New England Explorer Cruise (Portland Roundtrip)

Begin your journey in Portland, Maine—an enchanting coastal city brimming with charm and history. Nestled along the picturesque Casco Bay Peninsula, Portland is a delightful blend of maritime heritage and modern sophistication. Stroll through the cobblestone streets of the Old Port Exchange District, a lively hub of boutiques, galleries, and eateries housed in beautifully restored 19th-century red-brick buildings. This revitalized area offers a fantastic glimpse into the city’s maritime past while delivering a unique, contemporary feel.

For art and culture enthusiasts, Portland is a treasure trove. Explore its artistic soul at the Portland Museum of Art, showcasing stunning Beaux Arts and post-modern architecture and home to an impressive collection of regional and world-class art. Don’t miss a visit to the historic Portland Observatory, a fascinating relic from 1807, where signal flags once announced the arrival of ships. For those craving a taste of the sea, a variety of seafood restaurants await, serving up famous Maine lobster, fresh chowder, and other local delights. Portland takes pride in its culinary diversity, offering something delicious for every palate.

Beyond the city, you’ll find serene coastal escapes nearby, including the charming village of Kennebunkport, famous for its beautiful harbor and as the summer retreat of former President George Bush. Fort Williams Park and the iconic Portland Head Light offer stunning views and peaceful settings for nature lovers. For avid shoppers, the nearby town of Freeport boasts some of New England’s best outlet stores, perfect for uncovering hidden treasures.

Whether you are exploring its rich history, indulging in its vibrant culinary scene, or simply wandering its scenic waterfront, Portland offers a warm welcome and a journey full of memorable experiences.

Step into the charming, coastal town of Bar Harbor, a place that has inspired visitors for generations. Nestled on Mount Desert Island, this gem seamlessly blends its artistic roots with breathtaking natural beauty. Historically a retreat for the elite during the Gilded Age, Bar Harbor remains a vibrant destination where history and modern charm collide. Visit the grand mansions that tell stories of a bygone era—though some were lost to a fire in 1947, others have found new life as bustling local businesses. Wander the historic West Street, a National Historic District, to glimpse beautifully preserved homes that evoke the elegance of the past. Bar Harbor also serves as the gateway to Acadia National Park, offering travelers access to stunning landscapes and abundant wildlife. Look out for seals, whales, and eagles along the coastline, or spot deer and foxes in the area’s lush greenery. Its streets—Main, Mount Desert, and Cottage—are alive with boutique shops, unique galleries, and inviting eateries that capture the spirit of this coastal haven. Whether you're savoring fresh seafood, admiring local crafts, or simply soaking in the salt air, Bar Harbor promises a warm welcome and unforgettable experiences at every turn.

Step back in time as you stroll through Newport, a beautiful harbor town that whispers stories of early America. Founded in 1639 by William Coddington and Nicholas Easton, it became a haven for those seeking religious freedom. With its prime location at the mouth of Narragansett Bay, Newport blossomed as a bustling colonial port. Today, some of the city’s oldest landmarks, like the Wanton-Lyman-Hazard House and the White Horse Tavern, still stand to greet visitors. Other highlights include Trinity Church, Touro Synagogue, and the Redwood Library—testaments to an era of architectural splendor.Newport’s history also holds tales of British occupation during the Revolutionary War, which once emptied half the city. But this turmoil may have been a blessing in disguise, as the lack of development preserved many of its historic gems. By the 19th century, Newport had reinvented itself, becoming the exclusive summer retreat of America’s elite. Wealthy families built extraordinary mansions along Bellevue Avenue, known as “summer cottages.” These palatial homes, created by famed architects, remain a signature of the Gilded Age’s extravagant charm.For today’s visitors, Newport offers far more than its storied past. From scenic beaches and fresh seafood to art galleries and shopping, Newport packs a wealth of experiences into a small, walkable area. While summer brings bustling crowds, spring and fall reveal a quieter, equally enchanting side of this coastal treasure, making every visit an unforgettable journey.

Step into the charm of Portland, Maine, a picturesque destination that blends history, culture, and vibrant modern-day life. This coastal gem, Maine’s largest city, was founded in 1632 and flourished as a hub for shipbuilding, with its timber celebrated for creating towering masts used across the seas. Historic wharves once housed bustling trade and, today, some stand proudly preserved while others offer elegant condominium spaces. Over time, the community has beautifully transformed the city’s Old Port Exchange District, where cobblestone streets are now lined with shops, art galleries, and cafes that invite visitors to explore at a leisurely pace.Stroll through Congress Street, the heart of the Arts District, and find historic colonial mansions, the serene Portland Museum of Art, or inspiring statues scattered throughout town. Don’t miss favorite landmarks like the Portland Observatory, the Portland Head Light at Fort Williams Park, or the boyhood home of poet Henry Wadsworth Longfellow. And if adventure calls, take a short trip to Kennebunkport, a classic New England maritime village, famously known for its connection to U.S. presidential history.Food lovers will delight in Portland’s culinary scene. Known for its exceptional array of dining options—from fresh Maine lobster to global cuisine—this city boasts some of the finest seafood and dining experiences in the region. Visitors who enjoy shopping will find art, boutiques, and Maine-made treasures in the Old Port Exchange. For a more expansive retail experience, the designer outlets of Freeport are just a short drive away.With its rich seafaring heritage and friendly streets, Portland offers the quintessential New England adventure, perfect for both relaxation and exploration.

Nestled on Penobscot Bay, Rockland, Maine, offers a charming blend of history, art, and rugged beauty. Explore the iconic breakwater or stroll downtown, where art galleries and boutique shops await. Discover masterpieces at the Farnsworth Art Museum or savor fresh lobster in award-winning eateries. Rockland’s coastline invites adventurers for sailing and harbor walks, while its vibrant festivals create a lively, welcoming atmosphere. This small city captures the magic of coastal Maine—perfect for a day of exploration, relaxation, and discovery.

Discover the charm of Boothbay Harbor, a seaside gem nestled along Maine's stunning coast. Known for its rich maritime history, the town invites you to stroll quaint streets lined with shops, enjoy world-class dining, or cross the iconic footbridge. Explore rocky shores, serene coves, or embark on adventures like whale watching and island-hopping. Immerse yourself in the local culture during Windjammer Days, when majestic schooners grace the harbor. Whether you seek relaxation or adventure, Boothbay Harbor offers the perfect blend of natural beauty and coastal tradition.

Step into Bath, Maine, the "City of Ships," where maritime history and natural beauty meet. Wander through charming 19th-century streets filled with quaint shops and galleries. Discover the Maine Maritime Museum, a treasure trove of shipbuilding stories. Relax along the scenic Kennebec River or explore nearby Reid State Park's stunning beaches. Indulge in fresh lobster rolls at local eateries or experience the vibrant community spirit during annual festivals. Bath effortlessly blends heritage and serenity, making it a must-visit destination for history lovers and nature enthusiasts alike.

Experience the charm of Gloucester, America's oldest seaport, nestled on the scenic Cape Ann coast. This historic city offers a rich maritime heritage, from the iconic Fisherman's Memorial to the bustling working waterfront. Wander pristine beaches like Good Harbor or set sail on an unforgettable whale-watching adventure. Art lovers will delight in galleries at Rocky Neck, while history buffs can explore the grand Hammond Castle. Don't miss fresh, local seafood at quaint waterfront eateries. Gloucester blends coastal beauty with cultural treasures, making it an enchanting stop on your journey.

Step into the charm of Martha’s Vineyard, where lush landscapes meet rich history. Discover six quaint towns, from the Victorian appeal of Oak Bluffs to Edgartown’s harbor beauty. Visit iconic sights like the Aquinnah Cliffs or the Flying Horses Carousel. Savor farm-fresh flavors that celebrate the island's local farms. With its pristine beaches and gentle breezes, this New England island delivers a peaceful escape. Martha’s Vineyard invites you to soak up its serene atmosphere, admire its maritime past, and find your slice of paradise by the sea.

Nestled at the northern tip of Cape Cod, Provincetown is a blend of history, art, and natural beauty. Stroll along Commercial Street and explore vibrant shops, galleries, and cafes. Visit the iconic Pilgrim Monument, which commemorates where the Pilgrims first landed in 1620. Relax on the sandy shores of Race Point Beach or spot whales in the distance. Known for its embracing and lively spirit, the town is also a haven for artists and the LGBTQ+ community. Festivals and events throughout the year ensure there’s always something to celebrate here. Provincetown welcomes you with open arms!