There’s something special about coming home for the holidays — the familiar streets twinkling with lights, the laughter of family gathered around the table, and the comforting flavors that bring back fond memories. Whether you’re returning to Gloucester to visit loved ones or introducing your family to this charming coastal town for the first time, December is the perfect time to experience its holiday magic. Here’s how to make the most of a three-night stay full of nostalgia, tradition, and small-town warmth.

Day 1: Arrival and Settling In

Check In: Hampton Inn or Holiday Inn

Start your visit by checking into the Hampton Inn or Holiday Inn in Gloucester — the perfect home base for holiday travelers. You’ll be close to family, but with a cozy room waiting just for you… because as much as you love your relatives, it’s always smart to have your own space to retreat to after a full day of catching up, storytelling, and laughing until your cheeks hurt.

(After all, you don’t want to overstay your welcome — or lose the luxury of a peaceful night’s sleep!)

Dinner: Olivia’s In The Village

Ease into the evening with dinner at Olivia’s In The Village, where each dish tastes like it came straight from your grandma’s kitchen. Warm comfort food and hometown hospitality make this the perfect way to say, “It’s good to be home.”

Day 2: Holiday Cheer & Family Fun

Breakfast: Damon & Company

Kick off the morning at Damon & Company, where classic breakfast plates and hot coffee set the tone for a joyful holiday weekend.

Morning: Christmas at Buck’s in Guinea

Head over to Christmas at Buck’s for a dose of down-home holiday charm — music, crafts, treats, and the small-town spirit that makes Gloucester feel like home, no matter where life has taken you. They will have special programming on December 13, but any Saturday is special at Buck’s.

Lunch: Sal’s Sicilian Pizza & Restaurant

A cozy lunch at Sal’s Sicilian Pizza & Restaurant is the perfect midday pick-me-up. Nothing brings family together like sharing a few pies at a table filled with stories and laughter.

Afternoon: Holiday Glo Up Lights Display Tour

Next, pile into the car, crank up the holiday playlist, and enjoy Gloucester Parks, Recreation and Tourism’s Holiday Glo Up Lights Display Driving Tour, a self-guided adventure through the community’s most festive neighborhoods. It’s the kind of tradition that feels like childhood all over again, but this time guided by a festive map.

Be sure to stop at Tucker Pocket Park on Main Street for a sweet family photo under the twinkling lights.

Dinner: Hana Sushi

End the day with a relaxing dinner at Hana Sushi, where you can warm up beside the steaming hibachi grill.

Day 3: Holiday Traditions & Local Treasures

Breakfast Treats: Dough Haus

Stop by Dough Haus for a dozen donuts — the perfect treat to bring to family, or to enjoy on the go as you explore. (Around here, showing up with Dough Haus donuts practically guarantees hugs and smiles.)

Day: Main Street Browsing

No matter what day, Main Street offers both your classic favorite shops, plus new speciality shoppes and murals. You’ll always find something new and special on Gloucester’s Main Street.

Plan accordingly and your trip will be even more festive!

Christmas and Holiday Parade - December 6
Christmas Market at Abingdon Episcopal Church – December 5 & 6
Christmas Market at Ware Church – December 13

From handmade gifts to baked goods and holiday décor, these markets are packed with the spirit of the season.

Dinner: A Cozy, Home-Cooked Meal

After a full day of festivities, head “home” for a cozy, home-cooked dinner. Create a warm holiday table using beautiful settings and décor picked up from Timeless Treasures and York & Main, two local shops filled with charming pieces that make every meal feel special. Nothing says holidays like glittering and gold taper candles, cocktail glasses, dinner napkins, and table runners. Stop by Ware Neck Produce next door for fresh greenery.

If you’re visiting Gloucester on a couples retreat and want a special final dinner, we highly recommend Under the Stars Lavendar Farm’s Igloo Dining, where you can experience a private and cozy intimate dining experince.

Day 4: Stocking Stuffers & Farewell Moments

Before you pack up, make time to shop for last-minute gifts — instead of lugging presents from home, get everything you need right here in Gloucester:

Whitley’s Peanuts
Northern Neck Popcorn Bag
Virginia Made Products

Then swing by the Gloucester Visitor Center for a final keepsake or Gloucester-branded item. And don’t miss the Werowocomoco Exhibit, honoring the upcoming National Park site tied to Pocahontas, Chief Powhatan, and the region’s deep history.

A Holiday Homecoming to Remember

December in Gloucester wraps you in nostalgia — from glowing lights and cozy meals to family traditions and warm community charm. Whether you’re reconnecting with loved ones or rediscovering the town you once called home, this holiday getaway offers the perfect blend of togetherness, comfort, and festive fun.

And with your own cozy hotel room waiting each night, you’ll enjoy the best of both worlds: family by day, peace and quiet by night.

Coming Home for the Holidays: A Family-Focused December Getaway in Gloucester, Virginia