Well known as the “Sailing Capital of the U.S.,” Annapolis, Maryland, combines colonial charm and life on the water. Located on the shores of the Chesapeake Bay, this historic seaport is where you go when you’re dreaming of slowing down and enjoying a coastal getaway—sans the sand in your luggage. History buffs eager to explore centuries-old streets, foodies dreaming of fresh seafood and waterfront dining, and those who simply want scenic strolls and loads of small-town character, Annapolis offers something for every kind of traveler.
As one of the nation’s oldest cities, Annapolis was founded in the 17th century and once served as the temporary capital of the United States. It’s a beautiful city filled with landmarks that help tell the story of early America. That being said, you’ll want to explore the Historic District, where brick-lined streets and colonial architecture will transport you back in time.
The Historic District makes up most of downtown Annapolis, and it is collectively, designated as a National Historic Landmark. Iconic landmarks and features inside the area include the charming Main Street, filled with local boutiques, galleries, eateries, and more. Stroll down Main Street until you hit City Dock to watch the boats cruising in and out of Ego Alley—a popular pastime in its own right in Annapolis. City Dock is also where you’ll be able to see parades and displays during holidays, or of course, catch your water tour.
The U.S. Naval Academy is located in the heart of downtown and is steps away from City Dock. The grounds are open to the public, but there are guided walking tours available in addition to wandering the grounds—or “the Yard,” to visit the museum, visitor center, chapel, and more.
The Historic District includes modern buildings in addition to the main and more distinct landmarks and a collection of historic buildings dating back to the 1700s. The Maryland State House is one of such buildings—completed in 1779, it’s the oldest U.S. state capitol that’s been in continuous use as well as the only one to have ever served as the nation’s capital from 1783-1784.
Nearby is the Hammond-Harwood House. Built in 1774, the house is open to the public for tours and now holds the Museum of Architecture and Early American Fine & Decorative Arts. The William Paca House and Garden is another stop for visitors, as its another National Historic Landmark that allows people to see the restored Georgian-style mansion built for one of the signers of the Declaration of Independence, William Paca.
With such a rich history, it’s hard not to want to learn more about Annapolis’ past. At the Chesapeake Bay Maritime Museum, you can dive deeper into the stories that shaped not only Annapolis but the entire Chesapeake Bay region. With both indoor and outdoor exhibits, a working Shipyard, and narrated voyages out on the water, visitors can learn about the people and industries that have relied on the bay for generations.
Speaking of getting out on the water, we’d highly recommend finding a way to explore the area by water during your time in Annapolis. After all, this is the “Sailing Capital of the U.S.,” and the city’s connection to the Chesapeake Bay is part of what makes it so special. Regardless if you’re an experienced sailor or simply looking for some relaxing time on the water, there are plenty of ways to experience Annapolis from a different perspective.
As we’ve referenced before, a narrated harbor cruise is a great way to learn more about the city’s maritime history and for sightseeing. For a more memorable outing, consider booking a sightseeing sail aboard a traditional schooner or chartering a private sailboat for your group to spend a few hours on the Chesapeake Bay. Sunset sails are also especially popular if you’re looking for stunning views.
Visitors looking for a more active adventure are able to rent kayaks, paddle boards, or boats to set out to explore the area’s creeks, coves, and quieter waterways at their own pace. For the fishermen, fishing charters are also available for anglers hoping to reel in striped bass and a wide array of other local catches.
If you’d rather keep your feet on solid ground, Annapolis offers plenty of opportunities to enjoy the area’s natural beauty from the shore. Just a short drive from downtown is Quiet Waters Park, a beautiful space spanning more than 300 acres along the South River. Featuring walking trails, overlooks, gardens, and more, it’s a perfect place to stretch your legs and experience the quieter side of Annapolis.
Similarly, Sandy Point State Park offers ways to take a beat and enjoy the great outdoors in this region. With sandy beaches, swimming areas, and fishing spots, your group can decide on whether to stay busy or relax a bit. This is also a great spot for a different perspective of the region’s iconic waterways (and for a good old-fashioned picnic!)
Self-proclaimed foodies will feel right at home in Annapolis, where seafood lovers will be in paradise, where fresh Chesapeake Bay blue crabs, oysters, and dock-to-table seafood can be found throughout the city. Spend an evening dining along Ego Alley at waterfront restaurants that have prime views of the boats coming and going from the harbor. Downtown Annapolis boasts a growing culinary scene in general, featuring everything from casual taverns and bakeries to upscale dining experiences that shouldn’t be missed.
Thanks to its waterfront location and four distinct seasons, Annapolis offers something for everyone throughout the year. The best time to visit ultimately depends on the traveler and what kind of experience they’re looking for, but we will say that the peak travel season is during the summer. Warm temperatures make for beautiful days out on the water, and visitors have all the more daylight to pack the activities in.
If you’re looking for comfortable weather that bodes well for walking tours, waterfront dining, and outdoor sightseeing in general, spring can be a great time to visit. It’s not the off-season by any means—Annapolis is just waking up in springtime as the boating season ramps up. If you want fewer crowds and pleasant weather, try visiting in the fall. It tends to be the sweet spot where colorful foliage only adds to the beauty of the city’s historic streets, and popular events like the Annapolis Sailboat Show occur.
Travelers seeking lower rates will typically find the best deals during the winter months, specifically between January and early March. Winter sees less tourists, as temperatures can be chilly. If you’re ok with packing jackets and sweaters, visitors will love how the holidays look on the city. Festive decorations and twinkling lights dazzle visitors, and seasonal events ultimately create a cozy waterfront getaway.
Annapolis offers accommodations that suit nearly every travel style. Want to be in the heart of the action? Consider staying near Historic Downtown Annapolis in a charming inn or boutique hotel. Waterfront properties will place you within walking distance to popular attractions, restaurants, shops, and the City Dock. Want a quieter retreat? Stay along the Chesapeake Bay or South River for easy access to boating and other outdoor activities. Many properties in the greater Annapolis area may have less expensive rates and convenient access to shopping districts and nearby attractions.
Palmera Vacation Club members can use their Quest Travel Club membership to not only book their accommodations in Annapolis, but also reserve rental cars, book flights, and find fun activities!
Below are a few examples of accommodations you may find on Quest Travel Club:
Prices, discounts, and availability are subject to change.
