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Romantic 5-Day New England Honeymoon Itinerary

Viewed by 145 travelers

Day 1: Boston Exploration

Boston, MA

9:00AM

Brunch at The Paramount

Start your day with a leisurely brunch at The Paramount, known for its delicious pancakes and perfectly brewed coffee in a cozy atmosphere.
Walking distance from most downtown hotels.
USD30, 1.5 hours

11:00AM

Freedom Trail Tour

Take a guided walking tour along the historic Freedom Trail to explore Boston's rich history and iconic landmarks.
Starting point at Boston Common.
USD25, 2 hours

1:00PM

Lunch at Legal Sea Foods

Enjoy a famous New England chowder and fresh seafood at this iconic eatery, overlooking the harbor.
Short drive or a 15-minute walk from the Freedom Trail.
USD60, 1.5 hours

3:00PM

Visit the Boston Public Garden

Stroll hand-in-hand through the beautiful Boston Public Garden, known for its swan boats and vibrant flowerbeds.
Located adjacent to Boston Common.
Free, 1 hour

5:00PM

Check-in at a Romantic Hotel

Settle into your room at The Liberty Hotel, a beautifully converted former jail with upscale amenities.
Located in Beacon Hill.
USD350, 2 hours

7:00PM

Dinner at Top of the Hub

Dine at this upscale restaurant offering stunning views of the Boston skyline and an exquisite menu.
Short drive or taxi ride.
USD150, 2 hours
Find Hotels in Boston

Day 2: Cape Cod Retreat

Cape Cod, MA

8:00AM

Breakfast at the Inn

Enjoy a complimentary breakfast at the hotel before heading to Cape Cod.
Onsite at The Liberty.
Free, 1 hour

9:00AM

Drive to Cape Cod

Take a scenic drive to Cape Cod while enjoying beautiful coastal views along the way.
Route 3 South to Route 6.
Gas USD30, 1.5 hours

10:30AM

Explore Provincetown

Wander through the charming streets of Provincetown, known for its art galleries and vibrant shops.
Free parking available in town.
Free, 1.5 hours

12:00PM

Lunch at The Lobster Pot

Indulge in a lobster roll overlooking the beach at this beloved seafood restaurant.
Short walk from the center of Provincetown.
USD45, 1.5 hours

2:00PM

Beach Time at Herring Cove

Relax together on the sandy shores of Herring Cove Beach, perfect for sunbathing and strolling on the beach.
Short drive from Provincetown.
Free, 2 hours

5:00PM

Check-in at The Chatham Inn

Experience a romantic evening by checking into the luxurious Chatham Inn, set in a picturesque coastal town.
Located in Chatham.
USD300, 1 hour

7:30PM

Dinner at Chatham Bars Inn

Dine at this elegant restaurant on the waterfront, offering farm-to-table cuisine and breathtaking views.
Short drive from the inn.
USD180, 2 hours
Find Hotels in Cape Cod

Day 3: Nantucket Adventure

Nantucket, MA

8:00AM

Breakfast at The Chatham Inn

Start the day with a delightful breakfast at the inn, basking in the cozy ambiance.
Onsite at The Chatham Inn.
Free, 1 hour

9:00AM

Ferry to Nantucket

Board the ferry and enjoy scenic ocean views as you travel to the picturesque island of Nantucket.
Board at Harwich Port ferry terminal.
USD40, 1 hour

10:30AM

Nantucket Historic District Tour

Explore the historic charm of Nantucket's cobblestone streets and unique shops.
Walking distance from the ferry terminal.
Free, 2 hours

12:30PM

Lunch at Cisco Brewers

Savor a laid-back lunch with local craft beers and tasty food truck options at Cisco Brewers.
Short drive or a bike ride from downtown.
USD50, 2 hours

2:30PM

Whale Watching Tour

Embark on a thrilling whale watching tour to spot majestic humpback whales in their natural habitat.
Leave from the harbor in Nantucket.
USD75, 3 hours

6:00PM

Check-in at The White Elephant

Enjoy a romantic atmosphere while checking in at one of the best hotels on Nantucket island.
Located along the waterfront.
USD400, 1 hour

8:00PM

Dinner at Brant Point Grill

Indulge in a fine dining experience with fresh seafood and perfectly crafted cocktails at this waterfront restaurant.
Onsite at The White Elephant.
USD170, 2 hours
Find Hotels in Nantucket

Day 4: Newport Elegance

Newport, RI

8:00AM

Breakfast at The White Elephant

Enjoy a relaxing breakfast on the terrace with ocean views at your hotel.
Onsite at The White Elephant.
Free, 1 hour

9:30AM

Ferry back to Cape Cod

Return via ferry to Cape Cod where you'll drive towards Newport, RI.
Board at the Nantucket ferry terminal.
USD40, 1 hour

11:00AM

Drive to Newport

Enjoy a scenic drive to Newport featuring coastal views and charming towns.
Route 28 to US-6 E.
Gas USD20, 1.5 hours

12:30PM

Lunch at The Mooring

Feast on fresh seafood and enjoy beautiful harbor views at this popular waterfront restaurant.
Immediate proximity to the harbor.
USD80, 1.5 hours

2:00PM

Visit the Breakers Mansion

Explore the opulent Gilded Age mansion that showcases Newport's stunning architecture and history.
Short drive from the restaurant.
USD25, 1.5 hours

4:00PM

Check-in at Gurney's Newport Resort

Settle into your luxurious seaside accommodations at Gurney's where romance abounds.
Located on Goat Island.
USD300, 1 hour

7:00PM

Dinner at The Cliff Walk

Stroll along the famous Cliff Walk and enjoy dinner at a restaurant with views of the stunning coastline around Newport.
On-site dining options available.
USD150, 2 hours
Find Hotels in Newport

Day 5: Acadia National Park Bliss

Acadia National Park, ME

7:30AM

Breakfast at Gurney's

Enjoy a delightful breakfast while overlooking the harbor at Gurney's Newport Resort.
Onsite at Gurney's.
Free, 1 hour

8:30AM

Drive to Acadia National Park

Begin your drive to the breathtaking Acadia National Park, known for its rugged coastlines and scenic vistas.
Follow Route 1 N.
Gas USD30, 3 hours

11:30AM

Visit Jordan Pond

Explore the picturesque Jordan Pond, famous for its clear waters and the stunning Bubbles mountains in the background.
First stop inside Acadia National Park.
Free, 1.5 hours

1:00PM

Lunch at The Jordan Pond House

Dine on the terrace at The Jordan Pond House, famous for its popovers and lobster stew.
Located adjacent to Jordan Pond.
USD60, 1.5 hours

3:00PM

Hiking Cadillac Mountain

Take in sweeping views from the top of Cadillac Mountain, the highest point on the East Coast.
Short drive from Jordan Pond.
Free, 2 hours

6:00PM

Check-in at The Bluenose Inn

Relax in your charming room at The Bluenose Inn with ocean views after an active day.
Located in Bar Harbor.
USD250, 1 hour

8:00PM

Dinner at The Looking Glass Restaurant

End the day with a delicious dinner featuring local seafood and stunning views at The Looking Glass.
Conveniently located at The Bluenose Inn.
USD100, 2 hours
Find Hotels in Acadia National Park
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