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Wine & Waterfall Sunset Cruise with Island Style Charters

  • Island Style Charters 2001 S River Drive, Portland, Oregon 97201 Portland, OR, 97201 United States (map)

Trade the tasting room for the top deck. We're teaming up with Island Style Charters — home to Portland's first (and only!) tiki boat — for an evening cruise up the Willamette River to Willamette Falls, pouring a flight of Love & Squalor wines along the way.

On the ride up, Matt will walk you through our wines and the stories behind them — from Willamette Valley vineyard to bottle. On the return, kick back with a glass or bottle, take in live narration and river views, and watch the city lights come up as the sun goes down.

Expect tropical cocktails, onboard games, a little Portland history, and a full flight of our wines — all with unbeatable views of the falls and the river you won't get anywhere else.

Seats are limited and this cruise tends to sell out — reserve yours today.

This is an all-ages cruise. Wine tasting included with your ticket.

📅 Wednesday, August 19, 2026 | 5:30pm–8:30pm (approx. 3 hours)
📍 Departs from South Waterfront Park, 2001 S River Drive, Portland

Earlier Event: August 14
Celebrate Int'l Pinot Noir Day
Later Event: August 20
Wine Trends Weekend!!!