Summary

Begin your unforgettable small ship journey with a pre-night in Boston, giving you time to settle in and explore one of America’s most historic and vibrant coastal cities. From its iconic landmarks to its charming waterfront, Boston sets the perfect tone for the adventure ahead.

From there, embark on your Cape Cod Coastal Escape, sailing round-trip from Boston aboard an intimate small ship. Cruise to Cape Cod, where classic gray-shingled cottages, peaceful beaches, and lively clam shacks create a picture-perfect New England retreat.

Experience the colorful energy of Provincetown, a lively seaport known for its eclectic art scene, welcoming spirit, and exciting whale-watching opportunities. Continue on to Martha’s Vineyard, where you’ll explore charming villages, stroll past whimsical gingerbread cottages, and enjoy insights from engaging local guides.

In Newport, step into the grandeur of the Gilded Age as you tour magnificent seaside mansions set against the stunning Atlantic coastline. Then visit New Bedford, affectionately known as “The Whaling City,” where a rich maritime heritage meets a vibrant working waterfront.

A highlight of the journey is a classic New England lobsterbake—an authentic coastal tradition featuring freshly caught lobster, steamed clams, and sweet corn on the cob, all prepared over open coals. Paired with scenic harbors, charming seaside towns, and relaxed cruising, this experience perfectly captures the spirit of coastal New England.

Itinerary

Subject to change

Day 1 - June 1, 2027

Flight from Bloomington, IL to Boston

Upon arrival, meet your group transfer to the hotel. After check-in, enjoy free time to explore Boston.

History is around every corner—walk the Freedom Trail, enjoy views along the Charles River and Boston Harbor, or explore neighborhoods like Beacon Hill and the waterfront. Discover world-class museums, historic districts, and classic New England seafood at Quincy Market before your voyage begins.

Day 2 - June 2, 2027

Embark Cruise & Cruising the Cape Cod Bay

Enjoy free time in Boston before meeting your group to board the ship. Once onboard, settle in and become acquainted with the ship and its amenities. Sail into scenic Cape Cod Bay, where classic coastal views unfold, perfectly admired from the sun deck or a private balcony. Once on board, meet fellow guests and crew as enrichment programs bring the region to life. Learn about local history, savor culinary delights inspired by New England flavors, and enjoy relaxed social spaces as your Cape Codder cruise begins. 

Day 3 - June 3, 2027

Provincetown, MA

Originally established as an artist’s haven, Provincetown remains one of Cape Cod’s most vibrant and sought-after destinations. Today, it blends a thriving arts scene—filled with galleries and performance spaces—with a dynamic culinary landscape featuring fresh local seafood and diverse international flavors. Rich in history, Provincetown is home to the iconic Pilgrim Monument, commemorating the Pilgrims’ first landing aboard the Mayflower in 1620. A narrated trolley tour offers insight into this historic moment while showcasing the town’s unique character and scenic surroundings. You’ll also have time to browse eclectic shops, unwind on nearby beaches, and explore at your own pace. For a more adventurous perspective, set out on an exciting SUV excursion through the rolling dunes of the Cape Cod National Seashore. Along the way, pass the historic dune shacks that have inspired generations of American artists and writers from the 1920s to today.

Day 4 - June 4, 2027

Plymouth, MA

Plymouth is the site of the first Pilgrim settlement, founded in 1620. At the heart of its history is Plymouth Rock, believed to mark the Pilgrims’ landing. Nearby, step aboard Mayflower II, a full-scale replica of the original ship, and explore Plimoth Patuxet Museums, where costumed interpreters bring the 17th century to life. At Pilgrim Hall Museum, view authentic artifacts and gain deeper insight into the Pilgrims and the Wampanoag people through engaging exhibits.

Day 5 - June 5, 2027

Mass. Maritime Academy, MA

A visit to Massachusetts Maritime Academy offers a fascinating look at Cape Cod’s maritime heritage and the future of seafaring education. Explore a working campus where cadets train in advanced bridge and engineering simulators, guided by experienced staff and students who bring the Academy’s mission to life. Set along the scenic shores of Cape Cod, the campus overlooks the Cape Cod Canal and Buzzards Bay. Nearby, visit the Sandwich Glass Museum, known for its live glassblowing demonstrations and engaging exhibits of historic and contemporary glass art.

Day 6 - June 6, 2027

Newport, RI

Newport showcases its Gilded Age history along the famous Avenue of the Mansions, home to grand estates that reflect the wealth and elegance of a bygone era. Visit The Breakers, the opulent 70-room Italian Renaissance-style home of the Vanderbilt family. Explore the city’s cultural highlights, including the International Tennis Hall of Fame, a historic landmark celebrating the sport’s legacy. Continue to Fort Adams State Park for a traditional New England lobsterbake lunch featuring fresh lobster, clams, mussels, corn on the cob, and warm rolls—all served with scenic harbor views. Afterward, enjoy a guided tour of the fort or time to explore Newport at your own pace.

Day 7 - June 7, 2027

Martha's Vineyard, MA

Martha’s Vineyard, once a thriving whaling center, is now one of New England’s most charming island destinations, known for its picturesque harbors, local shops, and rich history. Enjoy a narrated tour through its scenic towns, beginning in Vineyard Haven and continuing through West Tisbury and Chilmark. Visit Aquinnah to see the iconic clay cliffs and Gay Head Lighthouse, with time for photos. Continue on to Edgartown, home to elegant sea captain homes and boutique shopping, before ending in Oak Bluffs, famous for its colorful gingerbread cottages and whimsical seaside charm.

Day 8 - June 8, 2027

New Bedford, MA

New Bedford was once the world’s leading whaling port and inspired Herman Melville’s Moby-Dick, published in 1841. Today, “The Whaling City” blends historic charm with a lively working waterfront. Visit the New Bedford Whaling Museum, the largest of its kind, featuring impressive exhibits such as whale skeletons, historic ship models, and maritime artwork. Later, enjoy a narrated harbor cruise showcasing the active fishing fleet, Palmer’s Island Lighthouse, Fort Phoenix, and the East Coast’s largest hurricane barrier.

Day 9 - June 9, 2027

Cruise Ends in Boston

As we welcome you back to Boston, we say goodbye to this New England voyage. Your luggage service and transportation to the airport have already been arranged for you.  

Included with this Tour

• Round Trip Air from Central Regional Airport in Bloomington, IL
• 1 pre-night hotel in Boston
• Airport & Hotel Transfers
• 7 nights on the American Maverick
• All meals on the ship
• All non-alcoholic drinks on the ship
• Alcoholic drinks with Lunch & Dinner
• Nightly Cocktail party with Hors d'oeuvres.
• One excursion at each port
• Wi-Fi
• Ship Gratuities
• Taxes & Port Charges
• WJBC Scott Miller & Direct Travel Host Kimberly Rowatt with 32 guests

Not Included:

• Meals & drinks off the ship
• One excursions is included at each port. There are others you can choose for an upcharge.
• Personal items
• Cost of Baggage/Airline Upgrades
• Travel Insurance
• Fuel surcharges

Deposit & Final Payment

A non-refundable deposit of $1,000 per person is required at the time of reservation. Space is limited and available on a first-come, first-served basis. Final payment is due by March 3, 2027. Please note that all payments become non-refundable once received. We strongly recommend the purchase of travel insurance to protect your investment.