Spring around the Bay means the pastel blooms of redwoods and dogwoods and the call of returning ospreys. Marinas are readying boats for their annual splash. As we wait for consistently nicer weather (and fewer April showers), it’s the perfect time for a road trip.
I love driving around the Bay to watch the landscape wake up from different vantage points. The region holds so many special weekend destinations that every getaway is unique.
With that in mind, here are five spring ideas to entice you to get out and enjoy the return of warm weather. Be it an adults-only grand estate, a floating home, a big-city high rise or a reimagined roadside stop from the 1930s, they each make a great excuse to get out on the road.
Great Oak Manor: (Practically) Your Own Private Estate
Chestertown, MD
When Werten Bellamy and his wife Kellye Walker decided they wanted to create a one-of-a-kind retreat, they searched up and down the East Coast for the right property. They finally found it in Great Oak Manor, at the mouth of Fairlee Creek and just outside Chestertown. This handsome Georgian-style estate was built in 1938 by Russell D’Oench, known as the “Great Gatsby of the Chesapeake.” The estate played host to guests including Ernest Hemingway and John F. Kennedy. For the last few decades, it served as a wedding venue but needed a new breath of life. It was just the opportunity Bellamy and Walker were looking for.
The couple purchased the property in 2022 and invested more than $1 million into an impeccable tip-to-toe renovation and redesign, turning the estate into a 12-room, adults-only boutique hotel that is elegant without feeling formal. The amply-sized guest rooms are beautifully appointed with plush beds, ample bathrooms (some with jacuzzi tubs) and thoughtful amenities like a stow bag for your phone, aimed to help you disconnect from the world outside and focus on where you are. An adjoining Carriage House accommodates four in a two-level suite with full kitchen. The airy solarium has huge windows overlooking the great lawn and the Bay beyond.
Guests mingle in the bar in the early evening, and then move into the dining room, which is for hotel guests only and serves a seasonal menu. A small study has a fireplace and a complimentary amenity bar with snacks, sodas and coffee, as well as a key-card wine dispenser offering by-the-glass pours whenever you wish. But my favorite room is the library, with another blazing fireplace, cushy sofas and walls of bookshelves filled with books handpicked by the owner himself.
The estate is an ideal size for renting out in its entirety, be it for weddings or family reunions. In the off season, Great Oak Manor’s monthly culinary series brings in award-winning chefs and sommeliers for deep dives into cuisine and wine, and they host creative retreats. (A section of shelves showcase authors who have been in residence here.) In the summer, you can watch the Bay from the shady gazebo, play nine holes on the adjacent course, or swim at the beach cove.
Chestertown is just 15 minutes away for shopping and restaurants. And Rock Hall is 25 minutes to the east. But if you’re anything like me, you’ll discover you don’t want to leave. After all, that’s kind of the point of a retreat. Greatoakmanor.com; two-night minimum stay.
FLOHOM: 360 Degrees of Waterfront Living
Baltimore, Anne Arundel County, Virginia Beach
If I were ever to live on a boat, it would look a lot like a FLOHOM. Co-owner Brian Meyer made a living celebrating the water with his first company, the Annapolis-based paddleboard business Capital SUP. When he and his wife looked into getting a houseboat, they stumbled onto the idea of creating a series of them to place at local marinas, like tiny floating hotels. Things started off rocky in downtown Annapolis, where there were questions about compliance with city codes, but they soon found more welcoming climates elsewhere. Today the company operates four FLOHOMs in Balimore’s Inner Harbor Marina, another on the Magothy River in Arnold, and they have two launching this summer in Virginia Beach. The long-term goal is to have a whole series of FLOHOMs around the Bay, giving people the chance to experience life not overlooking, but on, the water.
FLOHOM also wants to redefine the word “houseboat,” and these floating homes do exactly that. They are custom-made with a chic California-modern style, offered with either one or two bedrooms. They’re beautifully equipped with all you need, for a night or much longer. The two-bedroom/two-bath SEALUX has a full kitchen and living room, while the smaller HARBOR one-bedroom is studio-style, with a refrigerator, freezer, coffee setup plus microwave, and hot plate for cooking. The bathrooms have electric toilets (served by marina pumpouts) and tiled showers, the Wifi and TV setup is great, and there’s even a workstation if you can’t fully disconnect. The rooftop deck of each floating home has a gas fire pit and multiple seating areas designed for conversing or stargazing.
If you think a FLOHOM sounds like a place to party, think again. Being good neighbors is key to the company’s ethos, and the rental contract enforces it. The max occupancy is two overnight/four visitors total in the one-bedroom model, and four overnight/six visitors in the larger model. Quiet time runs from 10 p.m. to 7 a.m., there are audio volume sensors onboard to alert FLOHOM if anything gets out of hand.
You won’t miss the chance to socialize, however. There are plenty of social opportunities off the boat; each FLOHOM is located in a marina that’s walkable to restaurants and activities. (The one in Arnold is at the same marina as The Point Crab House & Grill.) Most people check in just to enjoy time on the water. A glance through the guest book shows that’s working. Most guests are local and check in for a night or two to celebrate a birthday or an anniversary, or just to get away from the world for a weekend. And if you want to make it more permanent, FLOHOM has an option to build your own and put it into the rental pool. Flohom.com
Cape Charles Tiny Livin’: Retro Reimagined
Cape Charles, VA
Virginia’s Eastern Shore has been luring vacationers as long as there have been vacationers. Back in the 1930s, the Esso Park Auto Court opened to cater to road trippers driving down to enjoy sun and sand. It featured standalone cottages along with a restaurant, gas station and general store.
Most of the motels of that era have been lost to time but thanks to owners Eric and Sheila Hawkins, this former auto hotel located just north of Cape Charles has been reborn as Cape Charles Tiny Livin’. The owners originally got into the travel business by operating Airbnb properties, but Tiny Livin’ allowed them to expand on that and create a community for travelers on their four-acre property.
The roadside complex features eight of the original cottages, all lovingly restored and updated with cheery colors and modern conveniences like A/C, full kitchens and flatscreen TVs. Each cottage has its own vibe, from the two-story, loft-style Barn to the beachy Stay Awhile, which is also pet-friendly. The restored Greenhouse offers a beautiful backdrop for small weddings or celebrations, and you can even rent out the whole property for exclusive use with a two-night minimum.
Whatever brings you there, it’s just a five-minute drive into Cape Charles proper for dining, shopping and strolling. Head out for wine tasting at Chatham Vineyards & Winery, just 20 minutes north, or go biking or beaching at Kitopepke State Park, 10 minutes to the south.
Each cottage has its own porch. If you’re feeling social come evening, you can gather with other guests under string lights around the shared fire pit and share tales from the road. That’s the kind of vacation memory-making that never goes out of style. Capecharlestinylivin.com
ROOST Baltimore: Luxury Apartment Comforts and City Waterviews
Baltimore Peninsula, Baltimore
If you’ve ever dreamed about living in a waterfront high-rise in Baltimore like a CEO, here is your chance. ROOST Apartment Hotels began in Philadelphia in 2014, with the aim of offering a boutique hotel vibe with the space and amenities of a luxury apartment complex. Since then, they’ve expanded to eight properties, including ROOST Baltimore, which opened in June 2023.
ROOST is set on the water in the evolving Baltimore Peninsula development near Locust Point. The 81 apartments range in size from studios to three-bedroom residences, featuring everything you need for a weekend or a longer stay, including full kitchens, in-unit washer/dryers, and plushy extras like Italian linens, Davnies bath amenities and Apple TV. To make it feel like home, ROOST welcomes pets under 40 pounds, and each apartment even has a collection of live plants—definitely not something you find in a typical hotel.
ROOST guests have access to 24/7 concierge service, a fitness center with Peloton bikes, and weekly cleaning service. Meet up with fellow guests and play a round of billiards in the communal lounge, with floor-to-ceiling windows over the harbor, or soak up the sun on the third-floor pool deck, open from Memorial Day to Labor Day. You’re close to attractions like the Baltimore Museum of Industry or waterside dining at Nick’s Fish House, and just around the corner from Sagamore Distilling. Don’t feel like going anywhere? Head up to Vessel onsite for craft cocktails and small plates, and watch the ships come and go. If you end your visit and find that you don’t want to check out, know that ROOST also has 40 residential apartments offering the hotel lifestyle 24/7. Myroost.com
Kitty Knight Inn: A Storied Stay and Destination Restaurant
Galena, MD
There are a lot of historic hotels around the Bay, but few have a backstory like the Kitty Knight Inn. As the story goes, during the War of 1812 British troops raided the then-thriving port of Georgetown, setting homes and businesses ablaze. Local resident Kitty Knight confronted Rear Admiral George Cockburn of the British Royal Navy, who would go on to burn Washington. Knight stamped out flames and demanded the Brits spare the home of her elderly neighbor, which sat next to the boardinghouse where Knight was a tenant. Her bravery persuaded Cockburn to spare both homes. Eventually, Knight bought both of the homes that were spared, joined them into one building, and operated them as an inn and tavern until her death in 1855.
The property has changed hands multiple times since then, and most recently was purchased by Jamestown Hospitality Group in 2021. This dining collective has won raves with their eight restaurants, including Giordano’s in Kennett Square, Pennsylvania, so it makes sense they started making changes with the restaurant. Now called Deep Blue, it’s a destination in itself for Sassafras River boaters and road trippers making their way along the Chesapeake Wine Trail.
To truly experience the inn, don’t just come for dinner. Check into one of the 11 bedrooms, with historic vibes from wooden furniture and swags of curtains that frame views of the river. The most popular room is Room Four, which was once home to Knight herself when it was a boardinghouse.
I also love the tavern, located on the back side of the inn away from the river. The most historic part of the inn, it features the original low-beamed ceiling and two-sided fireplace. Above the fireplace is a painting of a nude woman that some say is Kitty. Which leads to the inn’s other legend: Some stories say the boardinghouse where Kitty lived in 1813 was actually a brothel, which is why the British soldiers agreed to spare it. True or not? Check in and find out. Kittyknight.com
From big-city luxury to roadside tiny homes, from early 19th century lore to a modern floating house, it’s easy to find a favorite Chesapeake Bay destination to call home for the weekend. They’re easy to reach by land yacht this spring, as you await the warm promise of summer boating.
Susan Moynihan’s new book 100 Things to Do in Annapolis and the Eastern Shore, Second Edition, was released in April 2025. Look for it at a shop near you, and follow her adventures on Instagram at @chesapeaketraveler.
