— Escape to the Island Life —
Vacations for families, groups, couples, divers, corporate retreats and beyond!
No hassle bookings in paradise!
Let us find the ultimate yacht charter for you!
Island vibes & tan lines!
Water toys, snorkeling, & hiking galore - there's something for everyone!
previous arrow
next arrow

Caribbean & BVI Yacht Charters

Leave the daily grind behind as you cast off to delight in the turquoise playground of the Caribbean. With a trusted Captain to safely navigate your private yacht and a dedicated Chef to prepare gourmet meals aboard, you’ll have more time to soak up some rays, swim in the tranquil blue waters, bury your toes in the powdery white sand and enjoy sailing to a different island each day. The Island Life has something for everyone!

Why Choose Island Life Charters?

The premier charter yacht broker of the Virgin Islands and Caribbean – we are passionate about crafting an effortless, hassle-free vacation plan at no cost to you! We take great care to provide our customers with the ultimate island experience and carefully match yachts and crew with each group. When experience matters – choose Island Life Charters.

Why a Crewed Charter Vacation?

An all-inclusive crewed yacht charter takes the stress out of vacationing with an experienced Captain and Chef to tend to your every need. Island hop to local anchorages or find a hidden cove only accessible by boat. Your customized crewed charter frees you to enjoy all your preferred activities then unwind with five-star dining under the stars.

Best Destinations for Chartering?

Our team has sailed far and wide throughout the USVIs and BVIs and we know all of its secrets. If it’s pampering, peace, quiet, beaches, thrill seeking, foodie bliss you’re seeking – we know the prime anchorages and watering holes and we can’t wait to share all the juicy details with you! Escape for the stress of the Mainland and come live the Island Life.

Search Caribbean & BVI Yacht Charters

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

Types of Yacht Charter Vacations

Family Charters

Share quality time with family and enjoy the relaxation of a crewed charter. Watersports, shore-side activities, and time to chill – all-inclusive charters offer a well-deserved break from the hectic pace back home.

Couples & Friends Charters

Unwind from the mainland grind on a vacation of a lifetime with a group of your friends or couples. Laughter, food, and refreshing beverages are abundant in paradise!

Dive Charters

Explore the island life from deep below the big blue with crewed charters offering scuba diving right from your yacht. Not yet certified, inquire on dive courses or options for obtaining a certification while on vacation.

Tandem & Corporate Charters

Large groups of family or friends? Looking for a corporate retreat for team building or incentive travel? We can match multiple yachts and crews to accommodate your group.

Honeymoon & Romance Charters

Honeymoons, anniversaries and special occasions deserve to be celebrated. Enjoy quiet anchorages, sunset cocktails and walks on the beach with a private yacht and crew. Thinking of getting married? We’ve got a wedding officiant on staff!

Bareboat Charters

Lead your own island life adventure! We have access to hundreds of bareboat charter yachts throughout the Caribbean and can save you tons of time and help you find the best match.

Affordable Caribbean Yacht Charters

Once considered an indulgence of the rich and famous, Island Life Charters is on a mission to share chartering with couples, families, and groups seeking to explore the Caribbean the way it was meant to be enjoyed. Therefore, whether you’re a seasoned sailor looking to venture beyond your home lake or you’ve never sailed before, all-inclusive crewed yacht chartering is surprisingly affordable. From the time you cast off, your crew will provide for your wants and needs. Fancy a freshly brewed coffee on the front deck as you watch the morning rays dance on the water? Prefer a day packed with snorkeling and exploring ashore? Wishing for 5-star dining without the 5-star reservation headache? Most of all, crewed BVI yacht charters take the stress out of vacationing. An experienced captain familiar with the local anchorages – some of which are only accessible by boat – means you get to see coves and beaches that aren’t even in tourist guidebooks. Enjoy board games, movies, and water sports while your personal chef prepares gourmet meals. BVI sailing charters give you more time to relax, play and escape to the Island Life!

Crewed Yacht Options

Catamaran Charters

This is the most popular choice for charter vacations. Available in Sailing and Power Cat Options added benefits onboard include more spacious areas for dining and entertainment, ensuite baths, and multiple diving platforms. The shallower hauls increase stability on the water and allow for closer anchorage to pristine beaches that are plentiful throughout our islands or near the many scuba diving destinations.

Monohull Sailboat Charters

A great choice for the sailing enthusiast looking for a true thrill of action out on the water. Dreaming of a traditional sailboat charter vacation? We offer crewed yacht charters which include a seasoned captain (who will gladly show you the ropes) or you can just enjoy the views as you and your guests are chauffeured from island to island. Monohull Yacht Charters are ideal for a smaller group or for that romantic getaway.

Motor Yacht Charters

If sailing is not your thing but you still desire a luxurious vacation chartering the island chain, the comfort and efficiency of cruising around in a motor yacht is a great consideration. Amenities and comfort abound on our luxury motor yacht charters which come with an increased crew count. And with a bit more speed behind the helm, you can see and do more during your time in the BVI.

Don’t Just Take Our Word For It. Hear From Island Lifers:

“Feel the Magic” definitely lived up to its name. We were blown away by the beauty of the islands and the waters. But mostly we were in awe of the Magic of Hank and Micheale. With Hank’s amazing skills at the Helm and Micheale’s seemly effortless ability to serve up delicious meals, truly met every need we had. Truly an unforgettable trip. Thanks for all the great Memories. Conway Family

What an incredible week! You both made our trip special for our entire family. So many great memories – incredible meals, beautiful spots, fun sails, snorkeling, great Caribbean cocktails and service with a smile 24-7. You truly made the trip one our family will always remember & cherish. Hoine Family

Captain Steve and Admiral Janet spared no expense, time, and effort in making sure we had a memorable 25th wedding anniversary trip to include a surprise bottle of champagne on the night of our anniversary… You know it’s a good time when you walk away from a trip with insider jokes with the hosts and trip sayings and whatnot. We had a ball and laughed our asses off. We will definitely be doing this again. Kris & Rich Hoine Family


Destination Spotlight: British Virgin Islands (BVIs)

Known as “Nature’s Little Secret” the British Virgin Islands is a world-renowned playground for sailing, diving and charter vacations. The protected waters offer smoother boating and the islands’ close proximity to each other are ideal for island hopping.

Special Offers

Starting at $285 / night / person

All Inclusive Crewed Sailboat Charters Include:

Life onboard your own private luxury boat

A captain to navigate you through paradise

A chef to prepare gourmet meals

Provisions, including beverages for your trip

An arsenal of onboard water toys

Endless adventures and unrestricted access to the world’s best beaches

All-Inclusive Charter Specials


67 feet of luxury offering 4 guest cabins for up to 8 passengers.”Romantic getaway for two” 10% discount of the 2 pax rate + a complimentary Resort course dive for two or a couples massage in a spa.  12/16/2017 – 04/30/2018 – except holidays


With a spacious deck and lounge and 4 guest cabins, White House has plenty of room for fun and relaxation for up groups and families of 6. Save $1000 on charters taken November 2017 – January 2018 (except holidays)


56 feet of luxury with 4 guest cabins welcoming up to 8 guests.  Altesse offers 2 complimentary dives for 4 guests (incl. equipment). Take 10% off charters taken 10/19/2017 – 11/02/2017 – except holidays

Contact Us

Want to experience the Island Life? Our sailing charter specialists have got you covered.

Wild, exotic, remote, untouched and tranquil – discover over 25 incredible sailing destinations. Caribbean & BVI Yacht Charters afford a unique opportunity to experience spectacular scenery, colonial history, and flavorful foods. Whether your priority is chilling out on a fabulously deserted white sand beach, fishing the bountiful game, or socializing at a local watering hole, Island Life Charters has the perfect Caribbean sailing vacation for you. Come and escape to the Islands!

Request More Information