Island Windjammer Cruises

Get nauti group rates on selected sailings

Six is better when you sail with friends.
Get nauti group rates on selected sailings.
Six or more save up to $500 pp.
Call for available dates.
Now that's nauti.

More shipmates, more merriment!

Small groups save big on our small ships.

Have a group of 4 or more? Pick a ship and a date, and we'll give you the best rate.

Have a few more? Our ships are the perfect size for whole boat charters. Our smallest ship holds 10 guests, and our largest 26.

When it comes to sailing, the more the merrier is our motto! Clubs, corporations, friends, families, wedding parties…all have sailed the tall ships of Island Windjammers. Shipmates come to celebrate special events, major life milestones, or simply because they like each other's company!

We've hosted groups from across the globe, and from all walks of life.

Group or charter: sail away with us and experience an unforgettable week full of sun, fun, and delightful sips of rum!

Group discounts honored on phone-in reservations only.

Island Windjammers Caribbean Cruise Group Discounts
Island Windjammers