Top New England Cruises & Sailing - page 5

One hour walking tour - pirates, sardines, and a captured city - the history of Eastport and how life has changed in Downeast Maine. Leaving from the cruise pier, the tour will cover the downtown area of Eastport, stopping along the way for views of historic buildings, sweeping ocean views, and evidence of industries from long ago. Learn about the different fishing industries that shaped the town. Join this tour of downtown Eastport and learn about what makes this coastal village unique and how it's been important throughout history. The tour will meet and end near the cruise ship terminal making it perfect for those coming to port. We will stop for great views of the waterfront and your local guide will teach you about the way of life in Downeast Maine. This one-hour tour is a great opportunity to learn a little bit about the area and get recommendations from your guide about how to spend the rest of your time!

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.

Sailing regattas, Gilded Age mansions…Newport, Rhode Island, has quite the list of stories to tell (and secrets to reveal). Following your local guide—born and raised in Newport—you’ll dive head-first into cultural tales of America’s “First Resort,” learning about historic gems, social scandals, iconic spots, and more, getting a private, first-hand look at the “City-By-The-Sea.”

Experience the majesty of Lake Winnipesaukee during a narrated scenic tour aboard the historic M/S Mount Washington. Learn about the history of the region and local folklore, surrounded by some of the most beautiful scenery in New England.

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.

All our tours take place in a comfortable vehicle with a local driver-guide and can be tailored to your pace. This private tour is done in our larger passenger van that can take up to 12 passengers. We’re happy to customize the experience to match your interests. This particular tour covers all the major sights in Portland, followed by a visit to the South Portland lighthouses, including admission to Fort Williams Park to see the Portland Headlight. After exploring Portland, you'll journey down the highway to Kennebunkport, a charming coastal village that served as the summer retreat for former President George W. Bush and his family. While we have a standard route, as a private tour, we can personalize the itinerary to suit your preferences.

Discover the stunning Boston skyline from the unique perspective of the water with customized private boat charters on the Jess~Sea. Whether you're interested in a scenic harbor tour, historical sites like the USS Constitution, or a relaxing picnic on Spectacle Island, the experienced crew will tailor the adventure to your desires. With room for up to six guests, this intimate experience allows for personalized exploration of Boston’s hidden gems. Bring your own food and beverages for a perfect day on the water, all while enjoying expert guidance and local insights. - Private charters tailored to your interests, accommodating up to 6 guests - Explore historical sites, islands, and scenic views unique to Boston - Option to bring your own food and drinks for added convenience - Experienced crew dedicated to creating memorable experiences and sharing insider knowledge

Experience the ultimate in comfort and convenience with our black car service. Enjoy punctual, professional drivers, luxury vehicles, and a seamless, stress-free ride. With amenities like complimentary refreshments, and door-to-door service, we ensure your journey is as enjoyable as your destination. Book now for a premium experience from start to finish! A pet fee may apply.

See all of Boston and Cambridge from the comfort of a heated and air-conditioned modern minivan. This is a half-day driving tour that takes you through every highlight of Boston and Cambridge. The drive will include sights such as the Old North Church, Paul Revere's house, Faneuil Hall, Boston Common, Beacon Hill, Bunker Hill Monument, USS Constitution, Harvard, MIT, Copley Square, Boston Public Library and so much more! The tour is mainly driving, however we will (optionally) stop a few times to briefly (5-10 minutes) get out of the car for photo opportunities and a closer look at some sights! Listen to stories about Boston's past, learning about the American Revolution and the city's duality of religious morals and corruption.

What makes our black car service unique is the combination of luxury, reliability, and personalized service while traveling to top destinations such as airports, hotels, business districts, events, and popular city attractions. Guests enjoy a smooth, stress free ride in a premium black vehicle with a professional chauffeur who offers local insight, punctual service, and attention to detail. This service is ideal for business travelers, couples, families, and special-occasion guests who value comfort, privacy, and a refined travel experience.

Make this holiday season one to remember with this cocoa and carols holiday cruise on Boston Harbor. With dates offered throughout December, you can add a magical touch to your holiday, and easily find a date that works for you. Plus, you’ll cruise the harbor aboard a classic yacht with live music as you take in beautiful views of Boston.

This cruise is a perfect end to your day. Sit back, relax and breathe in the sea air while taking in the sights and sounds of Boston harbor under the Full Moon.

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.

Witness the stunning transformation of Portland Harbor and Casco Bay during a private sunset powerboat cruise. Aboard the classic Avelinda, enjoy a two-hour journey as the sun sets, painting the sky with vibrant hues. Marvel at iconic lighthouses like Portland Head Light and glide past charming islands, keeping an eye out for local wildlife such as seals and seabirds. This intimate experience is perfect for all ages, whether celebrating a special occasion or simply relishing the natural beauty of Maine's coastline. - Exclusive private cruise for up to 6 guests - Comfortable Maine-built powerboat with marine restroom - Experienced captains share local history and ecology - Flexible scheduling with multiple evening departures available - Alternative pickup available in Portland for added cost, saves 30 min of driving, contact us for availability

Experience the beauty of coastal Maine on this private guided tour featuring iconic landmarks, scenic harbors, and charming coastal villages. Your journey begins at Portland Head Light, one of the most photographed lighthouses in the United States, where dramatic rocky cliffs and sweeping Atlantic views create unforgettable photo opportunities. From there, travel along Maine’s scenic coastline to the picturesque harbor village of Boothbay Harbor. Walk across the historic Footbridge, built in 1901, and enjoy views of working lobster boats, quiet marinas, and classic New England waterfront scenery. Guests also have the option to enjoy lunch along the harbor at a unique restaurant built from a historic tugboat. With a knowledgeable local guide sharing stories and insights throughout the journey, this private coastal Maine tour offers the perfect blend of history, scenery, and authentic coastal charm.

Welcome Aboard Schooner Lazy Jack in Boothbay Harbor; your Maine Vacation starts here! Join the Schooner crew for a 2hr. day sail on Boothbay Harbor’s oldest windjammer. Help hoist sails or take a turn at the wheel as we set a course out past Burnt Island Light, Squirrel Island, Ram Island Light and the outer islands of Boothbay. Keep a sharp eye out for porpoise, Osprey, Bald Eagles, and harbor seals as we slip by local boats setting their pots or hauling in the lobster catch of the day.

Salem and Boston have been home to such a diverse range of historical events that it can be tough to take it all in on your own. On this full-day private tour, join your guide and discover the region’s Puritan history, learn about the 17th-century witch hunt hysteria, hunt for ghosts at several historical local landmarks, and much more.

Enjoy a laid-back evening on a social sunset cruise around Belfast Bay. This small-group boat tour accommodates up to 6 guests, making it perfect for solo travelers, couples, or friends looking to unwind together. Bring your favorite drinks and snacks aboard while you drift through the harbor, soaking in the stunning coastal views as the sun sets. With no set agenda, it's an unhurried experience that encourages good conversations and new friendships in a relaxed atmosphere. 2-hour sunset boat tour on Penobscot Bay Small-group experience with a maximum of 6 guests Bring your own drinks and snacks to enjoy during the cruise Relaxed atmosphere perfect for socializing and meeting new people

Spend a great day in Boston learning about history and exploring all the top attractions! The tour is designed to be fun for the whole family - we have quizzes, we have kid's guides, we have prizes, and we have interactive stops so kids can work off some energy!

Looking for a romantic way to watch the sunset while in Maine? How about chartering a vintage lobster boat and heading out to Casco Bay, where you'll take in great views of the sea and coastline. Your captain and guide will be on board to point out lighthouses, historic forts, and natural features. A round of drinks is included to toast the sunset with, but more beverages are available to purchase onboard.

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.

Maximize time in Boston with a private sightseeing tour. Get picked up at your hotel or the address of your choice in Boston and set out on a half-day excursion. Learn about the history behind top landmarks including the Paul Revere House, the USS Constitution, and the Bunker Hill Battle Monument. Explore several neighborhoods including Back Bay, Beacon Hill, and the South End.

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.

Spend a day tracing America's Revolutionary story in Boston, Lexington and Concord without the inconveniences of self-driving, buses and crowds on this private minivan tour. Sit back and view the sights as your driver-guide recounts facts and snippets you may not hear otherwise. Highlights include Boston's Paul Revere's House and Tea Party ships, plus Lexington's landmarks and Concord's gems, including the home of 19th-century 'Little Women' author, Louisa May Alcott.