Top North America Sailing Tours

Experience one of Hawaii’s famous sunsets on a cruise along Waikiki’s coast. Board your vessel and watch the sky change colors as the sun starts to dip below the horizon. While you sail, keep your eyes peeled for dolphins and, from November to May, even humpback whales. You can also enjoy views of Waikiki landmarks including Diamond Head.

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.

Sail along the beautiful crystal-clear waters of Cancun’s Caribbean coastline on this half-day sailing adventure to Islas Mujeres. Get geared up and go snorkeling, then take a break to enjoy a gourmet lunch on board your catamaran. Stop at the island of Isla Mujeres, and visit must-see spots either on a guided tour or on your own. Afterward, sip on complimentary beverages on the way back to port.

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.

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.

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.

Awaken your senses to the stunning sights and sounds of a Banderas Bay sunset on a tranquil 3-hour sunset cruise from Puerto Vallarta. Sip a cosmopolitan cocktail and nibble on premium cheese as your stylish Beneteau sailboat cruises on the calm waters of Banderas Bay; watch the setting sun sink into the crystal clear Pacific Ocean and absorb the impossibly romantic atmosphere of this enchanting excursion.

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.

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.

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.

Cruise the Bacalar Lagoon to the Black Cenote and Cenote Esmerelda on a half-day snorkeling tour of the spectacular ‘Lake of Seven Colors.’ You’ll pass through the Pirates' Channel, pause to make mud masks from sulfurous mud, and slip into the water to snorkel at both cenotes. Before returning to shore, navigate to the Island of Birds, a haven for some of the migratory birds that flock to the Bacalar Lagoon.

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.

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.

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.

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.

Sail across the shimmering seas of the Cabo coast on a luxury snorkel and lunch cruise from Los Cabos. Soak up the Mexican sunshine on board a sailboat, sipping cocktails or sparkling wine from the open bar. Snorkel in the ocean to discover troves of tropical fish and coral reefs before feasting upon a lunch of international specialties. Personalized attention from your guide is guaranteed on this small-group tour, where numbers are limited to 16 people.

Whether you're an experienced snorkeler or an absolute beginner, fully trained guides let you make the most of Cozumel's famous reef on this half-day snorkeling tour. Hit three of the island's hottest snorkeling spots: Palancar Reef, Columbia Reef and Playa el Cielo, known for the starfish that decorate its white sands. Your package includes drinks and snorkeling gear; marine fees are payable in cash on the day.

See Charleston from the water, and enjoy a luxurious way to admire the sights, with this private sailing charter. This flexible experience is tailored to your preferences: pick your own departure time, bring aboard a picnic and drinks (or upgrade for gourmet catering), and request a photographer if you want to capture the moment. As you go, circle the Charleston Harbor, see landmarks like Fort Sumter, and enjoy a relaxing ambiance.

Set out on a relaxing and informative sunset sailing cruise off Los Cabos. Board a luxury yacht for a 2-hour evening excursion, watching the sun slowly disappear below the horizon while listening to music and enjoying an array of drinks and appetizers. An expert crew will regale you with facts and history about the area as your boat makes its way smoothly across the sea, taking full advantage of the changing natural light reflecting off the water. Don't miss the illuminated sights along the coastline as you go. Departure time is dependent on time of sunset.

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.

Sail up the scenic Kona coastline, getting views of ancient lava flows and verdant cliffs, and stopping at the Captain Cook Monument, on this afternoon sail in Kealakekua Bay. Slip into the water using the provided snorkeling gear to see vibrant schools of fish, living coral, and even pods of spinner dolphins. Learn about the area's underwater flora, fauna, and ecosystem through guided commentary.