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Luxury Travel Agent, living on the beautiful Connecticut Shoreline, serving clients everywhere

Meet Jen Terra

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How to Plan the Perfect Girls Trip!



One of my favorite trips to plan and attend is the Girls Trip! Whether it be for a weekend getaway or longer international adventure, I strongly recommend prioritizing this type of travel on an annual basis. Traveling with friends has so many benefits- a much needed break from the family routine, a renewed connection with close friends and the chance to let loose!  And if you share a room, you have the added benefit of saving money! A well planned girls trip (with the right crew!) can produce memories–sometimes better left unsaid–and elicit laughs for years to come. 

Who to travel with?

T r u t h: your best friend is not always your best travel partner. Have you ever gone on a trip with someone only to find out that you will NEVER travel with them again?⁠ I strongly recommend that before you decide to get away with a friend, or group of friends, for the first time- sit down and have a truthful conversation about how you like to travel and your trip expectations. Here are some good talking points…

Budget– This is a no-brainer but often not discussed in detail. Determine if your total budget for items in addition to accommodations such as excursions, spa treatments, restaurants, transportation, etc. is on the same page.

Preference for downtime vs. active time– What is your vacation style? Do you live by an booked itinerary or are you a self-declared beach bum?⁠ Or do you need a bit of both?

Dining habits– Are you a vegetarian or churrascaria lover? Do you prefer fine dining, scouting out the best local food trucks, room service or is eating on vacation an afterthought?

Drinking patterns– When do you start consuming cocktails for the day-during lunch or at happy hour? Or do you start each morning with a bloody mary and keep up steam until brandy or you pass out? ⁠

Cleanliness– Are you the type -A unpacker upon check-in and clean before housekeeping type or could you care less about a sandy bed?

Sleep patterns– What time do you wake up? Do you have the ability to stay quiet in the morning if you wake up first? ⁠

Deal breakers– Do you have any? Like scuba diving, shamanic healings or night clubs?⁠

I’m telling you from experience, it is best NOT to be surprised by these answers. Talk first to save a vacation and a friendship!!

If you are planning to travel with a group of girlfriends, consider the energy of the entire group. If you are all type-A, fit it all in, overly opinionated ladies– that might be a bit overwhelming. I always find a balance of personalities works best.


Where to? Girls Trip Destination Ideas

Now that you’ve selected the perfect friend(s) to travel with, where should you go? Honestly, the possibilities are endless. There are few places that I wouldn’t want to getaway to with my best girls. But in the interest of time, here is a short list of my favorites…

Saint Barths- This French Caribbean island contains all of the vital girls’ trip ingredients- rose, beach, spa, shopping and day clubs. Stay at Hotel Christopher, Eden Rock or Villa Marie Saint-Barth. Party at Bagatelle and day drink at Nikki Beach.

Montana– Discover your inner cowgirls in big sky country where you can bond during the day on a challenging hike, ropes course or on horseback and by night with a glass of red by the fire pit under the stars. Glamp in luxury at The Resort at Paws Up, Under Canvas Yellowstone or The Ranch at Rock Creek.

Bali- Did reading Eat, Pray, Love put this stunning Indonesian island on your bucket list? Why not make the journey with your best friend where together you can experience nature, culture and hedonism. Hotel hop between Six Senses Uluwatu, Como Canggu and Capella Ubud. You’ll never forget this trip.

Napa Valley, CA- Wine tasting with girlfriends- it just makes sense. Add in spa, fine dining biking and hiking and you have the recipe for an iconic girls getaway. Stay at Auberge Du Soleil, the new Montage Healdsburg or take over Single Thread Farms’ 5 room boutique.

Sedona, AZ- Visit this spiritual mecca with friends where you can practice great yoga & meditation and potentially find healing at a vortex site. If all else fails, bask in views of the red rocks poolside, drink in hand. Stay and Spa at The Enchantment Resort and Mii Amo Spa or L’Auberge De Sedona.


So what are you waiting for?? Time to start planning your next (or first) epic girls trip!