Sailing Vacations for Couples & Friends

Share the time of your life with friends by treating yourselves to the experience of cruising on a private yacht in the Caribbean. With experienced charter crews, we can help build the perfect sailing vacations for couples so traveling throughout the islands with your friends becomes an epic adventure. Here at Island Life Charters, our team is ready to help you plan the perfect trip for your group. Whether everyone is looking to spend sunup to sundown in the water, on the beach, frequenting local watering holes, or with their nose in a book under the palms, we will plan all of the arrangements to give you ample time to do you. Upon arrival, your very able crew will be waiting for you all ready to attend to your needs and those of your friends. With the cooking and navigating taken care of, you get to soak up every second of your time in the islands.

The freedom to explore a new island every day… that is what the Island Life is all about!

Why Book a Group Yacht Charter?

Here are just a couple of the benefits of chartering a private yacht for you and your friends:


When you charter a yacht, you are assured the privacy that you need for you and your friends and/or significant other to bond and make memories. Crewed couple yachts only carry you and your friends meaning you can have private suites and en-suites. If you have a large group needing more than one catamaran, check out our Tandem Yacht Charters page. Just you and your crew (usually captain and first mate). You may even choose to cruise with a captain only, but consider the needs of your group such as food and cleaning. The first mate serves to provision the boat, prepare meals, and to keep the charter tidy.


Sailing vacations for couples are ideal for a get together with friends or even a group of couples to celebrate milestones and special occasions like birthdays, anniversaries, promotions, retirement and good health. With the ability to discover a new island each day, couples crewed charters put chain cruise line excursions to shame. Whatever your travel goals are, friends & couples yacht charters give you more options, more adventure, more destinations, and the best opportunity to create lasting memories with your squad.


Choose the pace at which to travel and experience pampering all through the vacation. Private charter boats for couples and friends are cost-effective for both small and large groups, offering privacy, comfort, and the added benefits garnered by having a sailboat to yourself!

Pricing on Sailing Vacations for Couples

With luxury Friends and Couples Yacht charters, you don’t have much reason to board a cruise ship that carries thousands of passengers ever again. Our Charter Specialist have access to charters for couples and friends that will suite any group seeking a Caribbean getaway. Save time, money, and the stress of cruising in a crowded ship and enjoy the luxury of a private catamaran together.

Contact Island Life Charters and find a sweet deal for you and your friends to island hop in the British Virgin Islands, U.S. Virgin Islands, Bahamas, Grenadines and beyond.