Sailing into Salem’s Gold: Sunset Aboard the 1939 Schooner When And If

SALEM SAILING FIELD GUIDE

Sailing into Salem’s Gold: Sunset Aboard the 1939 Schooner When And If

A two-hour evening cruise from Salem aboard the historic schooner When And If — this guide explains what to expect, what’s included, and how to make the most of the sunset sail.

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Sailing into Salem’s Gold: Sunset Aboard the 1939 Schooner When And If.

Duration
Contact operator
Location
Salem
Operator
Sunset Sail Salem
Category
Sailing
Robert Eric Crews
Founder & Editor, The Adventure Collective
Published Verified

Departing daily from Salem, the 2-hour Sunset Sail on When And If puts you aboard a 1939 wooden schooner built for General George S. Patton, skimming the North Shore coastline as the sun falls. Whether you want to turn the helm, help raise sail or simply settle into the aft rail and watch the light change, the cruise is structured to motor out to a safe spot, set sail, then drift with the evening breeze until you return to the dock two hours after casting off.

Highlights

Outing Highlights

A 1939 wooden schooner with a storied past
THE VESSEL

A 1939 wooden schooner with a storied past

When And If was built in 1939 for General George S. Patton and remains a living piece of maritime history — an elegant wooden schooner that carries you into the sunset aboard original lines and classic rigging.

Sunset on the North Shore coastline
THE LIGHT

Sunset on the North Shore coastline

The sail follows the North Shore shoreline at dusk, offering panoramic coastal views as the crew sets the sails and the engine is shut off to let the wind dictate your course — a quietly cinematic way to experience Salem at sunset.

Hands-on sailing or a relaxed evening
THE EXPERIENCE

Hands-on sailing or a relaxed evening

Guests are invited to take a turn at the helm or help raise sails, but can equally opt to relax while the captain and crew handle the passage — a short cruise designed to be accessible to first-time sailors and enthusiasts alike.

What the day feels like

What the two-hour sail actually feels like

You’ll board, cast off and motor out until the crew finds a safe stretch of water to raise sail; once the canvas fills and the engine is silenced, the schooner moves under wind power while the crew guides the experience. Over the course of two hours you’ll share the boat with other guests (When And If carries up to 28 people), enjoy onboard beverages and return to the dock where the voyage began.

A 1939 wooden schooner with a storied past

THE VESSEL

A 1939 wooden schooner with a storied past

When And If was built in 1939 for General George S. Patton and remains a living piece of maritime history — an elegant wooden schooner that carries you into the sunset aboard original lines and classic rigging.

Sunset on the North Shore coastline

THE LIGHT

Sunset on the North Shore coastline

The sail follows the North Shore shoreline at dusk, offering panoramic coastal views as the crew sets the sails and the engine is shut off to let the wind dictate your course — a quietly cinematic way to experience Salem at sunset.

Hands-on sailing or a relaxed evening

THE EXPERIENCE

Hands-on sailing or a relaxed evening

Guests are invited to take a turn at the helm or help raise sails, but can equally opt to relax while the captain and crew handle the passage — a short cruise designed to be accessible to first-time sailors and enthusiasts alike.

Suitability

Who it's for

Who this short sunset passage suits — and who should think twice.

1
First-time sailorsWell suited — the crew runs the vessel but invites participation, letting novices try the helm or help raise sails in a controlled setting.
2
Couples and photographersA good match — the two-hour sunset window and coastal vistas provide a concentrated opportunity for golden-hour photos and a scenic evening out on the water.
3
Groups and small partiesAppropriate for groups up to the boat’s capacity; When And If carries up to 28 guests, so expect a shared-boat atmosphere rather than private charter exclusivity.
4
Guests with strict no-alcohol policiesBe aware the vessel is a licensed premises with a full bar on board; outside alcohol is not permitted — bring cash or a credit card for purchases if you plan to drink.

Practical planner

Details to review before reserving

Timing & Check-in

The sail is a two-hour sunset cruise that departs daily; arrive at the dock 15 minutes before your scheduled departure time to board.

What’s included

Your ticket covers the 2-hour sail, the services of the captain and crew, and your spot aboard When And If (capacity up to 28). Coolers are stocked with bottled water and seltzer.

Food & drink

A full bar is available on board (credit card preferred). The vessel is a licensed premises and you may not bring your own alcohol.

Onboard participation

Guests may take a turn at the helm or help raise sail if they wish, or simply relax and enjoy the views while the captain and crew handle operations.

Booking Notice

Review cancellation policies before reserving.

Frequently asked questions

Planning Your Outing

How long is the Sunset Sail?

The cruise is a 2-hour sunset sail.

When does the sail depart?

The sunset sail departs daily; specific departure times correspond to the scheduled sunset sail you book.

Can I bring my own alcohol onboard?

No — the schooner is a licensed premises with a full bar, and outside alcohol is not permitted.

Is water provided on board?

Yes — coolers are stocked with bottled water and seltzer for guests.

How many people are on the boat?

When And If has capacity for up to 28 people; you will share the vessel with other guests.

Can I participate in sailing the boat?

Yes — guests are invited to take a turn at the helm or help raise sail, though the captain and crew run the vessel.