Romantic Winter Honeymoon Itinerary: Williamsburg & Washington D.C., Virginia with Evening Arrival

Day 1: Arrival & Relax

Williamsburg, VA on December 30, 2025

7:00pm

Check-in at Williamsburg Hotel

Arrive and settle into your cozy accommodations in beautiful Williamsburg to prepare for your honeymoon adventures ahead.
Varies, 1h0m

8:00pm

Light Dinner at Aromas Coffeehouse

Enjoy a casual light dinner with sandwiches, soups, and pastries in a relaxed setting ideal for a gentle start to your visit (Aromas typically closes by 9pm).
USD20, 1h0m

9:30pm

Evening Stroll around Colonial Williamsburg

Take a gentle evening walk near your hotel to soak in the historic ambiance and beautifully lit streets, perfect for a romantic start.
Free, 0h45m
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Day 2: Colonial Exploration & New Year’s Eve

Williamsburg, VA on December 31, 2025

8:30am

Breakfast at The Trellis Restaurant

Start the day with a Southern-inspired breakfast in a charming setting, fueling up for a full day of history.
USD25, 1h0m

10:00am

Colonial Williamsburg and Carriage Ride

Explore the immersive 18th-century historic area with engaging actors and enjoy a romantic horse-drawn carriage ride through historic streets.
USD50 per person for admission; carriage ride extra, 3h0m

1:30pm

Lunch at Christiana Campbell’s Tavern

Dine in a historic colonial tavern offering authentic period recipes in a cozy, atmospheric setting.
USD40, 1h30m

3:00pm

Williamsburg Winery Wine Tasting

Sample some of Virginia’s best wines in a relaxed, intimate tasting room, ideal for honeymoon celebrations.
USD25 per person, 1h30m

7:30pm

New Year’s Eve Dinner at The Fat Canary

Enjoy an elegant and intimate dinner with a special New Year's Eve menu, featuring fusion American cuisine and a warm ambiance.
USD80, 3h0m
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Day 3: Historic Jamestown & Leisure

Williamsburg, VA on January 1, 2026

9:00am

Breakfast at Aroma’s Coffeehouse

Start your New Year with fresh coffee and light pastries in a local favorite cafe with a cozy ambiance.
USD15, 1h0m

10:00am

Visit Historic Jamestowne

Spend the morning exploring America’s first permanent English settlement with interactive exhibits and well-preserved ruins. The site opens at 9am.
USD20 per person, 3h0m

1:30pm

Lunch at The Hound’s Tale

Savor a relaxed, flavorful lunch featuring locally sourced ingredients in a rustic yet stylish atmosphere.
USD35, 1h15m

3:00pm

Pack & Rest

Return to hotel to pack for the trip to Washington D.C. the next day and enjoy some rest time.
Free, 2h30m

6:00pm

Casual Dinner in Williamsburg Historic Area

Choose a relaxed spot such as The Public House for a comforting dinner with local brews and classic American fare.
USD40, 1h30m
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Day 4: Travel to D.C. & Iconic Sights

Washington D.C. on January 2, 2026

8:00am

Breakfast at Blue Talon Bistro, Williamsburg

Enjoy a French-inspired breakfast to start your travel day with a delicious meal.
USD25, 1h0m

9:30am

Drive to Washington D.C.

Travel approximately 3.5 hours northeast to the nation’s capital, settling into your hotel upon arrival.
Variable travel cost, 3h30m

2:00pm

Lunch at Founding Farmers DC

Enjoy fresh, farm-to-table American cuisine in a popular setting near the National Mall.
USD40, 1h15m

3:30pm

Visit National Mall Memorials

Take a romantic late afternoon walk exploring the Lincoln Memorial, Vietnam Veterans Memorial, and Korean War Veterans Memorial.
Free, 2h0m

6:30pm

Sunset at Jefferson Memorial

Experience the beautiful winter sunset by the Tidal Basin, a perfect photo moment for your honeymoon album.
Free, 1h0m

7:30pm

Dinner at Le Diplomate

Indulge in authentic French cuisine with a lovely atmosphere ideal for your first evening in D.C.
USD85, 2h0m
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Day 5: Museums & Culinary Delights

Washington D.C. on January 3, 2026

8:30am

Breakfast at Busboys and Poets

Enjoy a vibrant setting with coffee and diverse breakfast selections, blending culture and comfort.
USD20, 1h0m

10:00am

Smithsonian National Air and Space Museum

Explore fascinating aviation and space history exhibits. The museum opens at 10am and admission is free.
Free, 2h0m

12:30pm

Lunch at Mitsitam Native Foods Cafe

Sample indigenous American cuisine in the National Museum of the American Indian for a unique cultural experience.
USD30, 1h0m

1:45pm

National Gallery of Art

Admire art collections from Renaissance to modern masterpieces. Open 10am-5pm with free entry.
Free, 2h0m

4:00pm

Hot Chocolate Break at The Wydown Coffee Bar

Warm up with a delicious hot chocolate or crafted coffee at this intimate local café.
USD10, 0h30m

7:00pm

Dinner at The Pembroke

Enjoy creative American cuisine paired with elegant decor, perfect for a romantic evening dining experience.
USD90, 2h0m
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Day 6: Capitol Tour & Georgetown

Washington D.C. on January 4, 2026

8:00am

Breakfast at Eastern Market

Start your day with fresh pastries and coffee in the lively and historic Eastern Market setting.
USD15, 1h0m

9:30am

U.S. Capitol and Library of Congress Tour

Enjoy guided tours of these iconic institutions. Advance booking is required for Capitol tours, which typically start early in the morning.
Free (advance booking required), 3h0m

1:00pm

Lunch at Blue Duck Tavern

Savor refined New American dishes in a chic and welcoming environment near the White House.
USD60, 1h30m

3:00pm

Shopping & Walk in Georgetown

Explore Georgetown’s charming streets, boutique shops, and scenic waterfront for a leisurely afternoon outing.
Free (shopping varies), 2h30m

7:30pm

Dinner at Fiola Mare

Celebrate your last full night in D.C. with exceptional Italian seafood dining overlooking the Potomac River.
USD110, 2h0m
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Day 7: Relaxation & Departure

Washington D.C. on January 5, 2026

9:00am

Brunch at Ted’s Bulletin

Enjoy nostalgic comfort food and homemade treats in a cozy, welcoming diner setting.
USD25, 1h30m

11:00am

National Botanical Garden Visit

Experience tranquility strolling through the beautiful indoor and outdoor gardens before your trip home.
Free, 1h30m

1:00pm

Coffee at Compass Coffee

Have a final coffee at a local favorite before preparing for departure.
USD10, 0h30m

2:00pm

Hotel Checkout and Airport Transfer

Gather your belongings and head to the airport with time to spare for a stress-free departure.
Varies, Remaining day
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