Planning a romantic getaway to celebrate Valentines Day can be tricky no matter what stage your relationship is in, as it involves weighing a lot of factors and examining where you want the relationship to head, long before you’re actually heading there.

I thought I’d share a few guidelines that will help alleviate potential pressure points.

Newly Dating & Not Yet Committed

If you’re still playing the field, but it’s just too soon to know if they’re a keeper, then taking a Valentines Day escape can be a great idea. It guarantees that you won’t bump into anyone else who you’ve been out with recently and it’s a great way to get to know one another a little better.

Make it a city getaway, where you can fill your schedule with plenty of exciting things to do, which alleviates the pressure of too much solitary one-on-one time. Exploring a cultural town together, keeps the itinerary away from the ultra romantic zone, yet it allows you to learn each other’s likes and dislikes, gauge how open minded one another are and ultimately have the opportunity to make memories together in a special place.

West Coast residents can choose a city like San Francisco, which is full of quirky boutique hotels that are sexy, yet infuse sense of humor into every detail, not to be taken too seriously. Hotel Diva and Hotel Triton are my two picks, as they’re both unique, chic and affordable, so your city getaway won’t have to break the bank, and their Union Square locations make it easy to reach most spots on your tourism hit list.

Keeping the travel arrangements easy-breezy is a must when you’re still testing the waters of a relationship, so a weekend in SF is the ideal distance. Nothing more than a short flight and carry on baggage are needed, considering the logistics side of travel typically does not bring out the best in anyone, and we all want to put our best face forward early in the game.

Boyfriend & Girlfriend…Could This Be “The One”

I love a good road trip to test the boundaries of any relationship, especially if it’s someone whom you’re contemplating the next step with. It’s all about trust and teamwork, as you’ve got your clearly defined roles (driver and navigator / dj) and of course patience, because being on the road can throw anyone for a loop…traffic, accidents, missing an exit or two, etc…

This type of getaway is more about the journey and less about the destination. Create a play list of memory inspiring songs and your favorite sing alongs, pack a cooler of car safe snacks or even a picnic lunch that you can enjoy at a great roadside vista point mid way and make plenty of stops for photo ops along the way…first stop, that iconic landmark just outside of town for a quick photo to mark the beginning of your journey.

When you do finally arrive, make sure it’s to a more small town or rural destination.  For East Coasters, I love the New York Finger Lakes region as it’s the perfect road trip distance, just over 4 hours drive from NYC and is full of intimate B&Bs.  For West Coasters, how about getting back to nature in Sedona, Arizona, and stay at Enchantment Resorts, where the red adobe villas blend seamlessly into the natural landscape.

If you’re really looking to challenge your relationship strength one step further, try setting up camp at the end of your road trip (weather permitting that is) at someplace like Valley of Fire State Park in Nevada. There’s nothing more romantic than spending the night together in the wilderness, under the stars.  Pick up the necessary V-day camping supplies together as you’re heading out of town. 1. A little bubbly, 2. Marshmallows, chocolate and graham crackers for S’mores, 3. An assortment of fruit, cheese and charcuterie to dine on, as well as 4. A high quality air mattress & luxury sleeping bag combo to ensure a comfy cuddling. This is Valentines Day after all, so we’re not talking hot dogs and pork and beans…it’s the romantic side of the great outdoors.

Popping “The Big Question”

So your partner has clearly passed the road trip test or any equivalent milestone indicator that you have in your personal life, and you’ve decided that you want to spend your lives together. Well, not to sound cliché, but Valentines Day is at the peak of engagement season, so take advantage of your majestic getaway surroundings at Rancho Pescadero in Pescadero Beach, Mexico, and pop the question.

For my past 3 years, ever since setting foot in my Rancho Suite at Rancho Pescadero, I’ve had a crystal clear image of exactly where I would want to receive a marriage proposal.   It’s absolute heaven on earth with all the creature comforts that everyone needs, some additional ones that you don’t know you need, and none of the stuffy, excessive luxuries.

Why propose here? 3 simple reasons: 1. An unspoiled and pristine 360 degree view of the Pacific and the desert, from your private rooftop terrace, equipped with a comfy sun bed, as well as other amazing and private outdoor spaces to share time. 2. The important sexy “in room” details…large soaker tub and huge shower with double heads, both equipped for 2 and a bed to die for…literally, you won’t want to get out of bed for hours after waking! 3. The survival essentials of any great resort…amazing food and drink, exceptional service, fantastic common spaces with just the right number of guests so you don’t mind sharing them.

 

Married with Kids

Sometimes when your daily life is filled with the hectic schedules of everyone else in your family, the best gift you can give to you and your loved one is a little peace, quiet and pampering. Remove yourself from the rat race of your everyday lives and escape to a health spa resort where you can individually relax, re-center and refocus, as well as share in various therapeutic treatments, healthy activities and of course the much needed down time together.  Make sure to choose a spa resort that’s possible driving distance so that you can truly be worry free on your weekend away from the kids, knowing that if something pops up, you can always hop in the car and be home in a few hours.

The American Club at Destination Kohler, Wisconsin boasts one of the most impressive spas in the whole of the United States, amazing cuisine and wine, all at a driving distance from Chicago and other Mid West towns.   Here you’ll find such a relaxed environment that guests at The Carriage House literally can walk around in their robes when heading back and forth from their rooms to the multi leveled spa.  Don’t forget to spend some down time at their top floor relaxation room enjoying the jacuzzi or just lounging along the huge fireplace wall, and certainly allow some time in room to enjoy your spa tub, after all, this is Kohler’s resort, so when it comes to the bathroom, it’s only the best of the best.

For those West Coasters, try Cal-a-Vie Health Spa in Southern California for your rejuvenating Valentines Day getaway together. Their French Provencial style decor and open / airy feel of the resort is the epitome of a romantic setting and the spacious villas become an easy home away from home to settle into and reconnect after active days spent doing yoga, fitness programs, golfing or enjoying the spa.

The High Roller Looking To Impress

Whether your relationship is 5 days or 5 years long, some of us out there are truly looking to impress and will pull out all the stops to make an extremely memorable and one-of-a-kind Valentines vacation.

There are few places in the world where the hotels, cuisine and overall hospitality level are more lavish than Dubai so for those who tend to err on the eccentric side and money is no option, shoot for the stars and head to Dubai.

Be sure to stay at the Burj Al Arab, where you can experience the over the top luxury that they’re known for from the moment you arrive and are greeted at the airport by your chauffer driven Rolls Royce. Bask in the luxurious amenities of your guest suite and feel like a true sultan and sultana as you enjoy a bubble bath in the pillared marble Jacuzzi.

On Valentines morning, depart the hotel before sunrise via the rooftop helicopter pad and venture out into the desert, only to experience one of the most unique sunrises the world over, via a Balloon Adventures’ private hot air balloon taking flight over the desert.

Once back in town, be sure to stroll the lanes of the historical Gold Souk together, picking up a special token to remember the trip, and of course you must experience a taste of Dubai’s world class dining, some of my pics…Amaseena at the Ritz Carlton for traditional Arabic food, Amal indian cuisine at the Armani Hotel which boasts a spectacular view of the Burj Khalifa fountains and certainly not to be missed, the underwater dining sensation of Ossiano at The Atlantis.

You may not return home engaged, but the pure Wow factor of this Valentines vacation will leave you with bragging rights of a lifetime.