Specialty Yacht Charters

Our Island Life Charter team prides itself in our ability to customize yacht charter vacations to meet the needs of each charter guest and ensure that every sailing experience is unique and thought out. Because we are located in the Virgin Islands, we are your local experts to the Caribbean and some of the best things to see and do here. Below are a few of the specialty charters offerings we can help you book.

There’s a Perfect Crewed Charter Vacation for Everyone!


A family that plays together, stays together! Sailing charters are packed full of fun – there is something for everyone. Beach fun and snorkeling underwater marvels, kayaking, standup paddle boarding, hiking and exploring. As the sun tucks into the sea, play a board game under the stars or grab a bowl of popcorn and enjoy a movie in the salon.

Couples / Group

Nothing beats kicking back with a group of friends or other couples to unwind in paradise and share in some laughs. With your Captain and Chef tending to all the details, you can leave the responsibilities of your daily grind behind and have more time to create memories for a lifetime. Sailing, beach bars, snorkeling, hiking, shopping .. there’s something for everyone.


Explore the island life from below the waterline. The Caribbean waters are spectacular with color and abundant in marine life. Whether you are already a certified diver, or looking to get your certification, Island Life Charters can assist with finding the perfect dive charter for your vacation. The Virgin Islands are home to many renowned dive sites and underwater explorations.

Tandem / Corporate

Corporate hospitality meets corporate entertainment! Come enjoy “island time” while you open lines of communication and reinvest in your relationships outside of the office. A crewed charter yacht can offer a world-class business retreat. With an atmosphere that eliminates work distractions – bring your goals to crush and perspectives to open.


Congratulations! You’ve made it through the wedding planning and now it’s time to plan your Honeymoon. What could be more special than enjoying the privacy of your own yacht with a Captain and Chef to take care of all of the details. From remote anchorages and romantic dinners under the stars – it’s the perfect time to just enjoy one another.


Christmas and New Year’s are the most popular weeks of the year for crewed yacht charters in the Caribbean. If you’re thinking about getting together a group of close friends or surprising your family with a holiday sailing vacation, we encourage you to book early (at least a year in advance). This is a very special time of the season to enjoy the islands.

Spring Break

It’s the perfect time of the year to escape the cold and the routine of the daily grind. Grab some friends or gather the family together and head down to the Caribbean for some fun in the sun. Endless water sports, snorkeling, beach bars, hiking and enjoying the unique island local culture. Be sure to plan early for prime weeks during the spring.

Captain Only

A Captain Only charter can be a great option if you want the simplicity and freedom of a bareboat charter, but don’t want the responsibility of navigating the yacht (more time to relax). The charter rate includes the Captain, yacht and water toys. You purchase your food and beverage, cook your own meals or eat some ashore and pay for all running expenses.

Search for Specialty Yacht Charters

For additional yacht details, speak with our Charter Specialists toll-free 833-500-1794 or fill out our short contact form!