Destin, Florida, isn’t just about sugar-white beaches and emerald waters—it’s also a prime spot for sailing adventures. With its calm Gulf waters and plentiful marine life, Destin offers a variety of options that cater to all kinds of sea lovers. Whether you’re after a private escape, a family-friendly trip, or a sunset dinner with a view, there’s something here for everyone. We especially love the Private Catamaran and Snorkeling Tour for its intimacy and flexibility, and the Sunset Catamaran Cruise for a romantic wind-down.
If you want a laid-back, personal experience, a private charter like the Private Catamaran Sunset Cruise with Dolphin Watching is hard to beat. For family fun or lively outings, the Crab Island tours and dolphin-watching cruises bring the water alive. Whatever your style, Destin’s sailing scene will not disappoint.
Quick Overview
Our list covers private charters, group tours, and specialty cruises. Highlights include snorkeling and dolphin sightings, cruises to Crab Island, and spectacular sunset dinners. Prices vary from affordable per-person options to exclusive private charters, ensuring there’s a fit for every budget and interest. Dive into the details below to find the perfect match for your trip.
1. Destin Private Catamaran and Snorkeling Tour 3 or 4hrs
This private catamaran experience offers the chance to enjoy Destin’s waters with just your group—up to six people—for around $455. You’ll sail out to Crab Island, a local favorite, and spend plenty of time snorkeling, swimming, or just relaxing with the boat’s bean bag chairs and cooler. The short sailing time means more time at the island, where you can use snorkeling gear to explore underwater or simply soak up the sun.
What makes this tour stand out is its personalized approach. Captain Kip is praised for his professionalism and attentiveness, making sure your trip is smooth—even if the weather throws a curveball, as one reviewer noted passing a storm system gracefully. Guests love having the boat just for themselves, which makes for a peaceful, tailored experience. Bring your own snacks or buy from Crab Island vendors.
Bottom Line: Perfect for groups wanting privacy and a flexible schedule, with plenty of time for snorkeling and relaxing in style.
2. Destin: Crab Island Catamaran Tour with Dolphin Watching
For around $65 per person, this 3.5-hour group cruise takes you on a modern 45-foot catamaran to Crab Island, combined with a short dolphin cruise. It’s ideal if you’re looking to see dolphins in their natural habitat and enjoy plenty of water fun with included floats and toys. The boat’s comfortable design and licensed captain ensure a safe, enjoyable ride.
Many travelers appreciate the blend of sightseeing and playtime. The opportunity to spot dolphins, combined with free water toys, makes it a lively and interactive experience. The trip is well-suited for families, couples, or groups wanting a relaxed day on the water with a bit of wildlife viewing thrown in.
Bottom Line: A lively, affordable outing with the chance to see dolphins and enjoy the vibrant Crab Island scene.
3. 3 Hour Sunset Dinner Cruise by Solaris Yacht in Miramar Beach
Priced at $128 per person, this sunset dinner cruise combines a scenic sail with a delicious multi-course meal. The Solaris yacht boasts three decks, panoramic windows, and an open sky deck, making it one of the most elegant ways to experience Destin’s evening sky. As you cruise from Miramar Beach, you’ll enjoy a leisurely dinner, with options for the main course and the chance to purchase drinks from the bar.
The reviews highlight great service, quality food, and a romantic setting, especially as the sun dips below the horizon. It’s ideal for celebrating special occasions or just soaking in the stunning Gulf sunset with some good company. Dolphins sometimes appear, adding to the magic.
Bottom Line: An upscale, relaxed evening option for couples and those wanting fine dining combined with scenic sailing.
4. Private Catamaran Sunset Cruise with Dolphin watching
This private 2-hour cruise costs about $360 for up to six people, offering intimacy and flexibility. Captain Kip will take you to the best spots to view the sunset and watch for dolphins along the way. It’s perfect if you’re craving a peaceful, personalized experience where your group controls the pace and destinations.
Reviewers rave about the breathtaking sunsets and the chance to see dolphins, jellyfish, and even large jellies. It’s particularly suited for families or couples looking for a romantic, quiet evening on the water. The privacy and tailored itinerary make this cruise an excellent choice for special occasions.
Bottom Line: Ideal for a romantic or family sunset, with a personalized touch and plenty of wildlife sightings.
5. Sailing Adventures 3-Hour Activity in Destin
At $525 for a group of up to six, this sailing adventure on the Stiletto Catamaran promises an immersive experience of Destin’s emerald waters. Guests rave about Captain Bill’s expertise, with opportunities to see dolphins swimming alongside the boat and even swim in the clear waters.
What sets this apart is the pure sailing experience—no motors, just wind-powered fun. It’s perfect for those who want to feel the true sailboat experience while enjoying the scenic coast. The ability to stop for a swim and the chance to see dolphins up close make it a memorable trip.
Bottom Line: For sailing purists and families wanting active sea fun, this offers authenticity and close wildlife encounters.
6. 3 Hour Destin Dinner Cruise: Solaris Yacht in Miramar Beach
This dinner cruise costs $65 and features a luxurious yacht with indoor and outdoor dining options, plus live music. It is a great way to combine gourmet food and scenic views, cruising year-round from the Sandestin Golf and Beach Resort.
Guests highlight the high-quality food, lively atmosphere, and large open decks perfect for dancing or relaxing. The panoramic windows and skydeck provide superb views, making it ideal for celebrating a special night out or just enjoying Destin’s night scenery.
Bottom Line: For those wanting a combination of fine dining, entertainment, and scenic cruising, this offers excellent value.
7. Crab Island Explorer Catamaran Tours to Crab Island
At $60 per person, this daily group tour emphasizes a relaxed, fun day at Crab Island with a friendly local captain. A spacious 35-passenger catamaran takes you to swim, sunbathe, and explore in crystal-clear waters.
The highlight is the casual, fun vibe with plenty of opportunities to play in the water. It’s suitable for families, first-timers, or anyone wanting a straightforward but enjoyable day on the water.
Bottom Line: A budget-friendly, relaxed tour perfect for a casual day at Crab Island.
8. Destin Crab Island Tour in Catamaran
Offering a 3.5-hour trip at $59 per person, this tour features a newer vessel equipped with a marine bathroom and easy water access. The itinerary includes swimming at Crab Island and dolphin spotting, guided by experienced guides.
Guests appreciate the smooth operation and the convenience of onboard amenities. It’s a solid choice for those who want a relaxed, family-friendly boat ride with a bit of wildlife watching and water fun.
Bottom Line: Modern, comfortable, and well-run, this tour provides good value and dependable service.
$59.00 per person
9. Private Catamaran: Snorkel, Swim and Dolphin Watching
This customizable private trip costs $465 for up to six, allowing you to tailor your day to include snorkeling, dolphin watching, or swimming. Captain Kip’s passion for the waters shines through, making your private outing personal and engaging.
While reviews are not available, the flexible itinerary makes this an excellent option for those who want to craft their perfect day on the water.
Bottom Line: Best suited for travelers seeking a personalized, private experience with the freedom to choose activities.
$465.00 per group (up to 6)
10. Private Catamaran Charter to Crab Island for up to 13 Guests
For larger groups, this full-day private charter at $564 offers up to 13 guests the chance to customize their day. From mid-morning to evening, you control the pace and destinations—perfect for celebrations or family reunions.
Guests can enjoy swimming, snorkeling, or just relaxing aboard the spacious vessel. The private nature ensures your crew has a laid-back, exclusive experience.
Bottom Line: Ideal for big groups seeking a fully tailored, private day of sailing and water fun.
$564.00 per group (up to 13)
11. Snorkel, Dolphins, Crab Island, and Sailing Catamaran Activities
This 6-hour custom tour at $350 per group offers an all-in-one adventure—snorkeling, dolphin watching, Crab Island, and sailing. Its flexible approach lets you choose what you want to do, making it perfect for active families and groups.
While reviews are not available, the variety and duration suggest a comprehensive, engaging experience that covers all bases for sea lovers.
Bottom Line: For multi-activity lovers who want a full day on the water with the flexibility to pick their adventures.
$350.00 per group (up to 6)
12. Sunset Catamaran Cruise
At $375 for up to six people, this private sunset cruise offers a peaceful, intimate way to end your day. Feel the breeze, watch dolphins jump, and enjoy the spectacular colors of the sunset. Customization options like dinner or drinks make it a special occasion.
This cruise is great for couples or small groups wanting a quiet, romantic sail with wildlife sightings and a stunning view.
Bottom Line: A perfect choice for a romantic, sunset experience with the flexibility to customize.
$375.00 per group (up to 6)
How to Choose
When selecting your ideal sailing experience in Destin, consider your budget, group size, and interests. For a private, tailored outing, the Private Catamaran Snorkel and Sunset or Private Charter to Crab Island offer exclusivity and customization. If wildlife viewing and water toys appeal to you, Dolphin and Crab Island Tours or the Dolphin Watching Cruise fit the bill.
Budget travelers might prefer the Crab Island Explorer or the group dolphin and crab tours, both offering good value. Planning ahead and booking early is wise, especially for private or popular sunset cruises.
Final Thoughts
From luxury sunset dinners to adventurous dolphin safaris, Destin’s sailing scene is diverse and accessible. For those who want a romantic escape, a private sunset or dolphin cruise will impress. Families or groups seeking fun and affordability will find plenty of lively options around Crab Island. And if you’re after an authentic sailing experience, the sailing adventures on the emerald waters won’t disappoint.
Whatever you choose, Destin’s waters are calling. Book early, plan based on your interests, and enjoy some of the best sailing the Gulf Coast has to offer.