Welcome to Annapolis


Orientation

The historic district stretches along West and Main Sts near Church Circle, State Circle and the City Dock. The US Naval Academy and St John's College are also here. Walk across the Spa Creek Bridge or take a water taxi to the casual and more diverse Eastport, home to restaurants, outdoor outfitters and maritime businesses.


Top experiences in Annapolis

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Travel guides

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Annapolis activities

$63 Food, Wine & Nightlife

Historic Annapolis Food Tour

One of the first settled cities in America, Annapolis is one of the most historically significant cities in our nation. During The Historic Annapolis Food Tour, you will enjoy a series of dishes from restaurants in downtown Annapolis while weaving through historic sites. Your guests will hear fascinating stories about this quaint city, including when and why Annapolis was founded, and how it was named. Your host will walk your group at a leisurely pace throughout Annapolis, detailing stories and showing the group historical landmarks such as the Paca Gardens, the Hammond Harwood House, the State House, and the Governor’s Mansion, just to name a few. The Historic Annapolis Food Tour combines a cultural, historic, and architectural tour with a multi-course progressive meal. The result is a multiple hour dining experience that will expand and challenge the palette with an array of flavors, tastes, and textures. Your Food Tour may include the following specialties: • Specialties from a tavern frequented by George Washington, Thomas Jefferson, and Benjamin Franklin • Locally sourced dishes from one of the region’s top restaurants • Award winning she crab soup • Oyster shooters • Hand made pasta from an Annapolis dining institution that serves as a favorite for local lobbyists The amount of food provided throughout the duration of the tour is enough to be considered lunch for the average person.

$59 Food, Wine & Nightlife

Sweet Treats in Annapolis: Original Dessert Crawl Tour

Have a sweet tooth? We hope so! Annapolis might be known for its abundance of amazing seafood, but don’t discount the decadent desserts you can find here — with the help of a local, of course. Get ready to feel like a kid again as you dig into dessert, indulge your sweet tooth, and enjoy some of the best sweet treats Annapolis has to offer. And if you’re itching to see Annapolis from a local perspective, that’s exactly what you’ll be doing thanks to the expertise of a local city guide who can share insider tips you might not hear anywhere else. We’ll start the tour by hopping aboard our 5-passenger, all-electric EZCruiser from which we’ll take you on a dessert extravaganza, where you’ll be eating your way through the city’s sweetest offerings. But you won’t just be eating (don’t worry, we’ll get to that). You’ll also get a lesson in all things local when it comes to dessert. When possible, you might also get the chance to meet the owners of the restaurants we visit and hear their stories about why they love the dessert we’re eating and the history behind it. You’ll discover a local sweet dating back to colonial times, and learn why it’s still popular today. Not only that, but since America is known as a “melting pot,” we’ll enjoy an international pudding-style dessert along the way, that we’re pretty sure you’ll love as much as we do. We’ll also enjoy a dessert people enjoy each and every day - but this one will be better because it’s homemade. If you’re not too stuffed by the time the tour is over, why not cap off your local Annapolis experience with a speciality after-dinner (make that after-dessert) house drink? Before you go, don’t forget to ask your expert local guide for tips on what else to see, do and most importantly, eat during your stay in Annapolis. 

$22 Food, Wine & Nightlife

Haunted Pub Crawl Guided Walking Tour of Historic Annapolis

You'll stay in each bar approximately 30 minutes. The guide will provide you with a two-minute warning to finish your beverage, use the bathroom, etc. Then on to the next stop, your guide will share with you many ghost stories throughout the duration of your tour. Note: You will be spending most of the time inside sometimes noisy and crowded pubs, please bear this in mind. This tour's route varies with season, special events in Annapolis, bar availability and the whim of your tour guide. You will go to three or four bars on this crawl, but specific route information is not available until the moment you depart. Enjoy this tour whether you've just turned 21 or you're celebrating your 50th birthday! And you don't have to drink libations or crawl through the doors to participate - this tour is great fun for everyone 21 and over!

$22 Cultural & Theme Tours

Twisted History Tavern Tour of Historic Annapolis

You'll stay in each bar approximately 30 minutes. You will be given ample time to purchase your choice of beverage before the guide launches into their stories. Upon completion of said tales, the guide will provide you with a 5-minute warning to finish your beverages, use the bathroom, etc. Then on to the next stop...You will visit three or four bars on each crawl - locations visited may include some of the following: Middleton Tavern Rams Head Tavern Federal House Bar & Grille McGarvey's Saloon Dock Street Bar & Grill 1747 Pub at the Reynolds Tavern Harvest Wood Bar & Grill Drummer's Lot at the Maryland Inn Harry Brownes Galway Bay (formerly The Little Campus Inn) Drinks are not included in this tour; however, each bar usually offers a drink special to our guests. Your guide will have the details! This tour is limited to Adults (21+) ONLY! No children. You will be spending most of your time inside sometimes noisy & crowded pubs. This tour route varies with season, special events in Annapolis, bar availability and the whim of our tour guides. You will go to three or four bars on each crawl, but specific route information is not available until the moment you depart. So come join this tour, whether you've just turned 21 or you're celebrating your 50th birthday! (Even the Red Hats have taken this tour...apparently tea isn't the only thing these ladies drink!) And you don't have to drink libations or crawl through the doors to participate - this tour is great fun for everyone 21 and over!