Yankee Seaports Cruise
Boston, MA to New York, NY
New York, NY to Boston, MA
Set sail on this itinerary to see the best seaport towns of the Northeast aboard our innovative small ships, designed to expertly navigate New England’s pristine waterways. Explore the historic districts of Boston to New York, where each street still tells stories of the American Revolution.
Venture to Plymouth, MA, a charming coastal enclave with a rich history as the site of the Pilgrims' earliest settlement. Experience the splendor of Newport, Rhode Island, a testament to the opulence of the Gilded Age. Get to know the fascinating maritime legacy of New London, Mystic, and Essex, CT, led by a knowledgeable local guide through their charming streets and dynamic art scenes.
As the sun sets, take a cruise around New York Harbor, where the glittering skyline of the city unfolds before you. Take in these iconic views from the ship's bow, a fitting farewell to your unforgettable journey through the quintessential seaports of the Northeast.
Ask about our Current Savings and our Pre-Cruise Package which includes a stay at the Four Seasons Hotel, a Boston city tour, and transportation to the ship. See the Schedules & Rates tab for Current Savings.
Upcoming Dates & Fares
Itinerary
Map & Itinerary Overview
Aboard a brand-new Coastal Cat, explore the best seaport towns between the vibrant cities of Boston and New York. Step into American history in Plymouth and New London and discover the rich maritime influence of Mystic, CT; Sag Harbor, NY; and Newport, RI.
Pre-Cruise - Boston Four Seasons Pre-Cruise Package
With our exclusive Pre-Cruise Package, located in the heart of downtown Boston, you can begin your cruise early. This premier accommodation offers convenient access to the entire city, allowing you to leisurely arrive the day prior to your cruise.
Start your day with breakfast before joining a guided exploration of the city's renowned landmarks, including the historic Freedom Trail. Follow the red brick path as it winds through cobblestone streets, passing by significant sites such as the Paul Revere House, Old North Church, and Faneuil Hall, where you can stroll the lanes of Quincy Market.
Let American Cruise Lines handle all the details, including the smooth transportation of your luggage directly to your stateroom aboard the ship. Conclude your exploration at the ship, where you'll seamlessly transition to embarkation and set sail from Boston Harbor for an afternoon of relaxation and scenic cruising along the coast.
Pre-Cruise Packages must be reserved at least 30 days before your cruise date. Please call (800) 460-4518 for pricing and availability.
Day 1 - Boston, MA
Explore the charming streets of historic downtown Boston, where red-brick buildings line cobblestone pathways, holding centuries of rich history. Wander along the waterfront, where ships once docked to unload goods from distant lands and take in the panoramic views of Boston Harbor. Visit Beacon Hill, adorned with elegant brownstone homes and gas-lit streetlamps, harkening back to Boston's aristocratic past. Discover the verdant oasis of the Boston Public Garden, a retreat filled with colorful flowers, serene ponds, and iconic swan boats, offering a peaceful escape amidst the bustling cityscape. Let us welcome you aboard with a toast as you meet your dedicated crew and fellow cruisers.
Day 2 - Plymouth, MA
Discover the coastal beauty of Plymouth, Massachusetts, where sandy shores meet the gentle waves of Cape Cod Bay. Stroll along the historic shores, where weathered fishing boats bob in the harbor, reminiscent of Plymouth's seafaring past. Explore the charming streets of downtown Plymouth, lined with quaint shops and colonial-era architecture, providing a glimpse into the town's storied history. Visit Pilgrim Memorial State Park, home to the iconic Plymouth Rock, a symbol of the Mayflower Pilgrims' arrival in the New World and live the tales of America's early settlers.
Day 3 - Newport, RI
Uncover the enchantment of Newport, Rhode Island, where cascading cliffs meet the sparkling waters of the Atlantic. Take a leisurely stroll along the famous Cliff Walk, a picturesque pathway winding amidst grand Gilded Age mansions and wild coastline, offering breathtaking views of the rocky shore. Explore the historic downtown area of Newport, where colonial-era architecture blends seamlessly with bustling shops and waterfront cafes, reflecting the town's rich maritime history. Don't miss a visit to the renowned Newport Mansions, such as The Breakers and Marble House, once the extravagant playgrounds of America's elite, adorned with ornate ballrooms, gilded ceilings, and manicured gardens, for a step back in time to an era of pure luxury and indulgence.
Day 4 - New London/Mystic, CT
The perfect duo: New London and Mystic. Mystic is a charming maritime village known for its scenic New England beauty, featuring a harbor filled with historic tall ships and an eclectic waterfront area. The town has a rich art scene. Stop into the gallery of Russ Kramer, known for his realistic maritime paintings. This port gained additional fame from the 1988 film Mystic Pizza but pushes culinary boundaries at local restaurants and bakeries like the famous “Sift” with the best, melt-in-your-mouth chocolate chip cookies.
Nearby New London is a historic seaport city where the Thames River meets the Long Island Sound, characterized by its eclectic art scene, including the renowned Lyman Allyn Art Museum and frequent cultural festivals. The city's landscape features a mix of urban and coastal elements, with notable landmarks like the United States Coast Guard Academy and a vibrant waterfront district that offers sweeping views and a variety of dining experiences.
Day 5 - Sag Harbor, NY
Set sail for Sag Harbor, a historic port on the shores of Eastern Long Island. Established as a bustling whaling port, this village retains its 19th-century charm, with narrow lanes and whaler’s cottages that tell tales of the sea. Meander through the streets lined with art galleries and antique shops, each a treasure trove of artistic expression and bygone artifacts. Visit the Whaling Museum to trace the bold journeys of maritime adventurers and stand by the old windmill, a sentinel of the past. Experience Sag Harbor's unique blend of nautical history and cultural sophistication, where every corner reveals a story, and every sunset paints the harbor in pink and orange hues.
Day 6 - Old Saybrook, CT
Journey to Old Saybrook, where the Connecticut River greets Long Island Sound. As one of Connecticut's earliest settlements, founded in 1635, Old Saybrook boasts a legacy as the cherished home of silver screen icon Katharine Hepburn. Venture a short distance to the enchanting town of Essex, where you can wander along a waterfront framed by time-honored colonial and federal architectures that stand as elegant custodians of history along its idyllic streets. Uncover the maritime chronicles of the area at the Connecticut River Museum, a repository of seafaring lore and legends.
Day 7 - New York, NY
As we glide towards the iconic silhouette of New York City, prepare for the spectacle of its famed skyline: the Empire State Building pierces the sky, the Chrysler Building flashes its Art Deco brilliance, and the new One World Trade Center stands as a beacon of resilience and renewal. Once your ship docks in the energetic heart of Manhattan, you're perfectly positioned to step into city life. American Cruise Lines offers a curated selection of shore excursions—whether you’re keen to meander through the sprawling greenery of Central Park, take in a Broadway show, or explore the historic streets of Greenwich Village. Ready yourself to engage with New York’s storied museums, its endless markets, and the palpable buzz of Times Square. This isn't just a visit; it's a chance to take a bite out of the Big Apple.
Day 8 - New York, NY
Conclude your voyage in the city that never sleeps. From the dazzling neon glow of Times Square to the majestic elms of Central Park, and the chic boutiques and historic cobblestone streets of SoHo, Manhattan delivers an unmatched urban experience. Let Lady Liberty welcome you as you circle her and her famous torch. Enjoy one last breakfast on board and begin your journey home. American Cruise Lines thanks you for choosing to sail with us, and we look forward to welcoming you aboard again soon to explore America's beautiful waterways.
Arrive to Boston the night before your cruise and stay at the highly acclaimed Four Seasons Hotel, conveniently located in the heart of downtown. The morning of embarkation enjoy concierge luggage service, a full breakfast, and take part in a narrated city excursion which visits sites such as Faneuil Hall and Quincy Market, concluding at the ship for seamless embarkation where your luggage will be waiting for you in your stateroom.
Pre-Cruise Packages must be reserved at least 30 days before your cruise date. Please call (800) 460-4518 for pricing and availability.
As you embark upon your journey, enjoy a Welcome Aboard Reception with cocktails, hors d’oeuvres and entertainment. Meet the crew, your onboard experts, and fellow guests. Learn more about the wonderful adventure ahead of you.
A walking tour presented by Plimoth Patuxet Museums has been customized to connect your Plymouth experience to America's Founding Story. Visit Plymouth Rock, Cole's Hill and Massasoit's Statue; Leyden Street (original street of Plymouth Colony), Governor Bradford's statue, Brewster Gardens and Town Brook (water supply for the Pilgrims) and Town Square and Burial Hill (location of the Fort/Meeting House).
Step aboard the historic Mayflower II. Listed on the National Register of Historic Places, the Mayflower II is a full-scale replica of the 17th-century merchant ship that brought the Pilgrims in 1620. Also, see and learn how corn was stone-ground in 1636 at the Plimoth Grist Mill. Then, enjoy taking home a piece of history with freshly made cornmeal available for purchase at one of the three retail stores along the waterfront. Stop at the mill to purchase Plimoth artisan products.
Activity Level: High | ADA ACCESSIBLE: Partial
Guided by museum educators, you will visit Plymouth Colony as it comes to life in the recreation of the early English Pilgrim settlement. You will be living history, not just watching a reenactment. Historical performers, portraying real people who lived in Plymouth Colony, will educate, and captivate you with stories of Mayflower's crossing, life among the Pokanoket and other native people, Pilgrim courtship, faith, politics and trade.
Activity Level: Moderate | ADA ACCESSIBLE: Partial
This convenient option will transport you to one of these local favorites:
- Shoppes on Water Street - In 1920, for the 300th anniversary of the landing of the Mayflower, Water Street was converted from rows of factories to beautiful shops situated across from Plymouth Harbor. Shop for custom-made jewelry, unique gifts, local wines, and more.
- Plymouth Rock Brewster Gardens - Visit Plymouth Rock, where the Mayflower Pilgrims were said to have stepped in 1620 to land in the New World. A short walk away is Brewster Gardens with beautiful sculptures along Town Brook where the Pilgrims settled in what was then called Patuxet.
- Town Square - At the top of Town Square is the Mayflower Meetinghouse. Behind is Burial Hill and to the left is the 1649 Courthouse, a free museum filled with interesting items from Plymouths history. It is the oldest wooden Court House and the longest used municipal building in America.
- Plimoth General Store - Plimoth General Store combines the charm and character of a time gone by. Explore all its nooks and crannies, which feature dining, fine provisions, specialty gifts, unique jewelry, and home goods. To order goods ahead of time and have them delivered to the ship, refer to the flyer on the port information table or speak with your Excursions Director.
- Pilgrim Hall Museum - See actual Pilgrim possessions and learn about the Wampanoags and the Pilgrims who participated in the Mayflower story through an exhibit and unique hand-made tapestry project.
- National Monument to the Forefathers - Thought to be the largest solid granite monument in the U.S., this 81-foot-tall statue was built to honor the passengers of the Mayflower. Designed by Boston sculptor Hammatt Billings, the monument features allegorical figures depicting the virtues of Faith, Morality, Education, Law, and Liberty.
- The Mayflower Society House - The Mayflower Society House was originally constructed in 1754 and enlarged in the 1890’s.The house has a long a grand history, including being the home of the great-grandson of Mayflower passenger Edward Winslow; wedding venue of Ralph Waldo Emerson in the 1830’s; the summer home of the wealthy Willoughby family of retail fame; and was redesigned by famed architect Joseph Everett Chandler.It is now the world headquarters of the Mayflower Society, and shows off a tremendous collection of 19th century architecture and artifacts.
Activity Level: Low | ADA ACCESSIBLE: Partial
Travel back in time to the epicenter of 19th-century opulence as a knowledgeable guide takes you down one of the most architecturally impressive avenues in the world. Learn about the owners of the homes and their monetary successes as you travel along the spectacular Ocean View Drive and Bellevue Avenue, stopping at the “grande dame” of them all, The Breakers Mansion.
A portrayal of the social and financial prominence of the Vanderbilt family at the turn of the century, the architecture of this seventy-room Italian Renaissance-style palazzo is remarkable. Take a leisurely audio tour of the home and learn about the Vanderbilt family and the inspiration for their building this impressive summer “cottage.” At the conclusion of the tour, you will have time to explore the bustling Newport waterfront at your leisure.
Activity Level: Low | ADA ACCESSIBLE: Partial
Visit Fort Adams, the well-known fort used to protect the harbor, and puts us just a short ride away from Newport’s bustling riverfront. View the “Officer’s Quarters” and ascend to the scenic overlook for a breathtaking view of Newport Harbor. Learn about past and future plans for the restoration of the Fort and enter the restored casemates to visit the latest historical exhibit. The listening tunnels beneath the walls of the Fort are a marvel of architecture and engineering and represent 180 years of American military history and culture.
Activity Level: Low | ADA ACCESSIBLE: Yes
Watch the unveiling of a traditional, old-fashioned lobster bake, followed by a delicious buffet. Be treated to fresh lobster, steamed clams and mussels, warm corn on the cob, and baked rolls. A true New England experience!
Activity Level: Low / ADA Accessible: Yes
Enjoy a complimentary shuttle into the center of town to enjoy stops in Newport at your leisure. Stops include:
- International Tennis Hall of Fame - Set in The Newport Casino, it’s a National Historic Landmark that was first opened on July 26, 1880, as a social club for Newport’s turn of the century summer elite. Its mission is to preserve and promote the history of tennis and celebrate its champions.
- Audrain Auto Museum - Founded in 2014 in Newport, Rhode Island with a mission of "Preserving, Celebrating & Sharing Automotive History," the Audrain Automobile Museum and historic Audrain Building was transformed into a captivating exhibition space, fit specifically for our cultural needs. The museum welcomes visitors with access to collections containing over 400 cars and motorcycles ranging from brass era Veteran cars to Supercars of today.
- The Red Parrot Restaurant - In the heart of downtown Newport where streets lined with shopping boutiques, visitor information, local favorites, and gift shops await.
- The Sailing Museum – This museum features National Sailing Hall of Fame and America’s Cup Hall of Fame exhibits. In the space once used as the Press Room for the America’s Cup the heritage of sailing is celebrated, the legends of the sport honored, and new sailors and innovators inspired. Interactive educational exhibits provide real-world applications of STEAM concepts that come alive through sailing; and visitors of all ages, non-sailors, and sailors alike, experience the magic that happens when wind and water meet.
- Transit Station - Access hub for the Newport City public transportation system with buses and trolleys taking visitors to all the highlight areas of interest such as the Cliff Walk and Bellevue Mansions.
Activity Level: Low | ADA ACCESSIBLE: Yes
Take a narrated exploration of historic and famous Newport. With the brilliant Atlantic Ocean on one side and some of the country’s most impressive properties on the other, this celebrated trail is an unforgettable one. Drive along the 10-mile, spectacular Ocean View Drive and Bellevue Ave— “Avenue of the Mansions.” The highlight of the excursion is a stop at the Breakers, a seventy-room mansion and National Historic Landmark built for Cornelius Vanderbilt II in 1895. A short stop will be made for picture opportunities at a beautiful waterfront lookout at Brenton Point State Park.
Activity Level: Low | ADA ACCESSIBLE: Yes
Featured Excursion
For centuries, the New London Harbor has guarded the Thames River and entry to Long Island Sound with Navy and Coast Guard installations, the ship building industries that support them, as well as two forts that have seen battles, defeats and the birthplace of the Coast Guard and Merchant Marines. From the vantage point of the river aboard a water taxi, learn about the strategic value of this storied waterway.
Conclude at Fort Trumbull, which has a century-and-a-half-long legacy of service from the American Revolution to World War II to the Cold War. Originally built in 1777 to protect the New London Harbor from British attack, the first masonry structure was destroyed after Benedict Arnold successfully raided the fort and the British burned New London to the ground. Along with serving as a federal military facility, the fort played a pivotal role in the country’s coastal defense system and as the original site of the U.S. Coast Guard. Explore the massive granite fort and its ramparts, enjoy the view of the Thames River and Harbor, and walk along the riverfront boardwalk.
Activity Level: Low | ADA ACCESSIBLE: No
Visit Mystic Seaport Museum, the nation's leading maritime museum, with 19 acres situated along the Mystic River. Step aboard the 1841 whaleship Charles W. Morgan, a designated National Historic Landmark and the last wooden whaleship in the world. Explore a recreated 19th-century seafaring village, where you can meet blacksmiths, coopers, printers, and carvers hard at work. Discover world-class exhibitions of history, art, and more in one of the onsite galleries.
Activity Level: Moderate | ADA ACCESSIBLE: Partial
Expand your knowledge of art and art history through the fascinating collections and exhibitions of the Lyman Allyn Art Museum. Established by a gift from Harriet Allyn in memory of her seafaring father, the museum opened the doors of its beautiful neoclassical building in 1932. Today, the museum houses a fascinating collection of over 17,000 objects from ancient times to the present; artworks from Africa, Asia, the Americas, and Europe, with particularly strong collections of American paintings, decorative arts, and Victorian toys and doll houses. Docents are available on site.
Activity Level: Low | ADA ACCESSIBLE: Yes
Enjoy a self-guided exploration of the 33,000 artifacts found at the Submarine Force Library and Museum. Discover various exhibits featuring photographs and models that illustrate the history of submarine development. There will be docents available on site. Note – Submarine is undergoing renovations and may not be available for viewing.
Activity Level: Low | ADA ACCESSIBLE: Partial
Sag Harbor is truly one of Long Island’s hidden gems. Stroll down Main Street and discover the many unique boutiques and mouthwatering restaurants. Art enthusiasts will enjoy perusing the variety of galleries around the village. Wine connoisseurs can sip away happily at one of the local wine bars.
Experience the magic "behind the scenes" at Bay Street Theater and hear amazing stories and lure of the venue over the past 32 years. Peruse photos of Broadway greats and celebrities who have graced the stage. Learn about the Theater's history with performances by Broadway greats and celebrities including Bruce Springsteen, Julie Benko, Billy Joel, Jerry Seinfeld, Paul Reiser, Sarah Paulson, Cherry Jones, Richard Kind, Colin Quinn, Alan Alda, Alec Baldwin, Sutton Foster and so many more. You may even learn who resides in Sag Harbor today. This is a guided experience with restrooms on property.
Activity Level: Low | ADA ACCESSIBLE: Yes
Premium Excursion
Experience a one-of-a-kind piece of history in the heart of Sag Harbor. After a devastating fire took the iconic cinema in 2016, a plan was set into motion to raise the beloved landmark from its ashes. Reopened to the public in 2021, the new state-of-the-art facility that exists today honors the memory of the original cinema while providing new services and amenities. This unique institution celebrates a century of filmmaking excellence, as well as the rich history of Sag Harbor Village. This experience includes a guided exploration by the cinema docent, a short screening in the flagship auditorium, an exhibition of rare photos by film photographer James Hamilton, a Sag Harbor Cinema signature cocktail provided in the rooftop bar, a tasting of local foods, and a swag bag of Sag Harbor Cinema merchandise.
Activity Level: Low | ADA ACCESSIBLE: Yes
Premium Excursion
Enjoy an intimate beer tasting at Kidd Squid Brewing Company with beer named after many local icons. This unique brewery is located in the Historic Sag Harbor Train Depot. During your visit, the owner will provide interesting details about the history of the building, the creation of Kidd Squid, and the reason behind the name. The tasting will consist of four beers. It is a 0.3 mile walk that should take about 10 minutes at a slow pace.
Activity Level: Low | ADA ACCESSIBLE: Yes
Visit the home of Florence Griswold, where the Old Lyme Art Colony flourished in the early 1900s. Designated a National Historic Landmark in 1993, the museum brings to life the work of American Impressionist artists in the place where they once lived and painted. Explore this remarkable campus which encompasses 12-acres of historic buildings, grounds, gardens, and walking trails.
Start your day with private transportation to Downtown Essex. Enjoy a self-guided exploration of the Connecticut River Museum, which features exhibits that highlight artifacts with regional and historical significance. View the "Turtle Submarine," the first submarine used in combat and the first successfully launched in the early morning of September 7, 1776. Following the museum visit, walk down the street to The Griswold Inn for a delicious lunch. While on site, one of the owners will welcome you and explain the history of the Inn. You will also receive an Innkeeper's Log to take with you. After lunch, enjoy free time for shopping and strolling the charming streets of Essex, before boarding a boat for a 90-minute narrated exploration of the Connecticut River, during which you will learn about local history, wildlife, and nature found along the river. Notable landmarks include the Historic Essex Harbor and Hamburg Cove. This is a self-guided experience.
Activity Level: Low | ADA ACCESSIBLE: Yes
This is a Signature shore excursion and should be reserved in advance. Please call (800) 894-8570 for information.
Come experience a historic art colony with original structures. Explore the museum that consists of temporary and permanent American Impressionist works of art. After, relax and enjoy afternoon tea and cookies while you take in the beautiful landscape of the Lieutenant River.
Activity Level: Low | ADA ACCESSIBLE: Partial
Premium Excursion
Visit the Katharine Hepburn Museum, the only museum of its kind dedicated to preserving the legacy of Connecticut’s own Katharine Hepburn. Presenting an authentic view of the cultural and historical impact of Miss Hepburn and her family, exhibits feature costumes from her films, personal letters to family and friends, her 1975 Primetime Emmy Award, personal wardrobe clothing, framed artwork, and a special exhibits case. Join us for a showing of a famous Katharine Hepburn film in the historic theater dating back to 1911 and reopened in 2009 after state-of-the-art renovations.
Activity Level: Low | ADA ACCESSIBLE: Yes
Premium Excursion
Founded in 1635, Old Saybrook was the first English settlement along the Connecticut Shoreline, "Where the River meets the Sound." Walk to various points of historic significance, including markers that present the latest research on the Pequot War, the remnants of the 1871 Valley Railroad turntable, and Fort Saybrook Monument Park. View the imposing Lion Gardiner Statue and the Yale Boulder which tells the history of the founding of Yale University. Explore the ancient Cypress Cemetery where the unique tombstone and story of Lady Fenwick is told. Historic brochures and pamphlets are provided including one on the history of the lighthouses at the mouth of the Connecticut River, designated by The Nature Conservancy as one of the "40 last Great Places in the Western Hemisphere.”
Activity Level: High | ADA ACCESSIBLE: Yes
Be greeted by your guide at the ship as you board your motorcoach to travel to the 9/11 Memorial & Museum. Located at the World Trade Center, this museum honors those who were killed in the 2001 and 1993 attacks, those who risked their lives to help others, and the courage of those who survived. Enjoy a guided exploration, during which this poignant story is told through media, narratives, and a collection of monumental and authentic artifacts. After, explore the grounds on your own which include the Memorial Pools where the towers once stood, the Survivor Tree, and the 9/11 Memorial Glade.
Activity Level: Moderate | ADA Accessible: Yes
Be greeted by your guide at the ship as you board your motorcoach for your exploration of Midtown. You'll make a stop at Rockefeller Center to visit St. Patrick's and walk the outside of Rockefeller Center. Continue your drive down to Bryant Park for views of the Empire State Building. Next, you will visit Grand Central Station, a globally recognized landmark. End your exploration with a drive past the world-famous Central Park.
Activity Level: Moderate | ADA Accessible: No
Why not stay an extra night or two to immerse yourself in the spirit of this vibrant city? Ask your onboard Hotel Manager for recommendations on area hotels, attractions, and more.
There are a variety of activities scheduled on board when the ship is underway, which vary depending on the itinerary and scheduled date. Enjoy destination-focused enrichment programs with special guest speakers who present topics related to the region and ports of call, including Art Classes, App-titude Classes (Tech Made Easy), Cooking Demonstrations, Mixology (practice of making great cocktails,) Trivia, Game Shows, and more.
Map & Itinerary Overview
Aboard a brand-new Coastal Cat, explore the best seaport towns between the vibrant cities of Boston and New York. Step into American history in Plymouth and New London and discover the rich maritime influence of Mystic, CT; Sag Harbor, NY; and Newport, RI.
Day 1 - New York, NY
Prepare for the spectacle of NYC’s famed skyline: the Empire State Building pierces the sky, the Chrysler Building flashes its Art Deco brilliance, and the new One World Trade Center stands as a beacon of resilience and renewal. Once your ship docks in the energetic heart of Manhattan, you're perfectly positioned to step into city life. American Cruise Lines offers a curated selection of shore excursions—whether you’re keen to meander through the sprawling greenery of Central Park, take in a Broadway show, or explore the historic streets of Greenwich Village. Let us welcome you aboard with a toast as you meet your dedicated crew and fellow cruisers.
Day 2 - Sag Harbor, NY
Set sail for Sag Harbor, a historic port on the shores of Eastern Long Island. Established as a bustling whaling port, this village retains its 19th-century charm, with narrow lanes and whaler’s cottages that tell tales of the sea. Meander through the streets lined with art galleries and antique shops, each a treasure trove of artistic expression and bygone artifacts. Visit the Whaling Museum to trace the bold journeys of maritime adventurers and stand by the old windmill, a sentinel of the past. Experience Sag Harbor's unique blend of nautical history and cultural sophistication, where every corner reveals a story, and every sunset paints the harbor in pink and orange hues.
Day 3 - Old Saybrook, CT
Journey to Old Saybrook, where the Connecticut River greets Long Island Sound. As one of Connecticut's earliest settlements, founded in 1635, Old Saybrook boasts a legacy as the cherished home of silver screen icon Katharine Hepburn. Venture a short distance to the enchanting town of Essex, where you can wander along a waterfront framed by time-honored colonial and federal architectures that stand as elegant custodians of history along its idyllic streets. Uncover the maritime chronicles of the area at the Connecticut River Museum, a repository of seafaring lore and legends.
Day 4 - New London/Mystic, CT
The perfect duo: New London and Mystic. Mystic is a charming maritime village known for its scenic New England beauty, featuring a harbor filled with historic tall ships and an eclectic waterfront area. The town has a rich art scene. Stop into the gallery of Russ Kramer, known for his realistic maritime paintings. This port gained additional fame from the 1988 film Mystic Pizza but pushes culinary boundaries at local restaurants and bakeries like the famous “Sift” with the best, melt-in-your-mouth chocolate chip cookies.
Nearby New London is a historic seaport city where the Thames River meets the Long Island Sound, characterized by its eclectic art scene, including the renowned Lyman Allyn Art Museum and frequent cultural festivals. The city's landscape features a mix of urban and coastal elements, with notable landmarks like the United States Coast Guard Academy and a vibrant waterfront district that offers sweeping views and a variety of dining experiences.
Day 5 - Newport, RI
Uncover the enchantment of Newport, Rhode Island, where cascading cliffs meet the sparkling waters of the Atlantic. Take a leisurely stroll along the famous Cliff Walk, a picturesque pathway winding amidst grand Gilded Age mansions and wild coastline, offering breathtaking views of the rocky shore. Explore the historic downtown area of Newport, where colonial-era architecture blends seamlessly with bustling shops and waterfront cafes, reflecting the town's rich maritime history. Don't miss a visit to the renowned Newport Mansions, such as The Breakers and Marble House, once the extravagant playgrounds of America's elite, adorned with ornate ballrooms, gilded ceilings, and manicured gardens, for a step back in time to an era of pure luxury and indulgence.
Day 6 - Day of Cruising
Cruising through Buzzards Bay and the Cape Cod Canal, you'll hear the steady hum of the boat and the occasional call of seabirds. The fresh sea breeze swings in the air as you pass by charming coastal towns. Feel the sunlight and listen to the gentle sound of waves against the hull as you lounge on the top deck. Of course, you can enjoy the day on your private balcony or in any of our comfortable lounges.
Day 7 - Plymouth, MA
Discover the coastal beauty of Plymouth, Massachusetts, where sandy shores meet the gentle waves of Cape Cod Bay. Stroll along the historic shores, where weathered fishing boats bob in the harbor, reminiscent of Plymouth's seafaring past. Explore the charming streets of downtown Plymouth, lined with quaint shops and colonial-era architecture, providing a glimpse into the town's storied history. Visit Pilgrim Memorial State Park, home to the iconic Plymouth Rock, a symbol of the Mayflower Pilgrims' arrival in the New World and live the tales of America's early settlers.
Day 8 - Boston, MA
Disembark in historic Boston and enjoy one last breakfast onboard. Explore charming downtown Boston, where red-brick buildings line cobblestone pathways filled with centuries of history. Visit iconic sites like Boston Harbor or the Freedom Trail. If you're heading home, we hope to see you on the waters again soon.