A Summer to Remember
WhirlAway clients say it was one for the books—and now we’re already making our goals for 2026.
ITALY
Where: Castelfranci, Sorrento & Capri
Why Go: Together, these destinations create the ultimate Mediterranean trifecta—savor fine wines, bask in coastal elegance, and revel in Italian dolce vita.We’re talking about Castelfranci’s rolling vineyards, Sorrento’s cliffside glamour and sweeping Bay of Naples views, and Capri’s iconic blue grottos and chic boutiques.
Not to Miss: The annual Castelfranci Wine Festival is held in early August and celebrates the town’s winemaking traditions with tastings, local producer showcases, food pairings, and entertainment. Excelsior Vittoria is “a favorite hotel of all time,” says one WhirlAway client. Other musts: a hands-on pizza making class in Sorrento, and a private yacht excursion around Capri curated for family members of all ages.
ICELAND
Where: The Southern Coast
Why Go: Home to the earth’s largest glaciers, there’s no shortage of icebound experiences here!
Not to Miss: Hike the picturesque glacier outlet of Sólheimajökull and take in panoramic views of the surrounding mountains. Discover large sinkholes, called moulins, which drain into crystal-clear waterfalls beneath the black sand. And best of all: Explore the interior of a volcano on a journey that begins with a 40-minute hike to the crater. Once inside, you’ll be lowered into the volcanic opening with a specially designed lift. As your descent begins, the magma chamber puts on a display of magnificent colorations and eclectic textures.
CROATIA
Where: Dubrovnik, Hvar & the Island of Bisevo
Why Go: Sun-drenched days along the Adriatic, historic walled cities, and glittering turquoise seas make Croatia irresistible for summer adventuring. Luxury travelers will find secluded islands accessible by private yacht, Michelin-starred dining in Dubrovnik and Hvar, and boutique hotels carved into centuries-old stone palaces.
Not to Miss: When in Croatia, a boat tour on the Adriatic Sea is basically mandatory! Explore some of the bluest waters and take in the renowned sights between Dubrovnik and Hvar. While exploring the island of Bisevo, be sure to visit the large Monk Seal Cave—named after the Mediterranean creature who used to reside on its beach. And on Vis Island, Stiniva is one of the most Instagram-worthy beaches in all of Croatia.
HAWAII
Where: Kona & Maui
Why Go: Pristine beaches, dramatic volcanos, lush rainforests, and lavish resorts. Indulge in culinary journeys of hyper-local flavors and discover where culture meets nature—whale watching, private sailing, and star-gazing from volcanic heights.
Not to Miss: An evening manta ray snorkel—the most famous scuba dive or snorkel in Kona. A shallow, 25-foot depth allows both snorkelers and certified divers to get in on the action, as these gentle giants feed on a buffet of plankton attracted by dive lights. On Maui, the Haleakala Sunrise Guided Bike Tour takes you to the 10,000-foot summit of Haleakala, where you’ll learn about its significance in Hawaiian culture. As you enjoy bi-coastal views of Maui's central valley and the West Maui Mountains, you’ll spin through Maui’s most enchanting landscapes.
ALASKA
Where: An indelible cruise through the waters of Alaska with National Geographic-Lindblad Expeditions.
Why Go: There is no place quite like this—an untrammeled frontier of snow-capped mountains, breathtaking fjords, and extraordinary wildlife. Lindblad Expeditions has been exploring the region’s wildest corners for more than 40 years, seeking out inlets and coves where larger ships can’t sail.
Not to Miss: Glide among electric blue icebergs, hear the thunder of calving glaciers, and cruise shore-ward in Zodiacs for sightings of brown bears, pods of orcas, breaching whales, and bald eagles. When in Glacier Bay National Park, learn from First Nations peoples in Haida Gwaii, walk rainforest muskegs, or journey through the seldom-seen coastal inlets.
GREECE
Where: Anywhere you can island hop from your own private yacht!
Why Go: Imagine a trip for a family of six, including all ages and travel preferences. Add milestone moments like a retirement celebration, a son’s 30th birthday, and a daughter’s graduation, and this Greek sojourn will quickly become a favorite summer vacation.
Not to Miss: A beach club day at Scorpio’s on Mykonos, a biking excursion on Ios, and dancing with the yacht crew during your last dinner aboard. A happy WhirlAway client can attest: “It’s the easiest, most relaxing, and best quality family time they’ve ever had—a very special vacation!”
