Sea Island & A Last Minute Birthday Trip to New York City

If nothing else this has certainly been a summer of last minute trips.



For a type A planner like me this is pretty out of the ordinary. I knew earlier this year that I wanted to take a trip in June. The end of June would have been our original due date had we not lost our first pregnancy in December. I thought a trip would hopefully help us from being too sad as the date approached. Finding out we were expecting again in May definitely helped alleviate some of the sadness surrounding late June but it still seemed important to take a trip together to commemorate the event.

We talked about the trip a lot, but never pulled the trigger on a location. We wanted to go somewhere totally new but were reluctant to go too far away with a new pregnancy. Finally, at the behest of Robert’s cousin we decided on Sea Island, Georgia. We planned the trip so that it would coincide with our 3 year anniversary, only a few weeks away by the time we actually got around to the planning part.

Anniversary Dinner

The planning part entailed booking a room and making restaurant reservations. *Tip* Reserve your restaurants EARLY! We were too late to get into either of our top two choices 😦 A prime example of why I am typically a Type A advance planner. In the end, the restaurant choices mattered very little as I spent some of the trip sick (more on that later). Of the three options for lodging, we chose to stay at The Inn, the least expensive of the three. We quickly found out that Sea Island was pricey (especially during their peak summer season when we were there) so even the least expensive option cost a pretty penny. The Inn was closer to the Cloister (Most expensive option) and all of the amenities than The Lodge (second cheapest option) so it seemed like a solid decision. On top of our room rate we chose to pay extra to use the amenities and have access to the Cloister which I would definitely recommend because if you aren’t going to use their beautiful property and beach then why stay there at all? Wherever you choose to stay, there are free shuttles that run constantly which is a great feature.

We left for Sea Island on a Thursday, later than we had anticipated and hadn’t been on the road 30 minutes before hitting traffic. And by traffic I mean MAJOR traffic. Our easy 2 hour trip took us almost 4 hours 😦 On top of this being annoying (mostly for Robert, I had a book, thanks for always driving babe!) it also completely threw off our dinner plans so we decided to stop on the road. Robert chose Outback, a decision that I would sorely come to regret just a few hours later.

After dinner we continued our drive and checked in to our room at The Inn. I was very happy to find that The Inn was very nice. The staff were extremely friendly, the lobby was beautiful and our room was spotless and well appointed.

Unfortunately I didn’t get to enjoy it for long because within an hour of being there I got very sick. Presumably from the food at Outback (I ate french fries of all things?) because it lasted throughout the night and into the early hours of the morning but seemed to pass once I got it all out of my system.

As expected, this set us back quite a bit the next morning. Thanks to gatorade and saltines I finally rallied and we made it to the Cloister in time for lunch. The Cloister was gorgeous. Perfect lawns, beautiful open air Spanish style buildings, smiling families on bicycles, it truly looked like something out of a movie.


We made our way to the Beach Club, the activity hub of the Cloister, right on the beach and complete with three pools and several restaurants. I thought the adults only pool looked peaceful (and shaded) so we set up there for the afternoon.

Attendants came by often offering lunch menus, drinks, extra towels and free samples of various virgin daiquiris. The free daiquiri tasters were my favorite part about the adult pool and I ordered a few while Robert ordered us lunch. The food was tasty and the atmosphere was relaxing and quiet, too quiet for Robert’s liking. He informed me that night that he thought the adults only pool was a little too stuffy and that he’d like to try one of the family pools out the next day. After we’d had our fair share of pool we took a walk on the beach and then headed back to our room for a late afternoon nap.


Since we couldn’t get reservations at the Georgian Room (the fancy, fine dining restaurant The Cloister is known for) we had planned to eat the The Georgian Room Lounge, a slightly less dressy version of the former with a smaller but similar menu. Apparently neither of us slept well the night before because we both woke up from our “nap” around 8:30 PM! We quickly decided that showering and getting ready for a fancy dinner that late didn’t sound appealing in the least and Robert ventured out for some fast food instead. Certainly not what we had envisioned but sometimes eating take-out in a hotel bed is the best kind of vacation.

We were determined to make the most of the next day so we woke up early and rented bicycles to search out some breakfast. We biked to St. Simon’s Island and ate at a great bagel place, Sandy Bottom Bagels.


After breakfast we biked to some shops outside of the Cloister and did a little browsing. We then returned our bicycles and headed back to the Beach Club to sit by the pool. We found a shaded spot at the Family Pool and Robert declared it much more his scene.

We were both full from breakfast so we skipped lunch and opted for a sweet treat from Wonderland, the candy and ice cream parlor. Robert got an oreo milkshake (his standard) and I opted for the famous Gold Brick Sundae. Neither disappointed.

We DID have dinner reservations that night at Southern Tide, Sea Island’s ocean-side southern seafood restaurant, so we made sure to give ourselves plenty of time to get ready. The food was tasty, and it was nice to sit down at our first real restaurant of the trip.

After dinner we took a shuttle to Rainbow Island, a small island within The Cloister. When we booked our room, I saw that the Gin Blossoms were playing while we were there and like any good 90’s music fan I quickly snagged us two tickets. Despite a little rain to begin the show, the concert was great and the perfect way to end the trip.

Overall we both enjoyed Sea Island but agreed that for the price, we would give somewhere else a try next time. There is A LOT to do there, and I think it gets a lot cheaper in the off season so it is definitely worth looking into for a quick vacation stateside!

I did say it had been a summer of last minute trips, so on to the next one!

I turn 30 this Saturday (GASP!). Right now I don’t have too many feelings about this milestone birthday but ask me again this weekend and that answer may change. Being 4 months pregnant, our birthday celebration options seemed a little limited, so Robert and I decided about a week ago that we’d plan another quick trip, this time to New York City! If I can’t have anything fun to drink I CAN at least eat all the good food (read: ALL the pizza)! Despite the last minute planning we are both really excited. I haven’t been to New York since I was in high school and Robert hasn’t been since he was in the 6th grade! We’ve got a rough itinerary planned but I WELCOME all suggestions, especially those of the restaurant variety! Hopefully I’ll get around to sharing about that trip a lot sooner than I did this one!

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