What better way to share the holiday season with friends and family than an unforgettable trip together? Whether you’re looking for adventure or total relaxation, we rounded up some of the best destinations for you to explore this holiday season. 

Anguilla

Four Seasons Resort and Residences Anguilla

Immerse yourself in Anguilla’s unique culture and stunning natural beauty while staying at the Four Seasons Anguilla, where their award-winning hospitality team takes the Caribbean to new levels of sea-side luxury. Nearly 80% of the 181 villas and resort accommodations overlook the breathtaking beauty of two of Anguilla’s most spectacular beaches. Considered the culinary capital of the Caribbean, the restaurant offerings feature vibrant seafood dinners, sushi creations, and crisp wines. The complimentary daily oceanfront yoga is a favorite for guests looking to enhance their wellbeing while away.  Relax this holiday with those you love in a place where every sunset is theatrical. 

Miami, Florida

Four Seasons Surfside

The Surf Club has quite the storied past, with an impressive list of past guests such as Frank Sinatra, Elizabeth Taylor and Winston Churchill. The timeless glamour still glitters today, as the Four Seasons Surfside stands alone as one of the most divine destinations for total relaxation. Though it’s not on the famous strip, FS Surfside evokes privacy and exclusivity on one of Miami’s most Northern beaches. Home to one of the most iconic restaurants in all of Miami, Le Sirenuse offers a myriad of delicious entrees and cocktails. After dinner, head to the Champagne Bar - an award-winning and stunningly beautiful cocktail lounge. The elegant and contemporary accommodations are incredibly spacious and make it hard to leave. 

1 Hotel South Beach

1 Hotel South Beach boasts a world-famous rooftop pool and elegant, eco-friendly accommodations, making it the premier hotel on the strip. Focused on sustainability, 1 Hotel South Beach brings their expansive accommodations to life with reclaimed woods, organic cotton sheets, and other recycled materials - making each room one of a kind, naturally. The 4 outdoor swimming pools, including the largest rooftop pool in all of South Beach provide endless fun in the sun for everyone. The direct beach access and complimentary Tesla car service make 1 Hotel South Beach an easy choice for your holiday vacation. 

 Little Torch Key, Florida 

Little Palm Island

This island is considered to be one of the best hidden gems in The United States, and has been the escape of choice for Presidents, A-Listers and well-traveled individuals for generations. What makes this hotel so unique is the no cell-phone, television and guests under 16 policy that is set in place to ensure that the only distractions are the outdoors and each other. The beach accommodations and bungalows are inspired by a West Indies aesthetic, reminiscent of a jungle-like hideaway. The dining is unlike anything else with a world-renowned Chef who sources seafood and local spices from the island to provide an authentic culinary experience. Whether you arrive by the hotel’s private boat or a seaplane, you’ll begin your Keys escape in style. Restore your spirit this holiday season at Little Palm Island.  

Aspen, Colorado

The Little Nell

Known for bringing “downtown Aspen to your front door, and Aspen Mountain at your backdoor”, The Little Nell offers the best of Aspen to its guests. The hotel’s service is of the highest quality, ensuring they know each member of your family’s name upon check in. The accommodations are arguably the finest Aspen has to offer, each with their own layout and design. The custom touches - from original artwork to live plants lend an opulent and luxurious feel. Offering a myriad of outdoor adventures from world-class skiing to snowmobiling through the snowcapped mountains, your family will enjoy an epic holiday vacation.  

St. Barths

Le Barthélemy Hotel & Spa

Le Barthélemy is a haven of tranquility and restoration overlooking the spectacular, white-sand beaches in the chicest location known to man - St. Barths. This Caribbean island with a distinctly French flavor is known for a glamorous lifestyle of beach clubs, beautiful beaches and swanky restaurants. Despite its popularity with celebrities, the island is relaxed and friendly, a place of fun and unity. The vibe of the island and the beautiful scenery go a long way to getting you into a relaxed state of mind, making this the perfect getaway for you this holiday season. 

 Cheval Blanc St-Barth Isle de France

Set on the iconic Flamands Bay, Cheval Blanc is home to 61 luxurious accommodations that are either situated in the lush gardens or with stunning, panoramic beach views. Bringing Cheval Blanc’s Parisian flair to the Caribbean, this five-star resort brings French refinement with the utmost glamorous atmosphere. Whether you’d like to relax on the island and simply enjoy the charm of the West Indies or pursue outdoor adventures on the island, the team of ambassadors on property deliver highly personalized service and curate tailor-made experiences for ensure the perfect stay. 

 Dorado, Puerto Rico

 Dorado Beach, a Ritz-Carlton Reserve

Roughly 21 miles from the beautiful city of San Juan, Dorado Beach has long been one of the most exclusive resorts in the Caribbean. Once a pineapple plantation, conservationist and philanthropist Laurance Rockefeller purchased the property and developed this eco-friendly resort and natural sanctuary. You’ll be enamored with the lushness of the property, and the endless adventures that await you on Dorado beach - from the world-class snorkeling to the $12 million aquatic playground called the Watermill, there’s something for everyone. The Forbes Five Star-rated spa features locally-sourced ingredients for their handcrafted and all-natural products. The innovative dining option are plentiful, with four restaurants on property and cooking classes available upon request.