Top New England Wine Tasting Tours

Food lovers can explore Portland's historic Old Port independently, but to uncover the best places serving traditional local fare, you really need a guide to lead the way. Taste the best that Portland has to offer on this guided foodie walking tour, complete with stops at up to seven different eateries—and enough tastings to replace a meal. Along the way, your guide offers some stories about Portland's food scene, so you can get familiar with the local culinary stalwarts.

Embark on a boat to a private island historic fort that’s only accessible with this tour. Leave from Portland and for a boat ride on Casco Bay, landing at the privately owned Fort Scammel on House Island. There, explore the architecture and preserved ruins of the stone fort—the only fort in the Portland harbor to see battle. Discover underground passages and learn the history of this previously inaccessible site.

See a new perspective on the Providence waterfront—and enjoy a romantic, one-of-a-kind evening activity—aboard this sunset cruise. Make your own way to the centrally located docks at Fox Point Marina, board the vessel, and set off as twilight descends. With music playing in the background, you can sip Rhode Island-made wine and prosecco, glimpse architectural highlights and landmarks, and savor the tranquil ambiance.

Taste your way around the Federal Hill neighborhood of Providence with a guide to show you around and tell you about a unique side of the city’s history at the same time. Learn about mob bosses, corruption, and illegal gambling that ended in violence. Walk away from the tour with a delicious souvenir to take home with.

No matter the occasion—whether it's an anniversary, birthday, corporate event, day out with friends, or a girls' getaway—you'll likely need a designated driver, and that's where we come in. With a maximum of six customers per tour, this experience is intimate and feels like traveling with a group of friends! We are a small boutique tour company with over decade of experience! Available in spring and summer only, this guided tour visits three Vermont wineries, one hard cidery, and other local attractions. Most wines in Vermont are crafted from hybrid grape varieties suited to the harsh climate. When booking a hotel for this tour, please choose a location in either the Burlington, South Burlington or Killington areas. We offer door-to-door pick-up service! Available Wednesday – Sunday ONLY

Experience true local wines with a tasting at Plymouth Bay Winery, where talented vintners and chefs create wines, wine jellies and wine sauces from fruits that are native to the northeastern United States. Sample the entire collection of wines, and learn about using the jellies and sauces in your home cooking. Finish the tasting with an etched, commemorative glass from this unique winery in ‘America’s Hometown,’ just a stone’s throw away from historic Plymouth Rock.

Whether you’re a wine lover or just going along with others who are passionate about the drink, you won’t want to miss this White Mountains Seven Birches Winery Tour that takes you intimately through the wine-making process with the wine makers themselves. Enjoy tastings of both young and old wines, as well as a full-on tour of the winery’s wine production room.

Get ready for an unforgettable day along the stunning Outer Cape! Whether you're a foodie, an art lover, or just eager to soak in the best of what the Outer Cape has to offer, we'll work with you to create the ultimate itinerary! Our expert guides are here to take the hassle out of your adventure. Let us handle the driving while sharing fascinating insights into the Outer Cape’s vibrant history and culture. And if you need any personalized recommendations along the way, we’ve got you covered! What to Expect: • Once you book, we'll create a personalized itinerary just for your group. • Plan for up to 5 hours of Fun! (Can be longer if you want) • Self-Purchase: You’ll be in charge of buying your own drinks and goodies, but we’ve teamed up with some awesome businesses to offer exclusive perks for you to enjoy. • Convenient Transport: We’ll pick you up and drop you off anywhere on Cape Cod, so you can relax and enjoy the ride!

Travel from Boston to Woods Hole and Martha’s Vineyard without any stress on this private one-way chauffeured transfer. Avoid the hassle of parking or driving in traffic. Meet your driver in the city of Boston and make your way to Martha’s Vineyard. Some vehicles are equipped with WiFi so you can stay connected en route.

Cruise the Providence River as you sample a selection of beverages from a Rhode Island winery on this wine-tasting boat tour. Your captain will share information about downtown Providence landmarks while you savor and discuss six different wines. Experienced oenophiles and those new to wine-tasting can both enjoy this fun and festive twist on a sightseeing tour.

Whether you’re a cider lover or just going along with others who are passionate about them, you won’t want to miss this White Mountains Rhythm Cidery Tour that takes you intimately through the cider-making process with the cider makers themselves. Enjoy tastings of finished ciders and some experimental ones, as well as a full-on tour of the cidery production room. This intimate chat and tour of the facility with the cider maker is perfect for those that are new to cider, are learning about cider, or who are looking to expand their cider palate. You'll take a deep dive into the cider production process, while keeping it light, engaging and fun!

Explore the wines and meads of Maine! Take your tastebuds on a trip around the state and explore the wide variety of wines made right here in our state - including those made with imported grapes, those made with cold-hardy grapes grown in Maine, and those made from ingredients that aren't grapes at all! Participants will be introduced to six Maine-made wines and meads from six different producers - and hear the stories behind the wineries that brought them to your glass. This guided, 30-minute experience is a fantastic introduction to Maine's wine landscape and history. We recommend scheduling this class at the beginning of your time in Maine so you can take advantage of all you've learned during the rest of your trip. Stick around afterwards for personalized recommendations from your MTC host about wineries, breweries, markets, farms and other agritourism experiences to seek out while in Maine - customized to your interests and the regions you plan to visit while in Maine.

Explore the vibrant nightlife of Mystic, CT, on this exciting pub crawl. Begin your evening with three delicious slices of pizza at the iconic Mystic Pizza before venturing into the town's lively bar scene. Over the course of 3.5 hours, visit four local bars, enjoying one drink at each stop while soaking in the fun atmosphere. This social tour is perfect for couples, groups of friends, and anyone looking to make new connections while enjoying Mystic's nightlife. - 3.5-hour guided tour through downtown Mystic - Enjoy three slices of pizza at Mystic Pizza to kick off the night - Visit four lively bars with one drink included at each - Ideal for couples, bachelor/bachelorette parties, and friends looking for a fun night out

Engage in a unique wine tasting experience at Seven Birches Winery, guided by the founding winemaker, Mark LaClair. This intimate small-group session begins with a brief walk through the cellar, showcasing the heart of the winery. Savor four exclusive wines from the library, a collection not accessible to the general public, while enjoying personalized insights and education about each variety. This rare opportunity allows you to ask your most pressing wine questions and deepen your appreciation for these legacy wines. Perfect for enthusiasts seeking a memorable and informative tasting experience in a private setting.

Upon arrival, you will be greeted by your friendly staff and escorted to your cozy tasting room. The experience begins with an introduction to the tasting flight, carefully curated to showcase the best of your local offerings. As you sip on each variety, your vintner will share the captivating history of winemaking in the region, offering a deep dive into the processes and stories behind each bottle. You'll have the opportunity to ask questions, making this an interactive and educational experience. The tasting room's ambiance, combined with the stunning views of the farm and orchards, creates a perfect setting for a memorable outing. Included ~A guided tasting of a flight of wines and ciders ~A detailed presentation on the history and process of winemaking in the Maine Highlands ~Personalized attention from your expert vintner

What sets this experience apart is that it is designed around your group and brought directly to you. Choose a private sensory wine tasting or begin with an all-levels yoga practice before gathering around the table. I come to your Airbnb, vacation rental, private home, waterfront deck, or another Portland-area location. The tasting is relaxed, engaging, and approachable. I guide your group through the aromas, flavors, stories, and sense of place behind each bottle. No wine knowledge is needed. With WSET certification, I bring expertise without making the experience feel formal or intimidating. For groups adding yoga, the movement portion is tailored to your energy, experience, and occasion. First-time participants and regular practitioners are equally welcome. Ideal for bachelorette weekends, birthdays, girls’ trips, anniversaries, family gatherings, and corporate retreats, this private experience helps your group slow down, connect, and enjoy something memorable together.