Florida and The Bahamas have firmly established themselves as timeless vacation favorites, boasting top spots with pristine beaches, world-class luxury resorts, and stunning natural beauty around every corner.
With so many incredible spots to choose from, narrowing down a destination for your next trip isn’t the easiest task. While some places are most popular during the “high season”—roughly November through May, the discerning traveler can recognize the appeal and benefits that some of these destinations offer year-round.
With Tradewind entering the Southeast US travel market in Fall 2023, guests can now fly personal with private flights to the closest, most convenient airports relative to their final destination throughout the Southeast and Bahamas. Read on for our picks for the best vacation spots this fall and winter —and how Tradewind can elevate your journey to make your next trip unforgettable.
Amelia Island
Although Amelia Island often receives less attention than the coastal resort towns to the south, it’s just as desirable, and its location makes it a year-round destination unlike other parts of Florida. This pristine barrier island is an adventure-seekers paradise, offering activities such as canoeing, kayaking, fishing, wildlife exploration, and even horseback riding on the beach—a favorite among visitors of all ages.
During your stay, there’s no better home base than The Ritz-Carlton, Amelia Island, which is perched right on the beach. This expansive resort boasts an 18-hole championship golf course, a newly renovated spa and wellness area, as well as spacious pools and beach day beds, ensuring there is something to offer for everyone and making the resort an ideal choice for families. At the Ritz-Carlton, guests not only receive top-notch service but also experience southern hospitality is at its finest.
Where to Fly: Jacksonville International Airport or Jacksonville Executive at Craig Airport
Boca Grande
This secluded island on Florida’s west coast is renowned for its tarpon fishing, and its classic, historic charm makes it one of the top vacation spots in the state. The Gasparilla Inn & Club is the epitome of a classic Florida resort, having operated in various forms since the early 1900s and captures the essence of old-school Florida at its finest. For your stay, the resort’s new Beach Cottages offer beachfront accommodations and access to a private pool and exclusive amenities, including a golf cart for exploring the property.
Embrace the resort’s charmingly traditional atmosphere, which includes a “dress to fit the occasion” policy, which requires elevated attire and jackets for men at dinner from mid-December to late April. Keep in mind that the Gasparilla Inn closes seasonally from early July to early October, making it ideal for a winter or spring visit.
Tradewind’s ability to access to smaller airports is perfect for reaching this destination. Instead of needing to fly into the busier Fort Myers Airport before traveling more than an hour and a half to the property, guests can fly with a private charter into the Venice Municipal Airport, less than 45 minutes from Boca Grande.
Where to Fly: Venice Municipal Airport
Longboat Key
This west coast barrier island near Sarasota has long flown under the radar, but that’s likely to change with the addition of the brand-new St. Regis Longboat Key, which officially opened summer of 2024. One of just two St. Regis properties in Florida, the new resort is situated directly on 800 feet of private beach space and offers a front-row seat to the spectacular sunset views that the west coast of Florida is known for. Their 20,000-square-foot spa is massive by any standards, and its expansive pool complex includes a nearly 500-foot-long winding river, along with an adults-only “Serenity Pool.”
The addition of this St. Regis property is sure to attract new visitors to this part of the state, who will soon discover why loyal fans return to the island time and time again. Experience it yourself with a Tradewind private charter, which can land within 10 miles of the secluded destination.
Where to Fly: Sarasota Bradenton International Airport
St. Augustine
Spanish explorers landed on the shores of what is now St. Augustine in 1565, establishing it as the oldest continuously inhabited European settlement in the United States. The city has seen centuries of history, but in the current day it’s established itself as a charming seaside village with historic sites, Spanish colonial-era architecture, and stunning natural scenery.
Most visitors to St. Augustine are required to make the hour-plus-long journey from Jacksonville, but Tradewind’s private service provides access to the Northeast Florida Regional Airport, which is only five miles from downtown St. Augustine.
An ideal home base for a trip is Casa Monica Resort & Spa, a historic hotel located just steps from the 18th century Cathedral Basilica of St. Augustine and the stunning campus of Flagler College. History buffs will find no shortage of sites to explore in St. Augustine and the surrounding area, while still enjoying the classic elements of a Florida vacation—including beaches, nature preserves, and outdoor activities such as fishing and boating.
Where to Fly: Northeast Florida Regional Airport
Bahamas
In addition to private charter flights, Tradewind is launching scheduled flights to the Bahamas in December 2024, which will allow guests to bypass crowded airport terminals and fly directly to two of the most desirable airports in the Bahamas. Currently available for booking, Tradewind scheduled flights will operate five days a week from the private terminal at the Palm Beach Airport to Marsh Harbour and North Eleuthera. For those looking for ultimate flexibility and to travel on their own time, both locations, as well as all islands in the Bahamas, are accessible with a private charter.
Tradewind’s North Eleuthera flights make a visit to Harbour Island a no-brainer. The charming island, which is famous for its pink beaches and English colonial-style architecture, is relatively less easy to reach than other Bahamian islands and maintains an air of seclusion and sophistication.
The Dunmore on Harbour Island offers classic Bahamian charm with a 1960s vibe, while Pink Sands Resort provides an intimate and secluded atmosphere with unparalleled service and direct access to the island’s famous pink sand beaches.
Directly in North Eleuthera, The Cove Eleuthera offers a retreat that will make you feel like you’re on your own private island. Tradewind guests who fly to North Eleuthera and stay at The Cove are eligible to receive $100 resort credit for use during their stay as part of our exclusive partnership.
Looking for an under-the-radar destination? Norman’s Cay in The Exumas fits the bill, though it likely won’t remain so for long. This private island retreat features villas, bungalows, cabanas, and cottages to accommodate groups of varying sizes. The island is accessible only via private charter—which has its own runway within the property—and is guaranteed to provide a luxurious escape. Guests can enjoy stunning scenery, engage in activities such as deep-sea fishing or snorkeling around a sunken airplane, and unwind at the island’s Yacht Club, which offers 360-degree views of the island and surrounding waters.
Where to Fly: Marsh Harbour or North Eleuthera via Tradewind scheduled flights to the Bahamas, or Norman’s Cay via Tradewind private charter.
To learn more about Tradewind’s flights to the Bahamas and throughout Florida, please visit our website. To receive a private charter quote, please submit an inquiry here or contact our specialists at sales@flytradewind.com or 1-203-267-3305 option 2. For questions regarding scheduled flights, contact our scheduled service team at scheduledservice@flytradewind.com or 1-800-376-7922 option 1.