Things to do in Annapolis
Discover amazing Annapolis activities and premium in-home experiences.
Annapolis, the vibrant capital by the Chesapeake Bay, exudes a rich blend of American history and nautical charm. With its cobblestone streets, colonial architecture, and bustling waterfront filled with sailboats gliding through the harbor, this city warmly welcomes you to explore its spirited maritime culture. Whether you're savoring fresh seafood or strolling along picturesque docks at sunset's glow, Annapolis offers an unforgettable experience steeped in tradition and coastal beauty.
Popular Activities in Annapolis
Private Tiki Boat Cruise from Nautilus Point
BYOB private floating tiki bar for 8–16 to sip, cruise, and celebrate around Annapolis Harbor
U Street Jazz Clubs & Speakeasy Cocktail Walk
Sip craft cocktails as a guide shares U Street's vibrant jazz history and culinary highlights.
Southern Comfort: Old Town Alexandria Food Tour
Savor hearty tastings and local history on a guided walk through Old Town Alexandria
18' Picnic Boat Rental on Anacostia River in DC
Cruise the Potomac with your own food, drinks, and music on an 18-foot picnic boat.
The Harlem Renaissance in DC
Walk U Street’s Black Broadway to uncover jazz and literary history with a knowledgeable guide
Arlington Cemetery & Changing of Guard Tour
Explore Arlington National Cemetery with an expert guide and witness the solemn Changing of the Guard ceremony.
Smithsonian American History Museum Tour
Explore iconic American artifacts in an intimate group of no more than eight guests with an expert guide.
Smithsonian Natural History Museum Tour
Explore museum highlights in an intimate group of 8 with an expert guide.
National Portrait Gallery Semi-Private Tour
Explore two Smithsonian masterpieces with reserved entry and an expert guide in an intimate group of eight
Capitol Hill Walking Tour with Expert Guide
Explore iconic government buildings and rare artifacts on a 2.5-hour small-group walk with an expert guide.
National Archives & History Museum Combo Tour
Explore founding documents and iconic artifacts with an expert guide in an intimate group of eight guests.
National Archives & Portrait Gallery Combo Tour
Explore America's founding documents and iconic portraits in a small group led by a professional guide.
Semi-Private Smithsonian Museums Tour for 8
Explore Smithsonian highlights with an expert guide in a small group of no more than eight guests
Smithsonian Museum Tour: Natural History & Air/Space
Explore two iconic Smithsonian museums in one guided semi-private tour for an in-depth look at history, science, and innovation.
Small Group Tour of National Gallery with Expert
Explore masterpieces with an art historian guide in an intimate group of eight.
National Mall Walking Tour with Monument Ticket
Explore iconic memorials in a small group and enjoy Washington Monument entry on this 2.5-hour guided walk.
National Archives Skip the Line Small Group Tour
Explore America’s founding documents with an expert guide in a small group and skip the long entry lines.
Semi-Private Smithsonian Air & Space Tour for 8
Explore aviation and space milestones with an expert guide in a group of eight or fewer guests.
Private Mount Vernon & Old Town Alexandria Tour
Explore George Washington's estate and vibrant Old Town Alexandria with a private guide and luxury transport.
DC Monuments Tour with Capitol & National Archives Access
Explore Washington’s monuments in a glass-roof bus with reserved entry to the Capitol and National Archives.
VIP Capitol & Archives Tour with Reserved Entry
See DC’s iconic monuments by luxury bus with reserved entry to the U.S. Capitol and National Archives.
Private Yacht Charter in Washington DC with Captain
Host an elegant private cruise on the Potomac with crew, amenities, and classic DC views
Double Kayak Rental at The Wharf
Paddle the calm Washington Channel with easy sit-on-top doubles and flexible 1–4 hour rentals.
Single Kayak Rental at The Wharf
Explore DC's Washington Channel at your pace with flexible 1–4 hour kayak rentals
Paddleboard & Kayak Rentals in Annapolis
Explore scenic Back Creek at your own pace with high-quality paddleboards or kayaks
Single Kayak Rental at James Creek Marina
Paddle the Anacostia River with beginner-friendly gear and easy check-in at the marina
Double Kayak Rental at James Creek Marina
Paddle the Anacostia River in a double kayak with paddles and PFDs included
Stand Up Paddleboard Rental at The Wharf
Paddle the calm Washington Channel from The Wharf with board, paddle, and PFD included
Experience the Charm of Annapolis
Annapolis is a vibrant city where colonial history meets maritime culture, offering visitors a unique blend of old-world charm and nautical adventure. As you stroll along its cobblestone streets, you'll be greeted by the sight of historic brick buildings and the gentle sway of sailboats in the harbor. The city’s rich naval heritage is palpable, with landmarks like the United States Naval Academy providing an inspiring backdrop to your exploration.
Begin your day with a leisurely walk through downtown Annapolis, where sunlight dances off colorful storefronts and local cafes invite you in for a warm cup of coffee. The nearby Chesapeake Bay offers opportunities for sailing or kayaking, allowing you to feel the ocean breeze as you glide across tranquil waters. For those who prefer land-based activities, forested trails at Quiet Waters Park provide serene paths perfect for hiking or cycling amidst nature's beauty.
Whether you're exploring art galleries on West Street or savoring fresh seafood at one of many waterfront restaurants, Annapolis captivates with its blend of cultural experiences and natural wonders. Unlike other destinations in the region, this city offers an intimate connection to both history and sea life that feels authentic and refreshing. Book a Greetwell experience such as a guided walking tour or sunset cruise to make your visit truly memorable.