Windjammer Cruises on tall ships and cabin charters on the 3 mast Schooner Arabella in the Caribbean,  New England and Chesapeake Bay for Couples, Singles, Families and Groups

Our first hand knowledge of the area and the ships will help you to find the cruise that fits your needs. We will make the booking process easy and flawless - at no extra costs for you!

The more intimate Cruise vacation on the 160 foot sailing Schooner ARABELLA - sailing the Caribbean, New England and Chesapeake Bay

From her teak decks to her billowing sails aloft, Arabella brings you back to a time before the hustle and bustle of the modern world. So whether recharging your batteries, enjoying your second honeymoon or your first, or just seeking a winter getaway, join us on one of our castaway cruises!

•  Passenger Capacity: 40 Overnight or 149 for day trips
• US Coast Guard / SOLAS inspected vessel
• Beam: 24' / Draft 12'
• Rig: Three mast Staysail Schooner
• Staterooms: 20
• Large Inflatable Launches
• Satellite TV in each Stateroom
• Satellite Communication
• All Staterooms are individually Climate-Controlled
• In-Suite Head & Showers
• Viewing Port Hole in each Stateroom
• Afternoon Hors D'Oeuvres
• On Deck Hot Tub
• Traditional Salon & Bar
• Snorkeling
• Onboard Water Craft

Arabella is available for private, corporate and family sailing charters in the Caribbean in the winter, Chesapeake in the spring and fall, and New England throughout the summer.

Be it incentive travel groups, corporate seminars, family reunions, weddings, foreign tour groups, etc, your choice of itinerary are decided only by your own desires.

Category A: Queen bed, forward cabin
Category B: Double bed or Upper/Lower, forward cabin
Category C: Upper/Lower, aft cabin
Category D: Small Double, aft cabin

Cabin charter cruises starting at $1000 per person, double occupancy.

Contact us for more information and availability!

A sailing cruise in the Caribbean on one of the tall ships of the Windjammer Barefoot fleet could be the perfect alternative for you, if you think a sailing yacht is too small and a cruise ship is too crowded. The smallest ship takes 64 passengers; the largest ship carries 130 passengers. Compare that to 2,000 plus passengers on a cruise ship. Your group will get attentive service night and day. And there's no waiting in line for the buffet or anywhere else. Your group will never get lost in the crowd, because you are the crowd.

Cruises start under $1000 per person per week, depending on the ship, the itinerary and the cabin you choose. Group discounts are available.

Windjammer shipmates are a motley crew of interesting folks from all over the U.S. and abroad. You won't know if the guy or gal sitting next to you is the CEO of a Fortune 500 Company or an average "Joe." And the best part is... no one cares. Once your ship sets sail, it's all about relaxing and getting into the down-island groove. Any pretenses are quickly forgotten, and a familiar sense of camaraderie soon develops among passengers.

If you've never felt weathered teakwood beneath your bare feet, now's your chance. The spacious decks are a focal point of activity. It's where ship-mates gather to lounge, sunbathe, read, socialize, dance and party from sun-up to sundown. Above all, the atmosphere onboard is relaxed, casual and comfortable - a place where you can let your hair down. At night, bring your bedding to the top deck and sleep under the stars while the ship is under sail.

Dining aboard Windjammer is casual and relaxed. No tuxedos, ties or feather boas required. Come in a bathing suit and t-shirt if you like- just bring an appetite. Meals are social occasions for sharing stories and good food in the company of interesting and friendly shipmates. The good thing is, you can meet someone new at every meal, as there are no fixed seating arrangements. Shipmates are free to roam and sit with whomever they want.

Sailing is romantic, exciting, and adventurous. These historic ships captivate sailors and land lubbers alike. Ducking under booms, leaning against the railing a few feet above the sea, watching the crew work the winches and climb the masts are constant reminders that these are legendary vessels.

There are several Destinations for Windjammer Barefoot Cruises available, covering the whole Caribbean:

The Virgin Islands - Tropical adventure and near-perfect weather have lured seafarers and landlubbers to the Virgin Islands for centuries. Even the Gods were seduced … for they blessed this region with zephyr winds that keep Legacy’s sails billowing. From bow to stern, emerald islands, rocky outcrops and pretty yachts dot the panoramic seascape. Anchorages with names like Cinnamon Bay, Honey Beach and Watermelon Cay will entice you to linger in the surf and sand forever. And—there’s good reason why the Virgins are called the water sports capital of the Caribbean: the sailing, windsurfing and swimming are first rate. Beach-accessible coral reefs and calm lagoons make for excellent snorkeling and scuba diving. There’s good shopping and sightseeing in Yankee territory, while the British Islands offer healthy doses of barefoot R & R. Folks who are just getting their sea legs choose this relaxed voyage because the sailing is smooth. The distance between ports is short-and-sweet, allowing for ample time ashore.

The Leeward Islands - Anguilla - Nevis - Saba - Sint Maarten - St. Barthelemy (St. Barts) - St. Kitts - Tintamarre - St. Eustatius (Statia)

This is the perfect introductory cruise for Caribbean newcomers. It offers a taste of everything you’d expect in the tropics. During the golden age of seafaring, European nations battled for their place in the sun, leaving cultural footprints wherever they landed. There’s evidence everywhere you look. The sleepy Dutch islands reveal a gold-mine of artifacts and legends for divers and history buffs … The British colonies exude an air of relaxed sophistication amidst a tropical explosion of foliage and elegant architecture … And only the French isles greet the day with croissants and espresso. Chic boutiques and cafés line the avenue where the village baker sells warm baguettes for holiday-makers to whisk away on scooters. Geographically, the islands are as different as mangos and coconuts. Some are volcanic; bursting from the sea, their peaks are perpetually shrouded in clouds. Other islands are mountainous and smothered in rainforest; while Anguilla’s silken beaches barely rise above the waves.

The Eastern Caribbean - Antigua - Dominca - Ilse de Saintes - Nevis

Explore a chain of emerald isles... cascading waterfalls, rainforests, volcanoes, miles of beaches... contrasted with quaint sisewalk cafes and duty-free shopping.

St. Lucia and The Grenadines - The best way to appreciate the Grenadines is by boat. The region is visited by only a handful of yachties in search of eternal summer, making the Grenadines one of the most exclusive sailing grounds in the world. Sprinkled in the crystal-clear waters between the volcanic peaks of St. Vincent and Grenada is a 60-mile trail of palm-studded sandbars, coral reefs and tiny islets that haven’t changed much since Columbus first sailed these crystalline waters. Experience the Caribbean of long ago. Our ships can sail right up to an islet and anchor off a deserted beach. You could ride the tender ashore, or jump off the ship and swim, enjoying the ultimate beach day until your Captain gives the cue to hoist sails. If it’s nightlife and cultural stimulation you desire, the sassy, spice islands of Grenada and St. Vincent have just that, plus excellent beaches, lush rainforests and all kinds of water sports.

Windjammer Cruises are also available in the Bahamas and the ABC Islands.

Contact us for more information and to book your next Windjammer Barefoot Cruise in the Caribbean and sail the Islands on a tall ship.