Top Massachusetts Dining Experiences

Avoid tourist traps and eat like a local while you sample Boston’s most famous dishes on this small-group food tour along the Freedom Trail. Savor classics such as creamy New England clam chowder, a classic lobster roll, and Boston cream pie while learning the history behind these classics. Visit local eateries and landmarks and discover how the city's food culture and rich history go hand in hand. Perfect for foodies who want a sampling of Boston's most iconic foods.

Step into the heart of Boston's North End and embark on a delectable journey through its vibrant street food culture. With a knowledgeable local guide leading the way, you’ll wander through bustling streets rich in authentic Italian cuisine. From iconic dishes like fresh seafood and savory pastas to hidden gems known only to locals, each stop promises to tantalize your taste buds. Your guide will share captivating historical anecdotes, offering insider knowledge on the traditions and flavors that define this historic neighborhood. Perfect for food enthusiasts and curious explorers alike, this tour promises an immersive and unforgettable culinary experience.

Boston is famous for its donuts and has numerous artisanal donut stores, some hidden away from its tourist areas. Instead of hunting them down independently, let a guide lead you there and introduce you to some top donut varieties, enabling you to try flavors and gain insight into the local donut scene you might otherwise miss. Between tastings, browse a market, eat a delicious bakery treat and explore historical neighborhoods such as North End before one final, scrumptious donut sampling.

Enjoy a gourmet brunch on this scenic cruise of the Boston Harbor. Set sail aboard the Northern Lights at Rowes Wharf and settle in for a buffet filled with eggs, bacon, fresh fruit, and more. View popular Boston highlights such as Bunker Hill Monument, the USS Constitution, Old North Church, and Sea Castle Island. This brunch cruise offers a great overview of Boston and a lovely morning on the water.

Toast to Ptown’s past on a Commercial Street stroll blending craft cocktails and bohemian history. Perfect for drink lovers and history buffs, this tour celebrates our maritime, artistic, and LGBTQ+ legacy. Kick off at local establisment with a Cape Cod Blueberry Martini. Enter the Old Colony Tap Room, one of America's oldest, most weathered dives made completely from old shipwrecks. Pass the iconic Lobster Pot and Governor Bradford to stop at Lopes Square to see its 1801 anchor, and learn about the old colony railroad. Look up at the UU Meeting House’s 1847 Greek Revival steeple, then head into the Ptown Library to glimpse the grand schooner inside. Pay homage to literary history at the Atlantic House (A-House), a 1798 tavern loved by Tennessee Williams. Next, keep the energy high with a shaken Espresso Martini at a local favorite. Finally, wrap up at the famous Boatslip Resort for the legendary Tea Dance—a disco-fueled, open-air tradition pulsing since the 1970s.

Learn how to prepare a range of classic Italian dishes, from ravioli and tortellini to tiramisu and beyond—and receive hands-on guidance from your chef instructor—during this immersive cooking class. Upon arrival at 21 Kingston St, grab your apron, roll up your sleeves, and get ready to cook: with your instructor’s guidance, you’ll make a number of different delicacies. At the end of the class, sit down to enjoy the meal you created, plus light snacks.

Cruise Boston Harbor aboard a luxury yacht, complete with superb city views and a buffet brunch featuring both breakfast and lunch offerings. For 2-hours you'll explore the waters from Rowes Wharf to the Charlestown Naval Yard and back, sailing past sights such as Castle Island and Boston Light. Spend some time enjoying the yacht's three climate-controlled decks or dancing to the sounds of a live DJ mix.

Discover the South End in a fun and memorable way with this Sweet and Savory Food Tour. Make your way through this iconic Boston neighborhood, stopping for treats like French-Cambodian appetizers to a charming cheese market and locally famous sweets. As you walk, admire the architecture and learn about the area’s rich cultural history. Your guide will share insider knowledge and point out hidden gems along the way.

Many cooking classes teach you how to make authentic dishes, but few take place in a working distillery and allow you to sip on their craft spirits (own expense) as you cook. On this sushi-making experience, head to a Boston distillery and learn the secrets behind making restaurant-quality sushi rolls, while customizing your creations with your own unique flair.

This immersive cooking class offers a rare opportunity to explore history through food. Hosted by Andrew, a food writer and educator whose work has appeared in Gastro Obscura and Eaten, the experience blends hands-on cooking with storytelling, archaeology, and cultural insight. Drawing from historical sources, Andrew recreates authentic Ancient Roman recipes and explains the origins of the spices, ingredients, and techniques used thousands of years ago. Set in Quincy, just outside Boston, you’ll begin with a traditional Roman drink or snack before cooking 2–3 dishes inspired by ancient texts. As you prepare and share the meal together, you’ll discover how food connects us across centuries, making this class both a culinary experience and a living history lesson.

Enjoy lunch on the waters of Boston Harbor during this cruise aboard the "Odyssey Boston." You'll have the chance to admire views of the city skyline and seaport from the boat decks, plus listen to live music. The 3-course lunch includes a starter, main course, and dessert. This is a relaxing way to see the city from another perspective.

This macaron class is designed to help you build confidence while tackling one of baking’s most iconic pastries. Led by Chef Rita, the experience focuses on hands-on learning in a relaxed, encouraging environment. You’ll prepare and bake your own macarons, exploring rich dark chocolate and bright fruit flavors while learning how to achieve that signature crisp exterior and soft interior. Along the way, Chef Rita shares practical tips you can reuse for future baking projects, from proper mixing to baking precision. Ideal for friends, couples or solo bakers looking for something fun and skill-driven, this Boston class delivers both technique and creativity, with results you’ll be proud to share.

Get all the tips and tricks you need to learn to make mouthwatering dumplings while hearing stories about Chinese and Taiwanese cultural food traditions. Why we love this experience • Learn how to roll, stuff, and fold 4-5 styles of dumplings, and sample Taiwanese street food bites • Guest can BYOB and tea bar included • Public classes are held at the historical Windsor Inn, which is the oldest free-standing residence in the central square • Team building, birthday/bachelorette, couples night • Limited free parking on site

Celebrate a special occasion or just enjoy the company of your family and friends on this leaf-peeping Boston Harbor brunch cruise. On board a 1920s-style yacht, the Northern Lights, you’ll sail through Boston Harbor, cruise past the Harbor Islands, and spot landmarks and beautiful fall scenery along the way. Indulge in a fresh, gourmet brunch prepared by the onboard chef as you take in the waterfront views.

Immerse yourself in the autumn season while exploring beautiful Boston Harbor on a relaxing sightseeing cruise. Step aboard the Northern Lights vessel and catch spectacular views of colorful seasonal foliage on the Boston Harbor Islands. Then, enjoy a delicious gourmet lunch and sip a hot cider.

This cooking class is not just a meal; but a culinary adventure that enchants your mornings. Join us to transform your brunch into a celebration of flavors that will impress your friends and family for years to come.

This beginner-friendly dumpling class makes Asian-inspired cooking approachable, social and genuinely fun. Led by Chef Rita, the class walks you step by step through building flavorful dumplings with fillings tailored to your taste. You’ll practice shaping wrappers, experiment with multiple folding patterns and learn how technique affects texture and appearance. The atmosphere is relaxed and welcoming, making it easy to ask questions, laugh through the learning process and enjoy cooking alongside fellow food lovers. With hands-on instruction, flexible filling options and a complete meal included, this Boston class is perfect for friends, couples or anyone ready to level up their kitchen skills in a delicious way.

Step into the world of French culinary excellence and learn how to craft an exquisite steakhouse meal. Led by a seasoned chef with a passion for French cuisine, you'll explore the secrets of preparing classic French dishes, from perfectly seared steaks to sumptuous sauces and elegant side dishes.

Everyone loves dumplings, but learning how to cook it from scratch is just as much fun! Who better to teach you and your friends the ins and outs of dumplings than Chef Gary, who has over 15 years of restaurant experience in Boston! Your event includes a reception with light snacks, a hands-on cooking class, and a sit-down lunch.