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Romantic 5-Day Honeymoon Itinerary in Boston and Cape Cod

Viewed by 79 travelers

Day 1: Explore Historic Boston

Boston, USA

8:00AM

Breakfast at Tatte Bakery

Enjoy fresh pastries and artisanal coffee at this charming bakery that sets a romantic tone for your day.
Walk 10 minutes from your hotel.
USD30, 1 hour

9:30AM

Visit the Freedom Trail

Stroll hand-in-hand along the 2.5-mile Freedom Trail and discover Boston’s rich history at sites like the State House and Paul Revere’s House.
Follow the red brick line through the city.
USD0, 3 hours

1:00PM

Lunch at The Union Oyster House

Savor classic New England clam chowder in America’s oldest continuously operating restaurant, which adds a historic flair to your meal.
Walk 15 minutes from the Freedom Trail.
USD50, 1.5 hours

2:30PM

Explore Boston Common

Relax in the lush greenery of Boston Common, a perfect setting for a romantic afternoon, where you can enjoy a scenic swan boat ride.
Walk 10 minutes from lunch.
USD15 (for boat ride), 1 hour

4:00PM

Visit the Massachusetts State House

Take a guided tour of this iconic building with its golden dome, which offers a glimpse into the state’s history.
Walk 5 minutes from Boston Common.
USD0, 1 hour

6:00PM

Dinner at Oleana

Enjoy a romantic dinner featuring Mediterranean-inspired dishes made from local ingredients at this award-winning restaurant.
Take a short Uber ride (10 minutes).
USD150, 2 hours
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Day 2: Cultural Boston

Boston, USA

8:00AM

Breakfast at Flour Bakery

Indulge in their famous sticky buns and artisan breakfast sandwiches to fuel your cultural day ahead.
Take the subway to the South End.
USD25, 1 hour

9:30AM

Explore the Museum of Fine Arts

Immerse yourself in art and creativity at one of the USA's largest museums, showcasing everything from ancient artifacts to contemporary art.
Take the subway to the museum.
USD25, 2 hours

12:00PM

Lunch at The Salty Pig

Enjoy artisanal charcuterie and gourmet pizzas in a warm and inviting atmosphere, perfect for couples.
Take the Green Line subway.
USD45, 1.5 hours

1:30PM

Visit the Isabella Stewart Gardner Museum

Explore this charming museum filled with an eclectic collection of art within a beautiful Venetian-style palace.
Walk 15 minutes from lunch.
USD15, 1.5 hours

3:30PM

Stroll through the Public Garden

Wander among the beautiful flowers and take a picture with the famous Make Way for Ducklings statues.
Walk 10 minutes from the museum.
USD0, 1 hour

6:00PM

Dinner at No.9 Park

Revel in a fine dining experience that features French and Italian influences in a cozy atmosphere with views of Boston Common.
Take a short walk (15 minutes).
USD180, 2 hours
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Day 3: Journey to Cape Cod

Cape Cod, USA

8:00AM

Breakfast at George's Bakery

Start your drive with a delightful breakfast of freshly baked goods and coffee at this local favorite before your trip.
Drive to the bakery (30 minutes).
USD20, 1 hour

9:00AM

Drive to Cape Cod

Hit the road for a scenic drive to Cape Cod, known for its charming small towns and beautiful coastlines.
Drive for approximately 1.5 hours.
USD0, 1.5 hours

10:30AM

Check into your hotel

Settle into one of Cape Cod's cozy inns, known for their romantic ambiance and sea views.
Drive 15 minutes to your hotel.
USD200 (per night), 1 hour

12:00PM

Lunch at The Lobster Pot

Enjoy fresh seafood with a stunning view of Provincetown Harbor during this delicious lunch break.
Drive 30 minutes from your hotel.
USD70, 1.5 hours

2:00PM

Explore Cape Cod National Seashore

Stroll along the pristine beaches and witness the breathtaking views of the Atlantic Ocean.
Drive 10 minutes from lunch.
USD0, 2 hours

5:00PM

Dinner at The Pearl Restaurant

Dine on a seasonal menu featuring local ingredients with ocean views that enhance the romantic atmosphere.
Drive 20 minutes from the national seashore.
USD120, 2 hours
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Day 4: Relax and Unwind in Cape Cod

Cape Cod, USA

8:00AM

Breakfast at The Breakfast Room

Enjoy a delightful breakfast in a quaint setting, offering hearty American favorites and delicious coffee.
Walk 10 minutes from your hotel.
USD30, 1 hour

9:30AM

Beach Day at Nauset Beach

Relax on one of Cape Cod’s most beautiful beaches, where you can soak up the sun or take a romantic walk along the shore.
Drive 25 minutes to Nauset Beach.
USD0, 3 hours

1:00PM

Lunch at Arnold's Lobster and Clam Bar

Savor clams, lobster rolls, and fresh seafood in a casual setting that captures the essence of Cape Cod dining.
Drive 5 minutes from the beach.
USD50, 1.5 hours

2:30PM

Visit Chatham Lighthouse

Explore the picturesque lighthouse and its stunning surroundings, taking stunning photos to commemorate your trip.
Drive 20 minutes from lunch.
USD0, 1 hour

4:00PM

Wine Tasting at Truro Vineyards

Enjoy a romantic wine tasting session at this local vineyard known for its beautiful scenery and fine wines.
Drive 30 minutes to the vineyard.
USD35, 2 hours

7:00PM

Dinner at The Ocean House

Indulge in an exquisite dinner with cliffside views of the ocean, featuring fresh seafood and elegant service.
Drive 20 minutes from the vineyard.
USD150, 2 hours
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Day 5: Last Day in Cape Cod

Cape Cod, USA

9:00AM

Breakfast at The Red Inn

Enjoy a leisurely breakfast overlooking the water, featuring various breakfast favorites in a relaxed setting.
Drive 10 minutes from your hotel.
USD40, 1 hour

10:30AM

Visit Provincetown

Explore this vibrant town, known for its art galleries, unique shops, and beautiful beaches, making it an iconic Cape Cod destination.
Drive 20 minutes from the inn.
USD0, 2 hours

1:00PM

Lunch at The Crown and Anchor

Dine at this lively restaurant and enjoy a great meal while taking in the lively atmosphere of Provincetown.
Walk 10 minutes from your visit.
USD60, 1.5 hours

2:30PM

Relax at Race Point Beach

Spend your afternoon relaxing on one of the most beautiful beaches, with an option for a drowsy beach nap or a romantic walk.
Drive 15 minutes from lunch.
USD0, 3 hours

5:30PM

Farewell Dinner at The Mews Restaurant

Celebrate your last night with a candlelit dinner featuring fresh seafood and a stunning view of the water, the perfect ending to your romantic honeymoon.
Drive 20 minutes from the beach.
USD130, 2 hours
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