There’s nothing better than fresh oysters, crisp wine, and the open water—and I found all three on the Wine & Oyster Sail in Portland, Maine.
Hosted by Wine Wise Events, this sailing experience combines a scenic cruise with expertly curated wine tastings and local Maine oysters.
It’s the perfect way to spend a summer afternoon on Casco Bay.
Wine & Oyster Sail in Portland, Maine
Here is everything you need to know about his unique experience.
About Wine Sails in Portland, Maine
Wine Wise Events is a Portland-based company known for hosting creative wine experiences, from intimate wine dinners and vineyard trips to themed sails along the Maine coast.
Their popular Wine Sails are held on classic schooners departing right from Portland Harbor, making them a must-do for both locals and visitors.
Each sail has a theme, with options like rosé sails, champagne sails, wine & cheese sails, and of course, the crowd-favorite Wine & Oyster Sail.
Which I will talk about now!
My Wine & Oyster Sail Experience
We showed up at the dock right next to the Casco Bay ferry terminal, where the ferries leave for the islands.
This is also where you can take this $14 Portland,Maine Sunset Cruise, The Best Deal in Town!
Look for the small shack with the sign for the Frances schooner—that’s where you’ll check in and wait until boarding.
About ten minutes before departure, we made our way down the dock and stepped aboard.
I felt lucky the sail was still happening. Even though there was a hurricane far out at sea, the weather in Portland gave us a sunny August afternoon that was perfect for being on the water.
Before boarding, we were handed a plate and a real wine glass that fit right into it.
The plate for the oysters, the glass for the wine.
The Wines!
Once everyone found a seat, we were given a wine list for the day.
This sail focused mostly on whites, since oysters and white wine are a match made in heaven.
But I loved that each wine came with details about the region, grape, and even the price if you wanted to buy a bottle afterward.
First, you lifted your glass, and the crew poured in the wine while sharing history about the vineyard.
From there, the real fun began. We got to taste the wine!
Then we were able to drink it while enjoying the breathtaking views of the water.
Curated Oyster Pairing
A few minutes later, the team came around with a tray of oysters.
We were allowed to take two of each to start.
Then they would come around again if there were extras. Which there were each time!
I tried one topped with their homemade vinaigrette and one completely raw, and both were incredible.
We also learned about the oyster farm and how they’re harvested, which made me appreciate each bite even more.
This routine continued with all five wines, each one paired perfectly with Maine oysters.
My favorite moment was at the end when we tried the champagne.
They encouraged us to pour it right into the oyster, and it was one of the most unique pairings I’ve ever tried.
As a foodie, I loved it!
For more of my foodie finds, read Portland Maine Food Guide: 17 Must-Try Foodie Spots!
Enjoying the Views of Maine
We sailed around Casco Bay, passing lighthouses, forested islands, and other boats out on their own tours.
As a huge wine lover, this sail blew me away—literally and figuratively.
The balance of sailing, sipping, and slurping oysters felt like the perfect Maine experience.
I can’t wait to go back for one of their fall sails when red wines take the spotlight.
As a Maine local, I’d recommend this as one of the top things to do not just in Portland, but in the entire state.
You should also read 21 Best Lobster Rolls in Maine: From A Local! (2025)!
How to Book the Wine & Oyster Sail
The Wine & Oyster Sail is offered through Wine Wise Events and is one of their most popular experiences.
Tickets tend to sell out quickly, especially in the summer, so booking in advance is highly recommended.
The sails typically run from June through September, making them a perfect warm-weather activity in Maine. Prices vary depending on the theme and inclusions, but the value of tasting curated wines, eating fresh oysters, and sailing Casco Bay is worth every penny.
Book your Wine Sail today here!
Wine Sail Video!
Here is my YouTube short with my experience with added content!
Explore More of Portland, Maine
My favorite sunset cruise in Portland, Maine, is only $14! Read This $14 Portland Maine Sunset Cruise Is the Best Deal in Town!
You can also head over to Diamond Cove: Your Guide To The Ultimate Maine Day Trip.
Visiting Portland? Read my Portland Maine Food Guide: 17 Must-Try Foodie Spots.
Don’t forget to have a lobster roll after your sail! Here are 21 Best Lobster Rolls in Maine: From A Local! (2025)
If you are heading down east, read my Acadia National Park Travel Guides!
Or, check out all of my Maine Travel Guides!
Where Do You Want To Travel Next?