Maryland’s best tours deliver practical, no-nonsense experiences that connect you with the state’s core attractions. The standouts include Frederick’s crafted drink tours, which I found exceptionally well-organized and informative, offering intimate tastings at local wineries and craft breweries. Historic walking tours in Annapolis impress with their expert guides and manageable group sizes, while Eastern Shore seafood tours provide an authentic look at the region’s celebrated crabbing industry.
What makes these tours special is their blend of education and entertainment. The guides are true locals who share genuine insights rather than rehearsed scripts. In Baltimore’s food tours, you’ll learn the real story behind the city’s famous crab cakes while actually meeting the people who make them.
Let’s explore the top-rated Maryland tours that consistently earn high marks from travelers.
Key Points
- Maryland offers a variety of culinary and beverage tours, including wine, beer, and spirit tastings with transportation provided.
- Scenic and historical walking tours in Chesapeake Beach and North Beach highlight the region’s natural beauty and cultural heritage.
- Comprehensive tours in Cumberland provide an immersive experience, accommodating diverse traveler needs, including wheelchair accessibility.
- Many tours feature personalized and intimate experiences, with small group sizes for a more personalized experience.
- The tours offer engaging cultural insights, allowing visitors to explore the region’s culinary landscape, historical sites, and local charm.
Wine Beer and Spirit Tour in Frederick
Nestled in the heart of Frederick, Maryland, the Wine, Beer, and Spirit Tour offers visitors a delightful opportunity to explore the region’s thriving craft beverage scene.
This half-day small-group tour takes participants to three wineries, breweries, and distilleries, where they can sample a range of local wines, beers, and spirits. The tasting fees are included, and guests will receive a collectible wine glass and tote bag as a souvenir.
For added convenience, the tour includes round-trip transportation in an air-conditioned vehicle, as well as snacks and bottled water. Guests can upgrade their experience by adding cheese and charcuterie plates.
While gratuities aren’t included, the tour operates with a maximum of 10 travelers, ensuring a personalized and intimate experience.
With reviews highlighting excellent service and knowledgeable guides, this tour is a must-consider for anyone seeking to enjoy Maryland’s vibrant craft beverage culture.
Read our full review: Wine Beer and Spirit Tour in Frederick Review
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Chesapeake Beach: Guided Walking Tour of the Railway Trail
Though the Chesapeake Beach: Guided Walking Tour of the Railway Trail may not be as well-known as some of the region’s other attractions, it offers visitors a unique opportunity to explore the area’s rich history and natural beauty.
The 1.5-hour guided walking tour takes participants along the old Railway Trail, where they’ll learn about the trail’s role in establishing Chesapeake Beach. Along the way, they’ll have the chance to spot wildlife, including bald eagles, and visit an educational garden with tips on using plants to repel mosquitoes.
The tour also highlights the importance of supporting local wildlife through bat and purple martin houses. With a group size limited to 6 participants and available in English, the tour provides a personalized experience.
Pricing is €993 per person, and the tour can be booked with flexible and free cancellation policies. The tour starts and ends at Kellams Field, and itineraries may be subject to change.
Read our full review: Chesapeake Beach: Guided Walking Tour of the Railway Trail Review
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Chesapeake Region Wine Tour
Maryland’s Eastern Shore is home to a vibrant wine scene that often goes overlooked by visitors. The Chesapeake Region Wine Tour offers an exploration of this underappreciated region. Participants visit two local wineries, where they’ll meet winemakers and sample a variety of reds and whites. The small-group format ensures a personal experience.
The tour includes wine tastings, an optional cheese and fruit or charcuterie and bread plate, a collectible wine glass and tote bag, and lunch, bottled water, and snacks. Transportation is provided in an air-conditioned vehicle, and additional alcoholic drinks are available for purchase. Gratuities, however, aren’t included.
The tour begins at the Chesapeake Heritage & Visitors Center in Chester, MD, at 11:00 am and ends back at the same location. Confirmation is received at booking, unless within 2 days of travel. The tour isn’t wheelchair accessible, and the minimum age is 21 years. A moderate physical fitness level is required, with a maximum of 10 travelers per tour.
Read our full review: Chesapeake Region Wine Tour Review
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Chesapeake Beach: North Beach Scenic Guided Walking Tour
The North Beach Scenic Guided Walking Tour offers visitors an immersive experience in the charming coastal town of Chesapeake Beach. Priced at $41 per person, this 1.5-hour guided tour is limited to just 6 participants, ensuring an intimate and personalized exploration.
Visitors will start their journey at the Welcome Center on the Boardwalk, where they’ll uncover the area’s secrets with an English-speaking guide.
The tour highlights include the Sunrise Garden, a lush oasis featuring water features, native plants, rain gardens, and waterfalls. Guests will then visit the Wetland Overlook Park to spot migratory birds and local wildlife.
The fishing pier, where famous entertainers were discovered, is another stop on the itinerary. The tour concludes at the Bayside History Museum, where visitors can explore educational exhibits showcasing shark teeth, whale bones, Native American implements, sea shells, and coral.
Booking is flexible, with the option to reserve a spot without upfront payment and free cancellation up to 24 hours in advance.
Read our full review: Chesapeake Beach: North Beach Scenic Guided Walking Tour Review
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Heart of Savory Salisbury Foodie Tour
Travelers can embark on the Heart of Savory Salisbury Foodie Tour, an immersive culinary experience that showcases the vibrant food scene of Salisbury, Maryland.
This 5-star rated tour, with a perfect overall rating on Viator and Tripadvisor, takes participants on a delightful journey through the city’s most beloved eateries.
The tour begins at the Market Street Inn, where guests will meet their guide and set out to explore the local flavors. Participants can enjoy a complimentary lunch and private transportation throughout the experience.
The tour is accessible to wheelchair users, stroller users, and those with service animals, making it inclusive for all.
With a maximum of 12 travelers, the Heart of Savory Salisbury Foodie Tour offers an intimate and personalized experience.
Visitors can expect to savor the best of Salisbury’s culinary delights, all while learning about the city’s rich history and culture.
This tour is a must-do for any foodie visiting Maryland.
Read our full review: Heart of Savory Salisbury Foodie Tour Review
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Chesapeake Beach: North Beach Historic Guided Walking Tour
Situated along the scenic Calvert County coastline, the North Beach Historic Guided Walking Tour invites visitors to enjoy the charming seaside town’s captivating past.
Lasting 1.5 hours, the tour takes guests on a journey through North Beach’s historic landmarks, from the picturesque boardwalk lined with antique shops and cafes to the iconic pier that once hosted famous entertainers.
Along the way, the knowledgeable guide shares fascinating insights into the town’s rich history, uncovering hidden gems and local stories.
The tour culminates at the Bayside History Museum, where participants can explore educational exhibits showcasing the region’s natural and cultural heritage, from sharks’ teeth to Native American implements.
With a maximum group size of 6 and a minimum of 5 participants, this immersive experience offers a personalized and intimate exploration of North Beach’s captivating past.
Priced at $44 per person, the tour’s flexible booking and cancellation policies make it an accessible and convenient way to discover the charm of this coastal Maryland destination.
Read our full review: Chesapeake Beach: North Beach Historic Guided Walking Tour Review
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North Beach Historic – Guided Walking Tour
This 1.5-hour guided walking tour invites visitors to discover North Beach’s captivating past. At $41 per person, the tour covers the historic town, providing engaging insights along the way.
The tour starts at the Welcome Center on the Boardwalk and ends at the Bayside History Museum, with a maximum group size of 16 travelers.
The tour is wheelchair and stroller accessible, and service animals are allowed. However, it’s not recommended for those with back or heart problems. A moderate fitness level is required.
Water is provided, and radios are available for groups of five or more.
Confirmation is received at booking, with a minimum of four walkers required. Cancellations are free up to 24 hours before the tour. Visitors can also opt for the “reserve now, pay later” option.
Read our full review: North Beach Historic – Guided Walking Tour Review
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Chauffeured Vineyard Foodie Tour
Embarking on a gastronomic adventure, the Chauffeured Vineyard Foodie Tour invites visitors to savor the flavors of Maryland’s local vineyards and culinary delights.
This private tour takes guests on a journey through the region’s finest offerings, including a selection of starters such as Gucci deviled eggs, baked oysters, and shrimp macaroni and cheese. Theres some good bread pudding and other decadent desserts, all while enjoying included alcoholic beverages.
The tour provides a comprehensive experience, with taxes and tips at restaurants covered, as well as optional gratuities for the tour guides.
Departing from the entrance of Ocean Downs Casino, the tour offers a convenient meeting point and returns to the same location.
Whether you’re a wine enthusiast or a foodie at heart, the Chauffeured Vineyard Foodie Tour promises an unforgettable exploration of Maryland’s culinary landscape.
Read our full review: Chauffeured Vineyard Foodie Tour Review
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North Beach Scenic – Guided Walking Tour
The North Beach Scenic – Guided Walking Tour provides visitors with an opportunity to explore the picturesque coastal town of North Beach, Maryland. Priced from $41 per person, this guided walking tour takes participants on a journey through the town’s historic sites and scenic areas.
The tour starts at the Welcome Center and ends at the Bayside History Museum, covering a distance of roughly one block. Along the way, you will have access to radios for clear communication and be provided with water and handouts.
The tour is wheelchair and stroller accessible, though it’s not recommended for those with back problems, pregnant travelers, or those with serious medical conditions.
Travelers should note that this is a private tour, and only their group will participate. Smoking isn’t allowed, and the tour requires a minimum of 4 walkers. Participants are advised to check availability and call 24 hours in advance to confirm the minimum requirement is met.
With its scenic views and historical insights, the North Beach Scenic – Guided Walking Tour offers an engaging way to experience the charm of this Maryland town.
Read our full review: North Beach Scenic – Guided Walking Tour Review
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4-Day Tour of Cumberland
For those seeking a more comprehensive experience in Maryland, the 4-Day Tour of Cumberland offers an immersive exploration of this historic city. Priced from $1,300 per person, the tour accommodates a maximum of 8 travelers, providing the flexibility of private transportation and the convenience of included meals and fees.
Participants can arrive by various means, including private vehicles, Uber, rental cars, or train, and the tour begins and ends at the central meeting point in downtown Cumberland.
The tour’s inclusions ensure a well-rounded experience, with private transportation, accommodation, and all meals covered. Wheelchair accessibility and the allowance of service animals make the tour accessible to a wide range of travelers.
With free cancellation up to 24 hours before the start, the tour offers flexibility, allowing travelers to book now and pay later. The 4-Day Tour of Cumberland presents a comprehensive and convenient way to discover the charms of this Maryland destination.
Read our full review: 4-Day Tour of Cumberland Review
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Recap
Maryland offers a diverse array of tours, from wine and spirit tastings in Frederick to guided walking tours of historic and scenic coastal towns. Visitors can indulge in local cuisine, explore the state’s rich cultural heritage, and discover the picturesque Chesapeake region. These tours provide a well-rounded experience, catering to a variety of interests and preferences.