Wine Tastings, Dinners & Festivals

• May 22, 2025 (Thu)

Wine Around: An Evening Of Italian Elegance Summer Edition

• May 22, 2025 (Thu)

ReelHouse Marina Bay: Coastal Italian Supper Series

• May 22, 2025 (Thu)

Tour De France: Understanding French Wine @ The Spirited Gourmet

• May 22, 2025 (Thu)

Bubbles For All Budgets

• May 22, 2025 (Thu)

Wine Tasting In Support Of Next Generation Investment

• May 23, 2025 (Fri)

Maggiano's Little Italy - Boston & Titanic: The Artifact Exhibition

• May 23, 2025 (Fri)

Savory, Sweet & Salty Rum, Bourbon And Whiskey Nuts Paired With Wine!

• May 23, 2025 (Fri)

Hands-On: Ravioli Ricotta E Spinaci

• May 23, 2025 (Fri)

Rapid Run To Sun-soaked Croatian Wines

• May 23, 2025 (Fri)

Make Argentine Empanadas At Foundry

• May 23, 2025 (Fri)

Exploring Bruichladdich: A Journey through Whisky, Tradition and Innovation

• May 23, 2025 (Fri)

Sipping & Scripting

• May 24, 2025 (Sat)

Maggiano's Little Italy - Boston & Titanic: The Artifact Exhibition

• May 24, 2025 (Sat)

Taste, Tour And Bring Home A Glass At Averill House Vineyard And Winery

• May 24, 2025 (Sat)

Hermit Woods Winery Tour And Tasting

• May 24, 2025 (Sat)

Exploring Bruichladdich: A Journey through Whisky, Tradition and Innovation

• May 25, 2025 (Sun)

Sip & Savor: Wine Meets Mochi – A Tasting Experience Like No Other!

• May 25, 2025 (Sun)

Taste, Tour And Bring Home A Glass At Averill House Vineyard And Winery

• May 25, 2025 (Sun)

Share And Pair Sunday At Averill House Vineyard

• May 25, 2025 (Sun)

Maggiano's Little Italy - Boston & Titanic: The Artifact Exhibition

• May 25, 2025 (Sun)

Curd Your Enthusiasm

• May 26, 2025 (Mon)

Sip & Savor: Wine Meets Mochi – A Tasting Experience Like No Other!

• May 27, 2025 (Tue)

Hands-On: Tiramisu

• May 27, 2025 (Tue)

Hands-On: Pasta Alla Carbonara

• May 28, 2025 (Wed)

Maggiano's Little Italy - Boston & Titanic: The Artifact Exhibition

• May 28, 2025 (Wed)

Sip & Savor: Wine Meets Mochi – A Tasting Experience Like No Other!

• May 28, 2025 (Wed)

Around The World Through Chocolate & Wine

• May 28, 2025 (Wed)

Hands-On: Tiramisu

• May 29, 2025 (Thu)

Maggiano's Little Italy - Boston & Titanic: The Artifact Exhibition

• May 29, 2025 (Thu)

Sip & Savor: Wine Meets Mochi – A Tasting Experience Like No Other!

• May 29, 2025 (Thu)

Hands-On: Ragù Alla Bolognese

• May 29, 2025 (Thu)

ReelHouse Marina Bay: Coastal Italian Supper Series

• May 29, 2025 (Thu)

Decoy By Duckhorn Vineyards Wine Dinner

• May 29, 2025 (Thu)

May Paint & Sip

• May 29, 2025 (Thu)

Isa Bistro

• May 29, 2025 (Thu)

Hands-On: Pasta Alla Norma

• May 29, 2025 (Thu)

Pinot To The People! @ Sorriso In Brookline Village

• May 29, 2025 (Thu)

Exploremos America Del Sur

• May 29-Jun 1, 2025 (Thu-Sun)

Thames Voyager Evening Cruise (from Boston)

• May 29, 2025 (Thu)

Roman Night At La Pizza & La Pasta

• May 30, 2025 (Fri)

Cheesy, Meaty, Sweet & Salty Wine Chips. Potato Chips Paired With Wine!

• May 30, 2025 (Fri)

Hands-On: Lasagna

• May 30, 2025 (Fri)

Exploremos America Del Sur

• May 31, 2025 (Sat)

Taste, Tour And Bring Home A Glass At Averill House Vineyard And Winery

• May 31, 2025 (Sat)

3rd Annual Smuttynose Food Truck And Craft Beer Festival

• May 31, 2025 (Sat)

Hermit Woods Winery Tour And Tasting

• May 31, 2025 (Sat)

Summer Solstice Fizz Festival

• May 31, 2025 (Sat)

Wine & Food Walk In Portland, Maine's West End

• May 31, 2025 (Sat)

Spirits With A Twist - A Flavored Spirits Exploration

• May 31, 2025 (Sat)

Greased Lightning Rockabilly Dinner Party At LaBelle Winery Derry

• Jun 1, 2025 (Sun)

Princess Brunch

• Jun 1, 2025 (Sun)

Mimosas With Madam

• Jun 1, 2025 (Sun)

Sip & Savor: Wine Meets Mochi – A Tasting Experience Like No Other!

• Jun 1, 2025 (Sun)

Taste, Tour And Bring Home A Glass At Averill House Vineyard And Winery

• Jun 1, 2025 (Sun)

Share And Pair Sunday At Averill House Vineyard

• Jun 1, 2025 (Sun)

Summer Open House/Educational Tasting

• Jun 1, 2025 (Sun)

Exploring Bruichladdich: A Journey through Whisky, Tradition and Innovation

• Jun 3, 2025 (Tue)

Hands-On: Ragù Alla Bolognese

• Jun 3, 2025 (Tue)

Hands-On: Fresh Egg Pasta Shapes

• Jun 4, 2025 (Wed)

Sip & Savor: Wine Meets Mochi – A Tasting Experience Like No Other!

• Jun 4, 2025 (Wed)

Hands-On: Pasta Alla Carbonara

• Jun 4, 2025 (Wed)

Terrarium Workshop @The Hill Bar & Grille - McIntyre Ski Area

• Jun 4, 2025 (Wed)

Hands-On: Lasagna

• Jun 4, 2025 (Wed)

HCC X K&S: Steak & Cigar Night Series

• Jun 5, 2025 (Thu)

Savory, Sweet & Salty Rum, Bourbon And Whiskey Nuts Paired With Wine!

• Jun 5, 2025 (Thu)

Taste, Tour And Bring Home A Glass At Averill House Vineyard And Winery

• Jun 5, 2025 (Thu)

Wine Essentials: How To Taste, Describe, Pair And Enjoy Wine

• Jun 5, 2025 (Thu)

Hands-On: Pasta All' Amatriciana

• Jun 5, 2025 (Thu)

Roman Night At La Pizza & La Pasta

• Jun 6, 2025 (Fri)

Savory, Sweet & Salty Rum, Bourbon And Whiskey Nuts Paired With Wine!

• Jun 6, 2025 (Fri)

Taste, Tour And Bring Home A Glass At Averill House Vineyard And Winery

• Jun 6, 2025 (Fri)

Hands-On: Pasta Alla Carbonara

• Jun 6, 2025 (Fri)

Hands-On: Tiramisu

• Jun 7, 2025 (Sat)

Taste, Tour And Bring Home A Glass At Averill House Vineyard And Winery

• Jun 7, 2025 (Sat)

Hermit Woods Winery Tour And Tasting

• Jun 8, 2025 (Sun)

Sip & Savor: Wine Meets Mochi – A Tasting Experience Like No Other!

• Jun 8, 2025 (Sun)

Taste, Tour And Bring Home A Glass At Averill House Vineyard And Winery

• Jun 9, 2025 (Mon)

A Taste Of Terroir!

• Jun 9, 2025 (Mon)

Monday Funday Cocktail Class

• Jun 10, 2025 (Tue)

Hands-On: Ravioli Ricotta E Spinaci

• Jun 10, 2025 (Tue)

Fairy Garden Workshop & Wine Tasting With The Funky Squid:TUES 6/10

• Jun 11, 2025 (Wed)

Sip & Savor: Wine Meets Mochi – A Tasting Experience Like No Other!

• Jun 11, 2025 (Wed)

Downtown Sour Smash Disco Party & Beer Release

• Jun 11, 2025 (Wed)

Wine & Cheese Class: An Evening In France

• Jun 11, 2025 (Wed)

Single Mingle: Seaport Patio Edition

• Jun 11, 2025 (Wed)

Wine Wednesday Class @ Book Ends: Rosé

• Jun 12, 2025 (Thu)

Vive La France

• Jun 13, 2025 (Fri)

Wine Sail In Portland, Maine: Wine + Oysters

• Jun 13, 2025 (Fri)

Vive La France

• Jun 13, 2025 (Fri)

Wine Sail In Portland, Maine: Pinot Noir

• Jun 14, 2025 (Sat)

National Rosé Day With Whispering Angel

• Jun 14, 2025 (Sat)

Wine Sail In Portland, Maine: Delicious Whites

• Jun 14, 2025 (Sat)

Vive La France

• Jun 14, 2025 (Sat)

Wine Sail In Portland, Maine: Tuscany

• Jun 15, 2025 (Sun)

Wine Sail In Portland, Maine: California's Central Coast

• Jun 15, 2025 (Sun)

Sunset Champagne & Oysters Sail In Portland, Maine

• Jun 16, 2025 (Mon)

Maximum Flavor With Chef Adrianne: A Culinary Voyage

• Jun 20, 2025 (Fri)

Wine Sail In Portland, Maine: European Wines

• Jun 20, 2025 (Fri)

Wine Sail In Portland, Maine: Portugal + Spain

• Jun 21, 2025 (Sat)

Wine Sail In Portland, Maine: Greece

• Jun 21, 2025 (Sat)

Wine Sail In Portland, Maine: The Mediterranean

• Jun 22, 2025 (Sun)
• Jul 6, 2025 (Sun)
• Aug 24, 2025 (Sun)
• Aug 31, 2025 (Sun)

Wine & Raw Bar Sail In Portland, Maine

• Jun 22, 2025 (Sun)

Wine Sail In Portland, Maine: Wine + Oysters

• Jun 22, 2025 (Sun)

Wine Sail In Portland, Maine: France

• Jun 26, 2025 (Thu)

Discover New Wines From The Old World

• Jun 27, 2025 (Fri)

Wine Sail In Portland, Maine: Italy

• Jun 27, 2025 (Fri)

Discover New Wines From The Old World

• Jun 27, 2025 (Fri)

Wine Sail In Portland, Maine: California

• Jun 28, 2025 (Sat)

Wine Sail In Portland, Maine: South Africa

• Jun 28, 2025 (Sat)

Gin, Vodka & Tequila— A Battle Of The Clear Spirits

• Jun 28, 2025 (Sat)

Wine Sail In Portland, Maine: Sicily

• Jun 29, 2025 (Sun)

Chef Series Wine + Food Sail: Spain In Maine With Chefs Sansonetti + Lopez

• Jun 29, 2025 (Sun)

Wine Sail In Portland, Maine: Sparkling Wines

• Jul 4, 2025 (Fri)

Wine Sail In Portland, Maine: Oregon & Washington

• Jul 4, 2025 (Fri)

Wine Sail In Portland, Maine: Napa + Sonoma

• Jul 5, 2025 (Sat)

Wine Sail In Portland, Maine: European Whites

• Jul 5, 2025 (Sat)

Wine Sail In Portland, Maine: California

• Jul 6, 2025 (Sun)

Chef Series Wine + Food Sail With Chef Sansonetti Of Chaval

• Jul 6, 2025 (Sun)

Wine Sail In Portland, Maine: Wine + Oysters

• Jul 9, 2025 (Wed)

Chef Series Italian Wine + Food Sail With Chef Laboa Of Solo Italiano

• Jul 10, 2025 (Thu)

Under The Tuscan Sun

• Jul 11, 2025 (Fri)

Chef Series Wine + Food Sail With Chef Chris Gould Of Central Provisions

• Jul 11, 2025 (Fri)

Under The Tuscan Sun

• Jul 11, 2025 (Fri)

Wine Sail In Portland, Maine: Piedmont, Italy

• Jul 12, 2025 (Sat)

12th Annual Boston JerkFest Rum & Brew Tasting

• Jul 12, 2025 (Sat)

Wine Sail In Portland, Maine: Rosé

• Jul 12, 2025 (Sat)

Under The Tuscan Sun

• Jul 12, 2025 (Sat)

Wine Sail In Portland, Maine: Spain

• Jul 13, 2025 (Sun)

Wine Sail In Portland, Maine: Wine + Oysters

• Jul 13, 2025 (Sun)

Wine Sail In Portland, Maine: Tuscany

• Jul 17, 2025 (Thu)

Georgia On My Wine - The Lanchava Collection With The Lanchava Siblings

• Jul 17, 2025 (Thu)

Passport To Pour: An Introduction To Wines Of The World

• Jul 18, 2025 (Fri)

Wine Sail In Portland, Maine: France

• Jul 18, 2025 (Fri)

An Exquisite Wine Journey Around Argentina With Mascota Vineyards, El Esteco, And More!

• Jul 18, 2025 (Fri)

Georgia On My Wine - The Lanchava Collection With The Lanchava Siblings

• Jul 18, 2025 (Fri)

Wine Sail In Portland, Maine: Sparkling Wines

• Jul 19, 2025 (Sat)

Wine Sail In Portland, Maine: The Mediterranean

• Jul 19, 2025 (Sat)

Georgia On My Wine - The Lanchava Collection With The Lanchava Siblings

• Jul 19, 2025 (Sat)

Wine Sail In Portland, Maine: Italy

• Jul 20, 2025 (Sun)

Chef Series Wine + Food Sail With Chef Sansonetti Of Chaval

• Jul 20, 2025 (Sun)

Wine Sail In Portland, Maine: European Wines

• Jul 20, 2025 (Sun)

Wine Sail In Portland, Maine: Wine + Oysters

• Jul 24, 2025 (Thu)

Pop Open A Party—Great Sparkling Wines

• Jul 25, 2025 (Fri)

Wine Sail In Portland, Maine: The Loire Valley

• Jul 25, 2025 (Fri)

Pop Open A Party—Great Sparkling Wines

• Jul 25, 2025 (Fri)

Wine Sail In Portland, Maine: California's Central Coast

• Jul 26, 2025 (Sat)

Wine Sail In Portland, Maine: Delicious Whites

• Jul 26, 2025 (Sat)

Rum For All And All For Rum!

• Jul 26, 2025 (Sat)

Wine Sail In Portland, Maine: Sicily

• Aug 1, 2025 (Fri)

Wine Sail In Portland, Maine: The Loire Valley

• Aug 1, 2025 (Fri)

Wine Sail In Portland, Maine: Italy

• Aug 2, 2025 (Sat)

Hendrick's Marvelous Cocktail Masterclass

• Aug 2, 2025 (Sat)

Wine Sail In Portland, Maine: Wine + Oysters

• Aug 2, 2025 (Sat)

Wine Sail In Portland, Maine: The Mediterranean

• Aug 3, 2025 (Sun)

Wine Sail In Portland, Maine: Wine + Oysters

• Aug 3, 2025 (Sun)

Wine Sail In Portland, Maine: Greece

• Aug 3, 2025 (Sun)

Wine Sail In Portland, Maine: Portugal + Spain

• Aug 7, 2025 (Thu)

Sip N’ Snack Pairings

• Aug 8, 2025 (Fri)

Wine Sail In Portland, Maine: Tuscany

• Aug 8, 2025 (Fri)

Wine Sail In Portland, Maine: France

• Aug 9, 2025 (Sat)

Wine Sail In Portland, Maine: Rosé

• Aug 9, 2025 (Sat)

Sip N’ Snack Pairings

• Aug 9, 2025 (Sat)

Wine Sail In Portland, Maine: Napa + Sonoma

• Aug 10, 2025 (Sun)

Wine Sail In Portland, Maine: South Africa

• Aug 10, 2025 (Sun)

Champagne & Oysters Sail In Portland, Maine

• Aug 15, 2025 (Fri)

Wine Sail In Portland, Maine: French Whites

• Aug 15, 2025 (Fri)

Wine Sail In Portland, Maine: European Wines

• Aug 16, 2025 (Sat)

Wine Sail In Portland, Maine: The Mediterranean

• Aug 16, 2025 (Sat)

Wine Sail In Portland, Maine: Piedmont, Italy

• Aug 17, 2025 (Sun)

Chef Series Wine + Food Sail With Chef Sansonetti Of Chaval

• Aug 17, 2025 (Sun)

Wine Sail In Portland, Maine: Oregon & Washington

• Aug 17, 2025 (Sun)

Sunset Wine Sail In Portland, Maine: Wine + Oysters

• Aug 21, 2025 (Thu)

Summertime Sips

• Aug 22, 2025 (Fri)

Wine Sail In Portland, Maine: California

• Aug 22, 2025 (Fri)

Wine Sail In Portland, Maine: Italy

• Aug 22, 2025 (Fri)

Rosé All The Way: A Beginner's Guide To Pink Wines

• Aug 23, 2025 (Sat)

Wine Sail In Portland, Maine: Sicily

• Aug 23, 2025 (Sat)

Salud! An Introduction To Tequila & Mezcal

• Aug 23, 2025 (Sat)

A Premium Tequila Experience—The Art Of Agave

• Aug 23, 2025 (Sat)

Wine Sail In Portland, Maine: France

• Aug 24, 2025 (Sun)

Wine Sail In Portland, Maine: Wine + Oysters

• Aug 24, 2025 (Sun)

Wine Sail In Portland, Maine: The Loire Valley

• Aug 29, 2025 (Fri)

Wine Sail In Portland, Maine: European Whites

• Aug 29, 2025 (Fri)

Wine Sail In Portland, Maine: Spain

• Aug 30, 2025 (Sat)

Wine Sail In Portland, Maine: The Mediterranean

• Aug 31, 2025 (Sun)

Chef Series Wine + Food Sail With Chef Sansonetti Of Chaval

• Aug 31, 2025 (Sun)

Wine Sail In Portland, Maine: California's Central Coast

• Sep 4, 2025 (Thu)

California Uncorked—Napa Valley & Beyond!

• Sep 5, 2025 (Fri)

Wine Sail In Portland, Maine: Napa + Sonoma

• Sep 5, 2025 (Fri)

California Uncorked—Napa Valley & Beyond!

• Sep 6, 2025 (Sat)

Wine Sail In Portland, Maine: European Wines

• Sep 6, 2025 (Sat)

California Uncorked—Napa Valley & Beyond!

• Sep 7, 2025 (Sun)

Wine Sail In Portland, Maine: Wine + Oysters

• Sep 7, 2025 (Sun)

Wine Sail In Portland, Maine: Mediterranean Reds

• Sep 10, 2025 (Wed)

Chef Series Italian Wine + Food Sail With Chef Laboa Of Solo Italiano

• Sep 13, 2025 (Sat)

Wine Sail In Portland, Maine: Italy

• Sep 13, 2025 (Sat)

Wine Sail In Portland, Maine: Italian Reds

• Sep 14, 2025 (Sun)

Wine Sail In Portland, Maine: Sicily

• Sep 14, 2025 (Sun)

Wine Sail In Portland, Maine: Tuscany

• Sep 18, 2025 (Thu)

The King Of Grapes - Cabernet Sauvignon

• Sep 19, 2025 (Fri)

Wine Sail In Portland, Maine: Oregon & Washington

• Sep 19, 2025 (Fri)

The King Of Grapes - Cabernet Sauvignon

• Sep 20, 2025 (Sat)

Experience The Magic Of Amalfi: A Wine And Gastronomy Tour

• Sep 20-21, 2025 (Sat-Sun)

Salem Food Truck & Craft Beer Festival

• Sep 20, 2025 (Sat)

Wine Sail In Portland, Maine: Pinot Noir

• Sep 20, 2025 (Sat)

Wine Sail In Portland, Maine: France

• Sep 20, 2025 (Sat)

Singular Sensations - Getting To Know Single Malt

• Sep 20, 2025 (Sat)

Sip Happens: Wine Mistakes And How To Avoid Them

• Sep 21, 2025 (Sun)

Chef Series Wine + Food Sail With Chef Sansonetti Of Chaval

• Sep 21, 2025 (Sun)

Wine Sail In Portland, Maine: Wine + Oysters

• Sep 26, 2025 (Fri)

Fall Foliage Wine Sail In Portland, Maine: Cabernet Sauvignon

• Sep 27, 2025 (Sat)

Fall Foliage Wine Sail In Portland, Maine: Spain

• Sep 27, 2025 (Sat)

Fall Foliage Wine Sail In Portland, Maine: Sparkling Wines

• Sep 28, 2025 (Sun)

Chef Series Wine + Food Sail With Shef Mimi Weissenborn Of Sur Lie

• Sep 28, 2025 (Sun)

Fall Foliage Wine Sail In Portland, Maine: The Loire Valley

• Oct 3, 2025 (Fri)

Fall Foliage Wine Sail In Portland, Maine: Italian Reds

• Oct 4, 2025 (Sat)

Fall Foliage Wine Sail In Portland, Maine: Autumn Whites

• Oct 4, 2025 (Sat)

Fall Foliage Wine Sail In Portland, Maine: Piedmont, Italy

• Oct 5, 2025 (Sun)

Fall Foliage Chef Series Wine + Food Sail With Chef Sansonetti Of Chaval

• Oct 5, 2025 (Sun)

Fall Foliage Wine Sail In Portland, Maine: Napa + Sonoma

• Oct 10, 2025 (Fri)

Fall Foliage Wine Sail In Portland, Maine: European Wines

• Oct 11, 2025 (Sat)

Fall Foliage Wine Sail In Portland, Maine: Italy

• Oct 12, 2025 (Sun)

Fall Foliage Wine Sail In Portland, Maine: The Mediterranean

• Oct 12, 2025 (Sun)

Fall Foliage Champagne & Oysters Sail In Portland, Maine

• Oct 17, 2025 (Fri)

Fall Foliage Wine Sail In Portland, Maine: France

• Oct 18, 2025 (Sat)

Fall Foliage Wine Sail In Portland, Maine: Oregon & Washington

• Oct 18, 2025 (Sat)

Fall Foliage Wine Sail In Portland, Maine: Mediterranean Reds

• Oct 19, 2025 (Sun)

Fall Foliage Wine Sail In Portland, Maine: Sicily

• Oct 19, 2025 (Sun)

Fall Foliage Champagne & Oysters Sail In Portland, Maine

• Oct 31, 2025 (Fri)

Intro To Orange Wines: A Beginner's Guide To Skin-Contact Wines

• Dec 18, 2025 (Thu)

Intro To Sweet Wines: Understanding Dessert And Off-Dry Wines

• Sep 9, 2026 (Wed)

Howard's Wine Tour September 2026