Make this trip your own
Create your own free, personalized itinerary in seconds — then sign up to save and edit it.
Create my version

Romantic 5-Day Honeymoon Itinerary in Boston, Massachusetts

Viewed by 80 travelers

Day 1: Arrival and Exploration

Boston, MA

9:00AM

Breakfast at Tatte Bakery & Cafe

Start your honeymoon with a delightful breakfast at Tatte, known for its exquisite pastries and fresh coffee.
Head to Tatte Bakery located at 128 C. Newbury St, just a short walk from the Boston Common.
USD30, 1 hour

10:30AM

Visit Boston Common and Public Garden

Stroll hand in hand through Boston Common followed by a serene visit to the beautiful Public Garden, perfect for a romantic moment.
Walk from Tatte to Boston Common (10 min).
Free, 1.5 hours

12:00PM

Lunch at Legal Sea Foods

Dive into a classic New England experience with a delicious seafood lunch at this local favorite.
Head towards Legal Sea Foods at 26 S Market St, a 15-minute walk.
USD60, 1.5 hours

1:30PM

Freedom Trail Walking Tour

Take a guided tour along the Freedom Trail, uncovering Boston's historical significance while exploring its charm.
Start the tour at Boston Common, which is your earlier stop.
USD40 per person, 2.5 hours

4:00PM

Relax at The Lenox Hotel Rooftop

Unwind with a stunning view of the city while enjoying some champagne at the rooftop bar.
Take a 10-minute ride via Uber to The Lenox Hotel, 61 Exeter St.
USD50, 1 hour

6:00PM

Dinner at Mamma Maria

Indulge in an intimate dining experience with exquisite Italian fare in the heart of the North End.
A 10-minute Uber to Mamma Maria, 3 North Square.
USD100, 2 hours
Find Hotels in Boston

Day 2: Cultural Immersion

Boston, MA

9:00AM

Breakfast at Flour Bakery

Savor a hearty breakfast at Flour, known for its sticky buns and other delicious baked goods.
20-minute walk to Flour Bakery at 1145 Washington St.
USD25, 1 hour

10:30AM

Isabella Stewart Gardner Museum

Explore the enchanting art collections and breathtaking architecture of this unique museum.
A quick 10-minute ride or walk to the museum, 25 Evans Way.
USD20 per person, 2 hours

1:00PM

Lunch at Giacomo's Ristorante

Enjoy a flavorful Italian lunch at this cozy spot in the North End, famous for its pasta dishes.
Just a 15-minute ride back to the North End.
USD60, 1.5 hours

2:30PM

Visit the Boston Museum of Fine Arts

Immerse yourselves in world-class art collections that offer a romantic atmosphere.
15-minute T ride to the museum, 465 Huntington Ave.
USD25 per person, 2.5 hours

5:00PM

Sunset Cruise on the Charles River

End the day with a romantic sunset cruise on the Charles River, taking in the stunning views of the Boston skyline.
Cruise departs from the dock near the Museum of Science.
USD80 per person, 2 hours

7:30PM

Dinner at Oleana

Experience Mediterranean flavors and a cozy atmosphere at this acclaimed restaurant.
An Uber ride approximately 15 minutes to Oleana at 134 Hampshire St.
USD100, 2 hours
Find Hotels in Boston

Day 3: Historical Exploration

Boston, MA

9:00AM

Breakfast at The Paramount

Kickstart your day with a delicious and hearty breakfast in a quaint setting.
Head to The Paramount at 44 Charles St, close to Boston Common.
USD30, 1 hour

10:30AM

Tour the Boston Tea Party Ships and Museum

Learn about the significant event in American history with an interactive experience.
A 10-minute walk to the museum at 306 Congress St.
USD30 per person, 1.5 hours

12:00PM

Lunch at Union Oyster House

Savor a traditional New England clam chowder at the oldest restaurant in the United States.
A 10-minute walk to Union Oyster House, 41 Union St.
USD50, 1.5 hours

1:30PM

Explore the North End

Wander through the historic streets of the North End, stopping by charming Italian bakeries and shops.
A short walk through the downtown area.
Free, 1.5 hours

3:00PM

Visit Paul Revere's House

Step inside the home of the famous patriot and explore the exhibits portraying colonial life.
Located in the North End, just a few blocks away.
USD6 per person, 1 hour

5:00PM

Dinner at Antico Forno

End your day with delicious wood-fired pizza in a cozy setting.
A short stroll to the restaurant at 93 Salem St.
USD70, 1.5 hours
Find Hotels in Boston

Day 4: Nature and Relaxation

Boston, MA

9:00AM

Breakfast at The Coffee Shop

Enjoy a relaxed breakfast at this charming cafe, known for its delicious bagels and coffee.
Located at 9 Hunt St, a 20-minute walk from the Central Boston area.
USD20, 1 hour

10:30AM

Visit the Arnold Arboretum

Stroll through the beautiful landscapes filled with diverse plant species, perfect for a romantic walk.
Take the T to Roslindale stop, then an Uber to the Arboretum.
Free, 2 hours

12:30PM

Lunch at Mr. Bartley's Burger Cottage

Indulge in some of Boston's best burgers in an adorable diner atmosphere.
A 20-minute ride back to Harvard Square.
USD50, 1.5 hours

2:00PM

Explore Harvard University

Wander through the picturesque campus of America's oldest university, soaking in the educational ambience.
Easily accessible by foot from Mr. Bartley's.
Free, 1.5 hours

4:00PM

Visit the Isabella Stewart Gardner Museum

If you missed this artful gem, now is the perfect time to revisit and relive your experience or explore anew.
Return via T to the museum.
USD20 per person, 2 hours

6:30PM

Dinner at The Capital Grille

Savor an exquisite steak dinner in a refined setting, perfect for a romantic night out.
An Uber ride back to the center at 900 Boylston St.
USD150, 2 hours
Find Hotels in Boston

Day 5: Farewell Boston

Boston, MA

9:00AM

Breakfast at The Friendly Toast

Enjoy a quirky breakfast at The Friendly Toast, known for its eclectic decor and creative dishes.
A 15-minute Uber to The Friendly Toast at 35 Lancaster St.
USD40, 1 hour

10:30AM

Stroll Through the Boston Harborwalk

Take a romantic walk along the waterfront, enjoying the scenic views and breezy atmosphere.
Easily accessible from the restaurant.
Free, 1 hour

12:00PM

Lunch at Row 34

Taste some of the freshest seafood plates and craft beers in a chic yet laid-back environment.
Head to Row 34 at 383 Congress St, just a 10-minute walk.
USD70, 1.5 hours

1:30PM

Visit Boston's New England Aquarium

Explore the diverse marine life and indulge in the interactive exhibits together as a lovely couple.
A 10-minute walk to the aquarium at 1 Central Wharf.
USD30 per person, 2 hours

3:30PM

Last Shopping at Faneuil Hall Marketplace

Wrap up your honeymoon with some last-minute shopping and local souvenir hunting.
A short 10-minute walk from the aquarium.
Varies, 1.5 hours

5:00PM

Farewell Dinner at Top of the Hub

Enjoy a stunning view of the Boston skyline during your farewell dinner at this rooftop bar and restaurant.
Uber to Top of the Hub at 800 Boylston St.
USD150, 2 hours
Find Hotels in Boston
0
Like this trip? Make your own version.
A free, personalized itinerary in seconds — sign up to save and edit it.
Create my version

More About boston

Trip Packing List: Boston (Feb 27–Mar 5, 2026)
Packing List
Trip Packing List: July in Boston, NH (for a 9-year-old)
Packing List
Boston Weather Guide: Seasons, Coastal Breezes & Nor'easters
Weather Guide
Full Guide to Michelin Star Cities: 2025 Updated List
Travel Expert
Global Michelin Cities & US Travel Tiers from New York
Travel Expert
Itinerary created by AI-assisted, human-reviewed

Plan Your boston Trip

Cost Estimator
Estimate your trip budget
Packing List
Get a custom checklist
Weather Expert
Check weather & best time to go