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New Love: Tips For Planning Your First Romantic Weekend Getaway

couple in love

Photo courtesy of linh.ngan

As someone who’s constantly on the road, I often forget inviting a guy you’ve just been dating to Italy for the weekend or backpacking across South America isn’t a traditional first date idea. While I’ve gotten pretty good at resisting the urge to invite potential boyfriends to travel across the world with me, I love planning weekend getaways. To me, it’s a great way to really get to know someone before you make any official commitments (plus, it’s a great excuse to travel!). And, as someone who has experienced both wonderfully successful and awkwardly unsuccessful weekend getaways with new guys, I can say there are some basic tips to keep in mind before setting out on this type of adventure, including:

1. Take The Pressure Off

For some, the idea of going on a romantic weekend getaway for the first time with someone they’re dating can lead to non-stop daydreaming of perfect dinners, whisperings of sweet nothings and vows of commitment. Sure, these things can be part of it, but don’t expect anything more than having fun and getting to know each other. When you put pressure on the other person to deliver a flawless getaway and show that if anything goes wrong you’ll be disappointed, it can suck the fun out of the weekend — for both of you. Instead, keep things light and make jokes when the waiter spills wine on your shirt or you get lost and miss your dinner reservation. It’s all part of the adventure.

2. Plan An Activity That’s New For Both Of You

Maybe neither of you have ever zip-lined, or you both have an interest in cooking but haven’t yet taken a class. Experiencing something new together is a great way to strengthen your relationship while also crossing items off your bucket list. I recommend adding in at least one novel experience into your itinerary.

3. Be Spontaneous

While planning a few meals and activities can be a good idea, it’s also fun to be spontaneous and let the road take you. Ask for recommendations from your breakfast server on how to spend the afternoon, or get lost in a nearby town making local discoveries. This adds a bit of adventure into your weekend, and shows your partner you can go with the flow (see below).

4. Get A Room With At Least One Romantic Amenity

My suggestions: A Jacuzzi, plunge-tub, rain shower, balcony or fireplace. With amenities like these, romance is inevitable.

5. Talk About The Music

My current guy and I have completely different taste in music: while he loves metal I’m a big fan of electronic and dance. Because we were enduring a six-hour car ride together up to Lake Placid, I knew this was potential for one of us flinging ourselves from a moving vehicle. To avoid either of our ears bleeding (as well as sudden death), we each made mix tapes that included music we both could at least appreciate — i.e. he skipped the heavy metal and stuck to the hair bands, and I made sure no Justin Bieber or Britney Spears made the cut. It was fun to see what kind of music the other was into, and helped us find common ground in terms of artists we both liked.

6. Show You Can Go With The Flow

While throwing in a few ambient dinners and time in the hot tub can enhance the trip, this is also a great opportunity for you to show you can have fun in all kinds of situations. Romance on the road doesn’t always have to mean white linen and wine glass-set tables and expensive Champagne. Instead, plan some activities where you don’t need to get dressed up — like hiking, cycling, or drinks at a local dive — to show your ability to turn any situation into a romantic outing. Because really, romance is all about laughing together and sharing special moments no matter where you. Do you have any tips to add? Please share in the comments below.

About Jessie Festa

Jessie Festa is an New York-based travel content creator who is passionate about empowering her audience to experience new places and live a life of adventure. She is the founder of the solo female travel blog, Jessie on a Journey, and is editor-in-chief of Epicure & Culture, an online conscious tourism magazine. Along with writing, Jessie is a professional photographer and is the owner of NYC Photo Journeys, which offers New York photo tours, photo shoots, and wedding photography. Her work has appeared in publications like USA Today, CNN, Business Insider, Thrillist, and WestJet Magazine.

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  1. Sand In My Suitcase on at 3:32 pm

    Traveling together with a new love for the first time can also be too much togetherness! In such close quarters as one shared hotel room, you may learn things about each other you don’t like :-). So sometimes it can lead to Splitsville – or it can strengthen your relationship and add another layer of richness.

    • jess2716 on at 4:07 pm

      @Sand In My Suitcase: So true! Lucky for me my boyfriend and I — who went away together our second week of knowing each other — have now been together for a year 🙂 I’ve definitely had it go the other way, too, though! ha.

  2. Laurie on at 2:29 pm

    I think it is important to place no expectations or pressure on your trip and just relax. Enjoy your time together and do something fun together. Great tips, thanks for sharing!

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