New York & New England
15 day Fly Drive – from £1319
With flights from £1819
Journey from New York to Boston, exploring scenic New York State and beautiful New England. Drive along the Hudson Valley and explore the Catskill Mountains. Discover the panoramic views of Vermont and the White Mountains of New Hampshire.
Highlights:
- View the New York skyline from the top of the Empire State Building
- Visit Woodstock in the colourful Catskill Mountains
- Discover ‘Smuggler’s Notch’ near Stowe in Vermont
- Drive the Kancamagus Highway through the White Mountains
- Follow the Freedom Trail in Boston
Your Itinerary
Expand AllYou can customise your New York and New England fly drive by adding extra nights or stops along the way. Just let us know what you would like to do.
Arrive into your chosen New York airport, and once you have collected your bags, transfer independently to your Manhattan hotel.
New York City is renowned for its iconic skyline dominated by skyscrapers like the Empire State Building. In just a few days, you can experience world-class museums, catch a Broadway show, and dine in diverse neighbourhoods from Chinatown to West Village.
Once you have settled into your hotel, head out for your first taste of this electric city!
The New Yorker Hotel or similar
Day 2 & 3 – See the Sights of New York City
With two full days to explore New York you can end up doing a lot of walking, so it is best to group activities together and utilize the subway or taxis to travel some of the longer distance.
You may like to start in Midtown Manhattan, where you can take in the views from the Empire State Building, browse the shops along Fifth Avenue and see Times Square.
Wander to the Upper West Side, where you can visit the American Museum of Natural History and the Lincoln Center, before strolling through Central Park.
Continue through Central Park to the Upper East Side to visit the Guggenheim and the The Met.
Downtown Manhattan is where you will find Wall Street and the 9/11 Memorial. You can also catch the ferry from Battery Park to the Statue of Liberty, Ellis Island and Staten Island.
Greenwich and West Village are more relaxed neighbourhoods where you can enjoy the cafés around Washington Square Park and walk the High Line.
For food you should look no further than Little Italy and Chinatown, and then explore Soho for trendy art galleries and cobbled streets.
Optional Experience – Hop-on Hop-off Bus Tour
With stops at 30 key landmarks all around New York City, this sightseeing bus route will enable you to view all the sights and sounds of Manhattan and beyond.
The New Yorker Hotel or similar
Day 4 – The Hudson Valley
You can collect your car from downtown, or, if you prefer, catch the train to New York’s outer suburbs and pick-up your car from a local depot (speak to our Travel Consultants about the best option for you.)
As you leave New York City, take the Palisades Interstate Parkway for a scenic drive along the Hudson River. Enjoy views of the river, cliffs, and lush forests as you make your way north.
You may like to make a stop at Bear Mountain State Park, to take in the panoramic views of the river and the surrounding mountains from the Perkins Memorial Tower. Just to north, you could also visit the Storm King Art Centre, a world-renowned outdoor sculpture park, with over 500 acres of landscaped grounds dotted with large-scale artworks.
Before reaching Kingston, make a detour to Poughkeepsie to visit the ‘Walkway Over the Hudson’, the longest elevated pedestrian bridge in the world. You can walk or cycle across the bridge for stunning views of the Hudson River and surrounding valley.
Best Western Plus, Kingston or similar
Day 5 – Kingston & The Catskill Mountains
You could begin your day by exploring Kingston’s historic waterfront district, Rondout. Visit the Hudson River Maritime Museum to learn more about the region’s maritime history and stroll along the Rondout Creek waterfront, lined with charming shops, galleries, and restaurants. A perfect spot for a lazy brunch.
Alternatively, you can embark on a scenic drive into the Catskill Mountains, following Route 28 west from Kingston. This picturesque road winds through the heart of the Catskills, offering breathtaking views of rolling hills, forests, and streams. Along the way, you can stop at various scenic overlooks, roadside markets, and quaint towns like Phoenicia and Woodstock.
We also recommend making a stop at the Ashokan Reservoir, one of the region’s scenic gems. Take in the panoramic views of the reservoir and surrounding mountains from the Ashokan Rail Trail, which runs along the reservoir’s northern shore.
Another highlight of the Catskills is Kaaterskill Falls, one of the tallest waterfalls in New York State. You can follow the short trail to the viewing platform to admire the spectacular two-tiered waterfall cascading into a rocky gorge.
Best Western Plus Kingston or similar
Day 6 – Saugerties, Catskill & Hudson
Today’s relatively short drive takes you along the banks for the meandering Hudson River to three picturesque towns.
Your first stop will be Saugerties, where a short hike along a well-marked trail brings you to Saugerties Lighthouse on the river. The views from here are spectacular. The nearby Esopus Bend Nature Preserve is also good for stretching your legs.
In the town of Catskill it is possible to tour the former home of Thomas Cole, the founder of the Hudson River School of Painting. The House includes exhibits on the artist’s life and legacy, and the scenic grounds provide exceptional views.
The Hudson River Skywalk connects Thomas Cole House with Olana Mansion, the former home of landscape painter Frederic Church. Olana estate is adjacent to the town of Hudson on the eastern riverbank. This town is known for its beautifully preserved 19th-century architecture, fashionable boutiques, art galleries, and antique shops.
From Hudson, it is a short drive up the river to your next destination; Albany, the capital of New York State.
Hilton Albany or similar
Day 7 – Albany
From your hotel in Albany you will have a chance to explore the New York Capital on foot.
Begin your exploration at the grand 19th-century Capitol Building, a striking piece of architecture. Join a guided tour to uncover its fascinating history and marvel at features like the impressive Million Dollar Staircase.
Just steps away, visit the Empire State Plaza, where you can explore the New York State Museum with its exhibits on art, history, and culture. Afterwards, enjoy a leisurely walk through Washington Park, Albany’s very own version of Central Park, perfect for a relaxing afternoon in the heart of the city.
As evening falls, make your way to Lark Street, Albany’s vibrant arts and dining district. Here, you’ll find a variety of bars and restaurants to suit all tastes. For a local experience, stop by the Albany Pump Station to sample craft beers and enjoy a hearty meal.
Hilton Albany or similar
Day 8 – Saratoga Springs & Lake George
Just north of Albany is Cohoes Falls, one of the largest waterfalls in New York State then from there is is short drive on to Saratoga Springs.
Saratoga Springs is known for its natural mineral springs, thoroughbred horse racing, and its buzzing downtown. You can visit the Saratoga Spa State Park, home to hiking trails, mineral springs, and the stunning Geyser Island Spouter. You can also walk to Congress Park and sip fresh spring water from the fountains.
Travelling further north you can stop at Moreau Lake State Park or the small town of Glens Falls, known for is fine art museum and historic canal.
As you reach Lake George, stop by Fort William Henry. This reconstructed British fort from the 18th century offers guided tours, reenactments, and breathtaking views of the southern end of Lake George.
Hampton Inn, Lake George
Day 9 – The Adirondacks & Green Mountains
The scenic drive between Lake George and Stowe offers a stunning journey through the Adirondacks and Green Mountains.
If you haven’t already, before you leave Lake George, take a walk along the lake waterfront or join a steamboat cruise on the lake.
As you drive north, along the western side of Lake George, you will be able to stop at the historic town of Ticonderoga. Here you can visit Fort Ticonderoga, a key site during the Revolutionary War. It also has impressive views of the upcoming Lake Champlain.
You can then cross Lake Champlain Bridge into the state of Vermont, and head to the college town of Middlebury. You can stroll through the beautiful campus of Middlebury College and visit town’s cafés and shops downtown.
One final stop before you reach Stowe is Westbury. As well as being surrounded by beautiful scenery, Westbury has a culinary theme. You can grab a cup of fresh apple cider and a warm cider doughnut at Cold Hollow Cider Mill, or grab a coffee in the vintage train station. However, most people also stop at the original ben & Jerry’s factory, where you can complete a tour and sample som fresh ice cream.
It is then a short drive further into the Green Mountains and the resort town of Stowe.
Green Mountain Inn or similar
Day 10 – Stowe, Vermont
Today you can get out and about and explore around Stowe.
A good place to start is the Stowe Mountain Resort where you can take the cable car ride up Mount Mansfield, Vermont’s highest peak. It provides jaw-dropping views of the surrounding forests.
At lower levels you can also walk or ride a bicycle around Stowe’s very scenic Recreation Path. This 5 mile path meanders through fields and forests and bridges a number of rivers.
You can also visit the Trapp Family Lodge from Stowe. This Austrian-style lodge, founded by the famous von Trapp family from “The Sound of Music,” is a great spot for a drink, a meal, or just to take in the spectacular surroundings.
Green Mountain Inn or similar
Day 11 – The Kancamagus Highway
Today’s scenic drive takes you from Vermont’s Green Mountains to New Hampshire’s White Mountains.
Head east out of Stowe and drive through the Green Mountains in the direction of the Connecticut River and cross into New Hampshire.
A great place to stop is Franconia Notch State Park. Here you can walk through this natural gorge, where waterfalls, covered bridges, and beautiful granite walls create a magical scene. It is also possible to ride the Cannon Mountain Aerial Tramway for views of the White Mountains and beyond.
The town of Lincoln marks the start of one of America’s most scenic roads, the Kancamagus Highway. The route stretches for 34 miles to the town of Conway. Along the way you can stop for the short hike to Sabbaday Falls, or Rocky Gorge for cascading waterfalls. Alternatively you can pull off the road at Hancock and Sugar Hill Overlooks for panoramic views.
North Conway Grand or similar
Day 12 – Portland Lighthouse & Kennebunkport
North Conway is a bustling town surrounded by the White Mountains. If you haven’t already, you might consider driving or taking the cog railway up Mount Washington, the highest peak in the northeastern United States.
Just ten minutes outside North Conway you can take the short drive up Cathedral Ledge for views of the Saco River Valley.
Bridgton is a quiet lakeside town where you can take a scenic walk around Highland Lake with views of Shawnee Peak, which becomes a ski resort in winter months.
You will reach the Atlantic Coast at Portland, where you can visit the cobblestone streets of the historic waterfront area or just south of downtown, you can stop at Portland Head Lighthouse at Fort Williams Park that offers stunning ocean views
Your destination today is Kennebunkport, a charming harbour town known for its historic maritime homes and beautiful beaches. The town’s busy Dock Square is lined with shops, galleries and restaurants, so you can stop for a lobster roll whilst you are here.
Nonantum Resort or similar
Day 13 & 14 – Welcome to Boston
From Kennebunkport, it is a leisurely drive down the Atlantic Coast to Boston, one of America’s oldest cities.
You may like to stop at some of the maritime villages and towns along the way. You could choose to stop at Ogunquit or York, both of which have beautiful beaches. Alternatively the historic seaport town of Portsmouth features a blend of historic buildings and boutique shops.
Famous for the 1692 witch trials, the town of Salem offers a mix of history, art and coastal views, so is well worth a stop. Pickering Wharf is a lively waterfront area with a collection of historic building that are now a National historic Site.
Boston is a very accessible city, so we would recommend that as you approach the city you head to the airport to return your hire car. You can then transfer independently to your downtown hotel.
During your time in Boston you will be able to follow the Freedom Trail, a two and half mile walking trail that connects 16 historic sites, tracing Boston’s role in the American Revolution, you can also visit the Boston Tea Party Ships and the accompanying museum.
One of Boston’s most picturesque areas, Beacon Hill is known for its cobblestone streets, brick homes, and gas-lit lamps. Acorn Street is especially famous as one of the most photographed streets in the country.
If you have time you can also cross the river to Cambridge and explore the historic campus of Harvard University. In the evening you might like to choose to visit Boston’s North End, the city’s Italian Quarter, to visit some authentic Italian restaurants.
Optional Experience – Old Town Trolley Tour
The Boston Old Town Trolley Tour guides you through the North End and Beacon Hill, as well al the landmarks along the Freedom Trail.
Hilton Boston Park Plaza or similar
Day 15 – Farewell From New England
Sadly this New York and New England holiday has come to an end, although there may still be time for you to visit Faneuil Hall Marketplace or Quincy Market before you depart, for some last minute souvenir shopping.
When you are ready, transfer to Boston Logan International Airport in time to check-in for your return flight or onwards journey.
Your Itinerary
You can customise your New York and New England fly drive by adding extra nights or stops along the way. Just let us know what you would like to do.
Day 1
| Welcome to New York
Arrive into your chosen New York airport, and once you have collected your bags, transfer independently to your Manhattan hotel.
New York City is renowned for its iconic skyline dominated by skyscrapers like the Empire State Building. In just a few days, you can experience world-class museums, catch a Broadway show, and dine in diverse neighbourhoods from Chinatown to West Village.
Once you have settled into your hotel, head out for your first taste of this electric city!
The New Yorker Hotel or similar
Day 2 & 3
| See the Sights of New York City
With two full days to explore New York you can end up doing a lot of walking, so it is best to group activities together and utilize the subway or taxis to travel some of the longer distance.
You may like to start in Midtown Manhattan, where you can take in the views from the Empire State Building, browse the shops along Fifth Avenue and see Times Square.
Wander to the Upper West Side, where you can visit the American Museum of Natural History and the Lincoln Center, before strolling through Central Park.
Continue through Central Park to the Upper East Side to visit the Guggenheim and the The Met.
Downtown Manhattan is where you will find Wall Street and the 9/11 Memorial. You can also catch the ferry from Battery Park to the Statue of Liberty, Ellis Island and Staten Island.
Greenwich and West Village are more relaxed neighbourhoods where you can enjoy the cafés around Washington Square Park and walk the High Line.
For food you should look no further than Little Italy and Chinatown, and then explore Soho for trendy art galleries and cobbled streets.
Optional Experience – Hop-on Hop-off Bus Tour
With stops at 30 key landmarks all around New York City, this sightseeing bus route will enable you to view all the sights and sounds of Manhattan and beyond.
The New Yorker Hotel or similar
Day 4
| The Hudson Valley
You can collect your car from downtown, or, if you prefer, catch the train to New York’s outer suburbs and pick-up your car from a local depot (speak to our Travel Consultants about the best option for you.)
As you leave New York City, take the Palisades Interstate Parkway for a scenic drive along the Hudson River. Enjoy views of the river, cliffs, and lush forests as you make your way north.
You may like to make a stop at Bear Mountain State Park, to take in the panoramic views of the river and the surrounding mountains from the Perkins Memorial Tower. Just to north, you could also visit the Storm King Art Centre, a world-renowned outdoor sculpture park, with over 500 acres of landscaped grounds dotted with large-scale artworks.
Before reaching Kingston, make a detour to Poughkeepsie to visit the ‘Walkway Over the Hudson’, the longest elevated pedestrian bridge in the world. You can walk or cycle across the bridge for stunning views of the Hudson River and surrounding valley.
Best Western Plus, Kingston or similar
Day 5
| Kingston & The Catskill Mountains
You could begin your day by exploring Kingston’s historic waterfront district, Rondout. Visit the Hudson River Maritime Museum to learn more about the region’s maritime history and stroll along the Rondout Creek waterfront, lined with charming shops, galleries, and restaurants. A perfect spot for a lazy brunch.
Alternatively, you can embark on a scenic drive into the Catskill Mountains, following Route 28 west from Kingston. This picturesque road winds through the heart of the Catskills, offering breathtaking views of rolling hills, forests, and streams. Along the way, you can stop at various scenic overlooks, roadside markets, and quaint towns like Phoenicia and Woodstock.
We also recommend making a stop at the Ashokan Reservoir, one of the region’s scenic gems. Take in the panoramic views of the reservoir and surrounding mountains from the Ashokan Rail Trail, which runs along the reservoir’s northern shore.
Another highlight of the Catskills is Kaaterskill Falls, one of the tallest waterfalls in New York State. You can follow the short trail to the viewing platform to admire the spectacular two-tiered waterfall cascading into a rocky gorge.
Best Western Plus Kingston or similar
Day 6
| Saugerties, Catskill & Hudson
Today’s relatively short drive takes you along the banks for the meandering Hudson River to three picturesque towns.
Your first stop will be Saugerties, where a short hike along a well-marked trail brings you to Saugerties Lighthouse on the river. The views from here are spectacular. The nearby Esopus Bend Nature Preserve is also good for stretching your legs.
In the town of Catskill it is possible to tour the former home of Thomas Cole, the founder of the Hudson River School of Painting. The House includes exhibits on the artist’s life and legacy, and the scenic grounds provide exceptional views.
The Hudson River Skywalk connects Thomas Cole House with Olana Mansion, the former home of landscape painter Frederic Church. Olana estate is adjacent to the town of Hudson on the eastern riverbank. This town is known for its beautifully preserved 19th-century architecture, fashionable boutiques, art galleries, and antique shops.
From Hudson, it is a short drive up the river to your next destination; Albany, the capital of New York State.
Hilton Albany or similar
Day 7
| Albany
From your hotel in Albany you will have a chance to explore the New York Capital on foot.
Begin your exploration at the grand 19th-century Capitol Building, a striking piece of architecture. Join a guided tour to uncover its fascinating history and marvel at features like the impressive Million Dollar Staircase.
Just steps away, visit the Empire State Plaza, where you can explore the New York State Museum with its exhibits on art, history, and culture. Afterwards, enjoy a leisurely walk through Washington Park, Albany’s very own version of Central Park, perfect for a relaxing afternoon in the heart of the city.
As evening falls, make your way to Lark Street, Albany’s vibrant arts and dining district. Here, you’ll find a variety of bars and restaurants to suit all tastes. For a local experience, stop by the Albany Pump Station to sample craft beers and enjoy a hearty meal.
Hilton Albany or similar
Day 8
| Saratoga Springs & Lake George
Just north of Albany is Cohoes Falls, one of the largest waterfalls in New York State then from there is is short drive on to Saratoga Springs.
Saratoga Springs is known for its natural mineral springs, thoroughbred horse racing, and its buzzing downtown. You can visit the Saratoga Spa State Park, home to hiking trails, mineral springs, and the stunning Geyser Island Spouter. You can also walk to Congress Park and sip fresh spring water from the fountains.
Travelling further north you can stop at Moreau Lake State Park or the small town of Glens Falls, known for is fine art museum and historic canal.
As you reach Lake George, stop by Fort William Henry. This reconstructed British fort from the 18th century offers guided tours, reenactments, and breathtaking views of the southern end of Lake George.
Hampton Inn, Lake George
Day 9
| The Adirondacks & Green Mountains
The scenic drive between Lake George and Stowe offers a stunning journey through the Adirondacks and Green Mountains.
If you haven’t already, before you leave Lake George, take a walk along the lake waterfront or join a steamboat cruise on the lake.
As you drive north, along the western side of Lake George, you will be able to stop at the historic town of Ticonderoga. Here you can visit Fort Ticonderoga, a key site during the Revolutionary War. It also has impressive views of the upcoming Lake Champlain.
You can then cross Lake Champlain Bridge into the state of Vermont, and head to the college town of Middlebury. You can stroll through the beautiful campus of Middlebury College and visit town’s cafés and shops downtown.
One final stop before you reach Stowe is Westbury. As well as being surrounded by beautiful scenery, Westbury has a culinary theme. You can grab a cup of fresh apple cider and a warm cider doughnut at Cold Hollow Cider Mill, or grab a coffee in the vintage train station. However, most people also stop at the original ben & Jerry’s factory, where you can complete a tour and sample som fresh ice cream.
It is then a short drive further into the Green Mountains and the resort town of Stowe.
Green Mountain Inn or similar
Day 10
| Stowe, Vermont
Today you can get out and about and explore around Stowe.
A good place to start is the Stowe Mountain Resort where you can take the cable car ride up Mount Mansfield, Vermont’s highest peak. It provides jaw-dropping views of the surrounding forests.
At lower levels you can also walk or ride a bicycle around Stowe’s very scenic Recreation Path. This 5 mile path meanders through fields and forests and bridges a number of rivers.
You can also visit the Trapp Family Lodge from Stowe. This Austrian-style lodge, founded by the famous von Trapp family from “The Sound of Music,” is a great spot for a drink, a meal, or just to take in the spectacular surroundings.
Green Mountain Inn or similar
Day 11
| The Kancamagus Highway
Today’s scenic drive takes you from Vermont’s Green Mountains to New Hampshire’s White Mountains.
Head east out of Stowe and drive through the Green Mountains in the direction of the Connecticut River and cross into New Hampshire.
A great place to stop is Franconia Notch State Park. Here you can walk through this natural gorge, where waterfalls, covered bridges, and beautiful granite walls create a magical scene. It is also possible to ride the Cannon Mountain Aerial Tramway for views of the White Mountains and beyond.
The town of Lincoln marks the start of one of America’s most scenic roads, the Kancamagus Highway. The route stretches for 34 miles to the town of Conway. Along the way you can stop for the short hike to Sabbaday Falls, or Rocky Gorge for cascading waterfalls. Alternatively you can pull off the road at Hancock and Sugar Hill Overlooks for panoramic views.
North Conway Grand or similar
Day 12
| Portland Lighthouse & Kennebunkport
North Conway is a bustling town surrounded by the White Mountains. If you haven’t already, you might consider driving or taking the cog railway up Mount Washington, the highest peak in the northeastern United States.
Just ten minutes outside North Conway you can take the short drive up Cathedral Ledge for views of the Saco River Valley.
Bridgton is a quiet lakeside town where you can take a scenic walk around Highland Lake with views of Shawnee Peak, which becomes a ski resort in winter months.
You will reach the Atlantic Coast at Portland, where you can visit the cobblestone streets of the historic waterfront area or just south of downtown, you can stop at Portland Head Lighthouse at Fort Williams Park that offers stunning ocean views
Your destination today is Kennebunkport, a charming harbour town known for its historic maritime homes and beautiful beaches. The town’s busy Dock Square is lined with shops, galleries and restaurants, so you can stop for a lobster roll whilst you are here.
Nonantum Resort or similar
Day 13 & 14
| Welcome to Boston
From Kennebunkport, it is a leisurely drive down the Atlantic Coast to Boston, one of America’s oldest cities.
You may like to stop at some of the maritime villages and towns along the way. You could choose to stop at Ogunquit or York, both of which have beautiful beaches. Alternatively the historic seaport town of Portsmouth features a blend of historic buildings and boutique shops.
Famous for the 1692 witch trials, the town of Salem offers a mix of history, art and coastal views, so is well worth a stop. Pickering Wharf is a lively waterfront area with a collection of historic building that are now a National historic Site.
Boston is a very accessible city, so we would recommend that as you approach the city you head to the airport to return your hire car. You can then transfer independently to your downtown hotel.
During your time in Boston you will be able to follow the Freedom Trail, a two and half mile walking trail that connects 16 historic sites, tracing Boston’s role in the American Revolution, you can also visit the Boston Tea Party Ships and the accompanying museum.
One of Boston’s most picturesque areas, Beacon Hill is known for its cobblestone streets, brick homes, and gas-lit lamps. Acorn Street is especially famous as one of the most photographed streets in the country.
If you have time you can also cross the river to Cambridge and explore the historic campus of Harvard University. In the evening you might like to choose to visit Boston’s North End, the city’s Italian Quarter, to visit some authentic Italian restaurants.
Optional Experience – Old Town Trolley Tour
The Boston Old Town Trolley Tour guides you through the North End and Beacon Hill, as well al the landmarks along the Freedom Trail.
Hilton Boston Park Plaza or similar
Day 15
| Farewell From New England
Sadly this New York and New England holiday has come to an end, although there may still be time for you to visit Faneuil Hall Marketplace or Quincy Market before you depart, for some last minute souvenir shopping.
When you are ready, transfer to Boston Logan International Airport in time to check-in for your return flight or onwards journey.
This Self Drive Includes
Flights & More
Ask your FREEDOM Consultant to include Economy, Premium or Business Class flights for a complete ABTA and ATOL protected package.
They can also add extra nights and experiences in places you choose, to create the exact holiday you are looking for. Popular options include:
- Extra nights in New York, Stowe, Boston or any location on your route
- An upgrade to your car to an SUV, 4×4 or electric vehicle
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 York & New England
15 day Fly Drive – from £1319
With flights from £1819
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
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