Top USA Sailing Tours

Cruise to Shell Island and search for wild dolphins on a catamaran sailing trip from Panama City Beach. The catamaran’s broad, stable deck makes it a comfortable alternative to smaller boats prone to rocking in the waves, and since it’s stocked with paddle boards, snorkeling gear, and a waterslide, it’s the perfect base for playing in the clear water off Shell Island.

Watch the sun set and the moon rise off the coast of Key West on this sunset cruise. Enjoy the scenery and peaceful calm of a late afternoon sail aboard a 70-foot catamaran with plenty of deck space to stretch out and enjoy the breathtaking view. Then watch a legendary Key West sunset as the sun glistens and gently settles into the water. Hearty appetizers plus champagne, wine, full liquor bar, ice-cold beer and soft drinks are included.

Watch dolphins frolic through coastal waters on this scenic 2-hour sunset sail. Board your comfortable catamaran, and listen to music. Cruise through Grand Lagoon, passing elegant homes and St. Andrews State Park. See pods of dolphins travel together and leap above the water. Take photos and admire incredible sunset views. Don’t miss the chance to participate in games and dance when the boat docks.

Spend a relaxing two hours on an evening catamaran cruise from Waikiki. With maximum 25 passengers on board, you can enjoy the city without the hustle and bustle. Relax and watch the sunset from the deck and see Waikiki as it begins to light up for the evening. Your journey is further enhanced with provided drinks and snacks.

Go whale watching from San Diego aboard a replica of a historic sailing schooner that won the world’s first America’s Cup sailing competition in 1851. Throughout your cruise, your expert guide shares informative commentary about gray whales, dolphins, and other marine animals, along with details about the US Navy sites you pass as you head out on the Pacific Ocean.

From Las Vegas, exploring either Lower Antelope Canyon or Antelope Canyon X (depending on option selected) and Horseshoe Bend in one day is an ambitious itinerary. This small-group tour makes it possible—without the crowded big-bus experience. This small-group tour is limited to 14 people for a more intimate experience hiking through the slot canyon and taking in the views. Included , snacks, and bottled water make this an easy, hassle-free experience.

Get out on the waters of Charleston Harbor during this cruise aboard an 84-foot-tall (25-meter) classic tall ship. As the crew hoists the sails of the schooner, you'll glide past some of the city's historical sights and watch for dolphins in the water. Drinks are available for purchase on board. Select a departure time when booking.

If you’re looking to snorkel in Key West, but don’t know where to plan your experience, this Key West snorkeling cruise makes things easy. Just prebook this experience, and enjoy a cruise over to a coral reef area—perfect for snorkeling and spotting tropical fish. Plus, all equipment, as well as lessons, breakfast, showers, and a beer or soda is provided for you.

Discover all the vibrant marine life that calls Turtle Canyon’s reefs home—and enjoy an accessible way to snorkel and explore—on this family-friendly catamaran trip. Make your own way to the Kewalo Harbor, and hop aboard your well-appointed catamaran: snorkels, fins, masks, and more are all provided on board. Once you make it to the reefs, dive in, spot sea turtles and other marine life, and admire the underwater scenery.

A sailboat cruise from Hilton Head is a peaceful way to see stunning Lowcountry landscapes without the noise of a moor. Join a captain and crew aboard a 39-foot long (12 meter) sailboat that competed in America’s Cup—head through quiet waters and past gorgeous scenery without the roar of a motor. You can even try your hand on deck and help out with the sails.

Explore the only living coral reef in North America on this small-group snorkeling adventure aboard a sailing yacht in Key West. You will receive instruction on how to use the equipment, but it’s recommended that participants be comfortable underwater and have the ability to swim. Common sightings include tropical fish, eels, turtles, dolphins, anemones, and urchins.

There is no better way to soak up the beauty of Waikiki than by watching the sunset from the water. This evening cruise is timed to coincide with the sun slipping below the horizon and painting the sky in unforgettable colors. You can spend your time relaxing on the deck or take the opportunity to jump off board and swim in the ocean.

Set sail on a replica of the 1851 Schooner America on a cruise from Key West. See the top sights of the city, including Fort Zachary, Mallory Square, and Sand Key Lighthouse from a unique perspective. Your cruise is accompanied by complimentary hors d’oeuvres along with alcoholic and non-alcoholic beverages. Allow yourself to truly unwind as the sun sinks into the Atlantic Ocean.

Limited to an intimate number of passengers, this small-group sunset sail includes an up-close look at dolphins as well as views of Key West landmarks like the legendary Mallory Square, Sunset Key, and historic Fort Zachary Taylor. Then, relax on the luxury catamaran to watch the sunset as nibble on tapas such as shrimp cocktail served with wine and champagne.

Leave behind the crowds of Key West and catch a quintessential Florida sunset while enjoying drinks on a sailboat. There is no better vantage point for watching the sunset over the water than from the water itself. And, while larger sunset cruises can get overcrowded, this small group experience ensures you have a spot at the rail when it comes time to capture photos of the setting sun.

Enjoy Seattle’s cityscape, Olympic Mountain and Mt. Rainier views aboard Seattle's premier tall ship. After hoisting the sails, we’ll cut the engine and enjoy the tranquility on our beautiful schooner. As the sun sets, we will celebrate another beautiful summer day in the Pacific Northwest! Enjoy a beverage and the beautiful views as we sail back to the city.

Eat, drink, and be merry on a sunset cruise aboard a luxury catamaran. Sail the waters off Maui as you experience the ho’okipa (hospitality) of the crew and panoramic views. Enjoy an array of premium appetizers and a full bar—three alcoholic drinks are included in the price. There’s also a marine biologist on board to comment on any wildlife you may encounter or answer questions about the local flora and fauna.

The Na Pali Coast is one of the world's most spectacular coastlines. And one of the best ways to see it is with this sunset cruise. As the sun sets, glide past the jagged peaks and emerald valleys from aboard a luxury catamaran,

Enjoy views of Las Vegas from the STRAT Tower Observation Deck, which stands 1,149 feet (350 meters) in the air. You can visit both the indoor and outdoor decks, as well as purchase drinks from the Air Bar (own expense).

Set sail at one of the best times of day—sunset—during this San Diego Bay cruise. Board a comfortable sailing yacht and cruise along San Diego's coastline, taking in views of the scenic waterfront, military vessels, and historical landmarks. Catch sight of marine life and enjoy spectacular photo ops. Gorgeous sunset views and comfortable bean bag seating makes this tour a great choice for travelers celebrating a special occasion.

Cruise through the scenic waters of Frenchman Bay during a leisurely sailing trip. Admire views of Acadia National Park in Maine during this sightseeing boat tour. Keep an eye out for wildlife including eagles, seals, and porpoises during the sail. Check out views of the Porcupine Islands from the spacious decks on board a Windjammer. Picnics are welcome on board.

With a maximum of 13 people, this small-group tour takes in the beauty of Antelope Canyon X without the crowds. Travel round-trip by minivan from your Las Vegas hotel to Arizona, and explore the canyon with a Navajo guide. Hike out to the sheer rock face at Horseshoe Bend and stop at a scenic overlook for views of Lake Powell.

Experience a sunset you’ll never forget on this 2-hour catamaran cruise in Key West. Sip on your choice of wine, champagne, beer or sangria as you watch the sun go down over the water. As you sail you’ll catch glimpses of the island and marvel at the views from the turquoise water. Cocktails are also available at a cash bar on board.