Luxury Valentine’s Day Destinations in Italy, Costa Rica, Mexico & Beyond

With Valentine’s Day fast-approaching, many couples are searching for special ways to embrace the season of love together. Luckily, various destinations across both the country and the world provide romantic settings and offerings that make for an unforgettable getaway for couples looking to spend quality time together.

From Italy to Costa Rica to Chicago, there are plenty of options for couples to choose from for a romantic getaway, near or far. Please find details on the luxury properties, destinations and exciting attractions that are perfect for a Valentine’s Day retreat below.



Borgo San Vincenzo

Tuscany’s newest luxury boutique hotel, Borgo San Vincenzo, invites couples for a romantic getaway to experience the region’s vibrant culture, breathtaking views, historic wine scene and locally curated experiences. Located in the heart of Montepulciano, Italy, Borgo San Vincenzo is perfectly positioned for a picturesque engagement in the vineyards, breathtaking sunset wedding or unforgettably romantic escape. The hotel offers one-of-a-kind personalized experiences like touring the region by hot air balloon, cooking classes in a winery, truffle hunting, and olive oil tasting among others. Couples can wake up surrounded by dreamy panoramic views from a private Tuscan villa or one of the 21 luxury studios and suites. They can also soak up the Tuscan sun while having a poolside cocktail, enjoy a delightful countryside picnic or private dinner in a wine cellar. More information HERE. Images HERE.


Hotel Belmar

Recently named one of the Top 100 Hotels in the World as well as one of the 10 Best Resorts in Central America by Travel + Leisure World’s Best, Hotel Belmar is 26-room boutique eco-hotel located in Costa Rica’s lush cloud forest nestled in the mountains of Monteverde. Surrounded by naturally landscaped gardens and with the sounds of wildlife all around, the hotel is ideal for couples looking to connect with nature and with each other this Valentine’s Day. Offering a variety of elegant guestrooms and suites guests enjoy floor-to-ceiling windows with spectacular views, private terraces, private whirlpool jacuzzi, king size beds, showers with forest views and large terraces overlooking the mountains and the Pacific Ocean. Known for its gastronomy and farm-to-table program, the hotel features a restaurant, a microbrewery, an organic garden, a bar, a juice bar and tearoom, a spring water pond, a sun deck, a food store and a jacuzzi in addition to their Finca Madre Tierra farm, the first carbon neutral farm in the country offering a real Costa Rican farm experience for guests. Couples can also visit the hotel’s private reserve, SAVIA, for adventures with a purpose in the forest which can include a romantic picnic for two above the forest canopy. Images HERE.


Mount Cinnamon Resort

Tucked away on the hillside atop Grand Anse Beach, Mount Cinnamon is an eco-luxe hideaway with an enclave of 37 luxury villas and suites, each with their own veranda of sweeping views of natural unspoiled beauty. The resort treasures the natural beauty of Grenada and puts an emphasis on leading with environmentally friendly practices. This February indulge in romance and book a romantic stay at Mount Cinnamon with your significant other.  This package will transport you and your loved one to a tropical paradise where romance and relaxation are paramount. More information HERE. Imagery HERE and HERE.

Frangipani Beach Resort

Anguilla’s top luxury boutique resort, Frangipani Beach Resort, is inviting couples to celebrate love by planning their romantic engagements, chic destination weddings or memorable honeymoons along the stunning crystal-clear turquoise waters of Mead’s Bay. Those looking to plan the perfect proposal, or a destination wedding can captivate their significant other and their guests with exclusivity, elegance, unparalleled beauty and tranquility found at the resort.  The resort’s many activities offer couples a beach hopping day onboard Frangipani’s private catamaran or a day of beach-side fun kayaking and paddle boarding.  Customized experiences can be arranged including personal training, private yoga sessions and tennis lessons, a day at the Balinese Spa or a fishing trip. More information HERE. Images HERE.


Grand Residences Riviera Cancun

Grand Residences Riviera Cancun, a secluded coastal resort located outside of Cancun, sets the tone for couples to embark on a serene and peaceful luxe beachfront romantic escape. From taking a scenic route together on a guided bike tour followed by a tranquil couples massage in the afternoon and ending with a unique dining experience like a romantic candlelit dinner at the beach or a special chef in suite private dinner. This Valentine’s Day, couples looking to celebrate unforgettable moments and milestones, from moonlit engagements to romantic weekend getaways can book with 20% off in addition to receiving airport roundtrip transportation alongside welcome drinks and amenities. Images HERE.

Casa Kimberly

Once a gift from Richard Burton to his famed lover Elizabeth Taylor, Casa Kimberly is a gorgeous nine-suite boutique hotel in Puerto Vallarta, Mexico. Dick and Liz were the quintessential Hollywood romance, loving in secret at this hideaway, where Burton built a “Puente Del Amor” (Bridge of Love) to connect his villa across the street with Taylor’s so that the two could see each other without fear of paparazzi. Later marrying, divorcing, and remarrying, the couple’s infamous passion for each other can be felt everywhere within the hotel, from the rose petal-filled clawfoot baths to the private terraces overlooking the sparkling Banderas Bay. More information HERE.  Images HERE.



Hawks Cay Resort

Hawks Cay Resort, recipient of the Couples’ Choice Award presented by WeddingWire, is a 60-acre tropical lover’s paradise. The resort is cozy, the weather is breezy, and the destination creates the perfect setting for couples to rest, relax and reconnect on the sand and near the sea. This Valentine’s Day duos can enjoy a special date night movie on Feb. 13, then live music for dancing or the backdrop to their romantic dinner on Feb. 14. Home to spacious villas and suites; six restaurants; a saltwater lagoon; five swimming pools; on-site water sports; fishing, diving, spearfishing charters; and a Dolphin Connection facility, Hawks Cay is the ideal vacation spot for guests seeking the quintessential tropical escape centered around fun in the sun with virtually every water-related activity imaginable. Resort photos HERE.

Sofitel Chicago

This Valentine’s Day, rediscover romance with an elegantly styled staycation at Sofitel Chicago, the city’s most luxurious, French-inspired hotel. Make the night one to remember with a Magnifique Romance Package, featuring luxurious comfort, champagne, romantic welcome amenities and complimentary full American breakfast for two from CDA takeaway. Both guests and locals can take date night to the next level with Le Bar’s romantic prix fixe menu, featuring delightful French cuisine, exclusively available February 10-14, 2023. The menu has been specially created to help attendees embrace the season of love with delicious dishes including guest’s choice of Atlantic Cod with Sauce Vierge, Black Garlic Aioli and Pea Tendrils or Braised Short Rib with Taleggio Gnudi, Charred Endive and Bordeaux Jux. The menu is priced per person and rosé flights are available as an add on.  Reservations can be made on Tock. Images can be found HERE.

Swissotel Chicago

Swissôtel Chicago is an award-winning luxury hotel overlooking the Chicago River and Lake Michigan, and just steps from the Magnificent Mile. The distinctive all-glass four-diamond hotel offers spectacular wrap-around views from Navy Pier to Millennium Park, making for a romantic Valentine’s Day destination as you won’t need to leave your room to experience Chicago’s beauty! Book the Romance Package to sip champagne and enjoy hand-dipped Swiss chocolate strawberries complimented by sweeping views of the city. Wake up relaxed and refreshed and enjoy breakfast for two at The Palm Chicago and be in no rush to leave with complimentary 2pm late check out. Rates start at $249. As an additional add on experience, in-room spa services are offered through Windy City Massage. In the comfort of your own room, relax with treatments and services ranging from a Couples Massage to the Shea Butter Body Quench, which uses honey to cleanse pores and increase circulation, to the all-natural Hot Stone Massage. For a list of services and pricing, view the spa menu here. Images  HERE.

Fairmont Chicago

Fairmont Chicago, Millennium Park offers sophisticated, modern luxury in the heart of downtown Chicago. Overlooking Lake Michigan, Grant and Millennium Parks, and the legendary skyline, the hotel is the ideal backdrop for a romantic urban escape this Valentine’s Day. Spacious and impeccably appointed guestrooms provide city, park, or lake views, where the sights of Chicago will take your significant other’s breath away. Up the ante on your experience by staying in a Fairmont Gold room or suite, complete with a private lounge on the 15th floor, exclusive for Gold guests, that features breakfast, afternoon refreshments and early evening canapes; as well as concierge services available to assist in creating personal itineraries, spa appointments or dining reservations to make for a romantic and memorable stay. Images: HERE.

Hotel Zachary

Hotel Zachary at Gallagher Way is Chicago’s most distinctive boutique hotel. An authentic Wrigleyville neighborhood experience nestled just across the street from historic Wrigley Field, Hotel Zachary combines a vibrant, modern aesthetic and rich, classic elements with a unique neighborhood character that can’t be found anywhere else in Chicago. This Valentine’s Day, book the “Love, Alma” package which includes a $50 food and beverage credit at The Bar, upgraded Wrigley Field ballpark view accommodations, and an extended 1pm late checkout. Write your own love story with a special stay at Hotel Zachary! More information HERE. Images linked HERE.

Skydeck Chicago

Impress your sweetheart for Valentine’s Day Weekend with a visit to the Skydeck Chicago observation deck atop the iconic Willis Tower, and complete your romantic evening with a Pie in The Sky experience: a three-course meal featuring Giordano’s warm deep-dish pizza, salad, dessert, and a thrilling view of the city. This one-of-a-kind, after-hours experience is sure to be an evening you both remember forever. Book a table for Pie in the Sky on Valentine’s Day, and celebrate love with a heart shaped pizza at Skydeck Chicago at 10 p.m. To celebrate early, Pie in the Sky is also offered on Thursdays and Fridays at 10 p.m.  Skydeck has also launched their annual Love on The Ledge social media contest where four couples will be selected as winners of a vow renewal or wedding ceremony on The Ledge. The event will take place on February 12, 2023, the Sunday before Valentine’s Day. To enter, couples must submit a photo or video sharing their love story before January 25 and submit to the link located in Skydeck’s Facebook or Instagram.  Images linked HERE.

Museum of Illusions Chicago

This Valentine’s Day experience the ‘Illusion of Love’ at Museum of Illusions (MOI). MOI is the perfect date night spot if you’re looking for a fascinating adventure. The museum offers a wide variety of intriguing visual, sensory and immersive exhibits ranging from tried-and-true classics to the never-before seen! Located in the heart of downtown Chicago, just steps away from Millennium Park this museum is the perfect experience to spice up date night.

For one day only on Valentine’s Day Museum of Illusions will be offering a special discounted ticket deal. Tickets can be purchased on their website. Imagery HERE.


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