Caribbean islands, beach time on white sandy beaches, visiting famous beach bars like the Soggy Dollar on Jost Van Dyke, and enjoying live local music.

Activities are all customized to your group’s interests by the crew and your sailing itinerary is flexible. Wake up each morning and dive off the yacht for a swim, get out some water toys, catch up on some reading and relax or raise anchor and set sail to the next destination!

It depends on the individual yacht as to whether SCUBA equipment and diving is included in the charter rate.

Some of the charter yachts are fully equipped for SCUBA with dive equipment and a dive master / instructor as part of the crew. Some allow diving; however, you may need to pay for the equipment rental. SCUBA details are listed on each of the yacht’s ‘Specs’ tabs, and we are happy to provide details on individual dive policies for individual yachts.

If your boat does not provide SCUBA diving onboard, there is the option to do Rendezvous diving.  Rendezvous dive service is provided by local dive shops and is not included in the charter rate. The dive shop will bring their dive boat to your charter yacht, pick up your divers and take them to a dive site, and return the divers back to the yacht afterwards.

Rendezvous diving is a great option for groups if only a few members are interested, as the rest of your party can continue the charter with both the captain and chef on board in the meantime.

Kids are seldom bored on yacht charter in the Caribbean! They really enjoy sailing, snorkeling, and playing on the beach. Many vessels are kid-friendly, and most crews love family charters; however, some yachts do have age minimums or other requirements (e.g. swim safe).

The yacht’s crew is employed to maximize the enjoyment and safety of your vacation; however, please note that they cannot take responsibility for overseeing the welfare of children at all times. Children under the age of fourteen must be under the direct supervision of a parent, childminder, or other appointed adult.

We’ve put together a sample 7-night cruising itinerary that includes many of the sailing highlights in the Virgin Islands! This should give you an idea of what you can do during your all inclusive crewed yacht charter vacation. Remember, this is just a sample! The itinerary for each group will be customized and once on board, your crew’s local knowledge is an invaluable resource to help plan day-to-day activities.

Caribbean Virgin Islands: mid-November through end of July (winter through early summer)

Caribbean Leeward Islands: May – July (late spring and early summer)

Caribbean Grenadines: May – August (late spring through late summer)

Mid-December through the end of April is the high season in the Caribbean as travelers escape cold northern climates to bask in the tropical sunshine. For the peak holiday periods of Thanksgiving, Christmas, New Years, and the Spring Break months of March and April, crewed charter yachts should be reserved well in advance.

December through May is considered the dry season while June through November is generally the more humid season. However, in our experience, rain or clear skies can occur at any time during the year. Rainstorms often pass quickly and there is sunshine on most days during the year. Average air temperatures in coastal areas range from 72º to 86º F. The warm coastal water temperatures stay between 68º and 74º F.

The northern summer is the low season in the Caribbean. However the months of May, June, early July, and late November are still great times to visit the islands. In addition, all inclusive charter rates and flight prices may be lower and the beaches, roads, and restaurants are rarely crowded.

Atlantic hurricanes can occur any time from August through October with the most active month being September. The good news is that every year brings more sophisticated storm warning systems and it is unusual for any one island to be severely affected more than once or twice every 10 years and, with a bit of planning, your actual odds of experiencing a hurricane are very low.

The most popular sailing location in the Caribbean is the Virgin Islands. This includes the US Virgin Islands (primarily St. Thomas and St. John) and the British Virgin Islands (Tortola, Virgin Gorda, Anegada, and Jost Van Dyke, along with over fifty other smaller islands and cays).

This is one of the world’s best sailing areas due to the number and close proximity of islands, bays, and sandy beaches. Warm, clear tropical waters that offer great snorkeling, warm air temperatures year-round, quiet bays, fantastic evening star-gazing, and if you’re in the mood, world famous beach bars.

The Virgin Islands is a great sailing vacation destination for first time sailors and families. There are many crewed private yachts available to charter and the light trade winds and protected bays make for a fun, safe playground for kids and adults alike.

Ask us to place the yacht on hold for your dates, we’ll then email you over the charter agreement and reservation instructions. You’ll read and sign the charter agreement and pay the deposit by credit card or wire transfer.

For more details about the reservation process, including deposit amounts and after sales support, please see How to reserve a crewed Caribbean charter yacht vacation.

The all inclusive charter rate generally includes:

• Captain and Chef/Host/Crew
• 3 meals and snacks each day on board the yacht
• All drinks, including standard brand wine, beer, liquor, and mixers
• Air conditioned accommodations
• On board water sports equipment (SCUBA gear may be additional)
• Cruising permits, fuel, limited wifi and all on deck amenities unless otherwise specified

Extra charges for all inclusive yachts include crew gratuities, and optional: communications, marina berthing, shore based activities and any meals taken ashore, trip insurance.

 See more about crew charter vacation Costs here.

This means that in addition to the charter rate, you will be asked to pay an Advance Provisioning Allowance (APA) which is usually 25-30% of the charter rate. Power yachts and mega yachts are often plus expenses (we will let you know if the yacht is plus expenses in our quote).

 See more about crew charter vacation Costs here.

Payments are due in two or three payments depending on the time of your booking relative to your charter dates.

If the start of your charter is more than 6 months from your date of booking:

• 25% deposit is required to confirm your charter
• 25% payment is due 6 months prior to your charter
• 50% final payment is due 60 days prior to your charter

If the start of your charter is less than 6 months from your date of booking:

• 50% deposit is required to confirm your charter
• 50% final payment is due 60 days prior to your charter

We accept several different forms of payment with no fees. You can pay by wire transfer, check, Visa, MasterCard, and American Express.

We also offer the convenience of splitting credit card payments between charter group members through the customer portal on our secure website.

Standard crew gratuities are 15% – 20% of the charter rate depending on your satisfaction with the service.

The crew is an integral part of your yacht charter and they work hard to ensure that your vacation is a great one and will be remembered for many years to come. They are your chef, bartender, waiter, and tour guide.

Crew gratuity is generally given in cash prior to disembarking on the final day of your charter period. Certain crews accept checks on US bank accounts, and/or payment apps such as Venmo and/or PayPal. Let us know if you’d like to pay this way and we will double check that your crew can accept this payment method.

Travel insurance is optional.

Sailing Directions International does not sell or advise on trip insurance; however, the past few years have shown us that the unthinkable can and does happen, so we strongly encourage all clients to purchase travel insurance upon booking to ensure an additional layer of protection against financial loss.

When purchasing trip insurance, please make sure that the policy you choose provides coverage for your insurance needs. This may include:

• Medical coverage
• Delayed or canceled flights
• Lost or damaged luggage
• If you need to cancel the trip for any reason

Passports are required for all visitors in the Caribbean.

The United States Government will require a valid passport to regain entry into the US. Please remember to bring passports for each member of your group.

US Citizens: For information on renewing your US passport or obtaining your first passport please click here.

British Virgin Islands:
US Citizens can enter the British Virgin Islands with a valid passport – no visa is required.

Non-US Citizens may require a visa to enter the US and / or British Virgin Islands. For a list of countries that qualify for the US visa waiver program please see: US Visa Requirements

For more information on Visa requirements for the British Virgin Islands please see: BVI Visa Requirements

Many other Caribbean nations offer tourist visas, some of which must be applied for in advance. Please let us know if we can help you with any questions.

All vessels have VHF radios and the captain will have a cell phone where you can be reached in the event of an emergency.

You can also bring along your own cell phone. Please check with your provider that you have roaming capability in the area you are visiting. Many of the boats also have wifi internet available onboard available for guest use so you can receive calls or messages through an internet calling service such as WhatsApp, Skype or Messenger etc.

If we have not addressed your specific question, please contact us and we will be happy to help you further!

We typically provide same day responses by email, but if you have an urgent question please don’t hesitate to call us toll free at +1 877 669 224