The only thing better than the wedding of your dreams is the sweet escape for two that follows. And be it a place on the edge of the sea or in an alpine hideaway, Tradewind’s regularly scheduled shuttle flights or private charters in the Northeast and the Caribbean will ensure your first trip as newlyweds truly exceeds the ordinary.

Here are our recommendations for honeymoon accommodations, intimate date night venues, and romantic activities for two in some of our favorite destinations. 

Martha’s Vineyard

Photo Credit:  Harbor View Hotel

Photo Credit: Harbor View Hotel

In New England, there are few places so well known for romantic shorelines and quaint coastal cottages as Martha’s Vineyard.  Spanning just 100 square miles off the coast of Massachusetts, the picturesque island offers charming waterside towns, miles of farmland, and an abundance of activity on the water from sailing to fishing.

Newlyweds will delight in the lovely ambiance of Edgartown, which is close to both beaches and harbor and offers luxury accommodations such as Winnetu Oceanside Resort and Harbor View Hotel. For French-inspired contemporary cuisine, spend a night out at L’Etoile, and for fine Italian fare and cocktails, visit Chesca’s Restaurant—both located in downtown Edgartown.

During the day, you will want to explore the island on foot, by bike, or perhaps on the wings of an open-air biplane. Classic Aviators offers flights for two from Katama Airfield, and the Vineyard from above is simply stunning.


Photo Credit:  Wauwinet

Photo Credit: Wauwinet

History comes alive in downtown Nantucket, where cobblestoned streets are lined with flourishing elms and sycamores and homes built hundreds of years ago still abound. At the mouth of the harbor, Brant Point Light welcomes visitors to the island, and amidst the rolling hills you can discover the lush gardens of the First Congregational Church.

It’s the ideal place for a romantic New England getaway, especially when you stay in the historic Wauwinet, a sophisticated retreat known for its charming cottages and exceptional cuisine, or the classic White Elephant with its sprawling harbor-side lawn. Topper’s, located within the Wauwinet, offers gourmet New England fare, and Table No. 1 on Old South Wharf carries excellent wine and cheese perfect for a picnic on the beach.

When it comes time to explore Nantucket, go by bike. There are miles of paved paths around the island that make destinations like Siasconset on the Eastern coast easily accessible. We also recommend whale and seal watching on the Atlantic. 


The scenery in Stowe is beautiful year-round, whether the mountains are blanketed in snow or vibrant green. Honeymooners will discover new experiences during each season, including skiing and horse-drawn sleigh rides in the wintertime and canoeing and zipline adventures in the warmer months.

Stowe Mountain Lodge is the only ski-in-ski-out hotel in town, so it’s the perfect option for couples who will be spending time on the slopes. We also like Edson Hill, a cozy mountain lodge near the center of town that has an intimate and historic atmosphere. For an elegant dinner, take a drive to Michael’s on the Hill where the farm-to-table fare is fresh and seasonal and dishes like the pan-seared trout make the restaurant a local favorite.

Photo Credit:  Edson Hil

Photo Credit: Edson Hil

As for the outdoors, countless excursions will likely make it difficult to choose how to spend your getaway. We recommend hiking to Bingham Falls, a beautiful fluid waterfall in summer and a frozen sculpture in winter. It’s a great place for a photo to remember your time in Stowe. 

St. Barths

Photo Credit:  Le Seren o

Photo Credit: Le Sereno

Those wishing for a luxury retreat will find their honeymoon destination in St. Barths. The most glamorous island in the Caribbean offers 14 beautiful beaches, a collection of stylish designer boutiques, and trendy cafés with delicious French and Creole cuisine.

Newlyweds who enjoy a lively atmosphere will like Eden Rock for elegant accommodations overlooking St. Jean Beach, while those in search of a luxurious but secluded escape should opt for the palatial Cheval Blanc near Flamands Beach. For an intimate retreat in a world-renowned kite surfing destination, choose the romantic Le Sereno or the pastel-hued Le Guanahani alongside the crystal clear waters of Grand Cul de Sac. We also enjoy Hotel Christopher, isolated on the beautiful northern coast, and Le Toiny after its recent multimillion-dollar renovation.

Photo Credit:  Le Tamarin

Photo Credit: Le Tamarin

In the charming and historic capital of Gustavia, couples will find a delectable ceviche bar and inspired cuisine at Bonito. And across the island, Le Tamarin offers a lovely garden space for candlelit dinners and quiet conversation.

When you find yourself wishing to explore, Colombier Beach is a must-see on St. Barths. The hidden shoreline can be reached on foot or by boat from Gustavia, and it is here that honeymooners will discover bountiful coral reefs for snorkeling and incredible, color-drenched sunsets.


Photo Credit:  Malliouhana

Photo Credit: Malliouhana

Pristine beaches and historic neighborhoods await on the quiet island of Anguilla. The Caribbean destination is well known as a haven for food enthusiasts with a rumored 100 restaurants offering local specialties such as fresh lobster, crayfish, and goat curry.

Luxury hotels like the Mediterranean-style Cap Juluca and the boutique Malliouhana, located on a bluff overlooking the ocean, offer private suites and terraces perfect for newlyweds. There is also the culinary-focused CuisinArt Resort and Spa with gourmet cooking classes and an 18-hole championship golf course.

Photo Credit:  Pimms at Cap Juluca

Photo Credit: Pimms at Cap Juluca

As for dining, couples can experience an incredible variety of flavors including European and Caribbean fusion at Pimms, Moroccan specialties at Veya, and local fare like ginger teriyaki sea scallops just steps from the beach at da’Vida.

Adventurous couples who wish to explore the Caribbean Sea can snorkel or obtain diving certification from local experts like Shoal Bay Scuba Shack. There are seven marine parks located off the coast of Anguilla harboring beautiful rock formations, shipwrecks, and a vibrant array of marine life.

St. Thomas

Photo Credit:  Katlo Charters

Photo Credit: Katlo Charters

A beautiful destination for sailing, St. Thomas provides a state of calm among magnificent beaches, tidal pools, and rolling green hills.

Many couples seek a honeymoon on the water, and sailing companies such as Katlo Charters and Caribbean Cruising Vacation will have an experienced captain meet you at the airport for your ocean retreat.

Those who prefer to experience St. Thomas on shore will enjoy the elegant suites and outstanding scenery at The Ritz-Carlton overlooking Great Bay on the Eastern Coast. There is also Frenchman’s Reef & Morning Star Marriott Beach Hotel, a luxury oceanfront resort that pops with Caribbean designs, and the neighboring Marriott’s Frenchman’s Cove, which resembles a classic island village.

For a night out, dine al fresco with sunset views at Sunset Grille, or venture into the hills to Old Stone Farmhouse, a restored plantation stable and fieldhouse with an intimate ambiance and entrées that you can hand-select from the kitchen.

While sailing is our first recommendation, even if just for a day, couples should also opt for a zipline adventure through the canopy, and at day’s end, hike to Drake’s Seat for a panoramic view of Magen’s Bay and the romantic Caribbean sunset.