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Vacay By Gray Crafting bespoke travel experiences that allow you to rejuvenate your spirit and empower you to create unforgettable memories.

The scariest thing this Halloween? A “luxury” stay that isn’t so luxurious. That’s where I come in. I know which propert...
10/31/2026

The scariest thing this Halloween? A “luxury” stay that isn’t so luxurious.

That’s where I come in. I know which properties are worth the splurge, which rooms have the real ocean views, and how to make sure your trip is a treat, not a trick. 🎃

Spring Break PSA! 🏝️ I'm still booking LOTS of Spring Break trips right now, and I know plenty of you haven't made plans...
10/29/2026

Spring Break PSA! 🏝️

I'm still booking LOTS of Spring Break trips right now, and I know plenty of you haven't made plans yet!

With Travel Tuesday coming up on December 1 (I know, so soon!), here's what you need to know whether you've already booked your Spring Break trip or are still deciding what to do.

☀️ Already booked your Spring Break trip with me? Good news! My price-tracking tool is on and keeping an eye out for better rates. If something better comes along, I'll let you know so we can rebook at the lower rate.

☀️ Haven't booked yet? Let's get your Spring Break trip booked now! Some of my favorite properties are already filling up, and there's no need to wait until Travel Tuesday for a good deal. We can secure your trip now, and if a lower rate comes along, we can rebook!

Reach out and let's get to planning!

10/27/2026

An open thank you letter to Scales Restaurant in Portland, Maine. 🤍

Dear Scales,

On a Friday night in October, you helped my son and me make a memory. You reminded me to stop and appreciate little moments.

A friend told us about your restaurant, and without a reservation, we got in line at 4:15pm.

You welcomed us to the bar, and from the moment we sat down, we were made to feel special.

The bartender carefully described each type of bread offering and didn't blink when my child proceeded to go in depth on oyster farming. When we weren't interacting with the bar staff, we took turns sharing our favorite foods we've ever eaten and even played some cards.

My son declared it his favorite meal ever (which is a big deal for a child who would have previously stated it was Moe's).

And while I loved the food, I will mostly remember that a simple night out in a new town can be just as special as going halfway around the world.

So, thank you!

And to everyone reading this, consider it your reminder to make the trip, try the restaurant, and appreciate the little moments. If you're ready to make some travel memories of your own, I'd love to help you plan them. ✈️

From private island escapes to European adventures, my clients are off to some pretty incredible places! 🌎 Here's a peek...
10/22/2026

From private island escapes to European adventures, my clients are off to some pretty incredible places! 🌎 Here's a peek at where they're headed this month, part 2!

🇧🇸 Bahamas
Grand Hyatt Baha Mar

🇩🇰 Denmark
Admiral Hotel Copenhagen

🇬🇷 Greece
Luxury Penthouse Touching the Acropolis by GHH

🇮🇹 Italy
Gallery Hotel Art
ADLER Spa Resort Dolomiti
Palazzo Manfredi
Grand Hotel Minerva

🇧🇿 Belize
Matachica Resort & Spa

🇲🇪 Montenegro
SIRO Porto Montenegro

🇹🇨 Turks & Caicos
Ambergris Cay Private Island
Amanyara

🇺🇸 United States
The Tides Inn
Wynn & Encore Las Vegas
Blackberry Mountain
Nobu Hotel Miami Beach

Tried, Tested & Gray Approved ✅I’m always investing in travel, not just because I love it, but because it helps me plan ...
10/20/2026

Tried, Tested & Gray Approved ✅

I’m always investing in travel, not just because I love it, but because it helps me plan better trips for you!

I make a point to visit destinations firsthand, so I can experience the rooms, explore the property, meet the teams and get a feel for what makes a place special (and who it’s actually right for.) When I recommend something, there’s a real reason it made the list.

Want to learn more about my favorite destinations? Reach out to me!

When you think of Chile, Patagonia probably comes to mind first. And for good reason! 🇨🇱But what about after the hiking,...
10/16/2026

When you think of Chile, Patagonia probably comes to mind first. And for good reason! 🇨🇱

But what about after the hiking, glacier exploring, and horseback riding? I have a new travel guide to answer just that question!

Yes, you could go home to real life... but Chile offers so much more, including some incredible places to relax post-Patagonia adventure.

In my latest travel guide, I'm sharing my firsthand experiences at Clos Apalta and CasaMolle, two very different (and equally wonderful) ways to round out your Chile itinerary.

Read it for yourself:

https://tinyurl.com/4cb5ff9b

An active trip for an active couple! My clients Nora & Dave had a fantastic time exploring Italy from Rome to Florence, ...
10/14/2026

An active trip for an active couple! My clients Nora & Dave had a fantastic time exploring Italy from Rome to Florence, and the Tuscan countryside. 🇮🇹

We planned stays at two fabulous hotels, a private tour of Rome, a multiday hiking adventure through Tuscany, and restaurant reservations along the way. Plus, all the flights, trains, and details that make a trip run smoothly!

Hotel Savoy, a Rocco Forte hotel
Hotel Eden Rome
Backroads

Here, there & everywhere. ✈️ This October, my clients are going to Europe, Africa & beyond! Take a peek at where they're...
10/12/2026

Here, there & everywhere. ✈️ This October, my clients are going to Europe, Africa & beyond! Take a peek at where they're headed this month. 👀

🇭🇷 Croatia
Hotel Majestic

🇬🇷 Greece
St. Nicolas Bay

🇮🇹 Italy
Il Borro
Filario Hotel & Residences
Grand Hotel Ambasciatori

🇲🇽 Mexico
Rosewood Mayakoba

🇲🇦 Morocco
Selman Marrakech
Riad Fès
Eden Boutique Hotel

🇺🇸 United States
JW Marriott Marco Island Beach Resort
Four Seasons Resort Orlando at Walt Disney World Resort
Thompson Savannah
The Ritz-Carlton Reynolds, Lake Oconee
Warren Street Hotel
The London NYC
The DeBruce
Cambria Hotel Columbia Downtown the Vista
Rosewood Mansion on Turtle Creek
The Lodge at Primland, Auberge Collection
Caesars Virginia

What started as a quick trip to DC for the Commanders vs. Seahawks game turned into a fun family weekend away. 🏈🤍We came...
10/09/2026

What started as a quick trip to DC for the Commanders vs. Seahawks game turned into a fun family weekend away. 🏈🤍

We came for the game, but made a trip out of it with a day spent exploring the museums and a guided tour of the monuments and the National Mall.

With plenty of football still ahead of us, it’s not too late to plan a game day getaway of your own. Whether it’s an overnight trip to a nearby city or a trip across the country to see your family’s favorite team, I can help turn game day into a full weekend away.

And if tickets are the thing holding you back, let me make some magic happen. ✨ I have access to all kinds of hard-to-get tickets for sporting events, including sold-out games, premium seats, and boxes. Tell me what game you want to see, and we’ll go from there!

10/07/2026

I’m heading to Miami next month! 🌴 I’ll be there for a conference, meeting with hotel and travel partners, and touring properties around Miami Beach so I can continue to give the best recommendations to my clients.

Then I’m turning it into a girls’ weekend with a stay at Andaz Miami Beach Resort & Spa, a dinner at the Faena Miami Beach, and plenty of exploring in between.

So before I go, I want to hear from you: Is there a Miami Beach hotel you’ve been curious about? Want to know which hotels I’d pick for a girls’ trip vs. a family vacation? Want my Miami must-dos?

Drop your questions or requests below, and I’ll do my best to check them out while I’m there!

Address

37 Beach Ave
Kennebunk, ME
04043

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