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Sailing in Boston

Yankee Seaports

Boston - New York - Example 8 Day Cruise aboard American Glory
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Set sail on an 8-day Yankee Seaports cruise, sailing from Boston to New York aboard American Glory. This scenic journey takes you through the best seaport towns of the Northeast and learn about the historic neighborhoods of Boston. Visit the picturesque coastal town of Plymouth, MA, and experience the grandeur of the Gilded Age in Newport. Immerse yourself in the maritime history of New London, Mystic, and Essex, CT. Led by a local guide, explore the quaint streets and art galleries in Sag Harbor, NY. Lastly, experience an evening cruise around New York Harbor, admiring the New York City skyline from the observation area at the bow of the ship.
Zakim Bridge reflection on the Charles River in BostonVisit PlymouthAerial view of New York City at duskSkyline of Manhattan with Empire State BuildingSag HarborSailing in Boston
Highlights
  • Visit the Massachusetts Maritime Academy
  • Explore the Mystic Seaport Museum
  • Travel to Old Saybrook, where the Connecticut River meets Long Island Sound
  • Stroll around Sag Harbor, one of Long Island’s hidden gems
Places Visited
Activity Level: Variable
Activity options vary depending on destination and operator. Activity level is determined by the range and intensity of activities you choose to participate in. Discuss with your Trip Planner which options are best for you.
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Full Itinerary

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Day 1: Boston, MA | Embark

Walk through historic downtown Boston, where red-brick buildings and cobblestone streets reflect the city's past. Stroll along the waterfront, once a hub for trade and commerce, and take in views of Boston Harbor. Visit Beacon Hill, known for its stately brownstones and gas-lit lanterns. Relax in Boston Public Garden, surrounded by lush greenery, ponds, and the famous swan boats.

Welcome Aboard
Begin your journey with a reception featuring cocktails, hors d’oeuvres, and live entertainment. Meet the crew, connect with fellow travelers, and get an introduction to the experiences ahead.

Day 2: Plymouth, MA

Experience the coastal landscape of Plymouth, Massachusetts, where sandy beaches meet the calm waters of Cape Cod Bay. Walk along the historic shoreline, where fishing boats float in the harbor, reflecting the town’s maritime heritage. Explore downtown Plymouth, filled with colonial-era buildings and locally owned shops that highlight its past. Visit Pilgrim Memorial State Park to see Plymouth Rock, marking the arrival of the Mayflower Pilgrims and the beginning of America’s early settlements.

Plymouth Local Loop – Complimentary Excursion
Choose from several key sites on this convenient local tour:
Shops on Water Street – Once home to factories, this historic street was transformed into a shopping district for the 300th anniversary of the Mayflower’s arrival. Browse custom jewelry, specialty gifts, and local wines.
Plymouth Rock & Brewster Gardens – Visit Plymouth Rock, marking the Pilgrims’ landing in 1620. A short walk leads to Brewster Gardens, featuring sculptures along Town Brook, the site of the Pilgrims’ original settlement.
Town Square – Explore historic landmarks, including the Mayflower Meetinghouse, Burial Hill, and the 1649 Courthouse, the nation’s oldest wooden courthouse and longest-used municipal building.
Plimoth General Store – Step into a vintage-style general store offering dining, fine provisions, specialty gifts, and home goods. Pre-order items for ship delivery by referring to the port information flyer or speaking with the Excursions Director.
Pilgrim Hall Museum – View original Pilgrim artifacts and learn about both the Wampanoag people and the Pilgrims through exhibits and handcrafted tapestries.
National Monument to the Forefathers – Standing 81 feet tall, this granite monument honors the Mayflower passengers. Designed by sculptor Hammatt Billings, it features figures symbolizing Faith, Morality, Education, Law, and Liberty.
The Mayflower Society House – Built in 1754 and expanded in the 1890s, this historic home once belonged to Mayflower descendant Edward Winslow’s great-grandson. It later hosted Ralph Waldo Emerson’s wedding and now serves as the headquarters of the Mayflower Society.
Activity Level: Low | ADA ACCESSIBLE: Partial

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 a 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.

Fort Adams Exploration - Complimentary Excursion
Visit Fort Adams, the well-known fort used to protect the harbor, and puts you 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

Lobsterbake Luncheon – Complimentary Excursion
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

Newport Local Loop - Complimentary Excursion
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 the 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

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.

Submarine Force Library & Museum - Complimentary Excursion
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 – The submarine is undergoing renovations and may not be available for viewing.  
 Activity Level: Low | ADA ACCESSIBLE: Partial 

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.

Sag Harbor at Your Leisure – Complimentary Excursion
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.

The Bay Street Theater – A Behind the Scenes Experience & Wine Tasting - Complimentary Excursion
Experience the magic "behind the scenes" at Bay Street Theater and hear amazing stories and the 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 the property. Guests will enjoy a tasting of local wines at the conclusion of the experience. 
Activity Level: Low | ADA ACCESSIBLE: Yes

Sag Harbor Cinema – From Acts to Ashes and Back - Complimentary 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 swag bag of Sag Harbor Cinema merchandise, a Sag Harbor Cinema signature cocktail provided in the rooftop bar, as well as a tasting of local foods such as exquisite cheeses crafted on Long Island at Mecox Dairy Farm and Catapano Goat Farm. 
Activity Level: Low | ADA ACCESSIBLE: Yes

Kidd Squid Brewing Company - Complimentary 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.
Activity Level: Low | ADA ACCESSIBLE: Yes

Sag Harbor Historical Exploration – Complimentary Excursion
Explore Sag Harbor history with a personalized guided experience at the Annie Cooper Boyd House and a self-guided experience at the Sag Harbor Whaling Museum. Learn about the industry and people who established Sag Harbor from local historians.
Activity Level: Moderate | ADA Accessible: Partial

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.

Florence Griswold – A Historical Painters Colony – Complimentary Excursion
Walk in the footsteps of the artists who called this place home and inspired spectacular works of art. As you explore the museum and historic home, let the surroundings guide your creativity as you paint your own masterpiece! Once complete, your creation will be delivered to your stateroom later in the afternoon. The museum portion of this experience is self-guided with docents available on-site.
Activity Level: Low | ADA Accessible: Partial

The Kate - Hepburn's Life and Legacy – Complimentary 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 exhibit 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

Old Saybrook Historical Society Welcome – Complimentary Excursion
Learn about the first English settlement along the Connecticut Shoreline which was established in 1635, "Where the River meets the Sound.” This on-board introduction to Old Saybrook will feature 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. Historic brochures and pamphlets are provided, including one on the history of lighthouses at the mouth of the Connecticut River, designated as one of the "40 Last Great Places in the Western Hemisphere" by The Nature Conservancy.
Activity Level: Low | ADA Accessible: Yes

A Taste of Essex – Complimentary Excursion
Take a short drive to Downtown Essex for an afternoon of exploring. Visit the Connecticut River Museum, which features various exhibits that highlight artifacts with regional and historical significance. One collection found on the first floor of the museum is the "Turtle Submarine,” the first submarine used in combat which was successfully launched in the early morning of September 7, 1776. After the museum, spend time exploring the picturesque Main Street with its many shops and cafes. Or, choose to spend your whole afternoon strolling Essex. 
Activity Level: Low | ADA Accessible: Yes

Katherine Hepburn Cultural Arts Center – Complimentary Excursion
Enjoy a guided exploration of The Kate, 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 exhibit case.
Activity Level: Low | ADA Accessible: Yes

Day 7: New York, NY

As you 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.

Best of Midtown Manhattan - Complimentary Excursion
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 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

Day 8: New York, NY | Disembark

  • 1 Breakfast
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.

Ship/Hotel

American Glory

Dates & Prices

My Preferred Start Date

  • Sep 28, 2026from $7,070
  • May 29, 2027from $6,350
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Special Offers 23942
Promotional rates are available on select departures for a limited time. These offers cannot be combined with other discounts and are only valid on new bookings.  Please discuss with your trip planner about applicable dates and cabin types.
Applies to select departures

Per person starting at
$6,350
Rates are subject to change without notice. Book early to get the best rate.
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Single Balcony
A rarity in river cruising, our dedicated single staterooms are 280-square-foot enclaves for the solo traveler. Each room also includes a small wardrobe, drawer storage, under-bed suitcase storage, 54” inch led TV, writing desk, safe, and complimentary WiFi.
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Premium Waterview
310 square feet of interior space. Each main deck room features large picture windows with water views and a built-in reading nook. Premium Waterview rooms can be configured with a king or two twin beds. Each room has a large bathroom, wardrobe, ample drawer storage, under-bed suitcase storage, 54-inch LED TV, writing desk, safe, and complimentary WiFi.
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Premium Balcony
310 square feet of space and floor-to-ceiling sliding glass doors for sweeping views. Each room has an interior seating area, as well as a private balcony with a table and chairs.
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Vista Balcony
310-square-foot. Each room is available in king or two twin size bed configurations. Vista rooms have a large bathroom, wardrobe, ample drawer storage, under bed suitcase storage, 54” inch led TV, writing desk, safe, and complimentary WiFi.
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Sky Suite
These exceptionally large 470-square-foot rooms include a spacious private balcony with a table and chairs, as well as plenty of interior space to make yourself at home. Each suite has a seating area facing a 54” inch led TV, counterspace with replenished treats, and a stocked refrigerator.
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Grand Suite
620-square-feet. Each suite has a living room, bedroom, interior and exterior dining areas, and a spacious master bathroom.
Included
  • 7 Breakfasts, 6 Lunches, 7 Dinners
  • 7 Nights Accommodations
  • Accommodations as listed
  • Ground transportation as listed
  • Activities as listed
  • Meals as listed
  • Access to a 24-7 Emergency line while traveling
  • Snacks
  • Onboard Entertainment 
  • Onboard gratuities
  • Port charges and fees
  • Complimentary cocktail parties
  • Dining service
Excluded
  • Travel Insurance
  • Personal Expenses
  • Flight costs (please request a quote)
  • Additional excursions during free time
  • Fuel and transportation surcharges (when applicable)
  • Signature shore excursion - Should be reserved in advance due to limited availability.

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Beyond expectations! Then again we weren't sure what to expect. Lovely stay at the lodge, met other like-minded travelers (many had their trips planned by Adventure Life) and the owner was a gracious hostess. It felt like you were one happy family, visiting with a favorite aunt.
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