Dinner at a Waterfront Restaurant

One of the most romantic date night ideas is enjoying a delicious meal together at a waterfront restaurant overlooking the picturesque Plymouth Harbor. The setting provides the perfect backdrop for a cozy and intimate evening. Some top restaurants in the area include East Bay Grille, The Waterfront Bar and Grill, and RooBar.

Alternative options: Isaac’s Restaurant, CabbyShack, T-Bones Road House

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Romantic Stroll along Plymouth Harbor

After dinner, take a leisurely stroll along Plymouth Harbor and enjoy the breathtaking views of the water and boats. The serene atmosphere and cool sea breeze create a romantic setting for couples to walk hand in hand and have meaningful conversations.

Alternative options: Jenney Grist Mill, Brewster Gardens, Plimoth Plantation

Sunset Cruise on the Bay

For a truly unforgettable date night experience, consider booking a sunset cruise on Plymouth Bay. Watching the sun go down over the water while snuggled up with your significant other is sure to create lasting memories. Several companies offer sunset cruises, such as Capt. John Boats and Lobster Tales.

Alternative options: Viking Cruises, Plymouth Bay Whale Watch, Provincetown Fast Ferry

Wine Tasting at a Local Vineyard

Indulge in a wine tasting experience at a local vineyard and discover new flavors together. Sample a variety of wines, enjoy the beautiful vineyard scenery, and learn about the winemaking process. Some popular vineyards near Plymouth include Plymouth Bay Winery, First Crush Winery, and Cape Cod Winery.

Alternative options: Running Brook Vineyard & Winery, Truro Vineyards of Cape Cod, Westport Rivers Vineyard & Winery

Couples Massage at a Spa

Relax and unwind with a couples massage at a spa in Plymouth. This pampering experience allows you and your partner to de-stress, rejuvenate, and bond over a shared sense of relaxation. Treat yourselves to a soothing massage at Mirbeau Inn & Spa, Bella Day Spa, or Elements Massage.

Alternative options: Oasis Day Spa, Strategies for Wellness, Radiant Holistic Wellness

Live Music at a Jazz Club

Enjoy a night of live music at a local jazz club and groove to the rhythm of the music together. The intimate setting, smooth tunes, and cozy atmosphere make for a perfect date night activity. Check out The Spire Center for Performing Arts or local bars and pubs for live jazz performances.

Alternative options: British Beer Company, KKatie’s Burger Bar, Main Street Sports Bar & Grill

Cooking Class for Two

Get hands-on and learn a new culinary skill together by taking a cooking class for two. Whether you’re a novice in the kitchen or a seasoned home cook, a cooking class is a fun and interactive way to bond with your partner. Consider taking a class at The Kitchen at Mirbeau, Plymouth Farmers Market, or Sur La Table.

Alternative options: Milestone Kitchen & Bar, Chequessett Chocolate, Knotty Vines

Visit to Plymouth Rock and Mayflower II

Immerse yourselves in history with a visit to iconic Plymouth Rock and the Mayflower II. Explore the historic sites, learn about the Pilgrims’ journey, and deepen your appreciation for the town’s rich heritage. Don’t forget to take a romantic stroll along the waterfront afterwards.

Alternative options: Plimoth Plantation, National Monument to the Forefathers, Jenney Museum

Ghost Tour of Historic Sites

Embark on a spooky and thrilling adventure with a ghost tour of Plymouth’s historic sites. Delve into the town’s haunted past, listen to chilling tales of ghosts and legends, and hold each other close as you explore eerie locations under the cover of darkness.

Alternative options: Capt. John’s Boats, Plymouth Night Tour, The Ghost Lady Walking Tours

Comedy Show at a Local Theater

Laugh the night away with a comedy show at a local theater in Plymouth. Enjoy a night of humor, wit, and entertainment as you watch talented comedians perform live on stage. Check out shows at Thekla Macadonia, Memorial Hall, or Plymouth Community Theatre for a night of laughter and fun.

Alternative options: Improv Comedy at The Comedy Loft, Stand-up Comedy at DICK’S Last Resort, ComedySportz Boston

Whether you prefer a romantic dinner by the water, a leisurely stroll along the harbor, or an adventurous ghost tour, Plymouth, MA, offers a variety of date night ideas for parents looking to reconnect and have a memorable evening together. So, why not take some time for yourselves, hire a sitter through Wyndy, and enjoy a well-deserved night out with your partner? Happy date night!