If there’s ever a season to plan something special, it’s summer. Whether you’re mapping out a European escape or looking for a destination a bit more under the radar, now is the moment to get ahead of the season.
We reached out to Caroline McCray of Fora Travel to learn where she’s sending clients this summer, the destinations she can’t stop recommending, and her insider tips for making every getaway unforgettable.
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What destinations are you seeing clients gravitate toward this summer — both within the U.S. and abroad?
European summers continue to dominate with the same favorites leading year after year, like Italy, Greece, and Portugal. They offer the perfect mix of culture, food, and beautiful coastlines.
In the U.S., I’m seeing more and more clients head to the Carolinas. It’s such an easy, elevated getaway with great weather, charming towns, and a strong hotel scene. Properties like The Dunlin on Kiwah, Montage Palmetto Bluff, and The Cooper, a brand new waterfront hotel in Charleston, are getting a lot of attention.
HJ Pick for Europe: String Bikini Top and Tunnel Side Hipster in Lagos, Eyelet Trim Long Shirt Dress
What destinations do you love recommending for different types of summer travelers?
Families looking for a fun but easy getaway?
Mountains, hands down! It’s one of the easiest and most well-rounded family trips. You have hiking, horseback riding, fishing, rodeos, great food, and plenty of time to relax. There is truly something for everyone. I especially love Steamboat Springs in Colorado and Big Sky in Montana.
HJ Pick for the Mountains: Short Sleeve Pullover in Stone, Ankle Pant in Stone
Couples planning a romantic escape?
So many options, but in the summer, I love sending couples to the Northeast. It feels a bit more under the radar compared to Europe, but just as special. Hotels like Wildflower Farms in the Hudson Valley, Mayflower Inn and Spa in Connecticut, White Barn Inn in Maine, and The Vanderbilt in Newport are all incredibly romantic with beautiful settings and amazing service.
HJ Pick for the Northeast: Timeless Bandeau One-Piece in Hamptons Floral Blue, Nola Tunic in White
Friends planning a girls’ trip?
Santa Barbara or Newport Beach are always favorites. You get the perfect mix of beach time, great restaurants, shopping, and a fun social atmosphere. It is relaxed but still feels like a proper getaway.
HJ Pick for California: Tortoise Ring Banded Halter Top and Tortoise Ring Hipster in White Textured Metallic, Claudia Crochet Midi Dress in White
For those dreaming of sun and sea, what are a few of your favorite beach or seaside destinations for summer travel?
For Italian seaside glamour, I love Hotel Il Pellicano in Porto Ercole or Grand Hotel Tremezzo in Lake Como. Both feel iconic and effortlessly chic.
That said, it is hard to beat the Caribbean when it comes to truly beautiful beaches. Turks and Caicos is always a go-to for powdery white sand and that unreal turquoise water.
If you are staying in the U.S., Sea Island is such a classic. Easy, polished, and perfect for a summer escape!
HJ Picks for the Caribbean: Tortoise Ring Plunge One-Piece in Teal Cora Texture, Starburst Crochet Dress
Summer travel can be hectic. What are your best tips for making the airport experience smoother?
TSA PreCheck and Global Entry are non-negotiable if you travel, even a few times a year. It saves so much time and stress, especially during busy summer travel days.
What small things do you recommend travelers do or bring that make a vacation feel extra special?
It is usually the little things. I always recommend booking at least one really memorable experience, whether that is a special dinner, a boat day, or a spa treatment, so the trip feels elevated beyond just being there.
On a smaller scale, I love bringing a great outfit for dinners, a good book, and leaving space in your itinerary to wander. Those unplanned moments are often the most memorable.
What’s one piece of travel advice you wish more people knew before planning a summer trip?
Do not overpack your itinerary. If you have 10 nights in Europe, stick to two or three destinations max. The majority of cities are not meant to be rushed through, and constantly moving takes away from actually experiencing a place. Slowing down almost always leads to a better trip.
How soon in advance should you book a summer vacation? Are there still good last-minute options this season?
It really depends on where and when you are going. Places like Positano in June or Aspen over the Fourth of July are often booked months in advance.
That said, there are still great options if you are flexible. I always look to newer hotel openings like the Lake Como EDITION, Naples Beach Club, or The Venita Hotel in Palm Beach!
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If any of these destinations or properties have sparked your interest, Caroline would love to help plan your trip. Wherever summer takes you — from the cliffs of the Italian coast to the quiet charm of the Carolinas — packing with intention is part of the experience. Think pieces that transition seamlessly from beach to dinner, silhouettes that feel as effortless as the destinations themselves, and swimwear that’s as polished as it is practical.
Explore Helen Jon’s collection of refined resort wear and swim, designed for every kind of escape. Because the right pieces don’t just complement a trip — they become part of the memory.