Top Boston Wine Tasting Tours

Join Boston's only award-winning, original, Martha's Vineyard Day Trip! Leave the trouble of driving to someone else and enjoy a day trip to Martha’s Vineyard from Boston. Then, take a short cruise to Martha's Vineyard then enjoy free time to explore or upgrade to add an island tour. Complimentary snacks, bottled water, island guidebooks and a discount card with island perks are provided during the drive.

Relive the most important event leading up to the American Revolution on this guided tour of the Boston Tea Party Ships and Museum. Take a journey back in time to the famous Boston Tea Party, an incident that changed the course of American history. It’s more than a stroll through historic artifacts, though. It’s truly one of the top-rated museums in the city of Boston. Explore authentically restored tea ships and throw the fated tea into Boston Harbor.

Walk the Freedom Trail with a guide in historic costume on a tour from Boston Common to Faneuil Hall, a 1.2-mile route that covers important sites in the heart of Boston. This tour's shorter distance lets you follow in the footsteps of the founding fathers and American revolutionaries without making the more strenuous trek all the way across the Charles River, finishing in a spot that’s convenient to top Boston attractions.

Take a deep dive into the history of the American Revolution on this walking tour of Boston. Your historian guide will focus on the years between 1760 and 1775, a tumultuous time with plenty to talk about. Stroll the Freedom Trail and ask questions along the way; your small group will make for an intimate atmosphere.

Travel back in time to colonial New England on a 1 hour and 45 minute historic walking tour. With a length of 1.5 miles or less, this tour is perfect for people of most abilities. Your costumed and in-character guide gives you an immersive understanding of life during America’s infancy. Hear exclusive stories about the country’s Founding Fathers and discover iconic historical sites. 

Explore the best that Boston has to offer on this hop-on hop-off tour of the city. Visit nine of Boston’s top attractions — like the USS Constitution, the Boston Tea Party Ships and Museum and Fenway Park, to name a few — on a 1.75-hour loop. Select your pass, then board at any of the nine stops and get to know the city in custom fashion, with live on-board commentary from a professional tour conductor. Upgrade your experience to include a Boston harbor cruise.

Sample some of the most delicious bites that Boston’s North End has to offer—and enjoy a personalized, first-hand introduction to the area’s charms and Italian heritage—on this small-group walking tour. Choose between several convenient start times, and be sure to bring your appetite: you’ll follow your guide to a number of local businesses, where you’ll try everything from clam chowder and lobster rolls to pasta and cannoli. At the end, you'll enjoy a delicious Secret Dish, that will be revealed only on the day of the tour.

See the landmarks and highlights of Boston from the water on this sightseeing cruise in Boston Harbor aboard a 1920s-style yacht. Snap photos and enjoy a unique perspective of the harbor, very different than a typical walking or driving tour through Boston. Highlights include the USS Constitution, Bunker Hill Monument, Old North Church, and the USS Cassin Young.

Visit Martha’s Vineyard on a day trip from Boston to experience the island beauty without the hassle of booking ground and ferry transport. From hotel pickup and drop-off to included ferry tickets, snacks, water, and sightseeing maps, this Martha’s Vineyard excursion is designed for maximum time exploring, with the option to upgrade and include a guided tour of the entire island aboard a high-top, small-group van and explore all six towns on the island, indulge in lunch, and spend more time learning about scenic New England.

Walking the cobblestone streets of the most popular neighborhood North End is a must, but don’t waste time looking for the ideal place to eat. Join other passionate foodies to snack your way through the neighborhood. Your guide directs you to a hidden, a generations-old bakery, an authentic Italian salumeria, and a family run pastry shop. Visit the Old North Church (or equivalent alternative) and maybe even get a chance to talk with the neighborhood’s best bakers. Pizza, pastries, and other delights round out your experience.

Combine two attractions Boston has to offer—delicious food and rich history—on this tour that starts in the popular North End and continues along the Freedom Trail. Snack your way through this historic Italian neighborhood, trying fresh bread at a hidden bakery and enjoying an Italian salumeria. Once fortified, walk the Freedom Trail to discover the rich history of the American Revolution and experience the modern city Boston is now.

Pair your Boston sightseeing with a frothy brew or two on this combination history tour and tavern crawl. Meet your guide in the afternoon, and set off with just a small group for company. You’ll wander along the city’s Freedom Trail, and will see 10 key Boston attractions—all while your guide shares the stories and history behind the sights. As you go, stop for refreshing beers in several centuries-old taverns.

Take an evening cruise on Boston Harbor to watch the sunset from the water. Glide out to the Old North Church and Historic Site, the Charlestown Navy Yard, Leonard P. Zakim Bunker Hill Memorial Bridge, and the USS Cassin Young. As a bonus, listen to the cannon fire of the USS Constitution, which marks the sunset each night.

Enjoy views of beautiful Boston with this 90-minute sunset cruise. Watch the sun sink over the sparkling water as your guides point out the USS Constitution and other historic sights. Once the sun goes down, you’ll have a chance to see the city skyline illuminated. There is a full bar on every boat, with snacks and other beverages available for purchase.

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.

This is activity for travelers that are interested in learning and experiencing other Cultures. The host will share his Caribbean culture through food. Guests will have an opportunity to share their culture as well. We want everyone to learn something.