Monterey is a prime destination for sailing enthusiasts and those craving a scenic maritime adventure. Its calm, protected waters within Monterey Bay offer perfect conditions for relaxing cruises, wildlife spotting, and awe-inspiring sunsets. The abundance of marine life, including whales, dolphins, sea lions, and otters, makes it a natural playground for boat lovers. Plus, the area’s rich marine protected status means these tours often focus on eco-friendly sailing that respects the environment while providing unforgettable views. Whether you’re celebrating a special occasion or just want to experience the coast from a new perspective, Monterey’s sailing options are both varied and high-quality.
For those looking to explore, we’ve rounded up the top three sailing experiences—each offers something unique, from quick sightseeing trips to intimate whale watching escapades. If you want a romantic sunset, a family wildlife adventure, or a private boat for a special celebration, there’s a sailing experience for you.
Quick Overview
This list features three of the best sailing experiences in Monterey, each with distinct appeal:
- An eco-friendly sunset catamaran cruise ideal for romantic evenings Monterey Bay: Sunset Catamaran Sailing Cruise
- A short harbor cruise focusing on viewing sea lions, otters, and dolphins Monterey: Catamaran Sailing Cruise
- A private whale and dolphin watching tour perfect for small groups or special occasions Monterey: Private Whale Watching/Sailing Tour for 6
Below, each offers a detailed look at what makes them stand out.
1. Monterey Bay: Sunset Catamaran Sailing Cruise
At the top of our list is the Monterey Bay Sunset Catamaran Sailing Cruise — a perfect way to unwind and soak in the beauty of Monterey’s coastline. For around $95 per person, this 1.5-hour journey offers a peaceful and scenic experience in the Monterey Bay National Marine Sanctuary. The cruise departs from Sail Monterey, where you’ll step aboard a spacious, eco-friendly catamaran. The highlight is watching the gorgeous sunset reflecting on the water, with the chance to see marine life such as whales, possibly even during the early evening hours.
This tour is particularly appealing for its blend of relaxation and stunning scenery. The captain and crew—who have ample knowledge of the local marine environment—serve complimentary beverages and snacks, making it feel more like a leisurely evening with friends than a typical sightseeing trip. Reviews emphasize the peaceful atmosphere and the memorable experience of whales and sea lions in their natural habitat. One guest called it “absolutely wonderful,” praising the beautiful sunset and local beers served onboard.
Bottom Line: This cruise is ideal for couples or anyone wanting a relaxed, romantic experience with scenic views and marine wildlife in a quiet, eco-conscious setting.
2. Monterey: Catamaran Sailing Cruise
For a shorter, budget-friendly option, the Monterey: Catamaran Sailing Cruise offers an engaging 75-minute journey at $65 per person. Starting from Sail Monterey, this cruise emphasizes marine life viewing—especially seals, sea lions, and otters—while providing a taste of the Pacific Ocean’s fresh air. This tour is well-suited for those who want a quick but immersive wildlife experience without dedicating hours on the water.
During the cruise, you’ll enjoy sailing on a comfortable catamaran, with chances to spot whales, dolphins, and other marine creatures. The route includes sightseeing along the harbor and scenic views of the coastline, all with an environmentally friendly approach that respects marine habitats. Reviewers note the friendly crew and the opportunity to see sea lions and otters up close. One reviewer said, “It was a relaxing way to see the bay and observe wildlife — definitely worth the price.”
Bottom Line: This shorter cruise appeals to travelers seeking an accessible, wildlife-focused experience that fits into a busy schedule or a budget-conscious trip.
3. Monterey: Private Whale Watching/Sailing Tour for 6
If you’re looking for a truly personalized experience, the Private Whale Watching/Sailing Tour for 6 offers a 3.5-hour adventure for $950 per group. It’s perfect for families, couples celebrating a special occasion, or small groups wanting a tailored experience. The tour departs from 78 Old Fisherman’s Wharf, a prime starting point for exploring Monterey’s marine riches.
This private tour combines whale watching with dolphin sightings, scenic sailing, and up-close encounters with marine life. The captain and crew are highly experienced, and the boat’s small size ensures an intimate setting. Guests enjoy welcome refreshments before heading out to spot whales, which could include humpbacks or orcas, along with playful dolphins. The reviews commend its exceptional quality and personalized service, with one traveler describing it as “a memorable, private experience that exceeded expectations.”
Given its longer duration and private setting, this tour is best suited for those willing to spend more for a customized, in-depth marine adventure. It’s also ideal for celebrating special events in style.
Bottom Line: This is the best choice for small groups looking for exclusivity, whale sightings, and a flexible itinerary. It offers excellent value for a memorable, private day on the water.
How to Choose
When selecting a sailing experience in Monterey, think about your budget, time, and what kind of marine encounters interest you most. For a romantic evening, the Sunset Catamaran provides stunning views with minimal time commitment. If you’re eager to spot sea lions and dolphins quickly, the Harbor Cruise offers an affordable, shorter trip perfect for families or first-time visitors. For those celebrating a special occasion or wanting a personalized adventure, the private whale watching is an excellent choice, especially if you’re interested in seeing whales and dolphins in a more intimate setting.
Booking early is advisable, especially during peak seasons in the summer and early fall. Consider your preferred length of trip, budget, and whether wildlife viewing or sunset scenery is your priority. Each tour caters to different interests, so matching your expectations with their offerings will lead to a more satisfying experience.
In summary, Monterey’s sailing scene offers options suited for every mood and interest. Whether you’re after a romantic sunset, a quick wildlife fix, or a private marine adventure, the choices are both plentiful and high-quality. The sunset cruise is great for a relaxing evening, the harbor tour for a quick wildlife encounter, and the private whale trip for an exclusive, in-depth experience. To ensure you don’t miss out, it’s best to book early, especially during the busy months. No matter which you pick, a day on Monterey’s waters promises memorable views and marine encounters you won’t forget.