Sailing in the Caribbean is more than just a vacation, it's a lifestyle. Enjoy the freedom of choosing your day, whether it's anchoring at a private cove and swimming to a secluded beach or cruising between small, lush islands in the beautiful British Virgin Islands.

Sailors in the Virgin Islands can visit several islands in a single day, which, in part, is why the Virgin Islands are the most popular sailing destination in the Caribbean.

Those sailing and yachting also have an opportunity to see and experience the Caribbean in ways resort-goers don't. Sailors get the privacy and seclusion of the sea as well as the local experience, stopping and replenishing supplies or buying souvenirs at local markets along the way.

With the freedom of a sailing trip also comes more responsibility in planning. Here are a few of the key considerations to factor in when planning the sailing trip of your dreams.

Going bareboat: If a sailor decides to go without a captain and crew (called bareboat), yacht clubs and rental companies will match each potential sailor with the best boat for their experience level. Don't overstate your skill level on the resume as you don't want to be responsible for a boat too large to handle.

Beginner sailors can earn a bareboat certificate at sailing schools like Steve and Doris Colgate's Offshore Sailing School, the official sail school of the Moorings, one of the foremost rental leaders in the Caribbean. In just about a week, these courses will turn a novice into a sailor ready to take a boat out on their own.

Going bareboat in the Caribbean doesn't have to mean you're completely on your own. At Moorings, sailing groups have many different options to enhance their bareboat trip including packed meals. The Moorings also offers personal chefs or skippers for $170 and $185 a day, respectably - just make sure to leave room for them in the cabin!

Flotilla: A flotilla is when a group of boats, usually arranged by a charter company, follow a lead boat and travel together on a trip. This style of sailing is popular in the British Virgin Islands and is great for those who have just completed a bareboat certification class. Sailing in a flotilla doesn't necessarily mean always following the leader. Sailors can choose to be as independent as they want. This type of sailing also offers a great social aspect, as many of the boats will meet up at night for dinner or Caribbean cocktails.

Chartered: According to Sherry Yates, the owner of brokerage company Yates Yachts, picking the right chartered boat really depends on how the group plans to spend their time. You may be a family with active kids looking for a wide variety of water toys and diversions on board, Yates told the International Business Times. Or you may be professional couples, who need to get away from it all, relax, and be pampered, but with a healthy dose of nightlife thrown in. Some boats have top of the line entertainment systems, spa services, or everything needed for scuba diving - so picking a charter crew to match your travel style is key.

Some charter clients may be looking to participate and learn to sail, while others want a completely hands off vacation sunbathing on the hull. Explain in detail the experience you want to have to the charter company so that you'll be properly matched.

The Crew: Having a great crew is the secret to an amazing sailing retreat both in the Caribbean and elsewhere. Their local knowledge of secluded beaches, swim-in bars, and vibrant ports will turn the average tour into one you'll keep coming back for. It's important to also remember at the end of the day the captain will make the final decision on routes and places to go based on safety.

Some may wonder about privacy on a romantic cruise, however with a great crew this will be no problem. A good crew will be there when you need them, yet instinctively know when to disappear to leave you time to yourselves, said Yates.

Charter Broker: For those who need help with choosing the right boat and crew, a third party broker may be the way to go. The key to a successful charter is a good match between the guests, the yacht, and the crew - which is where a charter broker is essential, said Yates. Learning all I can about a charter group's needs and especially their expectations is so important.

A broker can match the number of guests, interests, and preferred locations with a crew and a boat suitable for their wants and needs. A broker is the primary contact person - and it's much easier to get in touch with a broker than the captain of a sailboat that's always on the move. Charter brokers are available to answer any concerns about sailing in the Caribbean, from seasickness to hurricane season dates.

Many reputable Caribbean brokers, including Yates, only recommend crews and boats others have had positive experiences on, so clients can rest assure they too will have an amazing vacation. In addition, the broker will hold the charter payment in escrow. This is great for travelers who are worried about paying upfront for a disappointing vacation.

All-inclusive trips: Most of the chartered Caribbean yachts and sailboats come all-inclusive. Many of the charter companies including Moorings and Yates Yachts will ask guests to fill out a food preference sheet in advance. This lets the chef know about favorite dishes and any allergies so they can plan accordingly. The majority of all-inclusive trips include meals, beverages (both alcoholic and nonalcoholic), snacks, and any onboard water sports if available.

Usually gratuity (customarily 15% of overall trip) and overnight dockage is not included. Most of the boats spend the night at anchorage points. Some additional food requests are typically available at an additional cost, including caviar, champagne, and certain wines.

What to bring: It's important to pack light on any sailing trip as space is often very limited. Remember to also bring lots of sunscreen, a hat, sunglasses, and a light long sleeve shirt. Travelers should also consider trading in their suitcase for a duffle bag, which can be folded and stored more easily.

Price Bareboat: According to a Moorings spokesperson, the price of renting a boat varies from $400 to $1,800 a day for the boat, regardless of the amount of people. For example, a monohull 37ft may cost about $2,300 for five days with a maximum of six people, while a larger catamaran will cost upwards $5,000 for five days.

Price Chartered: The price of a chartered boat varies greatly on the size and luxury amenities. For instance, on a large, luxury catamaran, the cost per person with 8 guests on board can be $5,000/week all inclusive, said Yates. A midsized catamaran will cost about $2,500 per person per week. An even smaller and affordable catamaran will cost even less at under $1,800 per person per week.