Travel Advisor

Jackie Garraffa

Expertise

  • Modern-luxe,
  • Caribbean getaways,
  • friend trips,
  • wine weekends
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Advisor - Jackie Garraffa

About

Professional vacationer, dog mom and wine enthusiast. Based in lower Westchester, but constantly living out of my suitcase.

Home airports

JFK (I practically live at T5), with the occasional trip out of EWR.

My travel style

Culture and history combined with amazing eats and drinks are at the heart of every trip I plan. I am here for new, trendy and Instagram-worthy spots just as much as I am for the local taco shack on the outskirts of town. Centrally located hotels with great architecture and character are my go-to (huge plus if they have a rooftop bar!). My passion is helping people create memories that will last a lifetime, whatever that may mean to them. I believe travel is an individual experience and I love curating trips that burst with personality. Above all, I’m always looking for once-in-a-lifetime experiences with the perfect mixture of relaxation and fun.

Favorite hotels

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Hotel El Convento

Long-time favorite in Old San Juan, with a traditional look and access to a sister beach club.

Fora Perks

  • ★

    Upgrade on arrival, subject to availability

  • ★

    Daily full breakfast for two guests

  • ★

    $100 USD equivalent Food & Beverage credit utilized during stay

Fontelunga Hotel

A successful mix of historic architecture and modern style at this guesthouse between Siena and Florence.

Eden Roc Cap Cana

Punta Cana’s most upscale resort, with a private beach, kids’ clubs, and golf course privileges.

Fora Perks

  • ★

    Upgrade upon arrival, subject to availability

  • ★

    Daily breakfast for two guests per bedroom, served in restaurant

  • ★

    $100 USD equivalent Resort or Hotel credit to be utilized during stay

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Recently returned from:

  • Wine touring and castle hopping through Tuscany.

  • Eating my way through Old San Juan.

  • Boating and beaching in Antigua.

  • Road tripping to Nashville and NOLA.

Dreaming of:

  • European Christmas markets.

  • Day of the Dead in Mexico City. 

  • Wine touring in Champagne. 

  • Beach clubs in Greece.

One thing I can't travel without...

A disposable camera.

Two truths, one lie:

  1. I once convinced a friend to fly from JFK to Ireland with me for three days. 

  2. I took a road trip from New York to Louisville to see Lil Wayne. 

  3. I missed my connection on an international flight and had to sleep in LAX for 17 hours.

Jackie's guides

Advisor - Jackie Garraffa

Travel Advisor

Jackie Garraffa

Get in touch with Jackie

Reach out to customize and book your own experience. Or, just to chat about travel in general.

You can normally expect a response from Jackie within a business day or so. You'll also be subscribed to our travel newsletter (you can unsubscribe at any time).