Set sail on an unforgettable adventure with Schooner Woodwind Sailing Cruises, located in the charming city of Annapolis, MD. Offering daily cruises on the scenic Chesapeake Bay, Schooner Woodwind provides an authentic sailing experience aboard their beautiful, 74-foot classic wooden schooners. Whether you're a seasoned sailor or a first-time passenger, you'll delight in the tranquility and breathtaking views as you glide effortlessly across the water.

Ideal for individuals, couples seeking a romantic outing, or families looking for a memorable experience, these cruises allow you to participate in the sailing process or simply relax and enjoy the journey. With a ticket, guests have the freedom to explore the deck, admire the sails, and capture stunning photos of the Annapolis skyline and historic landmarks.

Schooner Woodwind Sailing Cruises is particularly popular with tourists and offers a unique perspective on the rich maritime heritage of Annapolis. The knowledgeable and friendly crew are eager to share their passion for sailing, making your trip both educational and enjoyable. Each cruise typically lasts around two hours, providing excellent value for those wanting to experience the Chesapeake Bay's natural beauty without dedicating an entire day.

Located conveniently at 80 Compromise Street, visitors can easily access the dock in downtown Annapolis, making it a perfect addition to your itinerary when exploring this vibrant historic city. Embark on a Schooner Woodwind cruise for a refreshing way to see Annapolis and the Chesapeake Bay like never before. 

Schooner Woodwind Sailing Cruises

Nestled in the heart of Annapolis at 36 Market Space, Chipotle Mexican Grill offers a vibrant and modern dining experience. Known for its commitment to high-quality ingredients and sustainable sourcing, Chipotle serves a range of delicious Mexican-inspired dishes tailored to fit various preferences. Guests can enjoy customizable burritos, tacos, and bowls, with options for a hearty chicken, beef, or vegetarian filling made from tofu sofritas. The restaurant caters to a health-conscious and diverse audience, making it an excellent choice for those seeking vegan and gluten-sensitive options without compromising on flavor.

Chipotle's casual and welcoming atmosphere makes it a popular spot for families, friends, and solo diners alike. Its fast-casual service ensures you can enjoy a tasty meal without a lengthy wait, perfect for a quick lunch or a relaxed dinner. The convenient location in downtown Annapolis places Chipotle near local attractions, making it a favorite among both locals and tourists looking to refuel in the midst of exploring the city.

Whether you're a local resident or a visitor, Chipotle Mexican Grill offers a delightful taste of Mexican cuisine right in the heart of Annapolis. Its focus on fresh ingredients and customizable dishes guarantees a satisfying and enjoyable dining experience for a wide range of dietary preferences. 

Chipotle Mexican Grill

Nestled in the heart of Annapolis, Mangia - Italian Grill & Sports Bar offers a vibrant dining experience that merges authentic Italian cuisine with the lively atmosphere of a sports bar. Located at 81 Main St, this establishment is a must-visit for anyone craving a delicious meal in a dynamic setting. Mangia is renowned for its extensive menu that features a variety of Italian classics, from hearty pastas and pizzas to delectable meat and seafood dishes, catering to both locals and visitors alike. The casual ambiance makes it a perfect spot for groups to gather and enjoy a game together, as the sports bar component is equipped with large screens broadcasting the latest sports events. Whether you're a sports enthusiast or a lover of Italian food, Mangia has something for everyone. Ideal for a casual family lunch or a spirited dinner with friends, this restaurant captures the essence of Italy while providing the excitement of live sports entertainment. Come to Mangia for a taste of Italy and stay for the game — it's where good food and good times meet in Annapolis. 

Mangia - Italian Grill & Sports Bar

Nestled in the heart of Annapolis, Galway Bay Irish Restaurant and Pub offers an authentic slice of Ireland with a warm and welcoming atmosphere. Located at 63 Maryland Ave, this charming establishment is known for its genuine Irish hospitality and a delicious menu that celebrates traditional Irish cuisine. Patrons can indulge in hearty classics such as shepherd’s pie and fish and chips, paired perfectly with a fine selection of Irish whiskeys and craft beers. 

The ambiance at Galway Bay is both cozy and lively, making it an ideal destination for a casual lunch, dinner with family, or an enjoyable night out with friends. Its inviting setting makes it popular among locals as well as tourists exploring the historic streets of Annapolis. 

Whether you're looking for a place to catch up with friends over a pint, enjoy a relaxing meal with family, or simply soak in the rich cultural vibe, Galway Bay Irish Restaurant and Pub provides a genuine taste of Ireland right in the heart of Maryland. Come for the food, stay for the atmosphere, and experience the welcoming spirit of the Emerald Isle in Annapolis. 

Galway Bay Irish Restaurant and Pub

Nestled in the heart of Annapolis at 100 Main St, Buddy's Crabs & Ribs offers a delightful dining experience that seafood lovers will treasure. Known for its fresh and succulent crabs, Buddy's is a go-to destination for those craving authentic Maryland flavors. Whether you're a local or a tourist, this restaurant provides a warm and hospitable atmosphere perfect for enjoying a hearty meal.

Buddy's Crabs & Ribs is celebrated for its extensive menu, which, in addition to its standout crab dishes, features a variety of ribs that are perfectly seasoned and cooked to tender perfection. The restaurant caters to families and groups, making it an ideal choice for gatherings and special occasions. With its inviting setting and delectable offerings, it's a spot where memories are as richly created as the dishes themselves.

Buddy's emphasizes freshness and quality, ensuring that each dish reflects the culinary traditions of the region. Its location in the vibrant city of Annapolis makes it easily accessible for both locals and visitors who are exploring the area. Whether you're in town for sailing, sightseeing, or relaxation, stopping by Buddy's Crabs & Ribs is a must to experience an authentic taste of Maryland's coastal culinary heritage. 

Buddy's Crabs & Ribs

Lewnes' Steakhouse, located at 401 Fourth Street in the charming city of Annapolis, Maryland, offers an exquisite dining experience that has become a favorite among both locals and visitors. Renowned for its top-tier steak selections, this family-owned establishment is the go-to destination for lovers of classic American and steakhouse cuisine. 

The restaurant's intimate and inviting atmosphere is perfect for special occasions, romantic dinners, or a luxurious evening out. Lewnes' Steakhouse takes pride in serving prime aged beef, cooked to perfection, alongside a refined selection of seafood and gourmet accompaniments. The steakhouse's commitment to quality extends to its selection of fine wines, offering a thoughtfully curated list that enhances the flavors of each dish.

While the restaurant caters primarily to adults seeking a premium dining experience, it can also accommodate groups who desire an upscale and memorable meal. Lewnes' Steakhouse is known for its attentive service, ensuring each guest enjoys impeccable hospitality from the moment they arrive.

Whether you're a local resident seeking a fabulous meal or a visitor searching for a quintessential Annapolis dining experience, Lewnes' Steakhouse promises a truly unforgettable occasion. Engulfed in the rich ambiance of its Annapolis surroundings, it has secured its spot as a must-visit destination for those appreciating quality dining and excellent service. 

Lewnes' Steakhouse

Nestled in the heart of historic Annapolis, Harry Browne's Restaurant offers an elegant dining experience at 66 State Circle. This charming establishment is renowned for its upscale American cuisine, featuring both classic and contemporary dishes crafted with fresh ingredients. A popular choice among both locals and visitors, it serves a diverse menu that caters to a range of tastes, making it an ideal spot for a romantic dinner or a celebratory gathering.

Harry Browne’s prides itself on providing an inviting atmosphere highlighted by its sophisticated décor and attentive service. Its prime location makes it a convenient choice for those exploring the area's rich history and bustling State Circle. The restaurant is particularly noted for its refined ambiance, which pairs well with its extensive wine list and expertly crafted cocktails.

Whether you're looking for a place to impress on a special night out or simply wish to enjoy a fine meal, Harry Browne's stands out as a top choice in Annapolis. Its commitment to quality and excellence makes every dining experience memorable, inviting patrons to savor the tastes and elegance of this esteemed establishment. 

Harry Browne's Restaurant

Located in the vibrant heart of Annapolis at 122 Main St, Starbucks Coffee Company offers more than just a cup of coffee. Known globally for its premium coffees and welcoming ambiance, this Annapolis location is the perfect spot for locals and tourists alike to enjoy a wide array of expertly crafted beverages. Whether you're in the mood for a classic espresso, a frothy latte, or one of their innovative seasonal creations, Starbucks has something to delight every coffee enthusiast.

Alongside their signature coffee selections, Starbucks provides a variety of teas, refreshing cold drinks, and a tempting assortment of pastries and light bites, perfect for a quick breakfast or midday snack. The cozy and inviting setting makes it an ideal place to catch up with friends, settle in with a good book, or get some work done, thanks to the available Wi-Fi.

Starbucks at Main Street caters to a diverse audience, from busy professionals to social gatherers, ensuring everyone feels welcome. Its convenient location in bustling downtown Annapolis makes it a popular institution for both locals and visiting tourists eager to refuel before exploring the historic charm of the city. Consistently offering quality products and friendly service, this Starbucks delivers a reliable and enjoyable experience that keeps customers coming back for more. 

Starbucks Coffee Company

Nestled in the heart of historic Annapolis, O'Brien's Oyster Bar & Seafood Tavern offers a quintessential Chesapeake Bay dining experience. Established alongside the bustling docks, this welcoming venue specializes in fresh, locally sourced seafood, making it a must-visit for seafood enthusiasts. The menu highlights the best of Maryland's maritime heritage, including the famous Maryland crab cakes and a variety of succulent oysters expertly prepared by passionate chefs.

O'Brien's is perfect for those seeking a casual yet refined dining atmosphere, whether you're a local resident or a visiting tourist exploring Annapolis's charming streets. The tavern's inviting ambiance is complemented by a friendly staff committed to delivering exceptional service, ensuring every patron feels right at home.

Ideal for family dining and group events, O'Brien's also boasts a vibrant social scene, where friends gather to enjoy live music and upbeat conversations old and new. Its convenient location on Main Street makes O'Brien's an excellent spot for lunch or dinner as part of exploring Annapolis's rich colonial history and scenic waterfront.

With its dedication to quality seafood paired with a focus on community and hospitality, O'Brien's Oyster Bar & Seafood Tavern stands out as a beloved staple in the Annapolis dining landscape. Whether you're indulging in a hearty meal or simply savoring a drink, O'Brien's promises a memorable experience rooted in Maryland tradition. 

O'Brien's Oyster Bar & Seafood Tavern

Nestled in the heart of Annapolis, Kilwins Ice Cream - Chocolate - Fudge is a delectable destination for anyone with a sweet tooth and a love for indulgence. Conveniently located at 128 Main St, this charming spot offers a tantalizing array of handmade chocolates, creamy ice creams, and rich fudges, making it a must-visit for dessert enthusiasts in the area.

Step inside Kilwins and you’ll immediately be greeted by the delightful aroma of freshly made confections. Known for its quality and craftsmanship, Kilwins invites you to explore a world of flavors and textures. From their decadent variety of ice cream scoops to the velvety smoothness of artisanal fudge, each product showcases a dedication to using high-quality ingredients and traditional methods.

Kilwins is particularly popular with tourists seeking a local treat and families wanting to enjoy a delicious outing together. Whether you're looking to satisfy an afternoon craving or seeking a sweet souvenir from Annapolis, this shop offers a memorable experience for all ages.

With its inviting atmosphere and commitment to classic confections, Kilwins Ice Cream - Chocolate - Fudge promises not only delightful treats but also a slice of local charm. Indulging in their sweets is more than a treat—it's an experience you'll want to savor again and again. 

Kilwins Ice Cream - Chocolate - Fudge

This 786-acre Maryland State Park is located along the northwestern shore of the majestic Chesapeake Bay. The park’s beaches and picnic areas are well known for their breathtaking scenic water views that overlook one of Maryland’s true treasures, the Chesapeake Bay. The park was first opened on June 25, 1952 and has provided its guests with various activities and services ever since. The park also offers a marina store and boat rentals. Sandy Point State Park offers accessible food and beverage concession, fishing, picnic areas, shelters, bathhouses and playgrounds. For additional accessible amenities in Maryland State Forests and Parks, visit the Accessibility for All section of this website.

Boating/Sailing: 22 Launches, 6 Piers
Fishing: Shoreline and jetty fishing 
Swimming/kayaking: Open water swimming in the Chesapeake Bay

Sandy Point State Park

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