Wanderlusting: Sail San Diego

We are tied to the ocean. And when we go back to the sea, whether it is to sail or to watch – we are going back from whence we came. John F. Kennedy 

Annual Birthday Sail

It has become an annual tradition that around my birthday I go sailing. It began with my mertwin and I about five years ago going on a sail around Casco Bay in Maine on a two hundred year old schooner. Because we had such an amazing time we have gone every year since.


Last year we branched out and went sailing up in Acadia. Knowing I would be celebrating my birthday in San Diego with my other bestie Sarah, I still wanted to keep up the tradition.


Not only is it one of my favorite activities, but it would also be a great way to explore San Diego. Sarah, as only an amazing friend can be humored me and agreed to go with me.


Sail San Diego

Sail San Diego is the number one ranked sailing company rated by Trip Advisor. After our experience, I can completely understand why. They offer a wide range of tours from a two hour harbor sail to a three and a half hour booze fest channeling ol’ rum runners. They even do fishing expeditions. We picked their most popular, a three hour sunset cruise.


The nice thing about Sail San Diego is that they limit the amount of people to six per sail, or if privately chartering, eight people. It makes for a much more unique and intimate experience.


They also provide beverages and snacks which include wine and beer. As well as blankets for when it gets chilly and other boating necessities, such as binoculars and sunscreen. They pay attention to detail and their staff is attentive and incredibly knowledgeable further making it an amazing and fun experience.


The boat

Unlike the schooners I have been on, which are not only historical, but also very bare bones, this boat was decked out with a bathroom, a bedroom, a galley, and even a little sitting area. It was my dream boat and I very easily could have lived on it.


In fact while our captain didn’t live on THIS boat, he does live on one that was moored just a few boats down from the one we are on. Talk about a short and fun commute!


The aft (back of the ship) was spacious with benches on either side of the two wheels and two higher chairs directly behind them. You could walk towards the bow (front of the ship) and they actually had two beanbag chairs you could lay on and enjoy the wind in your face.


The Sail

It was one of, if not my most favorite sail I have been on. We had a great group of people, from a couple celebrating their anniversary and who lived right in San Diego, to the other couple who were from Houston, Texas and were in desperate need of a vacation after having been flooded, not once but twice by recent hurricanes.


Our captain was also incredibly informative and friendly, cracking jokes and interacting with us through out the boat. He not only helped to make the sail, but was enjoyable to talk to. We all got along great, and as the wine flowed so did the conversation and laughter.


We hung out mostly in the aft, but Sarah and I did venture to the bow to take a few hundred pictures.


It was Sarah’s first time on a sail boat and she ended up loving it. Much like Tiffany created an obsession six years ago, I think I may have done so in Miss Sarah now!


The Sail in My Hair

Because the couple from Texas, Sarah, and I had never been to San Diego before, the captain took us around the harbor giving us a tour from the water. It was stunning to see, not just downtown San Diego, but also to see it as the sun was setting.


The couple from San Diego, even joined the captain, and all three gave us the run down of things to do and see and included Coronado which we got to see from the boat.


The views were stunning. Just being on the water was so incredibly relaxing. At one point, I felt like the boat was lulling me to sleep.


Bucket List

Sailing is on my bucket list. I would LOVE to learn how. In fact when I was on another trip not to long ago, I saw people taking sailing lessons.


There is something so incredibly calming about being on a boat, but sail boats especially are so peaceful. Maybe because it is powered by the very forces of nature. You are at her mercy and their is something incredibly vulnerable albite freeing in letting go and trusting that.


I know I am a mermaid at heart, but I felt especially at home on the water surrounded by not just my bestie, but also the other amazing people we got to meet that night. It was one of my favorite things we did in San Diego and it was such an incredibly magical night.


Have you ever sailed? Have you taken a boat ride before?

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19 thoughts on “Wanderlusting: Sail San Diego

  1. How on earth do you manage all of these adventures? I would be jealous if I weren’t so happy for you and if I didn’t like you so much. 🙂 Your post reminded me of sailing with my friends Andrew and Patrick a few years ago on Lake Pepin. As you say, it was incredibly calming — though the beer probably helped too, ha ha. Anyway. Thank you for sharing this day on the water with us, miss mermaid!

    1. Your comments always make me smile! Thank you sweets! You will just have to come along one of these days! I love that! Bwahaha I agree beer, wine, it helps set the mood! ;p Yoda re most welcome sweets! Thank you for reading! <3

  2. I have never sailed before but it looks so calming and relaxing! Your outfit is lovely and you look beautiful <3 I think it's neat that you have created a sailing tradition 🙂

    1. Awe thank you beauty! Ferry boats are just as fun to ride! Really anytime I am on a boat I am happy! I hope you get to take a sail boat ride one of these days! <3

  3. How is it possible to have so many stunning photos in one place?!?! Also curious- is it possible for you to take a bad picture?! This is seriously the greatest tradition of ALL TIME. The people you were with sound like the best bunch too. What a magical time <3 <3 You know how to find the most incredible gems every single place you go!

    1. You are the sweetest! But I will let you in on a secret! I take probably five hundred pictures, and like maybe fifty of them! Lol. Awe thanks sweets! They really were! Awe thanks beauty! That last sentence means so much to me! <3

  4. I love boats and I love the sound of this fun sailing birthday tradition. The sunset sail sounds like the perfect option, those views are beautiful 😍 it sounds like a lovely, intimate setting with just a few people on the trip, perfect for a cosy Summer night! I’m glad you had a lovely time, you’ve made me want to go sailing now!

  5. I love boat trips and sailing round. I do one in most places I go. Just feeling the sea breeze, seeing the water it’s wonderful. I love all your photos they’re gorgeous xx

    1. I LOVE that! I typically travel to places with water and I think it is something I am going to try to do! It is a great way to explore! Awe thank you sweets! <3

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