Book a sail
Wingaway at anchor in a quiet cove at golden hour
New for 2027 · Overnight on Wingaway

Fall asleep at anchor. Wake up in a quiet cove.

Sail out in the afternoon, sleep aboard in a quiet island cove, and sail home after breakfast. Grill dinner on deck as the sun goes down, aboard a 40-foot yacht with your own skipper.

Check datesSee the night

For two (3 or 4 on request)Your own cabin and skipperYour own galley and barbecueSunday to Wednesday nights, May to September

Just you two

A yacht and a skipper for two

No strangers aboard. Your skipper sails, anchors and looks after the boat.

Quiet

A cove, not a marina

We anchor where the water is still and the city is out of sight, chosen for the night’s weather.

Easy

Just bring a bag

Bedding, towels and coffee are aboard. Bring your food, or let our caterer pack dinner and breakfast for you.

Two ways to stay out

A night aboard, or a night on Bowen.

Wingaway at anchor at golden hour
Overnight · Sunday to Wednesday nights

Island Sailing Escape

Sail out in the afternoon, sleep aboard in a quiet island cove, and sail home after breakfast.

  • Board at Jericho at 3 pm, back about noon the next day
  • Grill on the barbecue or use the galley; a catered hamper is available
  • Sleep in the forward double cabin; your skipper has their own cabin aft

From $2,990 for two, the whole boat · price depends on the date

Check dates
Wingaway at a calm island dock
Sail out, stay ashore · Sunday to Wednesday

Sail to Bowen

  • An afternoon sail from Jericho to Snug Cove on Bowen Island, up to 8 guests
  • Stay ashore at an inn or cottage of your choice
  • Ferry home the next day, or we sail you back (+$1,190)

From $2,190 for the whole boat · price depends on the date

Check dates
Island Sailing Escape

Your night aboard.

  1. 3:00 pm

    Welcome aboard

    Meet your skipper at Jericho Sailing Centre. Safety briefing, then settle into your cabin.

  2. 3:30 pm

    Sail for the islands

    Across English Bay and past Point Atkinson. Take the helm if you’d like.

  3. About 6:00 pm

    Drop anchor

    A sheltered cove off Bowen, Gambier or Keats Island, picked for the evening’s wind.

  4. Evening

    Dinner on deck

    Fire up the barbecue as the light goes gold, with your own food or our caterer’s hamper. Then the stars.

  5. Night

    Sleep aboard

    Your double cabin made up hotel-style, robes and fresh linens, heating if it’s cool. Your skipper has their own cabin aft.

  6. Morning

    Coffee in the cockpit

    Breakfast at anchor from the galley. A swim if you’re brave.

  7. About 12:00 pm

    Back at Jericho

    Sail or motor home, depending on the wind.

Sunrise over Wingaway’s bow
Wingaway’s saloon, seen from the companionway
Wingaway’s galley
Wingaway under sail below the North Shore mountains
Wingaway’s foredeck under sail
Sunset from Wingaway’s deck

The boat

Layout of Wingaway: forward double cabin, saloon with table, galley, head with shower, aft double cabin
Forward double cabinAft double cabinSaloon and galleyHead with separate shower

Included

  • The whole yacht and a professional skipper
  • A galley (stove, oven, fridge) and a barbecue on the stern rail
  • Coffee, tea, water and snacks
  • Linens, robes, towels, heating and hot water
  • A paddleboard, string lights, blankets and a proper coffee set-up
  • A photo of you at the helm and a signed ship’s log card
  • Lifejackets and all safety equipment

Bring

  • A soft bag (it stows more easily than a suitcase)
  • Warm layers: evenings on the water are cool
  • Soft-soled shoes
  • Your food, or add our caterer’s dinner-and-breakfast hamper when you book
  • Anything you’re celebrating

Good to know

  • Sunday to Wednesday nights, May to September
  • Weather is checked the evening before; if it’s not right, choose another date or a full refund
  • Made for two; 3 or 4 guests on request
2027

Prices for 2027.

ExperienceMay, June, SeptemberJuly and August
Island Sailing Escape · for two$2,990$3,490
Island Sailing Escape for 3 or 4 guests, on request+$400+$400
Sail to Bowen · up to 8 guests$2,190$2,490
Sail back from Bowen the next day+$1,190+$1,190

Per booking, for the whole boat, before tax. Price depends on the date. Self-catered: the galley and barbecue are yours; the catering hamper is an add-on.

Common questions

Before your night.

What if the weather turns?

Your skipper checks the forecast the evening before and again in the morning. If it isn’t right, choose another date or get a full refund. We anchor where it’s sheltered for that night’s wind.

Will I get seasick?

The coves are sheltered, and at anchor the boat is calm. If you’re prone to it, take something before you board.

Is there a toilet and shower?

Yes: a marine toilet and a separate shower with hot water. Your skipper shows you how they work.

Can we bring children?

Yes, with a grown-up for each child. Tell us their ages when you book so the right lifejackets are aboard.

Do we have to cook?

You can grill and use the galley with your own food, or add a dinner-and-breakfast hamper from our caterer when you book. It’s delivered to the boat before you leave, ready for the barbecue.

Can we charge phones?

Yes, there are charging points aboard.

Can we stay out more than one night?

Ask us about the Gulf Islands: two or three nights in quiet weeks.

Limited nights each month

Pick your night.

Choose a Sunday to Wednesday night between May and September 2027. Booking takes a couple of minutes, and you’ll get a confirmation straight away.

Book Island Sailing EscapeBook Sail to Bowen

Questions or a special occasion? info@vancouverbysea.com · (778) 200-9277

Departs Jericho Sailing Centre, 1300 Discovery St, Vancouver, BC.