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Tyringham, the Berkshires
Acorn Street, Boston
Paul Revere's Monument, Boston, Massachusetts
St Anthony's Monastery garden, Kennebunkport, Maine
Bar Harbor, Maine
Acadia National Park, Maine
White Mountains, New Hampshire
Winding road descending from Mount Washington, New Hampshire
Glen Moss Falls, Granville, Vermont
Rose Island Lighthouse, Newport, Rhode Island
Cape Cod, Massachusetts
Martha's Vineyard, Massachusetts
Plymouth Rock, Massachusetts

New England Explorer

13 day Fly Drive – from £1635

With flights from £2185

This 13-day fly drive holiday begins in the bustling city of Boston and weaves its way through the historic charm of New England’s towns, coastlines and mountains.

Highlights:
  • Walk the Freedom Trail to experience Boston’s rich history
  • Experience the artistic and natural beauty of The Berkshires
  • Discover the enchanting seaside town of Bar Harbor
  • Witness the lush beauty of the Green Mountains
  • Bask in the tranquil beaches and quaint charm of Cape Cod

Your Itinerary

Expand All

You can customise this itinerary by adding extra nights or destinations. Just let us know what you would like to do

Acorn Street, Boston

Day 1 – Welcome to Boston

Arrive in Boston make your way to your first hotel. The rest of the day is…

Arrive in Boston make your way to your first hotel. The rest of the day is yours to do as you please, a recommendation is to visit the Boston harbour where you can enjoy The Boston Harbour Walk. This walk is designed to connect the public to a clean and restored Boston Harbour. Alternatively, you could visit Faneuil Hall Marketplace comprised of a collection of boutiques, eateries and pushcart vendors housed in converted 18th-century warehouses.

    Boston Park Plaza or similar

Acorn Street, Boston
Paul Revere's Monument, Boston, Massachusetts

Day 2 – Boston

Spend a full day exploring this historic town. Take a walk along the famous Freedom Trail,…

Spend a full day exploring this historic town. Take a walk along the famous Freedom Trail, one of Americas’ first historic walking tours and the perfect introduction to Colonial and Revolutionary Boston. You will visit 16 historical sites covering two and a half centuries of America’s most significant past.

Optional Experience – Boston Old Town Trolley Tour
Hop aboard one of these trolleys and you’ll experience ‘Transportainment’, a delightful combination of transportation and entertainment. Turn back the pages of history and relive colonial Boston. Coming from various backgrounds, each conductor narrates the sightseeing tour with his or her own blend of trivia, colourful anecdotes, and humorous stories to ensure that your experience is both enjoyable and informative.

    Boston Park Plaza or similar

Paul Revere's Monument, Boston, Massachusetts
St Anthony's Monastery garden, Kennebunkport, Maine

Day 3 – Kennebunkport

Collect your car this morning and leave Boston behind as you drive north toward Salem, the…

Collect your car this morning and leave Boston behind as you drive north toward Salem, the infamous home to the witch trials of 1692. Well aware of its infamy, Salem has a number of attractions centred on this uneasy time, including haunted tours and re-enactments. Continue the drive passing Gloucester, America’s oldest fishing port, toward Kennebunkport, a great place for hiking and exploring.

    Boston > Kennebunkport | 127 miles

    Nonantum Resort or similar

St Anthony's Monastery garden, Kennebunkport, Maine
Bar Harbor, Maine

Day 4 – Bar Harbor

This morning get to know Kennebunkport and all its natural wonders like Spouting Rock and Blowing…

This morning get to know Kennebunkport and all its natural wonders like Spouting Rock and Blowing Cave. In the afternoon continue the journey to Bar Harbor. Located in Downeast, Bar Harbor was once considered a small fishing and ship-building community; today it’s a favourite destination for people throughout the world, offering spectacular beauty and natural wonder for those who would prefer to spend their time outdoors.

    Kennebunkport > Bar Harbour | 234 miles

    Bluenose Inn or similar

Bar Harbor, Maine
Acadia National Park, Maine

Day 5 – Bar Harbor

Today you can explore Bar Harbor and its surroundings at your leisure. Visit Mount Desert Oceanariu

Today you can explore Bar Harbor and its surroundings at your leisure. Visit Mount Desert Oceanarium which includes a lobster museum, a marsh tour, and a lobster hatchery. For a touch of nature, visit Acadia National Park, New England’s only National Park; it offers 6000 acres of mountains, rugged coastline, islands, forests and lakes where you can hike, bike, canoe, fish, and explore this Park’s trails.

Optional Experience – Lobster Boat Cruise
Experience a sample of the life and work of the Maine Lobsterman. Watch as the captain demonstrates how lobster traps are hauled while learning all the parts of a lobster trap and how the lobsters find their way to the bait inside. Learn all about the anatomy and life cycle of the Maine Lobster. In addition to lobster and crab, you’ll see and be able to touch sea urchins, starfish, and sea cucumbers. The kids will love it and so will you. About halfway through our cruise, we’ll stow all the lobster gear and then head off to a small island to look at harbour seals basking on the rocks or swimming in the nearby water.

    Bluenose Inn or similar

Acadia National Park, Maine
White Mountains, New Hampshire

Day 6 – White Mountains

Continue on your journey through coastal Maine to Jackson. Take a scenic drive to the White…

Continue on your journey through coastal Maine to Jackson. Take a scenic drive to the White Mountains National Forest, better known as the Whites. Take a train ride through this scenic area; choose one of the Valley routes to Conway or Bartlett, or the legendary Crawford Notch excursion.

    Bar Harbour > White Mountains | 219 miles

    Christmas Farm Inn or similar

White Mountains, New Hampshire
Winding road descending from Mount Washington, New Hampshire

Day 7 – Stowe

As you leave this morning, through the White Mountains, visit Franconia Notch State Park located in 

As you leave this morning, through the White Mountains, visit Franconia Notch State Park located in the heart of the White Mountain Region. Here you can ride a passenger cable car to the top of Cannon Mountain where on a clear day you can see mountains in Canada, and you can visit Mount Washington, the highest Mountain peak in the Northeast. After a scenic stop and some great photo ops, continue on to the Stowe area in Vermont.

    White Mountains > Stowe | 131 miles

    Green Mountain Inn or similar

Winding road descending from Mount Washington, New Hampshire
Glen Moss Falls, Granville, Vermont

Day 8 – Green Mountains

After a night in Stowe it’s time to head towards the Green Mountains. On your way,…

After a night in Stowe it’s time to head towards the Green Mountains. On your way, you will pass ‘Moss Glen Falls’, a roadside attraction featured in just about every photographic portrait of Vermont ever published. You can also visit the Smugglers’ Notch State Park in the Green Mountains; it’s great for hiking and offers several short, medium and long trails throughout the park.

    Stowe > Green Mountains | 78 miles

    Snowed Inn or similar

Glen Moss Falls, Granville, Vermont
Tyringham, the Berkshires

Day 9 – The Berkshires

The Berkshires are a beautiful place to visit any time of year, the area is known…

The Berkshires are a beautiful place to visit any time of year, the area is known widely as a cultural hub of museums, historic sites, music, dance and art venues. In addition, the region also offers outstanding opportunities for outdoor sports including golf, hiking and mountain biking, fishing, and even white-water rafting. All of these activities take place amid spectacularly scenic rural hills dotted with mountain streams and lakes.

    Green Mountains > The Berkshires | 68 miles

    Red Lion Inn Stockbridge or similar

Tyringham, the Berkshires
Rose Island Lighthouse, Newport, Rhode Island

Day 10 – Newport

Leave the Berkshires behind and drive on to Newport. Home to spectacular coastal scenery, awe-inspiring…

Leave the Berkshires behind and drive on to Newport. Home to spectacular coastal scenery, awe-inspiring architecture, a thriving waterfront, and welcoming hospitality, Newport is considered by many to be a shining gem in the coastal crown of New England. Take a walk through tennis history and explore six acres of historic grounds at the Tennis Hall of Fame, enjoy the peaceful waters of Narragansett Bay aboard the Newport Dinner Train, or visit Bannister’s Wharf, an old commercial seaport in the colonial days, now the hub of Newport’s harbour side shopping and dining. Here you can find eclectic boutiques and numerous restaurants from the sophisticated to the casual.

OPTIONAL EXPERIENCE – Newport Mansion Tour
Visit two of the famed Gilded Age mansions that once were the summer playground for socialite families. With names like Breakers, Astor and Vanderbilt, they are by far the most popular attraction in Newport. Built near the turn of the century, these magnificent structures are each a museum onto themselves. Here you will find a world of exceptional elegance and inspiration in architecture, art, interior design and landscapes.

    The Berkshires > Newport | 187 miles

    Newport Beach Hotel & Suites or similar

Rose Island Lighthouse, Newport, Rhode Island
Cape Cod, Massachusetts

Day 11 – Cape Cod & Falmouth

People come to Cape Cod to feel inspired; to walk the pristine beaches, revel in the…

People come to Cape Cod to feel inspired; to walk the pristine beaches, revel in the arts and culture, indulge in the freshest fried clams, play 18 holes on the lush fairways, and savour the breathtaking scenic beauty. Lighthouses, cultural landscapes, and wild cranberry bogs offer a glimpse of Cape Cod’s past and continuing ways of life.

    Newport > Cape Cod/ Falmouth | 97 miles

    Inn on the Square or similar

Cape Cod, Massachusetts
Martha's Vineyard, Massachusetts

Day 12 – Cape Cod

Today you can make a decision between visiting Martha’s Vineyard or Nantucket Island, both are next 

Today you can make a decision between visiting Martha’s Vineyard or Nantucket Island, both are next to Cape Cod and both are full of charm and typical New England atmosphere. The best way to see the prettiest spots on the islands are on foot, bicycle or a combination of the two. There’s so much to see and do on both Island’s the decision of which way to go may not be an easy one. 

    Inn on the Square or similar

Martha's Vineyard, Massachusetts
Plymouth Rock, Massachusetts

Day 13 – Farewell from Boston

On your last day, on your way back to Boston, you may wish to visit historical…

On your last day, on your way back to Boston, you may wish to visit historical Plymouth Rock a monument symbolizing the location where the Pilgrims disembarked from the Mayflower when they first landed on what was to become American soil. You can also see the Mayflower II, a replica of the ship that first brought settlers to New England. 

    Boston > Airport | 75 miles
Plymouth Rock, Massachusetts

Your Itinerary

You can customise this itinerary by adding extra nights or destinations. Just let us know what you would like to do

Day 1

|

Welcome to Boston

Arrive in Boston make your way to your first hotel. The rest of the day is yours to do as you please, a recommendation is to visit the Boston harbour where you can enjoy The Boston Harbour Walk. This walk is designed to connect the public to a clean and restored Boston Harbour. Alternatively, you could visit Faneuil Hall Marketplace comprised of a collection of boutiques, eateries and pushcart vendors housed in converted 18th-century warehouses.

    Boston Park Plaza or similar

Acorn Street, Boston

Day 2

|

Boston

Spend a full day exploring this historic town. Take a walk along the famous Freedom Trail, one of Americas’ first historic walking tours and the perfect introduction to Colonial and Revolutionary Boston. You will visit 16 historical sites covering two and a half centuries of America’s most significant past.

Optional Experience – Boston Old Town Trolley Tour
Hop aboard one of these trolleys and you’ll experience ‘Transportainment’, a delightful combination of transportation and entertainment. Turn back the pages of history and relive colonial Boston. Coming from various backgrounds, each conductor narrates the sightseeing tour with his or her own blend of trivia, colourful anecdotes, and humorous stories to ensure that your experience is both enjoyable and informative.

    Boston Park Plaza or similar

Paul Revere's Monument, Boston, Massachusetts

Day 3

|

Kennebunkport

Collect your car this morning and leave Boston behind as you drive north toward Salem, the infamous home to the witch trials of 1692. Well aware of its infamy, Salem has a number of attractions centred on this uneasy time, including haunted tours and re-enactments. Continue the drive passing Gloucester, America’s oldest fishing port, toward Kennebunkport, a great place for hiking and exploring.

    Boston > Kennebunkport | 127 miles

    Nonantum Resort or similar

St Anthony's Monastery garden, Kennebunkport, Maine

Day 4

|

Bar Harbor

This morning get to know Kennebunkport and all its natural wonders like Spouting Rock and Blowing Cave. In the afternoon continue the journey to Bar Harbor. Located in Downeast, Bar Harbor was once considered a small fishing and ship-building community; today it’s a favourite destination for people throughout the world, offering spectacular beauty and natural wonder for those who would prefer to spend their time outdoors.

    Kennebunkport > Bar Harbour | 234 miles

    Bluenose Inn or similar

Bar Harbor, Maine

Day 5

|

Bar Harbor

Today you can explore Bar Harbor and its surroundings at your leisure. Visit Mount Desert Oceanarium which includes a lobster museum, a marsh tour, and a lobster hatchery. For a touch of nature, visit Acadia National Park, New England’s only National Park; it offers 6000 acres of mountains, rugged coastline, islands, forests and lakes where you can hike, bike, canoe, fish, and explore this Park’s trails.

Optional Experience – Lobster Boat Cruise
Experience a sample of the life and work of the Maine Lobsterman. Watch as the captain demonstrates how lobster traps are hauled while learning all the parts of a lobster trap and how the lobsters find their way to the bait inside. Learn all about the anatomy and life cycle of the Maine Lobster. In addition to lobster and crab, you’ll see and be able to touch sea urchins, starfish, and sea cucumbers. The kids will love it and so will you. About halfway through our cruise, we’ll stow all the lobster gear and then head off to a small island to look at harbour seals basking on the rocks or swimming in the nearby water.

    Bluenose Inn or similar

Acadia National Park, Maine

Day 6

|

White Mountains

Continue on your journey through coastal Maine to Jackson. Take a scenic drive to the White Mountains National Forest, better known as the Whites. Take a train ride through this scenic area; choose one of the Valley routes to Conway or Bartlett, or the legendary Crawford Notch excursion.

    Bar Harbour > White Mountains | 219 miles

    Christmas Farm Inn or similar

White Mountains, New Hampshire

Day 7

|

Stowe

As you leave this morning, through the White Mountains, visit Franconia Notch State Park located in the heart of the White Mountain Region. Here you can ride a passenger cable car to the top of Cannon Mountain where on a clear day you can see mountains in Canada, and you can visit Mount Washington, the highest Mountain peak in the Northeast. After a scenic stop and some great photo ops, continue on to the Stowe area in Vermont.

    White Mountains > Stowe | 131 miles

    Green Mountain Inn or similar

Winding road descending from Mount Washington, New Hampshire

Day 8

|

Green Mountains

After a night in Stowe it’s time to head towards the Green Mountains. On your way, you will pass ‘Moss Glen Falls’, a roadside attraction featured in just about every photographic portrait of Vermont ever published. You can also visit the Smugglers’ Notch State Park in the Green Mountains; it’s great for hiking and offers several short, medium and long trails throughout the park.

    Stowe > Green Mountains | 78 miles

    Snowed Inn or similar

Glen Moss Falls, Granville, Vermont

Day 9

|

The Berkshires

The Berkshires are a beautiful place to visit any time of year, the area is known widely as a cultural hub of museums, historic sites, music, dance and art venues. In addition, the region also offers outstanding opportunities for outdoor sports including golf, hiking and mountain biking, fishing, and even white-water rafting. All of these activities take place amid spectacularly scenic rural hills dotted with mountain streams and lakes.

    Green Mountains > The Berkshires | 68 miles

    Red Lion Inn Stockbridge or similar

Tyringham, the Berkshires

Day 10

|

Newport

Leave the Berkshires behind and drive on to Newport. Home to spectacular coastal scenery, awe-inspiring architecture, a thriving waterfront, and welcoming hospitality, Newport is considered by many to be a shining gem in the coastal crown of New England. Take a walk through tennis history and explore six acres of historic grounds at the Tennis Hall of Fame, enjoy the peaceful waters of Narragansett Bay aboard the Newport Dinner Train, or visit Bannister’s Wharf, an old commercial seaport in the colonial days, now the hub of Newport’s harbour side shopping and dining. Here you can find eclectic boutiques and numerous restaurants from the sophisticated to the casual.

OPTIONAL EXPERIENCE – Newport Mansion Tour
Visit two of the famed Gilded Age mansions that once were the summer playground for socialite families. With names like Breakers, Astor and Vanderbilt, they are by far the most popular attraction in Newport. Built near the turn of the century, these magnificent structures are each a museum onto themselves. Here you will find a world of exceptional elegance and inspiration in architecture, art, interior design and landscapes.

    The Berkshires > Newport | 187 miles

    Newport Beach Hotel & Suites or similar

Rose Island Lighthouse, Newport, Rhode Island

Day 11

|

Cape Cod & Falmouth

People come to Cape Cod to feel inspired; to walk the pristine beaches, revel in the arts and culture, indulge in the freshest fried clams, play 18 holes on the lush fairways, and savour the breathtaking scenic beauty. Lighthouses, cultural landscapes, and wild cranberry bogs offer a glimpse of Cape Cod’s past and continuing ways of life.

    Newport > Cape Cod/ Falmouth | 97 miles

    Inn on the Square or similar

Cape Cod, Massachusetts

Day 12

|

Cape Cod

Today you can make a decision between visiting Martha’s Vineyard or Nantucket Island, both are next to Cape Cod and both are full of charm and typical New England atmosphere. The best way to see the prettiest spots on the islands are on foot, bicycle or a combination of the two. There’s so much to see and do on both Island’s the decision of which way to go may not be an easy one. 

    Inn on the Square or similar

Martha's Vineyard, Massachusetts

Day 13

|

Farewell from Boston

On your last day, on your way back to Boston, you may wish to visit historical Plymouth Rock a monument symbolizing the location where the Pilgrims disembarked from the Mayflower when they first landed on what was to become American soil. You can also see the Mayflower II, a replica of the ship that first brought settlers to New England. 

    Boston > Airport | 75 miles
Plymouth Rock, Massachusetts

This Self Drive Includes

12 nights hotel accommodation
10 nights car hire, with unlimited mileage

Flights & More

With FREEDOM, you can book your New England Explorer fly drive and flights together, as an ATOL protected package. Our Travel Experts can find the best priced Economy, Premium or Business Class flights for you.

You can also personalise your holiday. Why not add:

  • Extra nights in Boston, the Green Mountains or any location en route
  • A Boston Old Town Trolley Tour, Lobster Boat Cruise or Newport Mansion Passport

Next Step

Please get in touch with our America Experts to start planning your holiday. You’ll have a single point of contact from your first enquiry through booking.

New England Explorer

13 day Fly Drive – from £1635

With flights from £2185

Price is per person, based on two people sharing a double or twin room and includes pre-booked accommodation, air-conditioned car and unlimited mileage. One-way fees charged locally. Hotels specified are subject to availability and may be substituted by one of a similar or higher standard.

Map

New England Explorer Self Drive Map