Boston, Salem, and Cape Cod, Massachusetts—all sound like a song. When you arrive in Boston, explore. The Freedom Trail winds through the city, connecting 16 sites such as Paul Revere’s house and the Old North Church. Head to Faneuil Hall—the cradle of liberty—particularly glorious in the autumn, blazing with reds and oranges. Infamous Salem is nearby, home of witch trials, great shops, and old Clipper Ships.
Gloucester, a pleasant drive from Boston, is in the heart of Cape Ann. Imagine unique ocean adventures, fresh seafood dinners, art, and whale watching. Two other notables are Provincetown and the Cape Cod National Seashore—40 miles of beaches, dunes and nature trails. Provincetown is as far as you can go on the Cape, and artists began making their homes here a century ago. Breathe in that fresh, salt air!
Today you arrive to Boston Logan International Airport (BOS) to begin your vacation.
Enroute Sightseeing
Forty Steps Beach, Massachusetts
On the Map: Forty Steps Beach is a 100-yard stretch of beach 14 miles north of Boston, sandwiched between two rocky points and overlooking several offshore islands. The site is just north of Canoe Beach and the two are separated by a dramatic rocky point called Castle Rock, a cozy neighborhood beach located on Nahant Road in Nahant, Massachusetts.
A wide range of sea glass and mermaid loot abound in this tucked away hidden gem. Forty Steps Beach is in a magnificent location that's hidden from outsiders. The beach is small and located in the middle of an upscale residential area. There is no parking at Forty Steps, but if you stop at the police station beforehand and ask if you can park in the resident-only parking next to Canoe Beach they may allow it. Be considerate of the officers, for the best chance of success at scoring a parking spot but this site is worth it. The beach is tidy and loaded with millions of tiny smooth pebbles and not much sand, perfect for trapping colorful sea glass.
Overnight Location
Salem, Massachusetts
Salem located on the north coast of Massachusetts is famous for its 1692 witch trials, during which several locals were executed for allegedly practicing witchcraft. Landmarks include the Witch House which is the former home of a trial judge. The Peabody Essex Museum has a massive collection of global art and artifacts, including a rebuilt Qing-era Chinese house.
The town is all about witches, ocean ships, making waves through literature, settlers, pirates and trading. Take a tour and soak in its rich history. Stroll through the streets and visit the unique stores, an experience in themselves, buy everything from vintage clothes to spell-books and crystals. You'll also find many cafes and bistros dotted throughout the town.
Day 2
Daily Itinerary
Salem Sights - Witchcraft Tour
Set off to explore the many sights of Salem town such as the House of Seven Gables and Essex Street Pedestrian Mall and the Marblehead Lighthouse. Enjoy a Historical Witchcraft Walking Tour where you'll learn about Salem's colonial history, witchcraft, and the 1692 Hysteria and Witch Trials.
Included Unique Activities
Historical Salem Witchcraft Walk
Salem, Massachusetts
Learn about Salem's colonial history, witchcraft, and the 1692 Hysteria and Witch Trials. Examine the demographics, theories and personal stories comprising the dire events of 1692 and visit the locations that are full of witch trial history. This is a fascinating tour that will shed new light on what happened during the infamous witchcraft hysteria which turned neighbor against neighbor.
Note: No recording on the tour please, but photography is allowed. Tours run rain or shine.
Overnight Location
Salem, Massachusetts
Salem located on the north coast of Massachusetts is famous for its 1692 witch trials, during which several locals were executed for allegedly practicing witchcraft. Landmarks include the Witch House which is the former home of a trial judge. The Peabody Essex Museum has a massive collection of global art and artifacts, including a rebuilt Qing-era Chinese house.
The town is all about witches, ocean ships, making waves through literature, settlers, pirates and trading. Take a tour and soak in its rich history. Stroll through the streets and visit the unique stores, an experience in themselves, buy everything from vintage clothes to spell-books and crystals. You'll also find many cafes and bistros dotted throughout the town.
Day 3
Included Unique Activities
Marine Sanctuary Whale Watching Tour
Gloucester, Massachusetts
Take a Whale Watching Tour out of Gloucester harbor for an encounter with Whales in the wild. Start your tour from the busy working harbor where you will encounter fishermen at work and learn about the history and surrounding landmarks. Your naturalist will give a short presentation to familiarize you with the area you will be visiting (a National Marine Sanctuary) and the whale and other wildlife species you are likely to encounter while out on the ocean. Spend about 1.5 hours with the whales during which your naturalist will provide you with greater insight into their behaviors and characteristics. Return to shore with a deeper appreciation of these giant mammals and the unique marine environment you visited. Most trips are 3-4 hours in length but may be extended if the whales move further.
Suggested Sightseeing
Hammond Castle, Gloucester, Massachusetts
On the Map: Hammond Castle sits high on a bluff overlooking the Atlantic Ocean, in the Magnolia area of Gloucester, Massachusetts.
Hammond Castle was constructed in 1926 by inventor John Hays Hammond, Jr. as his residence. In the style of a European medieval castle, it was built to house his private collection of artifacts from ancient Rome through the Renaissance. Visitors can explore the many rooms of the castle, as well as enjoy the beauty of the castle grounds and view of the Atlantic shore line. The castle is listed on the National Register of Historic Places.
Overnight Location
Gloucester, Massachusetts
A short, pleasant drive from Boston, Gloucester is in the heart of Cape Ann, close to historic Salem and Rockport. Here you will find world-class museums to explore, gorgeous beaches to stroll, and interesting art galleries to visit, not to mention whale watching, schooner sails, foodie tours, and more. Discover all Gloucester has to offer!
Day 4
Daily Itinerary
Boston Bound - Walking Tour with a Local
Make your way back to ‘Beantown’ which is just about an hour's drive south. In the afternoon enjoy a walking tour for the perfect introduction to the history of Boston. You will be guided along by a passionate local who loves to share their knowledge and skills and tell a story about the great city they live in! Spend the night in a downtown hotel and enjoy all that Boston has to offer!
Included Unique Activities
Private Boston Freedom Trail Walk
Boston, Massachusetts
Enjoy a private Boston Freedom Trail Walk with a local guide for the perfect introduction to the history of Boston. Explore many of the Freedom Trail sights including the Old State House, Faneuil Hall, King's Chapel, the Old South Meeting House, and the site of the first public school in America. From the protests of Samuel Adams and James Otis to the Boston Massacre and the Boston Tea Party to the liberation of Boston in 1776 by General Washington and his army, the Freedom Trail takes you to the sites and tells the stories that led to American independence. You will be guided along by a passionate local who loves to share their knowledge and skills and tell a story about the great city they live in! As this will be a private tour it can be customized to suit your interests.
Suggested Sightseeing
Franklin Park Zoo, Boston, Massachusetts
The Franklin Park Zoo is a 72 acres zoo located in Boston, Massachusetts. It is currently operated by Zoo New England, which also operates the Stone Zoo in Stoneham, Massachusetts.
Overnight Location
Boston, Massachusetts
With Boston's rich history, diverse neighborhoods, and legacy of arts, culture, and education, Boston has something for everyone, making it a leading tourist destination.
Each of the city's neighborhoods has a remarkably different style and tone. From the Back Bay's cosmopolitan streets and ornate Victorian townhouses to the aromas spilling into the narrow and jumbled 17-century streets of Boston's North End to the spirited and funky neighborhood squares of Cambridge - all within easy distance from one another.
Boston dining is increasingly a destination all its own. The restaurant scene is delicious and dynamic. Even the shopping in Boston is of historic proportions from designer boutiques, eclectic galleries to prestigious department stores.
Day 5
Daily Itinerary
Drive to Provincetown, Cape Cod
Drive 2 and a half hours to get to Cape Cod from Boston. On arrival in Provincetown, check into your hotel. Just steps from the beach with commanding views of the ocean and a short walk into town, it is a perfect location to relax and unwind.
Overnight Location
Cape Cod, Massachusetts
The hook-shaped peninsula of Cape Cod is a popular summertime destination. It's the site of quaint villages, seafood shacks, lighthouses, ponds and bay, and ocean beaches. In the large town of Hyannis, the John F. Kennedy Museum is the first stop on the Kennedy Legacy Trail through downtown, where ferries depart to the resort islands of Martha's Vineyard and Nantucket.
Cape Cod is rich with recreation, from the artistic to the adventurous. It has been named one of the top ten spots in the world for whale watching, paddle boarding, kayaking, and windsurfing, and the region is also ranked among the ten most popular destinations in the U.S. for beaches and golf. Explore world-class bike trails, and some of the best shopping around, Cape Cod has it all for that perfect stay by the sea.
Day 6
Daily Itinerary
Explore Cape Cod - Sunset Sail
Kick back, relax, and enjoy beach life in this ideal location. Perhaps choose to visit the P-town Monument which commemorates the first landfall of the Pilgrims in 1620 or climb to the top of the 252-foot tower in the center of town with 116 steps. You can also rent a bike to explore the cape or take to the water with a kayak or paddleboard trip. End your day with a magical Sunset Sail.
Included Unique Activities
Cape Cod Sailing
Cape Cod, Massachusetts
Join Captain Bob Burns and the crew of the Bay Lady II for a memorable sail across Provincetown Harbor and into Cape Cod Bay. Depending on wind direction the 2-hour sail will take you either across the Bay towards the Bluffs of Corn Hill or around Long Point Light at the tip of the Cape in the direction of Wood End Lighthouse.
Overnight Location
Cape Cod, Massachusetts
The hook-shaped peninsula of Cape Cod is a popular summertime destination. It's the site of quaint villages, seafood shacks, lighthouses, ponds and bay, and ocean beaches. In the large town of Hyannis, the John F. Kennedy Museum is the first stop on the Kennedy Legacy Trail through downtown, where ferries depart to the resort islands of Martha's Vineyard and Nantucket.
Cape Cod is rich with recreation, from the artistic to the adventurous. It has been named one of the top ten spots in the world for whale watching, paddle boarding, kayaking, and windsurfing, and the region is also ranked among the ten most popular destinations in the U.S. for beaches and golf. Explore world-class bike trails, and some of the best shopping around, Cape Cod has it all for that perfect stay by the sea.
Day 7
Daily Itinerary
Return to Boston - Stay on the Water!
On this day, drive back to Boston. There is so much to do in Boston we have left this day free for you to choose. The city is easily explored on foot and is known as one of the most walkable cities you can find, you also have the option to hop on one of the many trolleys to get around and explore. Stay in a Unique Floating B&B with expansive views of the Boston Harbor skyline. Your B&B is located just four miles from Logan Airport. Enjoy your last night floating on the water!
Overnight Location
Boston, Massachusetts
With Boston's rich history, diverse neighborhoods, and legacy of arts, culture, and education, Boston has something for everyone, making it a leading tourist destination.
Each of the city's neighborhoods has a remarkably different style and tone. From the Back Bay's cosmopolitan streets and ornate Victorian townhouses to the aromas spilling into the narrow and jumbled 17-century streets of Boston's North End to the spirited and funky neighborhood squares of Cambridge - all within easy distance from one another.
Boston dining is increasingly a destination all its own. The restaurant scene is delicious and dynamic. Even the shopping in Boston is of historic proportions from designer boutiques, eclectic galleries to prestigious department stores.
Day 8
Depart From
Depart from Boston Logan Airport, Massachusetts
Today you depart from Boston Logan International Airport (BOS).
2025
Available Dates
Jan, Feb, Mar, Apr, May, Jun, Jul, Aug, Sep, Oct, Nov, Dec
From $3,463 per person
Based on 2 people traveling, customizable to your group size
Your Price Includes:
ACCOMMODATION
2 nights Modern Boutique Salem Center
1-night Seaside Hotel in Gloucester
1-night Downtown Boston Hotel with Views
2 nights Luxury Ocean Retreat in Cape Cod
1-night Unique Floating B&B in Boston
DINING OPTIONS INCLUDED
4 Breakfasts (Salem, Cape Cod & Boston B&B)
Daily Wine Reception in Cape Cod with Cheese & Snacks
UNIQUE EXPERIENCES
Historic Walking Tour of Bewitching Salem
Whale Watching with Naturalist in Marine Sanctuary
Explore Boston’s Historical Sites with a Local Guide
Sunset Sail on Cape Cod
Floating B&B Experience
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