- Home
- Romantic Rides & Proposal
Romantic Rides & Proposal
- Home
- Romantic Rides & Proposal
Private Catamaran Sailing for Couples in San Diego
Looking for the perfect romantic escape? Whether you’re planning a surprise proposal, celebrating an anniversary, or just want some quiet time on the water with the one you love, Fun Cat Sailing offers the most intimate and memorable romantic sailing tours in San Diego.
Leave the crowds behind and step onto your own private catamaran just for two (or invite close friends and family up to 12 guests). As the sun dips toward the Pacific, you’ll sail smoothly across San Diego Bay, surrounded by golden skies, gentle ocean breezes, and nothing but open water and each other.
We’ve hosted countless romantic boat rides, from spontaneous date nights to heartfelt marriage proposals at sea. Every detail is handled with care so that you can stay focused on the moment, not the logistics.
This isn’t just another boat ride. It’s your story, told on the water with unforgettable views, heartfelt connection, and that “just us” feeling you can’t find anywhere else.
Why Couples Love Our Romantic Catamaran Rides
-
Perfect for Proposals, Anniversaries & Dates
Whether it’s popping the question or toasting to years together, our private sailings create the ideal setting for meaningful moments. -
Golden Hour Sailing – Sunset Magic
Evening tours offer the most romantic light imaginable. The sunset over the Pacific creates a natural, cinematic backdrop for love.
-
A Private, Peaceful Experience
No loud music, no packed decks. Just your favorite person, the sea breeze, and the peaceful rhythm of the water. -
Optional Add-Ons
Want to bring champagne, flowers, or a photographer? We’ll help you make it unforgettable. Just let us know, we love creating custom moments.
Our Tours
Our Tours
Why Choose
Catamaran Sailing Tours?
Crew
Our Boat
Small Size
Conservation Minded
See What Our Guests Are Saying!
Fun Cat Sailing Adventure – San Diego Catamaran Sailing Tours & Charters
955 Harbor Island Dr Gate A-D, San Diego
4.9 235 reviews
-
Jenny Guzik ★★★★★ a month ago
Had the best time sailing with Fun Cat Sailing Adventures!!! Captain Ryan was very knowledgeable about the local history and current events happening around San Diego. He is a very experienced captain and one man show. We were able to sail … More all over the bay and my highlights included Coronado island and watching the local fisherman reel in their catch! Would highly recommend booking a trip if you are in the area! -
Kathy Mileski ★★★★★ a month ago
My kids (23 and 10) and I had a fantastic time on the water with Ryan as our captain! We were celebrating a successful junior year for my college son. We have been on many catamaran whale watch tours in Hawaii but this was a unique experience … More for us- it was true sailing! There were only 5 total passengers aboard which made for a personal experience. As Ryan expertly guided the boat all around Mission bay and out to Point Loma he told us cool facts about the area as well as how the sailboat works. My 10 year old daughter even hit to help Ryan sail at the end! It was a very memorable experience. Would love to go out again one day! -
Ariel Spencer ★★★★★ 4 months ago
Perfect Anniversary Sunset Sail with Captain RyanMy partner and I recently went sailing on a catamaran with Captain Ryan and had an amazing experience. It was my first time sailing, and Ryan immediately made us feel safe, welcome, and comfortable … More on board.He positioned the boat perfectly for the sunset, giving us absolutely beautiful views. Along the way he shared interesting history and knowledge about the area and kept the atmosphere fun and engaging.We were celebrating our anniversary, and even though another couple was on board, the catamaran was spacious enough that we still felt like we had plenty of privacy to enjoy the moment.The experience was also very comfortable. Complimentary drinks were included with wine, beer, and non-alcoholic refills, blankets were provided once the sun went down, and there was even a bathroom on board which was very convenient.If you're looking for a relaxing and memorable way to enjoy the water and sunset, I highly recommend sailing with Captain Ryan. We had such a great time and would absolutely do it again. -
Anna Gordon ★★★★★ 4 months ago
Highly recommend Fun Cat Sailing Adventure. We took our corporate team out on the bay for a team bonding activity and by the end everyone was dancing and singing. Their catamaran was very clean and extremely smooth. We were worried some … More might get sea sick but no! Even the most motion sensitive had a blast. Team bonding = success with Fun Cat! -
Christopher Isar ★★★★★ 4 months ago
Went on this sailing tour with Captain Ryan for our 4 year wedding anniversary and had the time of our lives! It best our wildest expectations with sea lions and up close up with dolphins! Ryan had beverages on board, explained everything … More we needed to know in simple terms, then took us on what can only be described as the sports car of cstermarans, we were flying down the bay, yet the boat felt so stable and it was easy to stand up. What really added an even better experience was that Ryan really knew the and answer to every question we threw his way from Portuguese history in the area to what the naval base was up to and lots of landmarks. And his knowledge of sailing is immense. Can't wait to go again! -
Jeff Whittle ★★★★★ 4 months ago
I had a wonderful time sailing with Fun Cat on San Diego Bay with my friends Mark and Nhela this past summer. Captain Ryan Wild took us on a smooth, relaxing cruise around the bay, while he told us about the sights we were seeing. He also … More answered all of the questions we asked about the fishermen, the vessels, the submarine base and Point Loma as we passed by them. It was a very "chill" sailing adventure, for sure. He never fired up the engines once, we did it all on wind power. I highly recommend Fun Cat Sailing Adventure for a family or business outing on the water! -
Kathleen Bracken ★★★★★ 5 months ago
San Diego is a great city to view from the water. This particular boat was so fun to be on. It’s light weight, so it’s fast and maneuverable. Because it’s so lightweight, you don’t really need to use the motor. You really experience the … More sounds of the water and the peaceful feeling of zipping through the waves. Somehow it was both exhilarating and relaxing. The boat can get into narrow and shallow places other boats can’t get into. You can see so much of the bay. The sunset was gorgeous. We saw dolphins and the historic Coronado hotel. The only thing I would’ve done differently is to bring a wind resistant layer, especially for February. Captain Ryan, who has his generational roots in San Diego, knew so much about all the landmarks, nature, and history of the area. He had answers in detail to every question I asked. I have been on other sailing trips even in this area, and this is one I look forward to returning to. If you’re looking for an immersive adventure where you can experience the natural beauty of the bay and the stunning city skyline, look no further. You won’t be disappointed! -
Ashley Cestra ★★★★★ 5 months ago
I had the best time sailing with Captain Tyler! He was super chill but also super professional at the same time. He answered all of my questions and then some! I saw the seals, had some wine and enjoyed some peace with my book! My only … More con was I wish it was more than 2 hours— I could spend all day out on the water -
Hillary Zucker ★★★★★ 7 months ago
Captain Matt took us on an amazing adventure around the harbor. What started as a nice afternoon with friends, became a fun bonding over our love of being on the water. He was knowledgeable about the area and shared the information with … More us! He made sure we had time for a quick swim. He was the absolute best! -
Jeremy Sells ★★★★★ 7 months ago
Such a great time, celebrated 17th year anniversary with the wife. Highly recommended experience, Captain Ryan was on point answing all questions and shared some great reastuarants to dine after our sunset cruise. Drinks provided to … More make the experience more memorable, we will return! -
Zach Eischen ★★★★★ 9 months ago
As a San Diego local who’s been on just about every kind of bay cruise in San Diego Bay, Fun Cat Sailing absolutely stands out. I’ve never sailed half as far on any other San Diego boat tour in the same amount of time. It really speaks … More to the experience of Captain Ryan and the unique Fun Cat catamaran, which is designed for both speed and comfort.The entire sailing experience was smooth, scenic, and incredibly relaxing. Captain Ryan made me feel completely safe and well taken care of while sharing great local insights about San Diego’s waterfront. Unlike most cruises that just loop around the harbor, we actually sailed across the bay and covered an impressive distance.Bonus points for the fact that this was real sailing! Captain Ryan only used the motor to exit and re-enter the marina. We were under sail for more than 95% of the trip. Whether you’re a local looking for something new or want to show off the best of San Diego to visiting friends and family, I can’t recommend Fun Cat Sailing enough. -
Ryan Lee ★★★★★ 10 months ago
Was in San Diego to visit friends and they suggested we take an evening to sail the bay with Fun Cat Sailing. The catmaran is stable and amazing to sail the bay while watching the sunset, having a few drinks, while hanging out with friends … More (including hanging our feet off the bow). Ryan was a great captain and sailed us beneath the Coronado bridge, alongside the navy ships, and cruised us along the banks as people waved, "hello." Great experience, highly recommend sailing with the Fun Cat catamaran!