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.
Sailing into Salem’s Gold: Sunset Aboard the 1939 Schooner When And If.
Adventure brief
Sailing into Salem’s Gold: Sunset Aboard the 1939 Schooner When And If
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.
Experience unforgettable sunsets with a 2-hour sailing adventure on 'When And If' in Salem, Massachusetts. Sunset Sail Salem offers a serene and scenic voyage along the Massachusetts coast, perfect for those seeking a peaceful escape and stunning photographic opportunities. As the golden hour approaches, you’ll glide across calm waters, watching the sky transform into vibrant hues of orange, pink, and purple. The intimate setting on this private sail provides a unique chance to connect with nature, enjoy fresh ocean air, and capture spectacular sunset views. Whether celebrating a special occasion or simply indulging in the tranquility of the sea, this trip promises a memorable experience that blends adventure with relaxation. The crew’s friendly hospitality and expert navigation ensure a smooth, safe journey, making it suitable for first-time sailors and seasoned explorers alike. Bring your camera to snap breathtaking vistas, or simply unwind as day turns into night surrounded by the beauty of Salem's coastline. This sunset sail is a perfect way to end your day, creating cherished memories and awe-inspiring moments on the water.
Route Schematic
Route Schematic: From dock to wind and back
A concise progression of the sail’s main phases, from departure through setting sail to the return.
Cast off from the dock
Guests board in Salem and the vessel casts off — plan to arrive 15 minutes before scheduled departure to embark.
Motor out to sailing position
The schooner motors out to a safe location where the crew can raise sail and switch from engine to wind power.
Under sail at sunset
With the sails set and engine off, the boat drifts and sails along the North Shore coastline while guests take in sunset views or help with sailing duties.
Return to dock
After roughly two hours on the water the vessel returns you safely to the dock where the cruise began.
The crew determines when and where it is safe to raise sail and will make operational decisions (motor out, set sails, engine-off) based on conditions and safety considerations.
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.
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.
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.
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.
Practical planner
Details to review before reserving
The sail is a two-hour sunset cruise that departs daily; arrive at the dock 15 minutes before your scheduled departure time to board.
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.
A full bar is available on board (credit card preferred). The vessel is a licensed premises and you may not bring your own alcohol.
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.
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.
How this guide was prepared
This field guide is synthesized using verified supplier specifications, route descriptions, and destination data. Some booking links may generate affiliate revenue for ADV Guides.
- Verified: 2026-08-12T21:54:29.633Z
Some booking links may generate revenue for ADV Guides or The Adventure Collective.
Availability, pricing, schedules and operating details can change.
Trip details and contextual sources were reviewed by ADV Guides Editorial.