Monterey is a standout destination for anyone who loves being on the water. Its crystal-clear waters, abundant wildlife, and dramatic coastline make it a top choice for sailing adventures. Whether you’re after a peaceful sunset cruise, a wildlife-filled day, or a private whale-watching trip, Monterey’s boats deliver unforgettable experiences. We’re particularly fond of the Monterey Bay: Sunset Catamaran Sailing Cruise for its tranquil vibe and stunning views, especially at sunset. Plus, it’s eco-friendly, so you can enjoy nature without guilt.
If you prefer a shorter, more budget-friendly outing, the Monterey: Catamaran Sailing Cruise offers a lively, wildlife-filled tour that’s perfect for spotting sea lions, otters, and dolphins. For those wanting the ultimate private experience, the Monterey: Private Whale Watching/Sailing Tour for 6 provides an intimate, three-and-a-half-hour adventure focused on whales, dolphins, and the open ocean. Below, we break down each tour to help you decide which fits your style.
1. Monterey Bay: Sunset Catamaran Sailing Cruise
This sunset cruise promises a peaceful 1.5-hour sail through Monterey Bay aboard a sleek catamaran. It’s perfect for those who want a relaxing evening with a view. The tour includes a complimentary beverage and snacks, letting you unwind as the sun dips below the horizon.
What makes this cruise stand out is the chance to experience the Monterey Bay National Marine Sanctuary in an eco-friendly manner. The boat’s design minimizes environmental impact, making it a responsible way to enjoy the coast. Guests consistently rate it highly, with a 4.9 out of 5 from 28 reviews, praising its intimate atmosphere and stunning sunset views. The guide’s narration enhances the experience, sharing insights about local wildlife and marine conservation.
During the cruise, you’ll witness the sky turn pink and orange as you glide over calm waters. The combination of gentle sailing, beautiful scenery, and complimentary drinks makes this a romantic and calming experience. It’s well suited for couples, honeymooners, or anyone looking for a serene moment on Monterey’s waters.
Bottom Line: A beautifully paced, eco-friendly sunset sail that offers a peaceful escape and spectacular views for roughly $95 a person.
2. Monterey: Catamaran Sailing Cruise
For those craving a shorter, lively adventure, the Monterey: Catamaran Sailing Cruise is a 75-minute tour that delivers a quick dose of coastal beauty. Priced affordably at $65 per person, it’s an excellent choice for families, first-timers, or travelers with limited time. The tour departs from the harbor and offers an up-close look at sea otters and seals basking on the rocks and floating in the bay.
What makes this tour special is its focus on wildlife spotting and active sailing. Guests often enjoy looking out for whales, dolphins, and sea lions while sipping a drink and feeling the ocean breeze. The captain shares local lore and wildlife facts, making it both fun and educational. The boat’s design allows for excellent views from all angles, giving everyone a chance to see marine life.
Reviewers particularly appreciate the relaxed atmosphere and the chance to breathe in fresh sea air. At 1.25 hours, it’s a perfect quick escape for those who want to experience Monterey’s waters without committing to a longer trip. It’s best suited for travelers with children or those seeking a casual, wildlife-focused outing.
Bottom Line: An affordable, wildlife-rich cruise that combines fun with education, ideal if you’re short on time but still want a memorable boat ride.
3. Monterey: Private Whale Watching/Sailing Tour for 6
If privacy and a tailored experience appeal to you, the Private Whale Watching/Sailing Tour for 6 offers a personalized 3.5-hour journey on Monterey Bay. Costing $950 for up to six people, this tour is ideal for families, small groups, or couples wanting a more exclusive outing.
This tour focuses heavily on whale watching, but also includes opportunities to see dolphins and other marine life. It’s led by an experienced captain who customizes the trip based on current wildlife activity, making each outing feel unique. The boat is private, offering comfort and flexibility — you can choose to relax, take photos, or focus on wildlife spotting.
Guests on this tour rave about the dolphin and whale sightings, with some even spotting humpbacks, gray whales, or orcas. The longer duration and private setting mean you get a more immersive experience, away from crowds, with plenty of room to enjoy the sea. It’s perfect for nature lovers or those celebrating a special occasion.
Potential drawback: It’s considerably more expensive than the other options, but the exclusivity and focus on whale watching make it worthwhile for serious wildlife enthusiasts.
Bottom line: A top-tier, personalized adventure for whale watchers and small groups willing to invest in a more intimate, in-depth marine experience.
How to Choose the Best Sailing Experience in Monterey
When deciding between these tours, think about how much time you want to spend on the water, your budget, and your wildlife interests. If a romantic sunset sounds perfect, go for the Sunset Catamaran Cruise. If you’re keen on a quick, wildlife-filled outing and value affordability, the Catamaran Sailing Cruise fits well. For a luxurious, private experience, especially if whale sightings are a priority, the Private Whale Watching/Sailing Tour is your best bet.
Booking early is advisable, especially for private tours, to secure your preferred date and time. Consider the time of year, as whale migrations and wildlife activity peak at different seasons, influencing your chances of seeing specific animals.
Final Thoughts
Monterey offers a diverse range of sailing experiences suited for varying interests and budgets. For a relaxed, romantic evening, the Sunset Catamaran Cruise is hard to beat. If you’re after a quick wildlife fix, the Catamaran Sailing Cruise offers excellent value. And for a truly personalized adventure focused on whales, the Private Whale Watching/Sailing Tour delivers a memorable, intimate experience.
No matter which you choose, Monterey’s waters promise scenic views and plenty of chances to spot marine life. With a little planning and early booking, you’ll be set for a sailing adventure worth remembering.