Valentine’s Weekend in Coastal Delaware is not just about candlelit dinners. 

Whether you are planning a romantic date night, a fun Galentine’s celebration, a relaxing spa day, or even a festive 5K on the boardwalk, there are countless ways to celebrate. 

From cozy wine pairings and curated tasting menus to comedy shows, creative workshops, and full weekend getaways by the ocean, this guide brings together the best events and experiences happening across Rehoboth Beach, Lewes, Milton, and beyond!

The Best Events Happening This Valentine’s Day Weekend

Don’t Tell Comedy Valentine's Day Show

If you are looking for something unexpected this Valentine’s Day, this secret comedy show delivers exactly that. 

Instead of the usual dinner plans, you will spend Valentine’s Day laughing your way through a carefully curated lineup of four to seven comedians, all kept completely under wraps until they step on stage. 

The show takes place in an indoor performance space, with the exact location revealed the morning of the event, adding a playful layer of mystery that feels perfectly on theme for Valentine’s Day. 

Once inside, you will enjoy 70 to 90 minutes of high-energy comedy that feels intimate, spontaneous, and refreshingly different. 

If you want Valentine’s Day plans that break the routine and give you something to talk about long after the weekend ends, this is it.

• Date: Saturday, February 14th
• Address: Secret Location in Lewes
• Hours: Shows at 7pm and 9pm
• Cost: $54

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Valentine’s Day Menu at the Avenue Apothecary & Spa

If Valentine’s Day for you means relaxing, the Avenue Apothecary and Spa is leaning fully into chocolate, florals, and glow-worthy treatments. 

The 2-hour Cookie Butter and Chocolate Body Treatment includes a full-body scrub, a CoQ10 and royal jelly chocolate mask, and a customized 60-minute massage with coconut and sweet almond oils for silky smooth skin.

You can also book the Love in Bloom hot stone massage with notes of white orchid and sandalwood, the Honey Berry Facial with organic plant-based skincare, and a lip treatment. 

Or seasonal manicures and pedicures featuring chocolate masks, sugar exfoliation, and vitamin-rich body butters. 

Whether you are planning Valentine’s Day with someone special or treating yourself, these services are designed to feel romantic and restorative.

• Dates: Throughout February
• Address: 110A Rehoboth Avenue, Rehoboth Beach
• Hours: Schedule by contacting them at (302) 227-5649 or [email protected]
• Cost: $335-$160

Massage at the Barefoot on the Beach

For another relaxing Valentine’s Day option, Barefoot on the Beach offers everything from classic Swedish relaxation massage to focused deep tissue work for stubborn tension. 

The Barefoot Signature Massage includes a guided breathing ritual and a full hot steam herbal towel treatment, while options like hot stone, Himalayan salt stone, bamboo massage, and CBD-infused bodywork add extra depth.

If you are celebrating Valentine’s Day together, the couples massage lets you unwind side by side in a dual suite. 

There are also prenatal sessions, myofascial release, and Reiki available, so you can choose exactly the level of therapeutic or calming support you want for the weekend.

• Dates: Various
• Address: 18389 Olde Coach Drive Unit 2, Rehoboth Beach
• Hours: Book your appointment here
• Cost: $320-$70

Spa Packages at Coastal Bliss Wellness

If you want to turn Valentine’s Day into a full spa experience, Coastal Bliss Wellness offers curated couples packages. 

The Sweet Escape for Two includes a 60-minute couples massage with aromatherapy, plus chocolate truffles and bubbly. 

The Blissful Romance Ritual adds customized facials for each person and chocolate-covered strawberries.

For a more elevated Valentine’s Day, the Ultimate Love Indulgence package includes a 90-minute couples massage with CBD balm, sculpting facials, and spa manicures and pedicures in a rose petal setting. 

Prefer to celebrate on your own? The Be Your Own Valentine package includes a full-body massage, facial, manicure, pedicure, champagne, and chocolate-covered strawberries, making self-love the focus of the day.

And if you are still deciding on the perfect gift, their spa gift cards offer a fantastic and thoughtful Valentine’s Day solution.

• Dates: Various
• Address: 323C Rehoboth Avenue, Rehoboth Beach
• Hours: Schedule by contacting them at (302) 260-9667 or [email protected]
• Cost: $1150-$350

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Nassau Valley Tour & Tasting

If you’re looking for a Valentine’s Day plan that feels thoughtful without being over-the-top, a visit to Nassau Valley Vineyards is a great option. 

The self-guided tour lets you explore at your own pace, which makes the experience feel personal instead of structured. 

As you walk through, you’ll learn fascinating bits about wine’s role in human history and see how grapes are grown and transformed into the bottles we love today. 

The displays include artwork, photos, and artifacts that make it feel more like a charming little museum than a typical winery stop.

There’s also a gallery space featuring local artists, adding a creative and slightly romantic touch to your Valentine’s outing. 

Afterward, you can settle in for a tasting, try a variety of wines, and even take home your glass as a keepsake from the day.

• Date: Various
• Address: 32165 Winery Way, Lewes
• Hours: Tuesday through Sunday from 11am to 5pm.
• Cost: Tour (free); Tasting ($15)

Milton Brewery Love at First Draft Book Fair with Browseabout Books

If your ideal Valentine’s Day includes craft beer and a good love story, this cozy book fair at Milton Brewery might be your perfect match. 

“Love at First Draft” brings together Browseabout Books and Dogfish Head for an evening that blends romance novels with your favorite brews.

You’ll be able to browse a curated selection of rom-coms, swoon-worthy romances, and heartfelt reads while sipping something delicious. 

The atmosphere is relaxed and welcoming: no pressure, no fancy dress code, just good drinks and stories that make you smile.

Whether you’re coming with a date, meeting friends for a Galentine-style night out, or simply treating yourself, it’s a low-key and genuinely fun way to celebrate Valentine’s Day.

• Date: Friday, February 13th
• Address: 6 Cannery Village Center, Milton
• Hours: From 4pm to 8:30pm

Valentine's Day Brunch at Chesapeake & Maine

Celebrate Valentine’s Day with a brunch that feels special but still comfortable.

Chesapeake & Maine offers a seafood-forward menu that puts creative twists on classic brunch dishes, blending indulgence with coastal charm.

Think beautifully plated dishes, fresh flavors, and the kind of meal you’ll want to linger over. 

Pair your food with a signature brunch cocktail and take your time soaking in the relaxed Rehoboth Beach atmosphere.

It’s perfect for couples looking for a romantic daytime date, but it also works wonderfully for friends who want to celebrate Valentine’s together over something delicious. 

• Date: Saturday, February 14th
• Address: 316 Rehoboth Avenue, Rehoboth Beach
• Hours: From 11am to 2pm
• Reserve your table here

4th Lovers Lane Valentines Boardwalk 5k

If you’d rather start Valentine’s Day with movement and ocean air, the Lovers Lane Boardwalk 5K offers a festive and feel-good alternative to traditional plans. 

Hosted by the Seashore Striders, the race begins at the Rehoboth Beach Bandstand and heads north along the scenic boardwalk toward Gordon’s Pond.

Runners and walkers of all levels are welcome, and many participants fully embrace the Valentine’s spirit with red, pink, and Cupid-themed outfits. 

There are playful awards for standout looks, and the energy is upbeat and community-focused.

Families will also love the free kids’ Cupid Dash just before the main race. 

With long-sleeve race shirts for pre-registered runners and post-race snacks that often include chocolate treats, it’s a fun and lighthearted way to celebrate Valentine’s Day together.

• Date: Saturday, February 14th
• Address: 1 Rehoboth Avenue, Rehoboth Beach
• Hours: Starts at 10am (Kids dash at 9:50am)
• Cost: $30 (until February 8th); $35 (from February 9th to 13th); $40 (on February 14th) 

Galentine's Day Party at Salted Vines

Valentine’s Day isn’t just about couples, and this Galentine’s celebration at Salted Vines makes that clear. 

It’s an evening dedicated to friendship, laughter, and raising a glass to the people who show up for you all year long.

You can enjoy seasonal wine selections crafted with Valentine’s flair while browsing local vendors offering handmade goods, boutique fashion, candles, pottery, baked treats, and thoughtful gifts. 

It’s the kind of event where you might leave with something special for a friend, or yourself.

Live music keeps the energy lively and full of good vibes, while food options help round out the night. 

• Date: Thursday, February 12th
• Address: 32512 Blackwater Road, Frankford
• Hours: From 4pm to 7pm

Love Notes to Yourself at Hammer & Stain Lower Delaware

Valentine’s Day can also be about self-love, and this creative workshop is designed with that in mind. 

“Love Notes to Yourself” invites guests to slow down and create something meaningful in a supportive, welcoming space.

Participants paint a bold canvas featuring either a heart or lips design surrounded by vibrant sunburst colors. 

Guided instruction makes it approachable for all skill levels, so no artistic background is required.

Once the base is complete, you’ll add handwritten affirmations and sparkling embellishments like gems and rhinestones to personalize your piece. 

The result is a one-of-a-kind keepsake that serves as a reminder of your strength and goals long after Valentine’s Day is over.

• Date: Saturday, February 14th
• Address: 18388 Coastal Highway #8, Lewes
• Hours: From 1pm to 2:30pm
• Cost: $35 (if available, the code is EARLYBIRD5); $40 (regular price)

Love Stinks, Let's Drink Party at Big Chill Surf Cantina

Not everyone wants candlelight and roses on Valentine’s Day, and this party proudly embraces that. “Love Stinks, Let’s Drink” is all about celebrating independence, laughing at dating disasters, and having an unforgettable night out.

The evening starts with live entertainment before transitioning into a high-energy dance party where you can fully let loose. 

The drink menu leans into playful Valentine’s-inspired flavors, and a digital photo booth lets you capture fun, slightly chaotic memories with friends.

One crowd-favorite activity even gives guests the chance to symbolically say goodbye to past relationships in a funny and surprisingly satisfying way.  

It’s bold, upbeat, and a reminder that Valentine’s Day can be whatever you want it to be.

• Date: Saturday, February 14th
• Address: 19406 Coastal Highway, Rehoboth Beach
• Hours: Starts at 7pm

Rehoboth/Dewey Beach Chamber of Commerce Merchants' Attic

If your Valentine’s Day vibe is more treasure hunt than candlelit dinner, the Merchants’ Attic is a fun and unexpected option. 

As Delaware’s largest indoor garage sale, it brings together up to 100 vendors offering antiques, handmade goods, collectibles, and unique finds.

It’s a great place to search for a one-of-a-kind Valentine’s gift or simply enjoy browsing together. 

The lively, social atmosphere makes the whole experience feel like an adventure, with surprises around nearly every corner.

Even if you don’t leave with a purchase, you’ll leave with stories, and maybe a new tradition for Valentine’s weekend.

• Date: Saturday, February 14th
• Location: Cape Henlopen High School
• Hours: From 10am to 3pm
• Donations will be accepted at entry for the benefit of the Chamber Event Fund

Parents' Night Out at Georgetown Campus

Valentine’s Day can be tricky for parents who want to plan a night together, and this event makes it easy. 

While you head out for dinner or a quiet evening, kids get their own Valentine’s-themed adventure filled with animals, crafts, and fun activities.

Children spend time interacting with adoptable animals, usually the highlight of the night, along with creating animal-inspired crafts and learning fun facts about pets and wildlife. 

The evening winds down with a themed movie so everyone can relax before pickup.

It’s a thoughtful Valentine’s option that lets parents enjoy meaningful time together while kids have a safe, engaging, and genuinely fun night of their own.

• Date: Saturday, February 14th
• Address: 22918 Dupont Boulevard, Georgetown
• Hours: From 4pm to 8pm
• Cost: $50

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Mead & Chocolate Pairing at Brimming Horn Meadery

Chocolate and sweet drinks are basically Valentine’s staples, and this tasting brings them together in a way that feels cozy, indulgent, and a little bit romantic. 

This pairing focuses on handcrafted meads matched with rich chocolate truffles, creating combinations that highlight the flavors of both in a really unique way.

Each pairing is meant to be savored slowly, making it a great option for couples looking for something different, friends wanting to celebrate together, or anyone who simply loves chocolate and trying new drinks. 

Live music with Bryan Scar adds an extra layer of charm and makes the whole setting feel warm and inviting. 

• Date: Saturday, February 14th
• Address: 106 Spring Street, Seaford
• Hours: From 12pm to 10pm

Love Is in the Air and on the Menu

Harvest Tide Steakhouse

Harvest Tide Steakhouse is a great pick for Valentine’s weekend if you’re craving a classic dinner that still feels special. 

The focus here is on dry-aged prime steaks, fresh seafood, and locally sourced ingredients, all prepared with care and big flavor without feeling overly complicated. 

The cocktail list is strong, the local draft selection is solid, and the wine list makes it easy to find something perfect for the table.

For couples who love bold flavors, their Bold Love and Fine Wine pairing dinner adds an extra layer to Valentine’s celebrations. 

The multi-course experience highlights Orin Swift wines paired thoughtfully with each dish, creating a meal that feels elevated but still warm and inviting. 

Whether you choose the pairing dinner or a traditional reservation, it is an easy place to settle in and enjoy a relaxed, memorable Valentine’s evening.

• Date: February 12th to 15th
• Address: 410 E Savannah Road, Lewes

Spirit Dinner: Thrasher’s Rum at The Federal

If you are looking for a Valentine’s season dinner that feels unique, cozy, and elevated, this Thrasher’s Rum spirit dinner at The Federal is a refreshing change from the typical date night. 

The evening blends amazing food, creative cocktails, and the stories behind the spirits, making it feel interactive and memorable from start to finish.

Part of a special distillery pairing series, the multi course menu is created by James Beard nominated Chef Todd Gray. 

The night begins with a rich black bean soup layered with bright, tangy accents that balance each bite. 

The main course features beautifully cooked duck served with comforting sides and a rich sauce that feels perfectly suited for a Valentine’s celebration. 

Dessert closes the evening with coconut cake paired alongside fruity, refreshing notes that give the night a sweet and indulgent finish.

Throughout dinner, guests hear directly from the people behind Thrasher’s Rum, adding personality and connection to every pour. 

• Date: Friday, February 13th
• Address: 62A Rehoboth Avenue, Rehoboth Beach
• Hours: Starts at 7pm 
• Cost: $105

Wine Dinner at Fish On Supporting SODEL Cares

The Valentine’s wine dinner at Fish On turns the evening into a full culinary experience built around intentional pairings and seasonal ingredients. 

Designed to be enjoyed slowly, the multi-course menu moves thoughtfully from bright flavors to richer, more indulgent plates.

The night begins with seared scallops served with shaved Brussels sprouts and citrus butter, paired with A to Z Wineworks Chardonnay from Oregon. 

The main course presents pepper crusted ahi tuna with ancient grains, roasted winter vegetables, and fennel soubise matched with Spring Valley Vineyards Nina Lee Syrah. 

Dessert finishes the experience with lemon bundt cake topped with cream cheese whip and white chocolate served with A to Z Wineworks Riesling.

It is a romantic and well paced way to celebrate Valentine’s while supporting a meaningful cause.

• Date: Saturday, February 14th
• Address: 17300 North Village Main Boulevard, Lewes
• Hours: From 6pm to 9pm
• Cost: $114

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Chesapeake & Maine

Chesapeake & Maine makes Valentine’s dinner all about sharing food, savoring flavors, and enjoying each other’s company. 

The menu is filled with options meant to be split, from appetizers like crab dip, fried artichoke hearts, crab wontons, beef tenderloin skewers, and a seafood quesadilla with lobster and crab. 

It also includes shareable entrees like crab cakes, lobster rolls, lobster carbonara, short rib tortellini, and braised pork chop with parmesan grits.

Dessert is designed for two, with choices like Smith Island Cake, crème brûlée, cheesecake, or a dessert-for-two assortment. 

Creative cocktails such as Lucy in the Sky with Diamonds and Garden of Eden add a playful, celebratory touch. 

With its warm, lively vibe, this dinner is romantic, festive, and perfect for couples looking to enjoy a Valentine’s night full of flavor and connection.

• Date: Saturday, February 14th
• Address: 316 Rehoboth Avenue, Rehoboth Beach
• Hours: Starts at 2pm
• Reserve your table

Bodhi Kitchen

Bodhi Kitchen offers a playful Valentine’s alternative with its Dumpling Date Night, perfect for couples who bond over sharing great food. 

Instead of a traditional plated dinner, the evening features a special dim sum spread filled with freshly made, steaming dumplings meant to be passed around and enjoyed together.

The variety keeps the table dynamic, encouraging conversation and connection as each basket arrives. 

The atmosphere feels casual and energetic without losing the sense of occasion, making it ideal for couples who want something flavorful and interactive rather than formal.

For Valentine’s couples who enjoy bold tastes and a more relaxed dining style, Dumpling Date Night turns sharing into the main event.

• Date: Saturday, February 14th
• Hours: From 5pm to 10pm
• Address: 10 N 1st Street, Rehoboth Beach

Heirloom

Heirloom in Lewes offers a charming, intimate dining experience that makes any night feel special. 

Housed in a Victorian white house with red shutters and recognized by the James Beard Mid-Atlantic Awards, the restaurant turns local, seasonal ingredients into beautifully crafted, flavorful plates.

The February menu features options perfect for sharing: French Onion Soup, Baby Red Romaine "Caesar" Salad, Steak Tartare, Winter Grain Salad, House-Stretched Burrata, and Kennett Square Mushroom Scrapple. 

Entrées range from Rotolo Pasta and Pan-Seared Filet of Beef to Shrimp & Grits, Cornmeal Fried Flounder, and Pan-Roasted Amish Chicken, with shareable sides like Mushroom Mix and Roasted Beets.

While Valentine’s Day is fully booked, Heirloom is open on Friday the 13th, making it a perfect choice for a romantic, memorable night during Valentine’s weekend.

• Date: Friday, February 13th
• Address: 316 Rehoboth Avenue, Rehoboth Beach

Eden

Eden in Rehoboth Beach has been a destination for fine dining and romance for over two decades. 

With a reputation for innovative cuisine, creative cocktails, and an award-winning wine list, it’s easy to see why Delaware Today calls it the “Most Romantic Atmosphere.” 

The elegant setting and attentive service make it a perfect choice for a special evening with someone you love. 

Valentine’s Day is also fully booked, but you can still celebrate on Friday the 13th.

• Date: Friday, February 13th
• Address: 20200 Coastal Highway, Rehoboth Beach

Drift Seafood & Raw Bar

Drift Seafood & Raw Bar brings the freshest local seafood and a refined, intimate atmosphere to Rehoboth Beach. 

With a carefully curated raw bar, seasonal dishes, and a thoughtful beverage program, every visit feels like a special occasion. 

The menu changes daily to highlight the best ingredients from the region, making each dinner a unique experience. 

While Valentine’s Day itself is unavailable, you can still enjoy a special dinner on Friday the 13th or Sunday the 15th.

• Date: February 13th or 15th
• Address: 316 Rehoboth Avenue, Rehoboth Beach

Turn Valentine’s Day Into a Weekend Escape

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Atlantic Sands Hotel

If waking up to sweeping ocean views and drifting off to the sound of the waves feels like your perfect Valentine’s weekend, Atlantic Sands Hotel offers exactly that experience.

Set directly on the Rehoboth Beach boardwalk, this oceanfront property places you just steps from the sand and only minutes away from the boutiques, cafés, and restaurants along Rehoboth Avenue. 

The atmosphere is relaxed and inviting, with modern guest rooms, convenient in-room amenities, and an outdoor pool that creates an easy setting to unwind together.

For couples planning a winter escape, Atlantic Sands is featuring a Stay and Save This Winter promotion that makes a romantic trip even more appealing. 

Guests receive 20 percent off when booking two nights or 30 percent off when staying three nights. 

This offer is available Sunday through Thursday during January and February 2026. 

Each morning also includes a full breakfast, giving you a warm and cozy way to begin the day before heading out to explore downtown Rehoboth.

• Address: 1 Baltimore Avenue, Rehoboth Beach
• Contact: (302) 227-2511

Dogfish Inn

Situated along the Lewes Rehoboth Canal, Dogfish Inn stands out as a great option for couples who want something a little out of the ordinary. 

With only 16 carefully designed rooms, this off centered basecamp combines relaxed comfort with the distinctive creativity that Dogfish Head is known for. 

The setting feels personal and intimate, ideal for couples who appreciate craft culture, unique experiences, and easy access to the outdoors.

What truly elevates a Valentine’s weekend stay here is the ability to personalize your visit with thoughtful add-ons, especially the Off-Centered Occasion bundle. 

Created for anniversaries, birthdays, and romantic escapes, this curated package includes a flower arrangement, an assortment of chocolates, two Dogfish Head glass tumblers, a s’mores kit, and even the option to display a personalized message on your guest room door.

To make the experience even more memorable, you can take a short walk to Heidi Lowe Gallery and participate in a hands-on class where you create custom jewelry together. 

With canal views, nearby bike trails, and meaningful personalized touches, Dogfish Inn is perfect for couples looking for a Valentine’s getaway that feels creative, cozy, and truly special.

• Address: 105 Savannah Road, Lewes
• Contact: (302) 644-8292; [email protected]

Boardwalk Plaza Hotel

Boardwalk Plaza Hotel provides one of the most romantic atmospheres in Rehoboth Beach, pairing oceanfront scenery with refined Victorian-style architecture and design. 

With 84 beautifully appointed guest rooms that blend antique furnishings with modern comforts, the property feels more like an elegant seaside residence than a typical resort. 

A glass-enclosed elevator with ocean views, fine dining at Victoria’s restaurant, and a heated indoor-outdoor spa pool all contribute to its timeless appeal.

For Valentine’s Day, the hotel offers its Victorian Valentine’s Package, a three-night escape created specifically for couples. 

Upon arrival, you will find champagne, chocolates, and keepsake champagne flutes waiting in your room. 

The package also includes a romantic Valentine’s dinner for two at Victoria’s with views overlooking the Atlantic Ocean. 

In addition, couples receive breakfast or Sunday brunch for two and a late checkout at 1pm so you can fully enjoy every final moment of the weekend.

Availability varies depending on the room type, so it is recommended to call early to secure the best option for Valentine’s weekend.

• Address: 2 Olive Ave & the Boardwalk, Rehoboth Beach
• Contact: (800) 33-BEACH or (302) 227-7169; [email protected]

Coastal Delaware always has something worth planning around, especially during Valentine’s season. 

If you want the inside track on standout dinners, local events, and the spots actually worth reserving, keep following the blog!