Highlights of New England: Rail & Drive

Arrive in Boston and transfer on your own to your centrally located hotel. Boston is a gorgeous destination, brimming with American history and fantastic seafood - much of which is easily accessible on foot. Spend the remainder of the day getting acquainted with the city's offerings. Overnight Boston.

From Beacon Hill's charming architecture to sites that made the city famous, this morning's walking tour offers an insider's look at Boston. This excursion is headed by an entertaining local guide that brings the local lore and history to life. As you walk, enjoy glimpses at landmarks like Boston Harbor, the Massachusetts State House, Quincy Market and Boston Public Garden. Walk along the Freedom Trail, soaking in its sites, and listen to stories about the Boston Massacre. Grab lunch at one of the many local options in the North End, famous for its seafood and delicious Italian specialties.

Make your way to the station to board Amtrak's Downeaster late afternoon train. The train takes us on a northerly route along the coast from Boston to Portland, Maine, over the course of approximately 2 1/2 hours. On arrival, transfer to your hotel on your own with the rest of the day evening free to sightsee or soak in the quaint seaside vistas. Diverse eateries and craft breweries abound throughout Portland and are the best place to get your first taste of Maine. Overnight Portland.

Lobster, chowder and clams - oh my! After an easy morning that affords time to explore Portland's cafés and coffee shops, join a local guide for lunchtime Seafood Lovers walking tour. This expedition takes you along the waterfront to see the lobster boats coming in from their morning's work. Your guide presents information about the industry and recounts interesting anecdotes that entertain as you walk. The prize after your walk: authentic Maine lobster rolls, clams and seafood chowder from a local restaurant. It is hard to top this.

The rest of the day is at leisure. Portland is all delightful scenery and vibrant culture. There is a thriving art community presented through galleries, theaters and museums. Commercial Street, sitting aside the water's edge, is the place to go for artisan goods, boutique shopping and fantastic drinks and eats. Marvel at the beauty of the cobbled streets and old-world buildings as you wander. Lighthouses are plentiful throughout the region, as are beaches and parks. 

For a more structured introduction to this working waterfront, consider a 2-hour tour of Portland's must see sights. This excursion includes three local lighthouses including Portland Head Light. Visits to Commercial Street and Old Port district are also included. (Lunch is not included on this tour) Overnight Portland.

• Lunch

Take the reins to this independent vacation into your own hands this morning when you pick up your rental car from Avis. The day's journey presents the contrasts of New England when you drive inland toward the White Mountains in New Hampshire. 

Stop in Bretton Woods, home to the Mount Washington Cog Railway - the world's first cog railroad. This popular attraction offers spectacular views over the White Mountains and is an impressive way to get acquainted with the region. Fully restored vintage rail cars make the one-hour trip to the summit. Once at the top of the highest peak in the Northeast, marvel at the 360-degree views that include up to five states, the Atlantic Ocean and even Southern Canada. Also at the top, peruse the visitors center, which includes a post office and a fascinating museum, and walk along the numerous hiking trails. After returning from your mountain adventure, continue your journey to White Mountains region hotel, drop off your bags, and begin your explorations. You may wish to go leaf peeping on the famous Kancamagus Highway or venture into Franconia Notch State Park for hiking, water activities or a ride on the aerial tramway. Or maybe you will sip a local brew at one of the microbreweries while looking over the colorful scenery. Overnight White Mountains Region, NH.

A day of endless possibilities lies ahead in the White Mountains. Downtown North Conway is a fantastic place to soak in quintessential New England, with its lovingly restored historic buildings and endless charms. Bakeries sit aside bookstores and lovely boutiques. Heading out into nature, Diana's Baths is all beautiful waterfalls surrounded by colorful forests. The town is also home to the Conway Scenic Railroad, which offers an intimate look at the mountains. Much like the rest of New England, the craft beer and wine scene is robust here, and there are plenty of places to taste artisan-created ales and sip tasty wine varietals.

Late this afternoon, soak in panoramic vistas of the lush White Mountains as you drive along the Kancamagus Highway to North Woodstock, where the Café Lafayette Dinner Train* awaits. Step aboard restored 1950s-era carriages and settle in for a two-hour ride through the mountains by way of the Pemi River Valley. As the scenery unfolds, a delicious five-course meal is presented, with each dish being more delicious than the last. Overnight White Mountains Region, NH.

*Please note the Café Lafayette Dinner Train Dress Code is Business Casual - Slacks, collared shirt, skirts, nice jean or shorts are all welcome.  Ripped clothing and tank-tops are discouraged. 

• Dinner

The small towns and lovely scenes of New Hampshire fade into the backdrop as you say goodbye to the White Mountains this morning and drive back to Portland. When you arrive, drop off your rental car and transfer to the train station for your return journey on Amtrak Downeaster. Reflect on quintessential New England adventures as you near Boston. On arrival, make your way to your hotel and take the rest of the day at leisure. Overnight Boston.

Your New England rail & drive vacation concludes this morning when you check out of your hotel. Feel free to continue your explorations on your own or make your way to the airport for your return flight home.