Travel Advisor

Gray Grandy

She/Her

Expertise

Florida,
Caribbean,
Europe,
Luxury Travel,
Family Travel

Based in

Norfolk, VA

Travel Advisor

Gray Grandy

Profile details

About

I bring that "oldest daughter energy" to all aspects of travel planning. Let my OCD create your itinerary! Let me plan the perfect vacay for your discerning family (even if that is an age seven tyrant).

Travel style

In high school, I won the 'I came, I saw, I conquered' award while on an eight week long Europe trip. To this day, I bring that energy to all my travels. Whether I am seeking the absolute best lounge chair and sunset to relax for a week or making sure no sight is missed, you can know that I will always go, see and conquer!

Gray's travel guides & trip reports

Guide

Ultimate Girls' Weekend: Todos Santos

Mexico has long been a favorite location for a girls' trip, but Todos Santos levels up. The combination of beach and desert, food and art and hiking and relaxation can't be beat. Both off the beaten...

large white houses next to palm trees during daytime

Guide

Family-Friendly Guide to 30A: A Taste of the Caribbean

30A is the best way to take your family on a high-end, Caribbean-style beach vacation without the hassle or extra work of actually leaving the country! Imagine crystal clear water, white sand beaches ...

Guide

Zermatt Ski Vacation With Kids: The Ultimate 7-Day Itinerary

Zermatt is a fantastic destination for skiing, winter sports, relaxation, and delicious food! It is the perfect place to go with a group that has diverse interests. Want to ski all day? Great! Have ...

Guide

Family-Friendly Guide to the North Carolina Mountains

Cashiers, North Carolina is an amazing family-friendly destination that allows you to unplug and enjoy the outdoors. Take your family and you'll feel like you have taken a step back in time, to a...

Guide

Explore Turks & Caicos: A Family-Friendly Guide

Providenciales, Turks and Caicos, holds a special place in my heart. You can explore different beaches every day or you can truly stay put on Grace Bay for a week. The water is calm, the food is...

Guide

Beyond Bourbon Street: NOLA with Kids

New Orleans is known for so much: Bourbon Street, open containers, beads and Mardi Gras! However, it is also one of the best places for a family. From outdoor spaces to kid friendly restaurants, plan ...

Three individuals standing in a field posing for a photo.

Guide

Family-Friendly 9-Day Botswana Safari

The diversity in safari type in Botswana is second to none. You can take a boat on the Chobe River and watch elephants swim from bank to bank, trek through the bush on a walking safari, ride a Mokoro ...

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Favorite hotels

Keswick Hall

Keswick Hall is a luxurious historic hotel and golf resort nestled in the picturesque countryside of Charlottesville, Virginia.

Fora Perks

★
$100 hotel / resort credit.
★
Breakfast daily.
★
Upgrade & extended check-in/out whenever possible.

Jade Mountain

Cliffside stunner made for romance, with gorgeous suites positioned for dead-on views of the mighty Piton peaks.

Fora Perks

★
$100 hotel / resort credit.
★
Breakfast daily.
★
Upgrade & extended check-in/out whenever possible.

Carmel Valley Ranch

This 500-acre stunner is a one-stop playground for golf, farm adventures, spa time and top cuisine, all with epic Santa Lucia Mountains views.

Fora Perks

★
$100 hotel / resort credit.
★
Breakfast daily.
★
Upgrade & extended check-in/out whenever possible.

Splendido Mare, A Belmond Hotel, Portofino

Once beloved by Elizabeth Taylor, this storied Portofino stay is a beacon of bygone glamour.

Fora Perks

★
$100 food / beverage credit.
★
Breakfast daily.
★
Upgrade & extended check-in/out whenever possible.

Gray's reviews

Everything was top notch with our trip. The airport transportation was seamless. Hotel was great. All of our tour guides were so good. ... Louvre, Musee d'Orsay, walking tour of latin quarter. I was impressed by all of our guides and their knowledge. I have their contacts and will refer to other friends! Gray planned this so easily and quickly for us. I will plan with Gray again.

Elizabeth G.
Booked travel to Paris
April 2025

Gray is amazing! Thank you for all of your help planning an amazing vacation.

Courtney P.
Booked travel to Bahamas
March 2025

Gray was super responsive and helpful in planning this trip. She responds extremely quickly and is able to make adjustments quickly. We truly loved her hotel and restaurant recommendations. And again, most definitely appreciated the hotel upgrade. Will definitely use her again in the future!

Kaylan R.
Booked travel to California
March 2025

Always wonderful to work with! Everything was so organized and we got an early check in which was so nice. Love not having to worry about planning! Can’t wait for our next adventure!

Muffy G.
Booked travel to Florida
March 2025

Get in touch with Gray

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

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