10 Extraordinary Valentine's Day Experiences for Couples

At Outlier Jets, we understand that every moment matters—especially when celebrating our partners. For those who value their time and exceptional experiences, Valentine’s Day is more than a holiday; it’s an opportunity to lean into experiences that focus exclusively on the two of you. That’s why we’ve curated a list of unique experiences perfectly paired with the convenience and efficiency of private air travel. Because when you choose to do something, it should be done well—no compromises, no wasted moments.

In addition to making your Outlier charter flight an experience unto itself by requesting Madame Zéro Champagne, Altima Caviar, and chocolate truffles to set the stage, here are a few unique ideas that make a great starting point for the rest of your planning. As your travel concierge, Outlier Jets can provide all transportation needs, including private drivers and helicopters. The Outlier Jet Card conveniently offers 24/7 365 access to flights to and from anywhere, so your Valentine’s experience can be as flexible and custom as possible.

Valentine’s idea for golf lovers

1. Golf and Spa on Kiawah Island, SC

   Arrive at Charleston Executive Airport (JZI) and head to Kiawah Island Resort, where you can disconnect and immerse yourself in spa indulgences and spark a friendly golf competition. Stay in the Sanctuary Hotel or one of several extraordinary private villas, cottages, or homes in the resort. The resort offers a private, full-service, exclusive access experience on this private island.

Valentine’s idea for History and Architecture lovers

2. Exclusive Evening at Hearst Castle, San Simeon, CA

   and at San Luis Obispo County Regional Airport (SBP) and be swept over to the incomparable Inn Paradiso to get yourself settled. Then, take a short drive to Hearst Castle to enjoy an extensive private tour of this historic estate, followed by a romantic dinner in one of its grand rooms.
    

3. Private Dinner at the Biltmore Estate, Asheville, NC

   Fly into Asheville Regional Airport AVL and enjoy a private, candlelit dinner on the stunning grounds of the historic Biltmore Estate, surrounded by the romantic charm of its sprawling gardens. The Grove Park Inn is the quintessential compliment to this experience, providing the ultimate environs for connecting with your partner and your soul, steeped in history, charm, and indulgence with one of the most unique spas in the U.S. A 43,000-square-foot subterranean spa with cavernous rock walls, arches and tunnels.

Valentine’s Idea for Boating Lovers

4. Private Yacht weekend in the Florida Keys

   Charter an Outlier jet to Key West International Airport (EYW) and enjoy a private yacht cruise to watch the legendary sunset at Mallory Square, followed by a secluded candlelit dinner on the beach with a private chef.
    

5. Private Yacht weekend in San Francisco Bay

   Fly into San Francisco International Airport (SFO) and embark on a private yacht weekend around the bay. Enjoy gourmet dining while taking in views of the Golden Gate Bridge and Alcatraz Island, and immerse yourselves in connecting. Short on time? Convert this to a private dinner cruise.

Valentine’s Idea for Nightlife Lovers

6. Private Dinner Viewing the Bellagio Fountains, Las Vegas

   Fly into Henderson Executive Airport HND and enjoy a private tour of the Lunar New Year display at the Bellagio Conservatory & Botanical Gardens, followed by a five-course gourmet dinner on a private terrace overlooking the Bellagio Fountains.

Valentine’s Idea for Nature Lovers

7. Hot Air Balloon Ride Over Sedona’s Red Rocks

   Arrive via Sedona Airport (SEZ) and enjoy a breathtaking private hot air balloon ride, capped with a champagne breakfast or dinner at sunrise or sunset. Book your stay at the Enchantment Resort for a profoundly grounded and intimate weekend of connecting.
    

8. Dinner and Stargazing in Jackson Hole

   Land at Jackson Hole Airport (JAC) and head to the Amangani Resort for a private fireside dinner with sweeping views of the Teton Range, followed by guided stargazing under one of the clearest skies in the country.
   

Popping the Question on Valentine’s? Proposal Ideas for a Memorable Moment.

9. Proposal at Top of the Rock, NYC

   Seeking an epic proposal experience? Charter a flight to Teterboro Airport (TEB) and arrange a private rooftop tour of Rockefeller Center, complete with Madame Zéro Champagne, Altima Caviar, all the city lights, and musicians doing covers of your favorite songs.
    

10. Reenactment of a Famous Movie Proposal in Chicago

    Fly into Chicago Executive Airport (PWK) and recreate the romantic ending of "Sleepless in Seattle" at the top of the Willis Tower Skydeck with a private dinner and breathtaking skyline views. For your stay, Nobu Hotel is just a stone’s throw away and offers a sanctuary of Japanese minimalism right on Restaurant Row.

Headquartered in Naples, Florida, Outlier Jets is here to ensure that your travel experience is nothing short of extraordinary. From the moment you step aboard our certified aircraft to the unforgettable experience waiting at your destination, we take care of every detail so you can focus on what truly matters. When you’re ready to celebrate, do business, or connect with family, Outlier Jets is ready to take you there every hour of every day. Life’s most meaningful moments deserve nothing less. Get there refreshed—for the moments that matter.