For the travel enthusiast in your life, memorable gifts are less about the materials and more about the experiences. Hence why this holiday season, we are proposing eight inspiring trips to surprise your family and friends as alternatives to material items.

Whether you are searching for a gift for a loved one or making your own holiday wishlist, here are our top choices for discerning travelers in the coming year:


Photo: Don Riddle / Four Seasons

Photo: Don Riddle / Four Seasons

Miles of secluded beaches, lush rainforest, and centuries-old plantations and sugar mills set the stage for a relaxing getaway on the island of Nevis. Abundant in natural beauty, the Caribbean destination has much to offer from snorkeling the vibrant reefs of Herbert’s Beach to visiting the beloved hot springs of Bath Village.

Plan to stay at the five-star Four Seasons Resort Nevis, the romantic Montpelier Plantation, or Nisbet Plantation Beach Club, the Caribbean’s only historic plantation inn on the beach. For exquisite cuisine, Bananas Bistro & Art Gallery provides a charming garden setting near the ruins of the Hamilton Estate sugar plantation, while Coconut Grove offers a local, sustainable menu and Wine Spectator award-winning wine list.

How to Get There: Fly Tradewind’s scheduled shuttle to Vance W. Amory International Airport (NEV).


Photo: Stowe Mountain Resort

Photo: Stowe Mountain Resort

Fresh powder and world-class skiing await this winter in Stowe, one of the most acclaimed ski destinations in the Northeast offering 40 miles of beginner-to-expert trails. Stowe Mountain Resort’s Mt. Mansfield is the highest mountain in Vermont at 4,395 feet and home to the renowned Front Four double-black diamonds.

After a day on the slopes, retreat to luxurious accommodations at Stowe Mountain Lodge, the only ski-in, ski-out resort in Stowe, then partake in winter favorites from ice skating to snowshoeing. Should your visit fall during January or February, check out the family-friendly Stowe Winter Carnival or the Stowe Derby, the oldest downhill ski race in North America.

How to Get There: Fly Tradewind’s scheduled shuttle to Morrisville-Stowe State Airport (MVL) from mid-December through March.


Photo: Montage Palmetto Bluff

Photo: Montage Palmetto Bluff

In the heart of the South Carolina Lowcountry, Bluffton’s Montage Palmetto Bluff spans 20,000 acres along the May River, encompassing a verdant nature preserve, walking trails, a marina, and a Jack Nicklaus signature golf course. Stay in Southern-style accommodations ranging from elegant guestrooms to entire village homes, and enjoy an array of activities from horseback riding to clay shooting. On the water, you can fly fish for redfish, paddleboard, or explore the marshlands by boat. And at just 30 minutes away each, Hilton Head and Savannah beckon.

How to Get There: Charter a flight with Tradewind to Savannah/Hilton Head International Airport (SAV) or Hilton Head Island Airport (HXD).

St. Barth


In the wake of Hurricane Irma, St. Barth has experienced an incredible revitalization. Restaurants and boutiques have reopened, beaches like Colombier have returned to their natural states, and annual events like the St Barths Bucket Regatta and Les Voiles de Saint-Barth are scheduled to go on as planned. There’s no need to be wary of planning a trip. In fact, tourism is essential to recovery, and the best thing you can do to help the island is to visit.

Most of St. Barth’s luxury hotels are slated to reopen in summer of 2018, so you should reserve your stay in one of the island’s exquisite villas – from expansive beachfront estates to intimate retreats tucked among the hills. Le Tamarin with its lovely garden and Jean Claude Dufour’s L’Esprit are both open, and Bonito is expected to welcome guests again by early 2018. Although recovery is ongoing, the island still offers the same stylish exclusivity that longtime visitors have come to love.

How to Get There: Fly Tradewind’s scheduled shuttle to Gustaf III Airport (SBH).


Photo: Omni Grove Park Inn

Photo: Omni Grove Park Inn

Tucked among the Blue Ridge Mountains in western North Carolina, Asheville is an elegant mountain getaway with a vibrant arts and restaurant scene. Miles of hiking trails leading to rushing waterfalls and scenic overlooks surround the city, while downtown and in the eclectic new River Arts District, you can find sculpture and painting galleries alongside farm-to-table dining experiences, breweries, and quirky live music venues.

Stay at the authentic Omni Grove Park Inn, built in 1913 on the western slope of Sunset Mountain, and dine on local, sustainable cuisine at chic eateries like Nightbell, Zambra, and Posana. Before your trip comes to a close, make time to visit the immense Biltmore House, a 175,000-square-foot French Renaissance-style home built in 1895 by George Vanderbilt.

How to Get There: Charter a flight with Tradewind to Asheville Regional Airport (AVL).

Martha’s Vineyard and Nantucket


Though traditionally regarded as summer destinations, Massachusetts’ iconic islands are peaceful, welcoming respites even during the cooler months. Plan a winter getaway filled with long walks on windswept coastlines, uncrowded dining experiences, and leisurely shopping.

On Martha’s Vineyard, Martha’s Vineyard Chowder Company and the Scottish Bakehouse are just a few of the restaurants that remain open year-round. You can find live music at The Wharf, and for shopping, head to Martha’s Vineyard Glassworks, Bunch of Grapes Bookstore, and Tuck & Holand Metal Sculptors – renowned for their weathervanes that have been designed for the likes of Steven Spielberg.

To the east, Nantucket welcomes visitors with snow-covered beaches and a harbor often completely covered in glistening ice. Visit Sankaty Lighthouse on the beach, the Dreamland Theater for movies and theatrical performances, and Cisco Brewers for local craft beer.

How to Get There: For trips in early 2018, charter a flight with Tradewind to Martha’s Vineyard Airport (MVY) or Nantucket Memorial Airport (ACK). Tradewind’s scheduled shuttles begin in May for Martha’s Vineyard and April for Nantucket.



One of the Caribbean’s top boating destinations, Antigua is home to endless stretches of white sand and turquoise waters with an estimated 365 beaches. Shorelines like Jolly Beach (among the widest on the island) and Half Moon Bay (an isolated snorkeling destination) tempt beachgoers, and weekly boat races and annual regattas like the spring Sailing Week draw experienced sailors from all over the world.

While the neighboring island of Barbuda was decimated by Hurricane Irma, Antigua was spared the worst of the storm. Luxury hotels like Jumby Bay Island, Carlisle Bay, and Hermitage Bay are open, along with exquisite restaurants from the oceanfront Catherine’s Café to the clifftop Sheer Rocks.

How to Get There: Fly Tradewind’s scheduled shuttle to V.C. Bird International Airport (ANU).

Fisher Island


Located three miles from mainland Miami, Fisher Island is an exclusive enclave for residents and few visitors that was once the home of the Vanderbilts. The destination is awash with exquisite, Spanish-style architecture from the residential mansions and apartments to the luxurious Fisher Island Club, the island’s only hotel. Reserve a room amid a lush, tropical landscape to enjoy the hotel’s beach club and marina, world-class spa, and seaside golf course with views of the Miami skyline.

How to Get There: Charter a flight with Tradewind to Miami International Airport (MIA).


*Featured Image: Starus