Weekend in Shelter Island

During the first long weekend of the year, we decided to have our first ever staycation in San Diego. We called up a couple of our friends who booked an adjacent room and joined us for some seaside fun!

We stayed at Humphreys Half Moon Inn, which we had previously passed when we went to eat at Bali Hai (delicious food and very strong drinks. In our search for an affordable but fun staycation, we used Hotel Tonight to book our hotel rooms at a discounted price. It wasn’t the first time we used Hotel Tonight, and we had good results in the past.

We only waited in line a few minutes to check in, and I have to give props to the guy who checked us in! He was accommodating when we asked to have a room next to our friends, he was very friendly, patient and overall super pleasant to deal with. At check in, we did have to pay a nightly resort fee (around $10) and $16 for parking. The resort fee isn’t unreasonable, considering you get free Wi-Fi, free one hour bike rentals, and a 20% discount on food at their adjacent restaurant (including $2 mimosas).

As soon as we checked in, we went to check out our rooms and get settled in. Since they were discounted rooms, we had a beautiful view of the parking lot, which was a bit disappointing. However, we did have sliding doors that faced our little outdoor patio with chairs and a table, where we all enjoyed drinks and snacks as the sun started to go down. The room was a decent size, and had a very comfortable bed, mini refrigerator, large closet and bathroom.

Around 5pm we went out to the famous Humphrey’s Backstage Live Music Lounge area, which was completely empty. This was great because it let us play around on the grass while we watched the sun reflect of dozens of boats that were docked right in front. The onsite fitness center has a nice view of the boats and water, but is tiny in size.


After our grass shenanigans, we took about an hour long walk south west hugging the water, obviously stopping to take pictures of a cotton candy sunset.

pano shelter island

After our sunset walk, we stopped at Vessel Restaurant inside the Kona Kai Hotel, for happy hour cocktails and snacks. We ordered mojitos and a piña colada cocktail and paired them with the seafood poke and the wild mushroom flatbread, both of which were on point! You have to have the poke if you eat at Vessel, as someone who lived in Hawaii for years, it is a delicious and well prepared plate. The view from Vessel is also exceptional, as you have already probably noted from the pictures above, Shelter Island is really an island, and you are surrounded by boats and beautiful views all around. Overall our visit to Vessel was ok, while the food and views were spectacular, the service was super slow, and the cocktails weren’t a part of happy hour so our bill was almost $80 with 4 cocktails and two appetizers.

We walked back to Humphrey’s after our cocktails and snacks, played some board games and headed off to eat a later dinner at Brigantine, which was a convenient 600 meters from the hotel! We had fish tacos and I had a caesar’s salad to compliment my meal, and a virgin piña colada which was perfect. Service was great and our food came out fast. We all left happy and full.

Around 10pm we headed over to the swimming pool and hot tub which was just what the doctor ordered. The swimming pool is a salt chlorinated pool, which is super pleasant, if you have never dipped your toes in a salt water swimming pool- you’re missing out. This pool is also the perfect temperature at day or night, as they keep it heated in the “cold” San Diego winter days.

The next morning we woke up and went to get breakfast at Humphrey’s Restaurant. There weren’t many people and we were seated next to the window as soon as we walked in. We ordered our $2 mimosas included with the $10 resort fee, and feasted on burritos, muffins, and all delicious things breakfast encompasses. I want to emphasize that once again, the view was what everyone probably wishes they could wake up to each morning.

breakfast view

Service was good and food was well prepared and generous in size. We were the only younger group of people dining in there that morning. We also looked like we were the only ones that didn’t have a boat docked up front…so we also cashed in that 20% discount on breakfast!

We walked back to the hotel and asked if we could have a late checkout, which they delayed for an hour. This gave us time to pack up, and go back to the pool to hang out until it was time to leave. We lounged and played ping pong which is another cool perk of the hotel (if you want to put golf balls, you can also do that on site for free).

When it was time to go, we had a smooth checkout. We returned out keys, signed out check out receipt and they gave us a parking ticket to get out without paying anything extra. Overall our stay was really relaxing and pleasing, the rooms were ok for the price, not out of this world but we weren’t planning on being cooped up in the room all day. Food was good everywhere we went (more details on other restaurants nearby below), drinks were delicious but pricey at times, and the views can’t be beat when you compare similar places that have way more people around.




Bali Hai– Highly recommend for a fancy and romantic dinner. The views are spectacular, absolutely reserve a table with a view if you can. The food melts in your mouth and the drinks are way stronger than they seem (more bang for your buck). I ate the Thai Caesar’s salad, the braised short ribs, and two…you probably guessed it by now…piña coladas. I was seriously buzzed by the end of dinner and these bad boys did not taste strongly of alcohol.

Tom Ham’s Lighthouse: This is a local favorite for a celebratory brunch, with all you can eat oysters, crab legs and salmon. Price also includes free flowing champagne for bottomless mimosas (you pick your juice). The food here really is endless, so bring your appetite and take advantage of the fancy spread. Only downside is the price ($48/head) so make it worth your tummy.


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