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🌿 RelaxedLong weekend · from Washington, DC

Sandy Shores, Gardens & Vineyard Wines

Escape the city for a sensory journey through Maryland's hidden gems, blending pristine beaches, botanical gardens, and award-winning vineyard tastings.

Day 1 — Sandy Point State ParkDay 2 — Cylburn ArboretumDay 3 — Catoctin Breeze Vineyard
Day 1 — Sandy Point State Park

Day 1 — Sandy Point State Park

🚗 1 hr 26 min driving📍 5 stops
🌅
Morning
🚗
Drive
Washington, DC → Sandy Point State Park
1 hr 3 min
Sandy Point State Park
Sandy Point State Park
★ Reviews →
Local beach & picnic area offering views of the Sandy Point Shoal Light & the Chesapeake Bay Bridge.
🍽️
Lunch
Libbey's Coastal Kitchen and Cocktails
Libbey's Coastal Kitchen and Cocktails
★ Reviews →
A Chincoteague, VA waterfront restaurant with a menu built around local clams, oysters, and blue crab. One of the best tables on Virginia's Eastern Shore, with the island's famous ponies as a backdrop.
☀️
Afternoon
🚗
Drive
Sandy Point State Park → Great Frogs Winery
14 min
Great Frogs Winery
Great Frogs Winery
★ Reviews →
Taste small-batch Maryland wines on a shaded terrace overlooking rolling vineyards. Relax with a flight of their signature blends while enjoying live music and local snacks.
🌙
Evening
🚗
Drive
Great Frogs Winery → Cantler's Riverside Inn
9 min
Cantler's Riverside Inn
Cantler's Riverside Inn
★ Reviews →
Crack fresh steamed crabs while watching the sunset over the Chesapeake Bay at this legendary waterfront institution.
🛏️
Chesapeake Bay Beach Club
A resort and event property directly on the Chesapeake Bay in Stevensville, just across the Bay Bridge from Sandy Point State Park — the waterfront rooms face west across the bay toward Annapolis, and the sunset from the pier is one of the best views on the Chesapeake's western shore.
Day 2 — Cylburn Arboretum

Day 2 — Cylburn Arboretum

🚗 1 hr 49 min driving📍 5 stops
🌅
Morning
🚗
Drive
Sandy Point State Park → Cylburn Arboretum
48 min
Cylburn Arboretum
Cylburn Arboretum
★ Reviews →
Tranquil park features 20+ gardens, century-old trees, a nature museum & a Civil War-era mansion.
🍽️
Lunch
R. House
A Baltimore food hall in a converted auto repair shop in the Remington neighborhood — chef-driven stalls in an energetic, high-ceilinged space. One of the city's best lunch destinations.
☀️
Afternoon
🚗
Drive
Cylburn Arboretum → Boordy Vineyards Inc
23 min
Boordy Vineyards Inc
Boordy Vineyards Inc
★ Reviews →
Sample award-winning estate wines in a historic stone winery, then stroll manicured grounds with panoramic views of Maryland's wine country. Pair tastings with local cheeses and charcuterie.
🌙
Evening
🚗
Drive
Boordy Vineyards Inc → Guinness Open Gate Brewery
38 min
Guinness Open Gate Brewery
Guinness Open Gate Brewery
★ Reviews →
Tour the only Guinness brewery in the Western Hemisphere and sample perfectly poured pints in a vibrant taproom just outside Baltimore.
🛏️
The Ivy Hotel
A 1889 Victorian mansion in north Baltimore's Roland Park neighborhood, converted to Baltimore's most acclaimed boutique hotel — six suites in the original mansion and new rooms in the carriage house, with a Michelin-starred restaurant and a garden that borders the arboretum. A 5-minute walk from Cylburn.
Day 3 — Catoctin Breeze Vineyard

Day 3 — Catoctin Breeze Vineyard

🚗 2 hr 57 min driving📍 3 stops
🌅
Morning
🚗
Drive
Cylburn Arboretum → Catoctin Breeze Vineyard
1 hr 19 min
Catoctin Breeze Vineyard
Catoctin Breeze Vineyard
★ Reviews →
Escape to this serene mountain vineyard nestled in the Catoctin Mountains where you can unwind with a glass of locally-produced wine while enjoying panoramic views and the gentle rustle of the breeze through the vines.
🍽️
Lunch
Rube's Crab Shack LLC
Rube's Crab Shack LLC
★ Reviews →
A laid-back Maryland crab shack near the Linganore wine trail — whole steamed blue crabs, crab cakes, and Old Bay by the fistful. The casual picnic-table setup is exactly what Chesapeake crab eating should feel like.
☀️
Afternoon
🚗
Drive
Catoctin Breeze Vineyard → Linganore Winecellars
33 min
Linganore Winecellars
Linganore Winecellars
★ Reviews →
Sip Maryland and regional wines in a rustic barn setting surrounded by vineyard views. Browse their gift shop and settle onto the outdoor patio with a glass of their popular fruit wines.
🌙
Evening
🚗
Drive
Linganore Winecellars → Washington, DC
1 hr 5 min
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