Tall Ships and Small Sailing Ships for Groups
Groups too big for a yacht can take a block of cabins — or the whole ship.
Ask About a Group SailingWhen your group is too big for a yacht, or wants a dining room and a cabin steward, tall ships and small sailing cruise ships are the answer. They sail like the real thing — masts, canvas and crew hauling lines — with cruise-ship comfort below deck.
Group Sailing on a Small Sailing Ship
There are two ways in. A group block reserves a number of cabins on a regular sailing; your group sails alongside other guests and can arrange its own events. A whole-ship charter takes every cabin, so the ship, the schedule and often the route are built for your group — a common choice for incentive trips, family milestones and clubs.
The Sailing Ships Groups Ask About
| Ship(s) | Guests | Notes for groups |
|---|---|---|
| Star Clippers: Star Flyer, Star Clipper | 170 each | Four-masted barquentines; private charters offered, and groups also sail alongside other guests |
| Star Clippers: Royal Clipper | 227 | Five-masted, fully rigged; a large group can take a big share of the ship |
| Windstar: Wind Star, Wind Spirit | 148 each | Motor-sail yachts with computer-controlled sails; listed for charters and incentives |
| Windstar: Wind Surf | 342 | The largest of the Wind-class ships |
| Maine windjammers (Camden, Rockland) | Small groups per schooner | Historic schooners, each run by its own captain; private charters available |
Ship facts as published by the lines and the Maine Windjammer Association, October 2026. Itineraries, charter rules and availability change; ask for current sailings.
Maine Windjammers: Group Sailing Close to Home
Along the Maine coast, a fleet of historic schooners sails multi-day trips out of Camden and Rockland in summer, anchoring in island coves at night. Each is owned and run by its own licensed captain, and guests often help with the sails. Because each schooner is small, a family reunion, a club or a group of friends can fill one entirely — a private charter without flying abroad. Expect simple cabins and hearty, shared meals; the appeal is the sailing and the coast, not luxury.
How to Set Up a Tall Ship Group
- Count your likely cabins early; a large share of a small ship disappears fast on popular dates.
- Ask about group terms: deposit dates, name-change deadlines and when unsold cabins go back on sale.
- For a whole-ship charter, decide what you want to change — the route, the program, private events — and ask what the line allows.
- Check accessibility: gangways, tenders and steep stairs are part of sailing-ship life.
- Book shore excursions as a group where it helps; port ideas are on Europe Port Excursions and Caribbean Cruise Ports.
Our cruise advisors at Mister Cruise can request group space and charter quotes from the lines. For expedition ships rather than sailing ships, see Explorer Cruising; for big-ship theme charters you can join, Cruising Groups. Thinking of turning group trips into a business? Be a Travel Agent explains how people start selling travel, and Best of the USA is our nonprofit parent.
Tall Ship Group Sailing: FAQ
Can a group charter a whole sailing ship?
Yes, on some ships. Star Clippers offers private charters on its square-riggers, Windstar lists its Wind-class sailing ships for charters and incentives, and many Maine windjammer schooners take private charters. Smaller groups book a block of cabins instead.
How big are small sailing cruise ships?
Star Clippers’ Star Flyer and Star Clipper carry 170 guests and Royal Clipper 227. Windstar’s Wind Star and Wind Spirit carry 148 guests and Wind Surf 342. That is small enough for a large group to feel the ship is theirs.
Request Group Space on a Sailing Ship
Tell us the ship or region, your dates and how many cabins you need.
Get Group Sailing Quotes