Valentine's Day Vacations
Dreaming of the perfect romantic getaway? Whether you’re seeking golden sunsets, charming old towns, or a cozy retreat for two, these destinations are filled with romance. From enchanting evenings to candlelit dinners by the sea, I’ve gathered my favorite spots to make this Valentine’s Day truly unforgettable, and I hope you enjoy them as much as I do.
1. Wild Side Specialty Tour in Hawaii
If you want to see dolphins on your trip to Hawaii, check out Wild Side Specialty Tours!
We left from the Wai‘anae coast early in the morning, the sun barely above the water, casting gold over a sea that stretched endlessly west. The crew was warm, funny, deeply respectful of the ocean.
We saw dolphins, green sea turtles, flying fish, and a massive manta ray.
Turtle Bay Resort was our go-to for romantic dinners, and unforgettable sunsets on O'ahu’s North Shore.
2. Largo, Florida
Largo may not be as widely known as its nearby neighbors, but it’s a wonderful hidden gem for a Valentine’s escape. Nestled in Pinellas County, just minutes from the Gulf, it combines lush parks, cultural gems, and easy beach access, perfect for a couples’ getaway.
We strolled through the Florida Botanical Gardens, had a picnic at Largo Central Park and had a romantic dinner at E&E Stakeout Grill.
Local tip: Just a 10-minute drive from downtown Largo, Indian Rocks Beach is less crowded than Clearwater and makes for a dreamy spot to toast with champagne while the sky turns pink.
3. Bradenton Beach
I thought Bradenton Beach was one of Florida’s most underrated Gulf Coast escapes, a sun-soaked blend of old-Florida charm, wide stretches of powdery white sand, colorful cottages, and a breezy island pace along the sparkling turquoise waters of Anna Maria Island!
From Tampa, we drove just over an hour south and spent three blissful days based at a laid-back beachfront inn. We wandered the sugar-soft sands at Coquina Beach, strolled the historic Bridge Street Pier with its quirky shops and ice-cream stands, kayaked through the serene mangrove tunnels of Leffis Key, and lingered over fresh-caught grouper tacos at casual dockside grills. In the evenings, we joined locals for live music under twinkling lights, watched fiery sunsets melt into the Gulf, and rounded off my nights with a cold craft beer at a friendly tiki bar right on the sand.
4. Ogden, Utah
Ogden was a vibrant mix of frontier history, adventurous spirit, and breathtaking Wasatch Range scenery all wrapped into a friendly, walkable downtown!
From Salt Lake City, we drove about 40 minutes north and spent three days based at a boutique loft near historic 25th Street. We explored the fascinating Hill Aerospace Museum, hiked into the stunning Ogden Canyon trails with cascading waterfalls and mountain vistas, and got my adrenaline fix at Snowbasin Resort, one of the 2002 Winter Olympic venues. Back in town, we browsed quirky art galleries, sampled inventive craft brews, joined a lively food tour of locally loved eateries, and capped off my nights with cocktails in restored saloons where old railroad stories still linger in the air.
5. Oshkosh, Wisconsin
I thought Oshkosh was one of the Midwest’s most underrated small cities. I enjoyed the charming lakefront community where aviation history, creative culture, and classic Wisconsin hospitality meet along the shores of sparkling Lake Winnebago!
From Milwaukee, we drove an hour and a half north and spent three days based at a cozy riverside inn. We explored the world-class EAA Aviation Museum, cruised the scenic Fox River, and discovered local art at the lively Paine Art Center and Gardens. I sampled hearty Wisconsin fare and craft brews at welcoming supper clubs, wandered through farmers’ markets bursting with regional flavors, and toured the historic Grand Opera House. Evenings ended with romantic golden sunsets over Lake Winnebago, live music at buzzing taverns, and a relaxed small-town vibe that made it easy to feel right at home.
6. La Junta, Colorado
We found La Junta to be one of Colorado’s most overlooked gems, a welcoming plains town where pioneer history, rugged landscapes, and wide-open skies create an atmosphere both adventurous and authentic.
About two hours southeast of Colorado Springs, we made La Junta my base for three days, staying at a rustic lodge with big western charm. WE wandered the fascinating Bent’s Old Fort National Historic Site, and toured the Koshare Indian Museum with its impressive collection of Native American art. My days were fueled by hearty local diners and family-run cafés, and our evenings slowed to golden sunsets, starry night skies, and quiet conversations in classic small-town watering holes that felt untouched by time.
7. Crystal City, Virginia
I thought Crystal City was one of the D.C. area’s most surprising Valentine’s Day getaways, a sleek and stylish urban pocket where modern city life, cozy dining spots, and Potomac River views create a perfect romantic backdrop.
Just minutes from the National Mall, we spent a long Valentine’s weekend in a chic high-rise hotel with skyline views. By day, we strolled hand-in-hand through nearby Long Bridge Park, wandered the underground Crystal City Shops, and took a scenic bike ride along the Mount Vernon Trail. Evenings were reserved for candlelit dinners at intimate bistros, craft cocktails in hidden lounges, and a moonlit walk along the river with the glittering monuments in the distance. We capped off the night with dessert and champagne in our suite, savoring the blend of city buzz and private retreat that made Valentine’s in Crystal City feel both effortless and unforgettable.
8. Kona Breezes & Garden Stillness at Holualoa Inn
I thought Kona was one of the dreamiest Valentine’s escapes in Hawaii, a sun-kissed paradise where volcanic shores, tropical breezes, and fiery sunsets set the stage for romance.
We spent our Valentine’s weekend at a serene oceanfront resort, waking up to the sound of waves and breakfasts on a lanai overlooking the Pacific. By day, we strolled hand-in-hand through fragrant Kona coffee plantations, shared quiet moments snorkeling in hidden coves, and explored sacred sites where history lingers in the lava rock. In the evening, we toasted with mai tais at a beachside bar as the sky blazed pink and gold, then dined under the stars with fresh island seafood and sweet lilikoi desserts.
9. Queens, New York
I thought Queens was one of New York City’s most unexpected Valentine’s escapes, a vibrant borough where global flavors, hidden gems, and skyline views create a love story all their own.
We based ourselves at LIC Hotel, a chic boutique hotel in Long Island City, starting the day with coffee and croissants at a cozy café before wandering Gantry Plaza State Park, hand in hand, with breathtaking Manhattan views across the East River.
In the afternoon, we explored the art-filled halls of MoMA PS1, then slipped into Astoria for a leisurely dinner at a candlelit Mediterranean bistro, savoring mezze and fine wine. As night fell, we shared rooftop cocktails with twinkling skyline lights all around us, then ended the evening on a sweet note with warm desserts from a tucked-away bakery, a Valentine’s Day in Queens that felt intimate, flavorful, and beautifully New York.
Conclusion
What made these trips special were the small, slow moments like watching snow fall in a quiet town, sharing a warm dessert after the beach, or catching our son’s laughter echoing down a city block. Each place gave us space to press pause, look at each other a little longer, and remember why we’re still choosing this, again and again. Valentine's Day wasn’t about one perfect day. It was about a few unexpected ones that brought us back to what matters.
Booking Checklist
1. Book Your Flight - I use Expedia because I like their mobile app with my itinerary. They've helped me re-book flights on many occasions. Once you reach their Gold tier, support is especially good.
2. Book Your Hotel - I use Booking.com or Expedia, depending on my destination.
3. Book Your Rental Car - I use Expedia.
4. Book your tours on Viator or Get Your Guide.
