Tess Woods


  • Solo Female Travel,
  • Couples Travel,
  • Weekend Getaways,
  • Girls Trips & Bachelorettes,
  • New England,
  • Florida,
  • Europe,
  • Caribbean
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Advisor - Tess Woods


Boston-based events professional. Dog momma. Believer in unlimited PTO and the phone eating first.

Home airports


My travel style

I believe every trip should be the trip of your dreams, and you should always have the memories – and pics – to show for it. I’ll do custom research and lay out the extensive details so you can live in the moment, relax and explore! I’m passionate about making your trip always feel luxurious, even when you’re ballin’ on a budget. Lover of upgrades, aesthetic-forward restaurants and one-of-a-kind local experiences.

Favorite hotels

Recently returned from:

  • Spending two weeks on a solo trip through France and Italy. 

  • Exploring Jamaica for the seventh time. 

  • Passing through Vegas for 48 hours.

  • Detouring to wine country on a PCH roadtrip.

Dreaming of:

  • A sushi and sake tour of Japan.

  • South African safari.

  • Girls spa trip to Quebec. 

  • Belize.

One thing I can't travel without...

A custom trip playlist.

Two truths, one lie:

  1. I met Naomi Campbell in Morocco.

  2. I shuck oysters on Cape Cod during the summer.

  3. I re-read The Alchemist on every (long) trip I take.

Advisor - Tess Woods


Tess Woods

Get in touch with Tess

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