Book a one-of-a-kind air journey crafted by award-winning tour operator George Morgan-Grenville, founder and CEO of Red Savannah, and hosted by American Viscountess, Julie Montagu. The inaugural Grand Tour of Europe by Private Jet will take just 15 travelers on a 12-day adventure from London to Sicily, then on to the Greek isles, the Adriatic Riviera, and the magical City of Canals, Venice. A private driver and guide for independent discoveries, plus private dining at Michelin-starred venues, make this a standout experience. September 12—24, 2023. From $139,500/person; email Camilla Davidson at inspired@redsavannah.com
The 750-passenger Regent Seven Seas Grandeur will launch in November 2023 with a 14-night cruise from Barcelona, Spain, to Miami via the Spanish city Seville, Madeira in Portugal, plus Bermuda. The best stateroom for that voyage (and any of the other 17 itineraries it will follow) is the Regent Suite at the ship’s prow. The standout, 4,500-square-foot stateroom boasts 270-degree views of the ocean, a private spa-like bathroom, unlimited treatments, and a personal car and guide in every port. Itineraries from $4,000/person; rssc.com
Plan a 14-day jaunt to the South Pole with an ultra-luxe charter specialist. The PelorusX Antarctica Heli-skiing and Forgotten Wrecks itinerary unlocks the untouched continent’s farthest reaches with an ice-class superyacht equipped with not one but two helicopters. Fly deep into the white desert to ski first-descent slopes; the copters will also visit an isolated Emperor Penguin colony. Take a literal deep dive into the continent via the onboard submersible to see 300-year-old shipwrecks. From $2 million for up to 12 people; pelorusx.com
For the Aspen Street Lodge Ski Experience with Chris Davenport, enjoy the expertise of the 11-room hotel’s in-house guide, who is a two-time World Extreme Champion and a big mountain ski icon. Davenport was the first person to ski all 54 of Colorado’s 14,000-foot peaks in less than a year and has logged more than two decades as a guide (including on mega peaks Everest and Denali). He will be on call for four of your group (he can bring in more pros if the group is larger) to finesse first-timers or take seasoned skiers roaming through the local backcountry. Sit down with him to discuss interests and experience levels, and Davenport will devise a custom itinerary. From $2,000 for up to four guests; aspenstreetlodge.com
The Fife Arms hotel in Scotland’s Braemar, close to Balmoral Castle, was reinvented four years ago by superstar gallerists Iwan Hauser and Manuela Wirth. The pair partnered with maximalist interior designer Russell Sage who created a whimsical collision of OTT Victoriana with cutting-edge contemporary art that resembles the inside of King Charles III’s mind. The on-site gift shop is packed with collaborations with classic British brands, including the waxed-cotton Fernweh for the Fife Arms Backpack, made by Aberdeen-based design studio Fernweh specially for the hotel. It’s trimmed with the property’s own signature tweed and features functional details like a D-ring for keys, a laptop sleeve, and a magnetic snap close to keep the roll top snug. $316; thefifearms.com
Vail Resorts’ unlimited Epic Pass to more than 40 properties has long been a snow bunny stocking filler. The season-long ticket accesses slopes everywhere from Park City, Utah, to Stowe, Vermont, as well as Vail proper without restrictions. European slopes, historically more limited in access with days-long allocations at partners like Italy’s Dolomiti Superski and the Trois Vallées in France, are now also unrestricted, as well as in Switzerland’s Andermatt-Sedrun resort, since Vail Resorts purchased a majority stake this year. It was a coup, for sure, to take on a resort that’s been a favorite of everyone from Queen Victoria to Elvis Presley. $841/person; epicpass.com
Winter Wellness at One&Only Portonovi includes seven nights at the 123-room outpost opened last spring on a mile-long strip of coast, right at the entrance to Montenegro’s fjord-like Boka Bay. You’ll stay at Villa One, a three-bedroom standalone home to hole up in while undergoing an intensive detox and wellness makeover courtesy the Swiss spa Chenot. It’s partnered with the brand to add signature clinics to properties like this, where guests can indulge in its fusion of Western and Chinese medical treatments. In this program, expect everything from daily energetic massages and Phyto-mud treatments to a body composition analysis, plus a custom low-calorie, plant-based menu for every meal. $66,000/seven nights for two guests; oneandonlyresorts.com
Entrepreneur Shelley Cline created an entirely new category of trip when she founded TCS World Travel: taking everything that’s great about high-end cruising but swapping out the ship for a private jet. Her guests fly on a 52-person A321neo, with custom-made leather seats and an 18-strong crew, including a chef and on-call doctor. Itineraries unlock far flung destinations, including the 17-day TCS South American by Private Jet Expedition that hopscotches between Colombia, Peru, Bolivia, Argentina, and Chile with highlights such as the Salar de Uyuni salt flats, Iguazu Falls, and a fishing expedition to land paiche, one of the world’s largest freshwater fish. $74,950/person; tcsworldtravel.com
The reimagined Kaimana hotel, a 122-room boho luxe property on the namesake beach, a smaller, quiet spit of sand close to Oahu’s Diamond Head, has partnered with a longboard surfing champion. Surf enthusiasts can book the five-night Design Your Own Longboard With World Champion Kai Sallas package to go one better than just a private lesson with Sallas (though that’s included, too). Sallas will custom design a board, via his new company, and help pick everything from shape to color. It’ll be finished off with a personal message from Kai, then shipped to the buyer’s home as the ultimate souvenir. $7,000/five nights, including an oceanfront suite, surfboard, and lesson; kaimana.com
Buy out the three-unit Presidential Skyhouse Wing at the Harbor View Hotel in Martha’s Vineyard. The 117-room historic inn, a favorite of the Obamas and Bradley Cooper, built the addition during a recent $15 million renovation. The hotel-within-the-hotel on the fourth floor overlooks Chappaquiddick Island. Order room service (or a private chef) from one of the two high-end restaurants on site, Bettina & Roxana, each named after the daughters of owner and Hong Kong–born tycoon Bernard Chiu. Presidential Wing buyouts from $5,995/night; harborviewhotel.com
