As one of America’s oldest and most storied cities, Annapolis continues to be a destination brimming with fascinating history, beautiful architecture, and great eats. A harbor for both foodies and history buffs, so dense are its many offerings, sometimes the easiest way to ensure you don’t miss anything is by taking a tour of this captivating town, exploring it through your lens of choice.
Let the Naptown locals show you around their storybook city, taking you to the doorstep of the very best eateries, drinkeries, and prominent sites. Whether you’re searching for tours drenched in history or ones filled with delectable dishes, Annapolis has no lack of spell-binding tours to keep you entertained.
Ashes and Apparitions of Annapolis Ghost Tour
With more than 300 years of history under its belt, America’s Sailing Capital has had plenty of time to amass an assembly of ghosts. Embark on an Annapolis ghost tour to travel down these cobblestoned streets heavy with history and discover a past awash with otherworldly tales and haunting figures.
Along this spine-tingling tour, your knowledgeable guide will regale you with tales of this city’s dark past, from salty sailors to murderous scoundrels. Experience the perfect blend of history and mystery as you walk down brick-lined roads roamed by ghosts and traveled by centuries of Marylanders before you.
Be transported to Annapolis’ bygone days of sea captains and bootleggers as you gaze upon some of the most haunted places in this nautical city. Hear stories of romance and tragedy at places such as the Maryland Inn, where a ghostly bride awaits her betrothed from beyond the grave. You’ll see the shadowy side of this colonial city known only to the brave!
Crabtown Ghosts Boos and Booze Haunted Pub Crawl
Those who possess a love for ghost stories and good drinks will delight in a Haunted Annapolis Pub Crawl. You’ll enjoy craft cocktails and great company at some of Naptown’s most haunted watering holes as you drink in the sinister history that has saturated these brick buildings for centuries.
As part of the boozy adventure, you’ll step inside Annapolis’s most haunted bar, the Middleton Tavern, where an unruly ghost likes to tip over drinks. Sip on a pint or two as you soak in tales of poltergeists and phantoms unwilling to leave their favorite haunts.
This adult-oriented tour is the perfect way to spend an evening, be it with friends or a special someone to hold your hand through these spirited tales. Combining delicious beverages with eerie tales of phantom-infested taverns, both longtime locals and first-time visitors to this seafaring city will find something new on this spirit-soaked tour of Annapolis.
Colonial Tour of Annapolis
Those who prefer their history spook-free may wish to instead opt for a Colonial Tour of Annapolis. Along this captivating walking tour, a colonial-garbed guide will shepherd you through Annapolis’ historic district as they transport you back to this city’s colonial past.
Along the way, you’ll stop by historic sites like the Maryland State House and St. Anne’s church, learning about what daily life was once like in this one-time colonial capital. It’s a tour perfect for the whole family, rich in both history and storytelling.
Historic Annapolis Food Tour
If signature fare and delicious dishes are more your speed, a food-based tour will satisfy your craving for adventure. Taste your way through this bayfront city on a Historic Annapolis Food Tour, exploring the culinary soul of this storied community by way of its most renowned restaurants.
Listen to the savory history of Annapolis’ famed eateries as you chew over their individual stories and sample iconic eats. There’s no better way to experience the culture of a city than through its local cuisine, whether you’re eating its world-famous seafood or drinking its craft beer.
Naval Academy Historical Walking Tour
Those with a penchant for maritime history will appreciate a tour of the Naval Academy, led by one of its expert guides. Historical Walking Tours spanning 90 minutes are offered daily at this patriotic location, giving guests an in-depth peek into the lives of midshipmen and more.
It’s an extensive experience that is fascinating for history buffs and former military members alike, providing thorough details about this esteemed landmark. Family rates and military discounts are offered as well.
African American Heritage Tour
Sometimes, Annapolis’ colonial and maritime legacy can overshadow its larger history. Those looking for a more comprehensive excursion will be immediately drawn to the African American Heritage Tour.
A two-hour walking tour, this remarkable venture will wind you through the lives of African Americans in Annapolis, beginning with the first slave ships that arrived 300 years ago, before the Old Line State became known as the Free State.
A guide dressed in period attire will direct you to multiple sites as they detail the tangled path African Americans have traveled over the past three centuries. Explore the lives of famous Marylanders like Harriet Tubman and Frederick Douglass as you take in the sights of the Alex Haley statue and the Maryland Statehouse. It’s a tour rich in history, culture, and lesser-told stories well worth a look.
Annapolis Boats Tour
What better way is there to take in the Sailing Capital of the World than by boat? Those who prefer to explore Annapolis by water will be enchanted by a private Annapolis Boat Tour. Along this leisurely 2-hour voyage, you’ll cruise the waters of the Annapolis harbor, Severn River, and Spa Creek as you take in this seaside town from its best angle.
A tour best taken during the spring and summer months, it’s one you’re sure to remember for years to come. Helmed by a native Annapolis sailor, passengers will be regaled by seafaring stories and maritime tales, from accounts of surviving the stormy seas to regatta races. It’s a briny adventure brimming with the beautiful sites and fascinating history that have come to define America’s Sailing Capital.