Day 1: Boston

On arrival in Boston take a taxi from the airport to your hotel downtown. 

Day 2: Boston

One of the best things to do in Boston is the Freedom Trail. 

I would recommend taking a walking tour to make sure you make the most of it. 

https://www.bostonbyfoot.org/tours/Road_Revolution

From the Boston Massacre to Paul Revere's midnight ride, Boston is renowned for its inciting events to the American Revolution. Come explore the streets of Boston's oldest neighborhoods and hear the extraordinary stories preserved in the meetinghouses, halls, and homes where the Revolution was born.

Our most comprehensive Freedom Trail offering, this tour includes historical landmarks such as King’s Chapel, the Old South Meeting House, the Old State House, the site of the Boston Massacre, the Paul Revere House and more.

What famous Boston restaurant originally served as headquarters for a Patriot paper called the Massachusetts Spy? Who devised the legendary “one if by land, two if by sea” signal at the Old North Church before Paul Revere’s ride? How did the British response to the Boston Tea Party help spread the revolutionary fervor throughout the colonies?  

Whether you are a history buff or just want a refresher on our nation’s Revolutionary past, our guides will gladly take you down the Road to Revolution on this fascinating tour!

Adult - $15 online price.

Tour lasts 2 hours.

May - October 
Daily Monday - Sunday 1:00 pm - 3:00 pm

 

Day 3: Boston

Day 4: Kennebunkport

This morning, you will collect your car from a downtown depot and head along the coast to Kennebunkport where you will check into your B&B. 

From September through mid-October, all of New England is awash in beautiful fall colour. Set out on a drive through the New England countryside and take in the gorgeous scenery. In addition to all of the wonderful colours on display, fall also means pick your own farm shops, and we have some great ones near our bed and breakfast for you to explore. Enjoy wandering the fields, eating fresh crisp apples and load up on locally grown, fresh Maine produce as you do.

Days 5 - 6: Kennebunkport

Your lovely Inkeepers would be happy to recommend activities which will enhance your stay, from schooner sailing to lobster tours, galleries and museums. Goat Island lighthouse is situated off Cape Porpoise and is one of the most popular tourist attractions in New England. The tower was built in 1833 to serve as a beacon light for mariners. When President George H.W. Bush took the office starting 1989 to 1993, the lighthouse served as a watchtower for some of his Secret Service agents. The Walker’s Point Estate is conveniently visible when viewed from the top of the tower.

 

Day 7: White Mountain National Forest

Head inland to the White Mountains and The Christmas Farm Inn. 

 

Days 8 - 9: White Mountain National Forest

Covered Bridges of the White Mountains

The Covered Bridges of the White Mountains are an integral part of the landscape and a place to wait out a summer shower or steal a kiss or watch raging river waters swollen by the melting winter snows. Covered Bridges were often called "courting bridges." Their distinctive shapes form a signature for New Hampshire. Why the first covered bridges were built has been obscured by time. Some say that horses were more comfortable crossing an enclosed span than an open trestle. Others point to the fact that a bridge lasts longer if its heavy timbers are protected.

There are tonnes of hiking and walking trails in the area so do seek out advice from the Inn workers on what would work best for your abilities. There are many waterfalls in the area so make sure you don't miss out!

Mount Washington Cog Railway

This historic Cog Railway up to the summit of majestic Mt. Washington is a great adventure for passengers of all ages. The colourful trains are powered by biodiesel or steam locomotives, traveling 5 mph past forests, ravines, wildlife (including the occasional moose or bear) and through three climate zones to reach the breathtaking summit. There, on top of the Northeast’s tallest peak, you can explore an interactive weather exhibit or look out over the mountains from the rooftop observation deck. You can also send a post card from the summit post office. Travelers will enjoy the commentary from train engineers and brakemen and brakewomen. Parking is free, and there are food courts or cafeterias at both ends of your exciting journey. Trains operate from late April through November.

 

Day 10: Lenox

The small village of Lenox is located in the heart of the Berkshires, a region in western Massachusetts renowned for its wooded, rolling hills.

The bucolic landscapes here have provided inspiration to successive generations of artists, musicians and writers and the village is home to both the Norman Rockwell Museum and Tanglewood, the summer home of the Boston Symphony Orchestra.

A multitude of artists, musicians, performers, painters, sculptors and writers come here every year to relax and enjoy the cultural activities.

 Whilst here, don't miss a drive along the Jacob's Ladder Trail Scenic Byway, affording lovely vistas of forested hills, rock-strewn rivers, farmland and steep rock ledges.

 

Day 11: Lenox

Day 12: Chatham

Chatham is a delightful, friendly, whitewashed old town located on the "elbow" of Cape Cod, tucked away in a sheltered harbour between Nantucket Sound and the Atlantic Ocean.

It is well known for its superb shellfish — clams, oysters and mussels are harvested here in abundance. There are some interesting art galleries and boutique shops in the heart of the town and the Old Atwood House Museum delves into the area's history.

Nearby lies the long strand of Chatham Light Beach whilst, just offshore, South Monomoy Island is a delightful bird sanctuary.

Days 13 - 14: Chatham

Overlooking Aunt Lydia’s Cove, Chatham Bars Inn Resort & Spa is one of Cape Cod’s best resorts. Travellers have stayed at the resort for over a century, and it’s easy to see why with its private beach, sweeping views of the Atlantic Ocean and close proximity to the shops and restaurants of Chatham.

Day 15: Overnight Travel

Make your way back to Boston in time to return your car and check in for the overnight flight home. 

Day 16: End of Itinerary

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