Private Luxury Sailing in the Virgin Islands & Florida

Customizable day sails, sunset cruises, snorkeling trips, and multi-night charters aboard a 50-foot yacht.

Featured Sailing Adventures

Private full- and half-day sails, sunset cruises, snorkeling trips, and multi-night voyages across the USVI, BVI and Florida.

About Summerwind Adventures

Summerwind Adventures operates luxury private sailing charters in the U.S. and British Virgin Islands, St. Thomas, St. John, and northeastern Florida.

The company specializes in customizable day sails, sunset cruises, snorkeling trips, and multi-night excursions aboard a 50-foot yacht designed for comfort and adventure. Private half-day and full-day charters are available, alongside two-hour exploratory sails, multi-night itineraries to St. Augustine, Cumberland Island, and Amelia Island, and extended passages through the USVI and BVI.

Professional crewing ensures safety and personalized service. Each charter includes two dedicated crew members who handle navigation, guest comfort, and on-board dining. Guests enjoy complimentary snacks and drinks on shorter sails, with gourmet meal options and caterable menus available for longer or private events. Water activities like snorkeling, fishing, and swimming are accommodated, and itineraries can be tailored for secluded beaches, open-ocean experiences, or relaxed coastal cruising.

Summerwind Adventures emphasizes small-group experiences, capping guests to maintain intimacy and quality. The yacht's amenities include a spacious deck, swim platform, and storage for snorkel gear and watersports equipment. Safety briefings, life jackets, and professional-grade equipment are provided for all participants.

Booking is streamlined for private groups seeking celebration charters, family outings, or romantic sunset sails. The operator supports custom itineraries and flexible scheduling to match guest priorities. Summerwind Adventures presents a reliable option for travelers seeking an upscale, personalized sailing experience in the Caribbean and along Florida's historic coastlines. Reservations include clear pricing, pre-trip communication, and the flexibility to adapt routes for weather and guest preference and timing requests.

Destinations

USVI, BVI, FL

St. Thomas, St. John, St. Augustine

Max Guests

6 guests

Intimate private charters

Vessel Size

50-foot yacht

Luxury yacht with full amenities

Summerwind Adventures — Private Sailing Charters

Summerwind Adventures offers luxury private sailing experiences tailored for small groups seeking adventure, relaxation, and curated itineraries across the U.S. Virgin Islands, British Virgin Islands, St. Thomas, St. John, and northeastern Florida. With a 50-foot yacht, two professional crew members, and a focus on personalized service, Summerwind delivers high-end private charters for day sails, sunset cruises, snorkeling trips, and multiday excursions.

Popular Trips and Destinations

Sailing Adventures (Full & Half Day) in the Virgin Islands — ideal for snorkeling, beach stops, and open-water sailing.
Sunset Sailing Adventures in St. Thomas and St. John — private sunset sails with complimentary drinks and light snacks.
Multi-night Sailing Adventures in the U.S. Virgin Islands and British Virgin Islands — multi-day passages with gourmet meals and island hopping.
Multi-night Sailing Adventure to St. Augustine, Cumberland Island, and Amelia Island — historic coastlines and secluded anchorages.
2-Hour Sailing and Exploring Adventure in St. Augustine — quick coastal exploration and scenic sailing.
Day Sailing, Snorkeling and Adventures in St. Thomas — tailor the day for snorkeling, swimming, and beach time.
Private Day Sail, Private Sunset Sail, and Multiday Sailing Excursions — fully private, customizable charters.

Why Choose Summerwind Adventures

Luxury vessel: The 50-foot yacht provides a comfortable deck, swim platform, and storage for gear.

Small groups: Maximum of six guests ensures an intimate, personalized experience.

Experienced crew: Two dedicated crew members handle navigation, safety briefings, and on-board hospitality.

Custom itineraries: Guests can prioritize snorkeling spots, secluded beaches, fishing, or relaxed cruising.

On-board dining: Complimentary snacks and drinks on shorter sails; gourmet and catered meal options for extended charters.

What to Expect on a Charter

Thorough safety briefing and professional-grade equipment
Flexible itineraries to match weather and guest preferences
Options for snorkeling, fishing, water sports, and beach exploration
Sunset sails with optional appetizers or full catering

Tips for Booking

Reserve early for weekend sunset sails and multi-night itineraries.
Specify snorkeling gear, dietary needs, or special events during booking.
Confirm guest count and preferred itinerary to ensure proper provisioning.

Book a Private Yacht Charter

Summerwind Adventures is a top choice for travelers seeking private sailing charters in the Caribbean and Florida. Whether the goal is a private sunset sail in St. Thomas, a full-day snorkeling adventure in the Virgin Islands, or a multiday voyage through the USVI and BVI, Summerwind provides luxury, safety, and bespoke experiences. Contact Summerwind Adventures to confirm availability, discuss custom itineraries, and secure reservations for an unforgettable sailing getaway.

Reserve a Private Sailing Charter Today

Secure Summerwind's 50-foot yacht for snorkeling, sunset, or multi-night adventures — limited availability for private charters.