A Romantic Getaway Steeped in History: Three Perfect November Nights in Gloucester, Virginia
Nestled along the scenic waterways of Virginia’s Middle Peninsula, Gloucester offers couples the perfect blend of history, charm, and Southern hospitality. Whether you’re celebrating an anniversary, escaping for the weekend, or just in need of some quality time together, Gloucester sets the stage for romance — from historic inns and fine dining to peaceful vineyards and cultural treasures. Here’s your guide to a three-night stay that will leave you refreshed, inspired, and completely smitten with this beautiful coastal town.
Day 1: Arrival & Indulgence
Check In: The Inn at Warner Hall
The Inn at Warner Hall - back patio over looking the river
Your romantic escape begins at The Inn at Warner Hall — a beautifully restored, newly renovated colonial estate with roots tracing back to George Washington’s ancestors. This elegant waterfront property combines timeless charm with modern luxury, making it the perfect setting for couples seeking tranquility and romance. Enjoy a stroll through the manicured grounds or unwind with a glass of wine as the sun sets over the river.
Dinner: Bangkok Noi
For your first evening, enjoy a taste of international flavor at Bangkok Noi, a local favorite known for its authentic Thai cuisine and intimate atmosphere. Dine on fresh curries, savory noodles, and delicate sushi appetizers crafted with care — the perfect way to start your romantic weekend.
Day 2: A Day of Art, History & Flavor
Breakfast: New Dough Haus
Wake up to a delicious start at Dough Haus, where you’ll find a creative spin on breakfast favorites. Don’t miss their famous breakfast pizza — warm, cheesy, and topped with all your morning favorites.
Morning: Gloucester Museum of History
Step back in time at the Gloucester Museum of History, where newly updated second-floor exhibits bring the county’s past to life. From colonial roots to maritime heritage, the stories here capture the spirit of Gloucester’s enduring legacy — perfect for history-loving couples to explore together.
Be sure to pick up one of the many self-guided tours to take your history travels even further, or stop by the neighboring Historic Colonial Courthouse for a personalized guided tour of six historic buildings, offered Saturdays 10-4 and Sundays 1-4.
Historic Court Circle
Lunch: Patriot’s Grill
Head to Patriot’s Grill for a casual yet flavorful lunch. This local gem is known for hearty American classics that keep visitors coming back.
Afternoon: Fine Arts Museum of Gloucester
Fine Arts Museum of Gloucester
Spend the afternoon hand-in-hand at the Fine Arts Museum of Gloucester, where the new exhibit This Is Us by Kacey Sydnor Carneal celebrates local artistry and identity through vibrant works of color and emotion. The collection offers a glimpse into Gloucester’s creative spirit — and is sure to spark a meaningful conversation or two.
Evening: Wine & Dine at Zoll Vineyards
Wine pouring
As the day winds down, make your way to Zoll Vineyards for an evening of elegance. Enjoy a wine tasting together or sit down for a locally inspired meal prepared by award-winning Chef Frank Zoll. From the first pour to the last bite, this is a dining experience that defines romance.
Day 3: Relaxation, Shopping & Local Flavor
Breakfast: Leisurely Morning at Warner Hall
Savor a slow morning at The Inn at Warner Hall with a homemade breakfast and the serene views that surround this historic estate.
Dining area at The Inn at Warner Hall
Late Morning: Explore & Shop Local
Start your day at the Gloucester Visitor Center, where you can find the perfect souvenir or a Gloucester-branded shirt to remember your getaway. Be sure to check out the Werowocomoco Exhibit, honoring what will become a National Park — the ancestral homeland of Chief Powhatan and Pocahontas.
If you’re shopping for something special, Vashti’s Jewelers offers timeless, elegant pieces to commemorate your romantic trip. For a more casual shopping experience, stop by Buoy 22 to find the perfect golf fit or Up South to pick out a new outfit for dinner.
Men’s hats and shirts at Buoy 22
Lunch: Nuttall’s Country Store
Nutall’s Country Store - Ware Neck
No visit to Gloucester is complete without lunch at Nuttall’s Country Store, a local treasure. Enjoy a freshly made sandwich or salad, and browse their shelves for local goods and gifts — the perfect way to take a piece of Gloucester home with you.
Evening: A Sunset to Remember
Spend your final evening relaxing together on the grounds of Warner Hall. Enjoy the peaceful quiet of the river, toast to new memories, and soak in the timeless beauty of one of Virginia’s most historic destinations.
Day 4: Farewell to Gloucester
After breakfast, take one last stroll through the gardens before checking out. Whether you explored history, art, wine, or simply each other’s company, you’ll leave Gloucester refreshed, inspired, and already planning your next visit.
A Timeless Escape Awaits
Romantic, historic, and full of authentic Virginia charm, Gloucester invites couples to slow down and reconnect. From the grandeur of Warner Hall to the artistry of local museums and the flavors of Zoll Vineyards, this three-night getaway promises moments you’ll treasure forever.