Day 1
Daily Itinerary
Arrival Boston - Drive to Marblehead
Arrive at Boston Logan Airport
Collect your rental car upon arrival. We are happy to make an advance car rental reservation for you, which you would pay for directly at the rental desk, thereby allowing you to use your personal auto insurance policy coverage and/or coverage provided by your credit card company, as applicable.
Drive from the airport to Marblehead, we recommend taking 1A along the water. The drive is only about 40 minutes.
Optional stops along the way:
• Nahant – 40 steps beach known for sea glass & colored pebbles/rocks
• Other great beaches, located in Nahant, for skyline views of Boston: Short Beach and Doggie Beach.
Once you arrive in Marblehead, check into your central quaint property with easy access to the harbor, shops, galleries, and restaurants.
Overnight Location
Marblehead, Massachusetts
Perched on a rocky peninsula that stretches out into the Atlantic, the seaside town of Marblehead features some of the most striking views and stunning scenery that northern Massachusetts has to offer. Due to its unique location, Marblehead’s coast became an irresistible draw to industrious colonists in 1629, who made quick work of turning it into a thriving fishing village.
Day 2
Daily Itinerary
Short Drive to Salem - Historical Walking Tour
Take the short 15-20 minutes to drive over to Salem.
Your day is pretty much free to do as you please, spend additional time in Marblehead, or set off to explore the many sights of Salem town such as the House of Seven Gables and Essex Street Pedestrian Mall.
Check into your boutique hotel in the heart of town.
Salem Historical Walking Tour
In the evening join a Historical Walking Tour. Learn about Salem's colonial history, witchcraft, and the 1692 Hysteria and Witch Trials.
Overnight Location
Salem, Massachusetts, USA
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
Daily Itinerary
Drive to Gloucester - Whale Watching Experience with Naturalist
Take a short leisurely drive north to Gloucester.
Marine Sanctuary Whale Watching Tour with Naturalist
Take a morning or afternoon 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.
Enjoy the rest of the day at your seaside location, spend the evening relaxing at your hotel which looks out to the ocean, or visit the charming downtown of Gloucester.
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 - Afternoon Private Walking Tour with a Local
Make your way back to ‘Beantown’ which is just about an hour's drive south. Drive the same route or set out to explore a new one.
If you wish you can drop off your car rental once you arrive in Boston.
Private Boston Freedom Trail Walk with a Local
In the afternoon enjoy a private walking tour 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.
Spend the night in a downtown hotel and enjoy all that Boston has to offer!
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
Travel to Provincetown, Cape Cod
If you dropped off your car rental the previous day, take the passenger ferry from Boston to Provincetown. It will take about 90 minutes to get there. This can be reserved in advance for you.
If you like having more flexibility and decided to hold onto your car it will take about 2.5 hours to get to Provincetown from Boston.
On arrival in Provincetown check into your luxurious hotel which will be your base for the next 2 nights. Your hotel has commanding views of the ocean, is just steps from the beach and a short walk into town, a perfect location to relax and unwind.
Your hotel offers breakfast and daily evening wine reception with a selection of cheese and snacks.
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
Day at Leisure on Cape Cod
Today you are free to plan your day as you wish.
After all your adventures of the last few days, you may just want to kick back, relax, and enjoy beach life and you are in the most ideal location to do so!
If you wish to explore or add some adventure...
Perhaps choose to visit the P-town Monument which commemorates the first landfall of the Pilgrims in 1620 and the signing of the Mayflower Compact in Provincetown Harbor. You can 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. We are happy to arrange your day activities in advance if preferred.
Day 7
Daily Itinerary
Return to Boston - Explore - Stay on the Water!
On this day take the ferry back to Boston or drive.
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.
Unique Floating B&B Stay
Set in the historic Charlestown Navy Yard, your B&B offers an expansive view of the Boston Harbor skyline along with the comfort and amenities of a modern bed and breakfast. Walk to the USS Constitution and the Freedom Trail to the North End and downtown Boston or take the water ferry to numerous points along the city's waterfront, 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
Daily Itinerary
Depart from Boston
Today you will depart out of Boston Logan Airport. Take a taxi from your B&B to the airport.
Depart for home basking in the many great memories made over the last few days, eager for more!
