2025 Chef Series Wine & Food Sails
If this isn’t the most exclusive and luxurious dining reservation of your summer, we don’t know what is. Sommelier Erica Archer has invited some of Portland’s most talented chefs to join her on a select few wine sails to craft five delicious courses, each paired with a fantastic wine. Each dish is thoughtfully designed to highlight the season’s best ingredients. Every wine is expertly selected to enhance the flavors and elevate the experience—making every sip and bite a moment to savor.
Set against the stunning backdrop of Casco Bay, you’ll enjoy this extraordinary culinary journey from your seat aboard the immaculate Tall Ship Frances, gliding past Maine’s iconic lighthouses, historic forts, and the picturesque Calendar Islands.
A One-of-a-Kind Experience
🍷 Sommelier-Selected Wine Pairings – Perfectly matched to complement each course with engaging insights from Erica Archer.
🥘 Five-Course Tasting Menu – Created by one of Portland’s top chefs, showcasing the best of Maine’s seasonal ingredients.
⛵️ Scenic Sailing Through Casco Bay – Take in the fresh ocean breeze and panoramic views as you dine.
🌟 An Intimate & Exclusive Setting – These sails offer an exclusive experience unlike any other.
Whether you're looking for an exceptional day out, a unique gift, or a special way to entertain friends and family, Chef Series Wine & Food Sails offer a luxurious yet laid-back way to savor great food and wine—all while taking in the beauty of the Maine coast.
They sell out fast! Secure your spot now for an experience that will be the highlight of your summer.
📅 See the schedule below, click through for full details, and grab your tickets while they last at winewiseevents.com. Waitlists are available for sold-out events.
Schedule:
JUNE
Sunday, June 29, 12:00-2:00 PM: Spain in Maine Wine & Food Sail with Chef Damian Sansonetti of Chaval
JULY
Sunday, July 6, 12:00-2:00 PM: Wine & Food Sail with Chef Damian Sansonetti of Chaval
Wednesday, July 9, 6:30-8:30 PM: Sunset Italian Wine & Food Sail with Chef Paolo Laboa of Solo Italiano
Sunday, July 20, 12:00-2:00 PM: Wine & Food Sail with Chef Damian Sansonetti of Chaval
August
Sunday, August 17, 12:00-2:00 PM: Wine & Food Sail with Chef Damian Sansonetti of Chaval
Sunday, August 31, 12:00-2:00 PM: Wine & Food Sail with Chef Damian Sansonetti of Chaval
SEPTEMBER
Wednesday, September 10, 4:45 - 6:45 PM Sunset Italian Wine & Food Sail with Chef Paolo Laboa of Solo Italiano
Sunday, September 21, 12:00-2:00 PM: Wine & Food Sail with Chef Damian Sansonetti of Chaval
Sunday, September 28, 12:00-2:00 PM: Fall Foliage Wine & Food Sail with “Shef” Mimi Weissenborn of Sur Lie
October & Fall Foliage
Sunday, October 5, 12:00-2:00 PM: Fall Foliage Wine & Food Sail with Chef Damian Sansonetti of Chaval