Self Drive Tour
Heritage Harbours and Hills

14 Days 13 Nights

Group: No minimum

United States

Comfort

Introduction

Heritage, Harbours, and Hills: Exploring New England by Road

Embark on the Heritage, Harbours, and Hills Tour for a quintessential New England experience. Begin in historic Boston, walking the Freedom Trail and indulging in iconic clam chowder. Explore quaint coastal towns like Salem, Rockport, and Kennebunkport, where maritime charm and lighthouses await. Journey along Maine’s rugged coastline, from Portland to Bar Harbor, savouring fresh lobster and breathtaking vistas. Venture inland to Acadia National Park and the White Mountains for serene landscapes and panoramic views. Discover picturesque villages, maritime history, and the rolling hills of Vermont before returning to Boston. This tour offers history, coastal beauty, and unforgettable memories.

Heritage Harbours and Hills self drive new england
Departure

Boston

Departure Time

TBC

Return Time

TBC

Dress Code

No dress code

Price Includes

  • 13 Nights' Accommodation

  • Intermediate Size Rental Car

  • Local accommodation taxes

  • 8 Breakfasts

  • Windjammer Sailing Trip (Bar Harbor)

  • Kayak the Creek Nature Tour (Cape Cod)

Price Excludes

  • Flights (please let us know if you would like flights including at the time of enquiry)

  • Meals (unless shown in inclusions)

  • Anything not shown as included

Tour Gallery
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Itinerary
  • Day 1: Boston

    Arrive in Boston and settle into your accommodation. Begin your day with a walk along the iconic Freedom Trail, featuring 16 historic stops such as the Old North Church and Paul Revere’s House. Visit the Boston Tea Party Ships and Museum, where interactive exhibits bring history to life. Stroll through Boston Common, the oldest public park in the U.S., and the serene Public Garden.

    Highlights: Freedom Trail, Boston Tea Party Museum, Boston Common, Public Garden

    Meal Suggestion: Union Oyster House for classic New England fare.

  • Day 2: Boston to Kennebunkport

    Collect your hire car and drive north along the scenic coast. Begin with a stop in Salem to visit the Salem Witch Museum and House of the Seven Gables, a literary and architectural gem. Continue to Manchester-by-the-Sea for a brief stroll along the harbor before reaching Rockport, known for Motif Number 1, one of the most painted buildings in America. Stop in Portsmouth, New Hampshire, to explore the charming downtown area before arriving in Kennebunkport, a picturesque coastal town. Enjoy a leisurely evening exploring boutique shops or take a stroll along Dock Square.

    Highlights: Salem Witch Museum, House of the Seven Gables, Rockport’s Motif Number 1, Portsmouth’s Historic Downtown
    Meal Suggestion:

    Dine at The Clam Shack in Kennebunkport for a classic lobster roll.

  • Day 3: Kennebunkport to Camden

    Start your day with a visit to Old Orchard Beach, a classic seaside destination with retro amusements and a scenic pier. Drive to Portland and explore the historic Old Port District, filled with cobblestone streets, unique shops, and restaurants. Don’t miss a visit to Portland Head Light, Maine’s most iconic lighthouse. Continue to Rockland, home to the Maine Lighthouse Museum, before reaching Camden, where the mountains meet the sea. Spend your evening enjoying the harbour views or dining at a waterfront restaurant.

    Highlights: Old Orchard Beach, Portland Head Light, Maine Lighthouse Museum, Camden Harbor

    Meal Suggestion: Enjoy fresh seafood at Peter Ott’s on the Water in Camden.

  • Day 4: Camden to Bar Harbor

    Travel along the scenic coast, stopping in Lincolnville for coffee and views of Penobscot Bay. Continue to Blue Hill, an artsy town filled with galleries and cafes. Arrive in Bar Harbor, the gateway to Acadia National Park. Spend your afternoon walking the Shore Path, which offers stunning views of Frenchman Bay. In the evening, consider a sunset cruise to take in the rugged coastline.

    Highlights: Lincolnville, Blue Hill, Bar Harbor Shore Path, Frenchman Bay

    Meal Suggestion: Savor fresh lobster at Stewman’s Lobster Pound.


     Harbor.

  • Day 5: Free Day in Bar Harbor

    Spend the day exploring Acadia National Park. Begin with a drive to Cadillac Mountain, the highest point on the U.S. East Coast, offering panoramic views. Hike the Jordan Pond Path, known for its serene scenery and famous popovers at the Jordan Pond House. In the afternoon, set sail on a Windjammer Cruise to experience Frenchman Bay’s rugged beauty. End the day with a relaxing walk along the Shore Path or visit the Abbe Museum, which highlights Native American culture.

    Highlights: Acadia National Park, Cadillac Mountain, Jordan Pond Path, Windjammer Cruise

    Meal Suggestion: Enjoy a seafood dinner at a Bar Harbor favorite.

  • Day 6: Bar Harbor to Bethel

    Leave the coast behind as you journey inland to the charming mountain town of Bethel. Start your morning with a visit to Acadia National Park, walking along Ocean Path to see Thunder Hole and Otter Cliffs. Drive through scenic countryside and forests to Bethel, a perfect retreat for outdoor enthusiasts. Spend your evening strolling through the quaint town center or relaxing at your accommodations.

    Highlights: Acadia National Park, Thunder Hole, Otter Cliffs, Bethel’s charm

    Meal Suggestion: Try a local tavern for hearty comfort food.

  • Day 7: Bethel to North Conway

    Begin your day driving through Pinkham Notch, surrounded by the dramatic peaks of the White Mountains. Stop at Glen Ellis Falls, an easy walk to a picturesque waterfall. Ascend Mount Washington via the Auto Road or Cog Railway for spectacular views. Arrive in North Conway, known for its boutique shops and proximity to outdoor adventures. Spend your evening exploring the town or relaxing at a local brewery.

    Highlights: Pinkham Notch, Glen Ellis Falls, Mount Washington, North Conway

    Meal Suggestion: Dine on hearty New England fare at a local favorite.

  • Day 8: North Conway to Londonderry

    Take a scenic drive along the Kancamagus Highway, a legendary route through the White Mountains known for its breathtaking views and stunning foliage in the fall. Stop at Albany Covered Bridge and hike to Sabbaday Falls, a beautiful waterfall surrounded by lush forest. Continue to Franconia Notch State Park to explore the Flume Gorge, a natural wonder with cascading streams and towering granite walls. Arrive in Londonderry, where the rolling hills of southern New Hampshire offer a peaceful retreat.

    Highlights: Kancamagus Highway, Flume Gorge, Sabbaday Falls, Albany Covered Bridge

    Meal Suggestion: Enjoy a farm-to-table meal at a local Londonderry restaurant.

  • Day 9: Londonderry to Stockbridge

    Drive through Vermont’s lush countryside to Manchester, where you can explore the historic Hildene Estate, the Lincoln family home. Continue to Bennington to visit the Bennington Battle Monument and several covered bridges, offering a glimpse of classic New England. Arrive in Stockbridge, a charming town in the Berkshires. Spend your evening exploring the Norman Rockwell Museum, dedicated to the famed American illustrator, or stroll through the quaint streets lined with galleries and shops.

    Highlights: Hildene Estate, Bennington Battle Monument, Norman Rockwell Museum

    Meal Suggestion: Dine at the elegant Red Lion Inn in Stockbridge.

  • Day 10: Stockbridge to Mystic

    Start your morning with a relaxing walk through Stockbridge or a visit to a local cafe. Head south to Old Saybrook, Connecticut, where you can visit the Saybrook Breakwater Lighthouse and enjoy a stroll along the waterfront. Arrive in Mystic, a coastal town steeped in maritime history. Visit the Mystic Seaport Museum, showcasing historic ships and seafaring heritage, or the Mystic Aquarium, home to beluga whales. Spend your evening exploring the town’s charming streets and waterfront restaurants.

    Highlights: Saybrook Breakwater Lighthouse, Mystic Seaport Museum, Mystic Aquarium

    Meal Suggestion: Enjoy fresh seafood at Mystic Pizza, made famous by the movie of the same name.

  • Day 11: Mystic to Cape Cod

    Drive to Narragansett, Rhode Island, to visit its beautiful beaches and enjoy a quick seaside stroll. Continue to Newport to explore its Gilded Age grandeur. Walk the iconic Cliff Walk, which combines dramatic ocean views with the backdrop of historic mansions like The Breakers. Head to Cape Cod, where you can relax by the beach or explore quaint villages.

    Highlights: Narragansett Beach, Newport Cliff Walk, Cape Cod Beaches

    Meal Suggestion: Have lunch at The Mooring in Newport, renowned for its fresh seafood and harbor views.

  • Day 12: Free Day in Cape Cod

    pend the day discovering Cape Cod’s scenic beauty and maritime heritage. Visit Cape Cod National Seashore for unspoiled beaches and picturesque lighthouses. Explore charming villages like Chatham or Provincetown, known for its vibrant arts scene and whale-watching tours. End the day with a classic New England lobster bake.

    Highlights: Cape Cod National Seashore, Chatham, Provincetown, Whale Watching

    Meal Suggestion: Enjoy a traditional lobster bake at a seaside restaurant.

  • Day 13: Cape Cod to Boston

    On your way back to Boston, stop in Plymouth to visit Plimoth Patuxet Museums, which bring the Pilgrim and Wampanoag stories to life. See Plymouth Rock, a symbolic landmark of the Pilgrims’ landing, and tour the Mayflower II, a replica of the original Pilgrim ship. Return to Boston for an evening stroll along the waterfront or a celebratory dinner.

    Highlights: Plimoth Patuxet Museums, Plymouth Rock, Mayflower II

    Meal Suggestion: Dine at Legal Sea Foods, a Boston institution.

  • Day 14: Farewell, Boston

    Spend your final morning exploring Beacon Hill, known for its cobblestone streets and charming brownstones. Take a leisurely stroll through the Boston Public Market for local treats and souvenirs. After lunch, return your rental car and head to the airport for your departure.

    Highlights: Beacon Hill, Boston Public Market

    Meal Suggestion: A light farewell lunch at Panza in the North End for classic Italian cuisine.

Hotels
  • Boston

    The Colonnade Hotel

    Overview: A stylish, modern hotel in the heart of Boston’s Back Bay. Famous for its rooftop pool and prime location near Newbury Street, Fenway Park, and the Prudential Center.

  • Kennebunkport

    Kennebunkport: Waldo Emerson Inn

    Overview: A historic and charming bed-and-breakfast offering personalised service, cosy rooms, and a tranquil atmosphere. Perfect for a relaxing New England getaway.

  • Camden

    Blackberry Inn

    Overview: A charming and colourful Victorian inn located near Camden's harbour. Known for its comfortable rooms, homemade breakfasts, and warm hospitality.

  • Bar Harbor

    Acadia Inn

    Overview: A family-friendly hotel just minutes from Acadia National Park. Offers comfortable accommodations, an outdoor pool, and convenient access to Bar Harbor’s shops and restaurants.

  • Bethel

    Holidae B&B

    Overview: A cosy and welcoming bed-and-breakfast with antique furnishings, homemade breakfasts, and a peaceful mountain setting ideal for a quiet retreat.

  • Londonderry

    Coho Inn

    Overview: A serene boutique inn surrounded by natural beauty, offering charming accommodations, modern amenities, and easy access to Vermont’s Green Mountains.

    the Virginia State Capitol and historic Shockoe Slip.

  • Stockbridge

    The Red Lion Inn

    Overview: A historic boutique hotel with New England charm, featuring antique-filled rooms, a renowned restaurant, and a classic porch overlooking the quaint town of Stockbridge.

  • Mystic

    Taber Inn

    Overview: A cosy and peaceful inn offering spacious rooms, a heated indoor pool, and a quiet garden setting. Located close to Mystic’s attractions, including the Seaport and Aquarium.

  • Cape Cod

    Inn on Main – Yarmouth Port

    Overview: A lovely boutique inn set in a historic home. Known for its elegant rooms, gourmet breakfasts, and central location for exploring Cape Cod’s beaches and villages.

Extras and Optional Fees Payable Locally
National Park Fees
  1. Acadia National Park (Day 6)
    • Fee: $35 per vehicle for a 7-day pass.
    • Details: This pass covers access to all areas within the park, including Cadillac Mountain, Jordan Pond, and Ocean Path.
State Park Fees

  1. Franconia Notch State Park (Day 8)

    • Fee: $5 per adult for access to attractions like Flume Gorge.
    • Details: Some specific activities or parking areas may have additional costs.

  2. Pemaquid Point Lighthouse Park (Day 3)

    • Fee: $3 per person for access to the lighthouse and park.
    • Details: This fee supports the maintenance of the historic site.
Local Fees

  1. Mount Washington Auto Road (Day 7)

    • Fee: $45 per vehicle for the driver, plus $20 per passenger.
    • Details: Includes access to the summit and a tour guide booklet.

  2. Mystic Seaport Museum (Day 10)

    • Fee: $28.95 per adult, $19.95 per child (ages 4–14).
    • Details: Includes access to exhibits, historic vessels, and the village.

  3. Newport Mansions (Day 11)

    • Fee: Approximately $25–$35 per mansion, depending on the property.
    • Details: Discounts are available for bundled mansion tickets.
Optional Fees

  1. Cadillac Mountain Summit Reservation (Acadia National Park)

    • Fee: $6 per vehicle for timed entry reservations during sunrise or peak hours.
    • Details: This is separate from the Acadia park entry fee.

  2. Swan Boats in Boston (Day 1)

    • Fee: $4 per adult, $3 per child (ages 2–15).

  3. Mount Washington Cog Railway (Day 7)

    • Fee: $72 per adult, $39 per child (ages 4–12).
    • Details: An alternative to the Auto Road.
Tips
  • Consider purchasing an America the Beautiful Pass ($80) if you plan to visit additional national parks within a year, as it covers Acadia National Park and other federal lands.
  • Local fees for museums and guided tours vary but are generally noted in the itinerary for budgeting.

Enquiry Form

HIGHLIGHTS

  1. Freedom Trail, Boston – Walk this iconic route to explore 16 historic sites, including Paul Revere’s House and the Old North Church.
  2. Boston Tea Party Ships & Museum – Relive the events that sparked a revolution with immersive exhibits.
  3. Quincy Market & Union Oyster House – Savour Boston’s famous clam chowder and local seafood.
  4. Salem Witch Museum – Dive into the history of the 1692 witch trials.
  5. Motif Number 1, Rockport – Snap photos of this famed red fishing shack.
  6. Portland Head Light – Visit Maine’s most photographed lighthouse near Portland.
  7. Old Orchard Beach – Enjoy retro amusements and stroll along the pier.
  8. Acadia National Park – Explore Cadillac Mountain, Jordan Pond Path, and stunning coastal views.
  9. Windjammer Sailing Trip, Bar Harbor – Sail past picturesque islands and spot marine wildlife.
  10. Marginal Way, Ogunquit – Walk this scenic coastal path with sweeping ocean views.
  11. Pemaquid Point Lighthouse – Admire breathtaking coastal vistas and early settlement history.
  12. Flume Gorge, Franconia Notch – Wander through dramatic granite walls and cascading streams.
  13. Kancamagus Highway – Drive this legendary byway, known for foliage and mountain views.
  14. Mount Washington Auto Road – Experience panoramic vistas from the summit.
  15. Norman Rockwell Museum, Stockbridge – Discover the works of America’s iconic illustrator.
  16. Mystic Seaport Museum – Step into maritime history at this living museum.
  17. Newport Mansions – Tour Gilded Age marvels like The Breakers and Marble House.
  18. Cape Cod Beaches & Lighthouses – Relax on pristine beaches and visit historic lighthouses.
  19. Plimoth Patuxet Museums, Plymouth – Immerse yourself in the Pilgrims’ and Wampanoag’s stories.
  20. Boston Harborwalk – Stroll along the waterfront with views of the city skyline.

This tour itinerary is flexible and can be adapted as required. 

A family friendly option is available on request. 

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