New Chat

Download App

Ask me about your trip!

There are no messages for this conversation.

Free AI trip planner

Ultimate 5-Day Trip to Washington D.C. and Surroundings

Ultimate 5-Day Trip to Washington D.C. and Surroundings Itinerary

Last updated: 2024 Jun 14

Monuments and Museums

Morning
Begin your day with a hearty breakfast at Not Your Average Joe's to fuel up for a morning of exploration. After breakfast, take a guided tour of the iconic Washington Monument and enjoy panoramic views of the city.
Afternoon
For lunch, indulge in gourmet burgers at Melt Gourmet Cheeseburgers. Spend your afternoon visiting the historic Lincoln Memorial and the thought-provoking Smithsonian National Museum of American History.
Evening
Dine at The Wine Kitchen, offering a cozy atmosphere and a selection of over 20 wines by the glass. End your evening with a twilight tour of the enchanting Jefferson Memorial.
Bedtime
Find amazing hotels in Washington D.C..

Winery Tour and Culinary Delights

Morning
Start with a delightful breakfast at Lightfoot Restaurant, known for its elegant ambiance. Then, embark on a scenic drive to the countryside for a morning of wine tasting at the renowned Loudoun County Wineries.
Afternoon
Enjoy a leisurely lunch at Tuscarora Mill, housed in a historic grain mill, and savor farm-to-fork cuisine. Afterward, take in the natural beauty with a visit to the picturesque Harper's Ferry, just a short drive from Leesburg.
Evening
For dinner, experience the vibrant atmosphere and eclectic menu at Delirium Cafe Leesburg, known for its extensive beer selection. Cap off the evening with a stroll through downtown Leesburg's charming shops and galleries.
Bedtime
Find amazing hotels in Leesburg, Virginia.

Capitol Exploration and Evening Cruise

Morning
Kick off the day with a delicious breakfast at Blue Ridge Grill, offering a menu of American classics. Then, immerse yourself in the history of the United States with a tour of the US Capitol Building.
Afternoon
Enjoy a leisurely lunch at Firebirds Wood Fired Grill, known for its upscale-casual dining and bold flavors. Spend your afternoon exploring the fascinating exhibits at the Smithsonian National Air and Space Museum (NASM).
Evening
Dine in style at Cocina on Market, which features a blend of Latin American flavors in a chic setting. Conclude your day with an illuminating Monuments by Night Electric Bike Tour with Experienced Guide to see the iconic landmarks in a different light.
Bedtime
Find amazing hotels in Washington D.C..

Honoring Heroes and Scenic Views

Morning
Start with breakfast at King Street Oyster Bar, known for its fresh seafood and lively atmosphere. Then, pay your respects at the solemn Arlington National Cemetery.
Afternoon
Have a casual lunch at Not Your Average Joe's, where you can enjoy a diverse menu. Afterward, visit the US Marine Corps War Memorial (Iwo Jima) and enjoy the views of the city from this vantage point.
Evening
For dinner, head to The Wine Kitchen for a sophisticated dining experience with a focus on local and seasonal ingredients. Wrap up your day with a relaxing stroll along the vibrant Reston Town Center, known for its shops and entertainment.
Bedtime
Find amazing hotels in Arlington, Virginia.

Historic Estates and Evening Entertainment

Morning
Enjoy a delightful breakfast at The Wine Kitchen before embarking on a journey to the past at the George Washington's Mount Vernon. Explore the historic estate and gardens.
Afternoon
Savor a sumptuous lunch at Cocina on Market, where the flavors of the Mediterranean come to life. Spend your afternoon at the Smithsonian National Museum of Natural History, discovering its fascinating exhibits.
Evening
Dine at Blue Ridge Grill for a refined yet relaxed meal, and then experience the vibrant nightlife of Downtown Leesburg. Enjoy live music or a performance to cap off your trip.
Bedtime
Find amazing hotels in Washington D.C..

Top Washington D.C. Travel Videos

kayakFind the right stay during your trip.
Got a question about your trip?