Top Massachusetts Cruises & Sailing - page 2

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.

Learn about Boston’s revolutionary history on a walking tour that emphasizes good storytelling. Enjoy personalized attention from your guide in your small group as you walk a curated route that includes the Freedom Trail. Visit well-known sites as well as more local places and develop an understanding of modern Boston along with its history.

If you've always wanted to see Plymouth Rock, this 4 hour tour lets you check it off the bucket list. It can fit snuggly into a Boston city break without using up too much of your time in the city. We pick up in downtown Boston and travel 50 minutes directly to Plymouth. There we'll do a walking tour around the town, explaining why the Pilgrims landed here and how they settled in to the area. Go aboard the Mayflower II (seasonal) to see for yourself how awful their journey must have been and stop by the memorial for the legend of the rock. Quick stop at an impressive monument, built to honor the Pilgrims and then it's back to Boston. Boston is 50 minutes drive from Plymouth, so you will be in the car a chunk of time on this tour. You will have approximately 2 hours in Plymouth.

Explore Boston on a trolley tour that’s timed to catch sunset over the Charles River. Many Boston sites are illuminated—and uncrowded—at night, making this an ideal time to explore Boston Harbor, Cambridge, the Public Garden, and more. Live narration from an experienced guide showcases the stories and culture behind each place you visit, from stylish seaside neighborhoods to revolutionary war–era landmarks.

Explore Boston at your own pace with this hop-on hop-off trolley tour. Visit landmarks like Faneuil Hall, the Boston Tea Party Ships and Museum, and the Prudential Center, while enjoying insights from engaging guides. With flexible routes, discounted attraction admissions, and trolleys departing regularly, this tour is the perfect way to experience Boston’s history and charm.

Beat the Boston heat and get out on the water on this dog-friendly harbor cruise. With your group and your canine companion, board the cruise boat and set sail. Learn about Boston's history and sights including the Seaport District, Castle Island, USS Constitution, and North End from live narration onboard, and relax during Boston’s long summer days in the company of your dog.

What a way to celebrate the weekend! Enjoy a lovely two hour sail on Boston Harbor with unbeatable views of the city. Your ticket includes complimentary coffee and fresh-baked pastries from the incomparable Flour Bakery + Cafe. Feel free to bring your own food along if you prefer, but please no outside beverages and no coolers. Mimosas are $5 all morning! We also have our full drink menu available including local craft beers, cocktails, wine, soda, juice, and water. We accept Apple Pay, credit cards, or cash onboard.

Explore Martha’s Vineyard efficiently on a private tour designed for travelers with limited time. This narrated drive offers a personalized overview of the island’s towns and scenic coast without navigating on your own. Learn local history and context from a dedicated guide while traveling comfortably between key areas, making the most of a short visit ashore.

Take a cruise along the Charles River for a chance to see some of Boston’s most beautiful historic and contemporary architecture. Pass important landmarks such as Marriott’s Custom House, the Prudential Building, and the Hancock tower and listen to live commentary onboard about the history, architecture, and design of these buildings.

Travel to or from Boston Logan Airport hassle-free and in comfort with this private one-way transfer. Choose an arrival or departure transfer and meet your driver at the airport or your hotel. Ride in a comfortable air-conditioned vehicle with a phone charger and relax while your driver navigates the route.

If you have limited time but still want to see all that Martha’s Vineyard has to offer, then book this private sightseeing tour. You’ll pass through the island towns and scenic landmarks with a local guide, who will tell you all about the area, and allow time for plenty of photo stops. You’ll also be driven from place to place in a comfortable, luxury minivan.

If you've always wanted to visit this infamous town, then let's do it during your visit to Boston. This half day Boston to Salem tour consists of: - Downtown Boston pick up, ~45 minute drive to Salem - Stories of what happened before, during & after the Salem Witch trials - Walking tour of movie scenes, sites and fun facts of Salem - Go into one of the main Salem attractions (entry fee not included, and availability not guaranteed) - 45 minute drive back to Boston If you'd rather skip going into any of the sites, we use that time to take you to Marblehead for some amazing ocean views. The return journey and tour is 4 hours, we're happy to customize it to accomplish the things you're most interested in.

This half day private car tour is a perfect way to visit the Revolutionary War towns of Lexington and Concord and see the site where the "shot heard round the world" was fired. We'll take the same route as Paul Revere, stopping at the most significant sites along the way to give a detailed account of what and how things unfolded in April 1775. The travel time from Boston to these towns is 45 minutes each way and you'll be in one of our comfortable private vehicles with an experienced, knowledgeable and licensed tour guide.

Take a private day trip from Boston to the North Shore, combining coastal scenery with two of Massachusetts’ most distinctive historic sights. Enjoy door-to-door hotel pickup and flexible pacing that lets you explore without group constraints. Travel comfortably while your guide provides context on regional history, architecture, and folklore, with meaningful time for exploration and photos.

This 90-minute journey on a catamaran is the fastest and most luxurious way to travel to Cape Cod, where restaurants, beaches, shopping and nightlife await.

Explore the best of Boston at your own pace on a hop-on hop-off trolley tour of the city. Choose from a 1- or 2-day pass and see Boston’s top attractions, including the USS Constitution, the original bar from TV show “Cheers,” and the Faneuil Hall Marketplace, to name a few. The pass includes discounted admission to the Boston Tea Party Ships and Museum, to enjoy during or after the tour.

Don’t waste time looking for the ideal place to eat as you walk the cobblestone streets of Boston’s North End. Join other passionate foodies to snack your way through the neighborhood’s hidden gems. Your guide directs you to a hidden Italian bakery, an authentic Italian salumeria, and a family-run pastry shop. Visit the Old North Church (or equivalent alternative) and enjoy a rich cappuccino or bold espresso with a pastry.

Book your Private Departure Transfer from Flynn Cruiseport Boston to Boston Logan Intl Airport (BOS) . Don't go through all the hassle of waiting in a long taxi or shared shuttles queues and use our private, door to door airport transfer. Your driver will be waiting for you at a scheduled time and you will travel comfortably to your destination. • Meeting with a Nameplate • We track your Flight • Door-to-door Service • No Hidden Charges • Clean cars & Professional drivers

Enjoy your Martha's Vineyard Private 4-Hour Tour - experience the full Island tour with a few added stops. For example, you might include a stop for lunch, or at scenic areas along the way for some photos, maybe a stop by an art gallery, farm stand, or beach. • Include a stop (or two) to shop in Edgartown, Vineyard Haven • Is Chappaquiddick on your ‘bucket list”? We can definitely include this in your tour. (please note that, depending on traffic for the Chappy ferry, a Chappy tour may take about to 2 hours…and you always have the option to extend your tour beyond 4 hours)Cost of ferry for van & passengers not included. • Experience a Martha’s Vineyard sunset – possibilities include: Menemsha, Cliffs of Aquinnah, West Chop beach or East Chop Light! Let us help you Customize can make your tour and make it special just for you

Discover some of Boston’s deepest, darkest secrets that lots of tourists miss out on by joining this “frightseeing” tour aboard the Trolley of the Doomed, which roams around the haunted streets and burial grounds of Boston. Your costumed host provides illuminating insights into the history of the city's spookiest sights, such as Copp’s Hill Burying Ground.

Experience the best of Newport, Rhode Island on a private, guided day trip tour in a comfortable luxury vehicle. If you value privacy, comfort, and the flexibility to explore at your own pace, our tour is the perfect choice for you. We will take you to all of Newport's most important sights, and our tour is completely customizable to suit your preferences. Whether you want to explore the opulent Gilded Age mansions, take a scenic drive along Ocean Drive, or stroll through the charming downtown area, we will create an itinerary that meets your needs. With our private tour, you can relax and enjoy the sights of Newport without having to worry about keeping a schedule or sharing your experience with strangers.

Set sail on the magnificent tall ship Denis Sullivan, a Great Lakes schooner offering a unique opportunity to connect with the sea. Whether you choose to help the crew raise the sails or simply soak in the stunning views, this public sail is a perfect outing for family and friends. All ticket proceeds contribute to the World Ocean School's educational programs, ensuring a meaningful experience on the water. Enjoy an enriching day while supporting maritime and experiential education.

Discover the New Hampshire and Maine coasts, plus the highlights of Kennebunkport, all in one day: this private, full-day tour from Boston makes exploring easy. Meet your guide in the morning at your departure point, and hop aboard your private van. You'll stop in the historic town of Portsmouth, will discover the Cape Neddick Nubble Lighthouse, can tour the President Bush Compound at Kennebunkport, and upgrade to add on a lobster tour.

This full day private tour combines some of the best coastal views in the region with Pilgrim history. First stop focuses on the Presidential history of John Adams and then for something completely different we swing by the first Dunkin' Donuts (how's that for random). Then it's sit back and enjoy the views, through south of Boston towns Hingham, Cohasset, Scituate and Duxbury. There's some great photo opps along the shoreline that you won't be able to resist. Next onto Plymouth and it's Pilgrim history as well as it's own lovely ocean views. This is a break from your city break. We pick up and drop back to downtown Boston, will stop for lunch along the way (not included in price of tour) and will make sure you have a calm and relaxed day.