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Self-Drive: Towns of New England

15 days from £2199 per person

This itinerary is a fantastic option for those wishing to combine a New York City break with an unforgettable self-drive journey through New England. During this 14 night itinerary, you’ll visit historical villages and towns that offer a wealth of history, each with their own stories to tell.

Packed with a selection of highlights, enjoy exploring charming villages, rolling farmlands, mountain peaks and gleaming lakes. Search for hidden gems at your own pace as you scratch below the surface of New York, Connecticut, Massachusetts, Vermont, New Hampshire and Maine.

Route: New York – Mystic – Lenox – Woodstock - Meredith – Kennebunkport - Boston

Itinerary Highlights

Lose yourself exploring streets lined with world-class attractions, incredible art galleries and some of the best shopping and dining experiences; New York is a truly eccentric and alluring city.

Whilst in Mystic, visit Olde Mistick village, a re-created 18th century village that offers a refreshing change to the modern day we are all used to.

Enjoy fresh seafood along the rocky coastal shores in Kennebunkport, a delightful town brimming with lighthouses, lovely inns and ample opportunities for whale watching.

Itinerary: Self-Drive: Towns of New England

Today, begin your journey by boarding your international flight to New York City. On arrival, make your own way to your hotel in New York City (it is far cheaper to grab a taxi at the airport or use public transportation, but we can pre-book a transfer for you if you prefer – just let us know). The rest of the day is free for you to explore the city at your leisure. (N)
Accommodation in New York: Belvedere Hotel (or similar)
New York is a fast-paced, dazzling and vibrant city. With so much creativity in the air and endless sightseeing options, the streets feel like they come alive as you wander through them. Spend today hopping from one attraction to the next, you might choose to book a city pass that enables you to see as many attractions as you wish, or cherry pick the ones that take your fancy. (N)
Accommodation in New York: Belvedere Hotel (or similar)
Today is again free for you to continue sightseeing and shopping your way around New York. If you want something a little more relaxed for today, you could hire bikes to cycle around central park, or book a helicopter ride to see the city from a bird’s eye view. (N)
Accommodation in New York: Belvedere Hotel (or similar)
This morning you will make your way to the car depot in Manhattan. Once you have collected your car, you’ll begin your 3 hour drive out of the city and through the beautiful Connecticut countryside until you reach Mystic. Mystic is a historical old town that’s home to the tall ships of Mystic Seaport, it’s also a great place to enjoy fine dining and shopping. (N)
Accommodation in Mystic: The Whalers Inn (or similar)
There’s plenty for you to see and do in Mystic today. You might choose to explore the scenic Connecticut River Valley or cruise around the Mystic River. If you fancy something a little more historical, visit Olde Mistick village, a re-created 18th century village that offers a refreshing change to the modern day we are all used to. (N)
Accommodation in Mystic: The Whalers Inn (or similar)
Today you will drive for around 3 hours until you reach the Berkshires scenic country roads and Lenox, the cultural heart of the region. Lenox is a gracious town that’s nestled amongst rolling hills and woodlands. It’s a popular summer retreat for creative and musical artists who wish to enjoy the cultural activities and serenity of the area. Lenox is also home to the Norman Rockwell Museum and Tanglewood music venue. (N)
Accommodation in Lenox: Brooks Farm Inn (or similar)
Today is free for you to explore Lenox. If you are feeling active you might choose to hike part of the Appalachian Trail mountain path followed by an afternoon tea. Alternatively, browse around the town, popping into the arts and crafts stores or go and watch a concert at Tanglewood. (N)
Accommodation in Lenox: Brooks Farm Inn (or similar)
Today you will drive for around 3.5 hours until you reach Woodstock in Vermont, the iconic festival town. When you arrive at this quaint little village, admire the beautifully restored Georgian houses that surround the town’s green and covered wooden bridge, situated in the town centre. With picture postcard scenery, Woodstock oozes character and offers great restaurants, bars and shops right on your doorstep. (N)
Accommodation in Woodstock: Kedron Valley Inn (or similar)
Today is free for you to venture from Maple Syrup Farm to the cider brewery and dairy farm and museum, or drive out to the nearby 165 foot deep, mile-long Quechee Gorge, Vermont’s little Grand Canyon. (N)
Accommodation in Woodstock: Kedron Valley Inn (or similar)
Enjoy taking in the passing sights of traditional white steeple churches, charming villages and ever-changing landscapes as you drive for around 2 hours east until you reach Meredith. Located in the heart of New Hampshire’s lake region and a Gateway to the White Mountains, Meredith is the perfect spot for outdoor enthusiasts as there are a wide variety of activities on offer, on and off the water. (N)
Accommodation in Meredith: The Oliver Lodge (or similar)
Today is free for you to explore Meredith at your leisure today. This beautiful town is conveniently located on a pristine bay to the northwest of Lake Winnipesaukee. Today you might choose to take a cruise onboard the MS Mount Washington, drive to the mountains and visit the scenic villages of North Conway and Jackson or ride on the Conway Scenic Railroad through Crawford Notch. (N)
Accommodation in Meredith: The Oliver Lodge (or similar)
Today you’ll journey back towards the coast. New England’s largest state, Maine, is well known for its dramatic coastline, adventurous outdoor activities, rich heritage, over 60 working lighthouses and, of course, its famous tasty lobster. After a 2 hour drive you’ll reach the coastal town of Kennebunkport. Settle into your delightful country inn and head out to explore the town or relax on the beach. (N)
Accommodation in Kennebunkport: Kennebunkport Inn (or similar)
After breakfast, today is free for you to explore the Kennebunks at your own pace. Go for a drive and snap a picture of Walker’s Point - the Bush Compound, head out on a whale watching boat tour or hop from local museum to quirky craft store. This evening, enjoy a tasty bite of lobster beneath the mesmerising sky, a blend of purple and orange which makes for a really romantic setting. (N)
Accommodation in Kennebunkport: Kennebunkport Inn (or similar)
After breakfast, check out of your country inn and begin your 2 hour journey back to Boston International Airport; stop off at the historical town of Salem if you have time. When you reach the airport, drop your hire car off and board your international flight back to the UK. (N)
Today you will arrive back into the UK, where you will continue your journey home. (N)
**KEY: N = No meals, B = Breakfast, L = Lunch, D = Dinner

What To Do Next?

We design unique, tailor-made holiday itineraries to suit you, by combining your ideas with our knowledge and experience. Once you have an idea of what you’re looking for, or if you require some advice, please call us or complete the enquiry form online for a quotation.

What's included

  • International flights from the UK
  • Hotel accommodation and taxes
  • Car hire as specified

What's not included

  • Cost of visas
  • Travel Insurance
  • Expenses of a personal nature
  • Meals unless specified

Guide to Price

The above price is based on two people travelling together and sharing accommodation in low season. The price is only a guide and can vary according to selected airlines, hotels and date of travel. If you wish to travel with your family, friends or on your own we will be very happy to assist you with your arrangements.

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Experts in Tailor-Made Holidays

For over 30 years, Pettitts Travel have led the way in creating authentic, tailor-made holidays. Our knowledgeable team have first-hand knowledge of our destinations and no two itineraries we prepare are the same.

Please call us for more information or complete the online enquiry form to request a quotation.

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