SALEM SAILING FIELD GUIDE
Schooner Spectacle: Aboard the Malabar X for Gloucester’s Mayor’s Cup
A day sail from Gloucester aboard the 2024 medium-size gaff schooner champion Malabar X to view traditional boats and watch the Mayor’s Cup Race—this guide collects the verified boarding, route, and race details you need.
Schooner Spectacle: Aboard the Malabar X for Gloucester’s Mayor’s Cup.
The Gloucester Schooner Festival gathers traditional sailing vessels and enthusiasts for a day of boat viewing and racing along the Massachusetts coast. Aboard the celebrated Schooner Malabar X, passengers join a parade of sail and then watch the Mayor’s Cup Race—an afternoon that pays homage to the working fleets and maritime craft that shaped New England.
Highlights
Outing Highlights
Malabar X: a class winner
The voyage is aboard the Schooner Malabar X, the 2024 winner in the medium-size gaff-rigged schooner division and ranked second only to the Schooner Columbia in class competition.
The Mayor’s Cup off Eastern Point
After a parade of sail past the Fishermen’s Memorial, the cruise moves to the Mayor’s Cup Race area; the official race start is scheduled for 1pm off Eastern Point.
A festival of traditional boats in Gloucester
Gloucester Schooner Festival is a vibrant gathering where owners and fans of traditional schooners come together to admire classic rigs and watch competitive sailboat racing from the deck of a historic vessel.
What the day feels like
What the Day Feels Like
Passengers board in Gloucester in the morning and get underway for a parade of sail—passing the Fishermen’s Memorial—before moving to the race area for the Mayor’s Cup’s 1pm start. The itinerary combines up-close viewing of traditional schooners, the energy of a formal race, and time aboard a celebrated racing schooner.
THE BOAT
Malabar X: a class winner
The voyage is aboard the Schooner Malabar X, the 2024 winner in the medium-size gaff-rigged schooner division and ranked second only to the Schooner Columbia in class competition.
THE RACE
The Mayor’s Cup off Eastern Point
After a parade of sail past the Fishermen’s Memorial, the cruise moves to the Mayor’s Cup Race area; the official race start is scheduled for 1pm off Eastern Point.
THE SCENE
A festival of traditional boats in Gloucester
Gloucester Schooner Festival is a vibrant gathering where owners and fans of traditional schooners come together to admire classic rigs and watch competitive sailboat racing from the deck of a historic vessel.
Suitability
Who it's for
Who this day sail suits—and what the provided information says about limits.
Practical planner
Details to review before reserving
The event date is August 31, 2025; the published rate is $300 per person. Boarding is scheduled to begin at 9:30am with the Mayor’s Cup Race starting at 1pm off Eastern Point.
No gear list or explicit what-to-bring guidance was provided in the supplied information; confirm with the operator for recommended clothing, sun protection, or motion-sickness remedies.
Board and disembark at Gloucester, MA. The public description frames the day as a round-trip sail that includes a parade of sail and the Mayor’s Cup Race.
Review cancellation policies before reserving.
Frequently asked questions
Planning Your Outing
When is this Gloucester Schooner Festival sail?
The published date for the trip is August 31, 2025; the listed price is $300 per person.
Where and when do we board?
Passengers board in Gloucester, MA; boarding begins at 9:30am.
Which vessel will I be on?
The trip is aboard the Schooner Malabar X, the 2024 winner in the medium-size gaff-rigged schooner division and rated second only to the Schooner Columbia.
When and where does the Mayor’s Cup Race start?
The Mayor’s Cup Race is scheduled to start at 1pm off Eastern Point.
Where do we disembark?
Boarding and disembarkation occur in Gloucester, MA.
Who operates this sail?
The operator named for this sailing is Sunset Sail Salem.