Top Maryland Holidays

Drink your way through the haunted side of historic Fells Point on Spirits of Fells Point, Baltimore’s adults-only haunted pub crawl. Along the route, guests will visit atmospheric bars and historic streets while hearing stories of Edgar Allan Poe, vanished sailors, smugglers, gamblers, haunted taverns, waterfront crime, and the bad decisions that helped give Fells Point its notorious reputation. This is more than a night out at the bars. It is a haunted walk through the places where sailors once spent their wages, privateers and merchants chased fortunes, and legends of restless spirits still linger near the harbor. Guests will have time to purchase drinks at select stops while enjoying spooky storytelling, local lore, and a fun social atmosphere. Perfect for adults who want ghosts, history, drinks, and a little chaos, Spirits of Fells Point offers a memorable way to experience Baltimore after dark. Guests must be 21+ with valid photo ID.

Sunshine, Good Vibes, and Island Beats—All Aboard! Get ready to cruise into the day aboard your custom-built party boat! This 90-minute daytime escape is all about fun in the sun, tropical cocktails, and a Caribbean-inspired playlist that sets the tone for an unforgettable experience on the water! Whether you're celebrating with friends or just looking for the ultimate vacation vibe, this cruise is your ticket to pure island-style fun. Boats departing at various times throughout the day. Start or end your adventure with world-famous dining and live music at Seacrets, Jamaica USA—a true Ocean City hotspot where the party never stops! Bathing suits are welcome, but guests will remain on board for the entire 90-minute cruise—so relax, sip, and enjoy the view! This cruise is 21+. What's included - Friendly, knowledgeable crew sharing local insights - Music on board to set the vibe - Partially covered deck with sun & shade bench seating - Clean onboard restrooms

Step into Baltimore’s darker side on Devil in the Harbor, an adults-only ghost tour through historic Fells Point where the city’s sins, scandals, and spirits come out after dark. Explore one of the city’s oldest waterfront neighborhoods through the theme of the Seven Deadly Sins. Along the route, you’ll hear stories of pride, greed, lust, gluttony, wrath, envy, and sloth — not as a sermon, but as a chilling look at the ambition, corruption, violence, vice, and weakness that shaped Baltimore’s harbor. Atmospheric, mature, and historically inspired, Devil in the Harbor is perfect for adults who want a ghost tour with sharper edges, darker storytelling, and a deeper look at the sins that still haunt Baltimore after dark. Guests must be age 16+.

Put a ghoulish twist on your night out with a haunted pub crawl through historic Annapolis. Visit three bars over the course of the night, each with a ghost story behind it that will scare you sober. Drinks available at your own purchase.

Explore Baltimore after dark for a different, darker perspective on Charm City. With a guide leading the way, skip the planning and get hear about the city's spooky side at several popular pubs and haunted sites. Start at Max’s Taphouse before continuing to other notorious watering holes, and uncover more eerie local history than you could on your own.

Watch the sun set over Assateague Island on your own private boat, with 75 minutes of quiet, open bay all to yourselves, and plenty of time to look for wildlife along the way. Your USCG-licensed captain takes up to six guests into the calm back bays behind Ocean City and along the Assateague shoreline, where the famous wild ponies roam free. Look for the ponies along the beach and keep an eye out for dolphins, ospreys, herons, and egrets as the sun sets. Your captain shares what you are seeing and answers whatever your group is curious about, whether that is the wildlife, the barrier island, or life on the water. With no other guests aboard, the evening runs on your schedule. Bring your own beverages, play your music, and settle in for quiet water, open sky, and one of the finest sunset views on the Eastern Shore. It is a favorite for families, couples, and anyone who wants to end the day on the water!

Step inside some of Baltimore's most haunted sites on a Fells Point pub crawl that delivers far more than drinks. Hear ghost stories from your guide as you make your way around the historic maritime neighborhood and in and out of 3–4 historic taverns, each known for their ghostly experiences.

Baltimore's Fell's Point neighborhood is filled with great places to eat. But, if you are new in town, it can be difficult to find the best spots. This tour guides you through the historic district, visiting family-run restaurants along the way to sample specially made dishes including Polish, Baltimore-style pit beef, and Spanish tapas.

Join Chef Jesse at a local brewery in Baltimore for a pasta-making experience that combines Italian flavors with craft beer! This hands-on class will teach you how to make fresh ravioli from scratch, from kneading the perfect pasta dough to rolling it to the ideal thickness. Then, create a creamy ricotta filling enhanced with bright lemon zest and Parmesan before shaping and sealing your ravioli with expert precision. Once cooked to perfection, you’ll savor your handmade masterpiece while enjoying the relaxed atmosphere of the brewery. Pair your pasta with locally brewed beer available for purchase and enjoy a fun, social evening of culinary creativity. Whether you're looking for a unique date night, a social outing with friends, or a way to sharpen your cooking skills, this class is the perfect mix of hands-on learning and great flavors. Book your spot today for a memorable ravioli-making and craft beer experience in Baltimore!

Explore and relish the enchanted day trip to California's famous wine country on this full-day tour of Napa and Sonoma County. Tour and taste wine at a Napa Valley landmark—Castello di Amorosa. You’ll stop for photos of the iconic Golden Gate Bridge, enjoy wine tastings in both Napa and Sonoma, where you'll take in the delightful notes of each region, and have free time to explore historic Sonoma Square. Many of the wineries that will be visited are some of the oldest wine making families wine in the Napa and Sonoma Valley. You’ll learn of their family histories and first beginnings in California’s most famous Wine Country.

Celebrate the holiday season with the Holiday Candlelight Stroll, a delightful 75-minute walking tour through Annapolis. Led by a period-attired guide, this tour takes you through Maryland’s capital, adorned in festive greenery. Learn about the rich holiday traditions as you pass by charming colonial mansions, Victorian homes, and quaint shops. The tour culminates at the grand Christmas tree in Market House Park, where you'll receive a goody bag featuring George Washington’s famous eggnog recipe. - 75-minute guided evening walking tour of Annapolis - Explore colonial and Victorian holiday traditions - Enjoy insights into local holiday traditions from your guide - Receive a goody bag at the end of the tour that includes George Washington's eggnog recipe

Join Chef Jesse at a local brewery in Baltimore for a pasta-making experience like no other! This hands-on class will teach you how to craft fresh pappardelle pasta from scratch using simple, wholesome ingredients. Learn the essential techniques of mixing, kneading, rolling, and cutting pasta dough, followed by preparing a flavorful roasted garlic tomato sauce with crushed tomatoes, garlic, olive oil, and classic Italian seasonings. As you refine your skills, enjoy the laid-back brewery atmosphere and sip on locally brewed craft beer available for purchase. Whether you're looking for a unique date night, a social outing with friends, or a fun way to expand your cooking repertoire, this class offers a perfect mix of culinary creativity, delicious flavors, and craft beer. Book your spot today for a memorable evening of fresh pasta and brews in Baltimore!

Celebrate the holiday season with a delightful 45-minute cruise along Spa Creek, guided by Captain Santa or Mrs. Claus. This family-friendly adventure includes hot cocoa served by an onboard elf and cozy blankets to keep warm as you enjoy the festive sights. A portion of the proceeds supports Historic Annapolis, making this a jolly way to give back while creating cherished family memories. Perfect for families and holiday enthusiasts, the cruise offers private bookings for larger groups. Reserve your tickets in advance for this limited-capacity experience. - 45-minute festive cruise along Spa Creek with holiday characters - Enjoy complimentary hot cocoa and cozy blankets on board - Supports Historic Annapolis with a portion of proceeds - Perfect for families and private group bookings available for up to 21 passengers

Welcome the holidays with Watermark's Christmas in the Capital Tour: Annapolis Traditions and State House Trees. Meet your period-attired guide inside our cozy office before embarking on your tour. Stroll with your colonial guide around Maryland’s capital city, trimmed in greenery for the season. Hear holiday traditions of times past and present as you walk by colonial mansions, Victorian homes, and quaint shops A highlight of the tour is the Maryland State House, with decorated Christmas trees representing the different counties of Maryland, presented by the Federated Garden Clubs of Maryland. The tour ends at Annapolis's grand Christmas tree at Market House Park. Take home the holiday cheer with a goody bag of treats including George Washington’s famed eggnog recipe!

Skip the frozen aisle and discover just how fun dumpling making can be. In a relaxed culinary studio, this beginner-friendly cooking class breaks the process into simple, hands-on steps that make every fold feel achievable. You'll prepare a savory dumpling filling, learn how to fill and seal wrappers with confidence, and practice shaping dumplings using techniques you can recreate at home. Along the way, you'll pick up practical skills for portioning, folding and creating tightly sealed dumplings that cook beautifully. Finish by serving your handmade dumplings with a flavorful dipping sauce and enjoy every warm, satisfying bite. It's equal parts comfort food, creativity and a skill you'll be happy to show off.

Explore and relish the enchanted day trip to California's famous wine country on this full-day tour of Napa and Sonoma County. Tour and taste wine at a Napa Valley landmark—Castello di Amorosa. You’ll stop for photos of the iconic Golden Gate Bridge, enjoy wine tastings in both Napa and Sonoma, where you'll take in the delightful notes of each region, and have free time to explore historic Sonoma Square. Many of the wineries that will be visited are some of the oldest wine making families wine in the Napa and Sonoma Valley. You’ll learn of their family histories and first beginnings in California’s most famous Wine Country.

Many sightseeing tours can feel exhausting, as you rush from one top sight to another. This sailing experience on Baltimore's Inner Harbor, on the other hand, offers the chance to soak up city views at a relaxed pace from the water. Sailing in a small group also means that the experience is amore personal one.

Get views of a sunset over Baltimore's Inner Harbor on this evening sunset cruise. Snap photos of your loved ones against the backdrop of the sun sinking below the horizon and relax on board the boat. Listen to relaxing music and feel free to bring along your favorite bottle of wine, with corkscrew and glasses provided.

Immerse yourself in the Chesapeake Bay's rich maritime history on a sailing tour of the Baltimore Harbor. Take in the sights of the Inner Harbor and listen to a guide detail Baltimore's and the Chesapeake's roles in the shaping of American history.

Short on time but ready to sip your way through Virginia Wine Country? The 4 Hour "Ride to The Vines"** is the perfect escape to explore the *Passion of the Grape* without the rush and crowds on the weekends. Perfect for visitors and area residents! Join us to experience a customized, door-to-door wine tour designed around your group. Book a romantic afternoon with a glass in hand, a birthday celebration, or a just-because getaway. Visit boutique wineries, scenic estate vineyards, and select breweries or distilleries, all safely guided by fun, knowledgeable local drivers. We handle the reservations so you can relax and soak in the views while stopping at award-winning venues along the way. Savor tastings, discover unique spots, and make lasting memories with friends or loved ones. Ideal for solo travelers, couples and larger groups, with convenient Sunday through Friday pickup available. from your location. Cheers to a perfectly paced wine country adventure!