Gray Grandy
She/Her
Based in Norfolk, Virginia
Gray Grandy
Ask me about
My Story
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!
Reviews (99)
Christopher K.
2 months ago
We won't use anyone else! She is great with a quick one night getaway (always gets us VIP'd and perks) and just as fantastic at a multi stop itinerary. She listens and understands our preferences.
Wiley G.
2 months ago
We only use Gray! She is amazing-she recommends hotels, restaurants, and activities from actual experience. She makes sure we get the best perks and helps plan our personal and work travel. I highly recommend her.
William C.
7 months ago
We've been working with Gray for about 2 years and can honestly say that it has changed our travel experience. She takes care of everything and we just show up. We trust her suggestions and she always makes us feel cared for. We can't recommend her enough!
Kathryn C.
8 months ago
Gray was fantastic throughout the process—literally amazing to work with and would recommend her to anyone planning a trip or any kind!!! She went above and beyond and was unreal!!
Edith G.
9 months ago
Gray is the absolute best! She is quick to respond and listens to my requests. She shares honest feedback on hotels and experiences and even provides options for places I didn't consider. I appreciate having a proactive advisor and trust her for all of my travel.
Christopher K.
2 months ago
We won't use anyone else! She is great with a quick one night getaway (always gets us VIP'd and perks) and just as fantastic at a multi stop itinerary. She listens and understands our preferences.
Wiley G.
2 months ago
We only use Gray! She is amazing-she recommends hotels, restaurants, and activities from actual experience. She makes sure we get the best perks and helps plan our personal and work travel. I highly recommend her.
William C.
7 months ago
We've been working with Gray for about 2 years and can honestly say that it has changed our travel experience. She takes care of everything and we just show up. We trust her suggestions and she always makes us feel cared for. We can't recommend her enough!
Kathryn C.
8 months ago
Gray was fantastic throughout the process—literally amazing to work with and would recommend her to anyone planning a trip or any kind!!! She went above and beyond and was unreal!!
Travel ideas (8)
A Multigenerational Alaskan Escape with Lindblad Expeditions
Alaska is the perfect destination for those who love nature, wildlife, and stunning views. There is plenty to see from land, but to get to the unspoiled and seemingly untouched areas, an expedition cruise can’t be beat. Imagine seeing whales off your bow and stopping for an hour to follow them—this is a regular occurrence with an expedition cruise.
A Multigenerational Alaskan Escape with Lindblad Expeditions
Alaska is the perfect destination for those who love nature, wildlife, and stunning views. There is plenty to see from land, but to get to the unspoiled and seemingly untouched areas, an expedition cruise can’t be beat. Imagine seeing whales off your bow and stopping for an hour to follow them—this is a regular occurrence with an expedition cruise.
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 path and accessible (an hour from Cabo), you'll feel like you're worlds away in your own special haven designed for you to connect with your group.
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 path and accessible (an hour from Cabo), you'll feel like you're worlds away in your own special haven designed for you to connect with your group.
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 and European-esque villages around every corner.
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 and European-esque villages around every corner.
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 no desire to throw on uncomfortable ski boots? Perfect! Interested in winter hiking? The list of trails is endless. Rather stay inside by the fire and the spa? You can try a different one each day! Traveling to Zermatt with kids? This 7-day itinerary is for you!
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 no desire to throw on uncomfortable ski boots? Perfect! Interested in winter hiking? The list of trails is endless. Rather stay inside by the fire and the spa? You can try a different one each day! Traveling to Zermatt with kids? This 7-day itinerary is for you!
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 time when kids spent the day outdoors and away from screens, skipping rocks, climbing mountains, and splashing their way through the day. If you have enough of the outdoor life, your family can quickly and easily be spoiled by luxury with delicious food, spectacular views and luxurious accommodations. Once you've left, you will feel as if you discovered a hidden gem!
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 time when kids spent the day outdoors and away from screens, skipping rocks, climbing mountains, and splashing their way through the day. If you have enough of the outdoor life, your family can quickly and easily be spoiled by luxury with delicious food, spectacular views and luxurious accommodations. Once you've left, you will feel as if you discovered a hidden gem!
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 delicious, and the sand is soft as sugar.
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 delicious, and the sand is soft as sugar.
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 to go beyond Bourbon street to enjoy this lovely city with a family!
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 to go beyond Bourbon street to enjoy this lovely city with a family!
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 on the Okavanga Delta and of course, ride in a traditional safari vehicle while searching for the big five! With the right support, it is the perfect spot to take a family for their first safari experience.
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 on the Okavanga Delta and of course, ride in a traditional safari vehicle while searching for the big five! With the right support, it is the perfect spot to take a family for their first safari experience.
A Multigenerational Alaskan Escape with Lindblad Expeditions
Alaska is the perfect destination for those who love nature, wildlife, and stunning views. There is plenty to see from land, but to get to the unspoiled and seemingly untouched areas, an expedition cruise can’t be beat. Imagine seeing whales off your bow and stopping for an hour to follow them—this is a regular occurrence with an expedition cruise.
A Multigenerational Alaskan Escape with Lindblad Expeditions
Alaska is the perfect destination for those who love nature, wildlife, and stunning views. There is plenty to see from land, but to get to the unspoiled and seemingly untouched areas, an expedition cruise can’t be beat. Imagine seeing whales off your bow and stopping for an hour to follow them—this is a regular occurrence with an expedition cruise.
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 path and accessible (an hour from Cabo), you'll feel like you're worlds away in your own special haven designed for you to connect with your group.
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 path and accessible (an hour from Cabo), you'll feel like you're worlds away in your own special haven designed for you to connect with your group.
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 and European-esque villages around every corner.
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 and European-esque villages around every corner.