This will forever be one of my favorite vacations of all time. Every time I scroll through the photos I still can’t believe it was all real and we experienced everything we did. From the color of the water [they aren’t lying, the Exumas have to be some of the clearest, bluest water to ever exist], to the royal treatment of having delicious home-cooked meals provided for breakfast, lunch, and dinner to feeling completely immersed into the sea life at every turn. It was truly a trip of a lifetime and one I would recommend to anybody and everybody.

I’ve received so many questions since our travel to the Bahamas on a catamaran that I wanted to have a place to answer all of those and lay out our trip from start to finish! If you’d like to see videos from our travels [from the boat we were on to the activities we did, make sure to watch this Instagram highlight where it is all captured]! Let’s dive into this trip of a lifetime…

The Catamaran

We were on Penny Jo Sailing Charters and it was incredible to say the least. It is a brand-new Bali 4.4 catamaran that has 4 bedrooms with queen beds [all with their own bathrooms], a fully stocked kitchen, a dining area with incredible views 24/7 [the wall that went up and down to create an open-air dining environment was our favorite], and plenty of outdoor areas to lounge [our hot spot was the front of the boat where there was ample space to lay out, play cards, drink our coffee at the table, get a YouTube workout video in [let’s be real – this only happened once] and relax as we sailed to each new destination]! There is also a large area to relax up top at the Fly Bridge which is an awesome spot to take in the sunsets from! The best part of the charter? The staff. When you sail on Penny Jo, your captain Ainsley and his first-mate, Mispah will be your hosts for the week. From making sure you travel to all of the best spots, to cooking up all of your meals, blending up your favorite drinks, and cleaning up after you, they are there for whatever you need [and are awesome, fun, friendly people at that]!

We traveled with my sister and brother-in-law so there were four of us + the captains. The boat has three rooms available [as Ainsley and Mispah use one of the rooms] so you could travel easily with 6 [3 couples or adults and kiddos] and be comfortable!

The Food

Oh, but the food. Mispah was our chef onboard and when I say her meals were better than some that we experienced at restaurants, I mean it. Everything she made was incredible – both the taste and the presentation were spot on. Prior to our vacation, we received a very detailed preference sheet to fill out to indicate what types of foods we like for breakfast, lunch, and dinner along with drink preferences, snacks, how we like our coffee, when we prefer to eat, and so on! They make sure every single detail is catered to your liking beforehand so that while you are on board you can be assured they will have everything you like. They even went as far as to make me a different meal whenever seafood was served because I am not a seafood lover while the others were!

Note: All food and beverages [alcohol included] on board are included in the price of your trip!

Activities

All activities are included in the price of your trip!

This is what made sailing on Penny Jo even more special. Our captain, Ainsley, knew exactly all of the best spots to go [and when to take you to avoid the cruise ship crowds]! We often felt like we were the only ones in the universe because he knew the most serene, picturesque, hidden gems to take us that the everyday traveler may never see. From snorkeling in the most beautiful coral reef with thousands of fish right outside of Johnny Depp’s island to parking the boat overnight where we’d constantly have a firsthand look at sharks and sea turtles as we sipped our morning coffee and pulling up to private beaches where not a single other person was for us to explore, every day we couldn’t believe the adventure we were on. I’ll go into more detail on the activities we did in our itinerary below, but one thing I want to note is that on board the catamaran they have paddle boards, kayaks, underwater scooters, floating toys, and more!

Our Itinerary

Before I jump into our itinerary, it should be noted that we didn’t have to plan anything you see! Our captains took care of arranging all of the itineraries and every morning would sit us down for our “daily briefing” to show us where we were going to go that day and what activities we’d find ourselves in! I loved this!

Day 1:

We flew into Nassau, Bahamas, proceeded through customs [which fortunately only took 15-20 minutes or so] and from there were whisked off in private transportation that Penny Jo Sailing Charters arranges for you. It was approximately a 30-minute drive to the marina where Penny Jo was docked awaiting our arrival. Once we were all boarded, we toasted with our Penny Jo Punches [these are delicious!], got settled in our rooms, and we took off on our first sail toward the Exumas. It is this initial sail that is one of your longest of the trip, approximately 4 hours. That evening we docked in Highbourne Cay and went to one of our two dinners off the boat for the week at Xuma’s Restaurant which was stunning and delicious.

My Dress [size up one, wearing in medium]

Day 2:

For starters, waking up and instantly seeing nothing but the bluest of blue waters surrounding you is amazing. On this day we made our way to Norman’s Cay where we were able to snorkel around a sunken airplane and then sailed an hour or two to Shroud Cay where we took the Dingy through the Exuma Cays Marine Park to the most gorgeous beach to hang out on for a few hours!

Day 3:

On day 3 we made our way to Hawksbill Cay where again – we were able to anchor, jump off the boat and swim, paddleboard and make our way to a beautiful isolated beach with the bluest of waters and purest white sand.

From there we sailed to Warderick Wells where we would anchor for the evening. The best part about this stop? Sharks like to swarm the boats which give you a firsthand look at them while you are [safe] on the boat! We fed them and watched them swim around all night. Another awesome spotting at this spot? Sea turtles. I could have watched these cuties all day long.

Day 4:

This was my favorite day of the trip [and also the one I have the least amount of photos from – coincidence? probably not ;)] We woke up, enjoyed a delicious breakfast like always, and headed towards O’Briens Cay [on the way we were able to sail past Johnny Depp’s Island and scope his property out from afar which was fun]! Once we reached our destination, we snorkeled at The Aquarium at O’Briens Cay [a gorgeous coral reef] with so many different varieties of fish everywhere. It was a magical day I’ll never forget!

Day 5:

Let’s be real – every day was pretty epic. To start things off, we made our way to Compass Cay where we swam with nurse sharks [yes, I was petrified and first and no, it wasn’t scary at all when I actually got it]. After surviving, we set sail for our final destination of the trip, Staniel Cay. Out of all of the Cays we stopped at, this was the only one I believe that was really habited [people live here, there are restaurants, stores, etc]. One awesome must-see is Thunderball Grotto. You are able to snorkel in it and around it and it is a site to be experienced. After “ooohing and ahhhing” from that, we walked around Staniel Cay and ended our day at our second restaurant off the boat for the week at the Staniel Cay Yacht Club.

Dress [true to size, wearing in small]

Day 6:

Things started off like most days in life do – swimming with pigs 😉 I had never thought as a child “someday you’ll be in the Exumas standing in the most beautiful water surrounded by pigs” but here we were. I can’t say I thought they were overly cute and I can’t say I didn’t freak out a little. As soon as they realize you have no more food to give them, they leave you alone but during that short period of time when you do have food, watch out, pigs like to eat.

My swimsuit [true to size] // Shawn’s swimsuit

Because good ole Tropical Storm Nicole was making her way to the Bahamas, we had to cut our trip a wee bit short and start to make our descent back toward Nassau to avoid getting caught in her path!

Day 7:

Made it back to Nassau to end our trip!

FAQ’S I’ve Received:

What is the cost to do this?

It depends on how many are in your group, but if you have 6 guests [the max] it is $20,000 for the group. Yes, it is a more expensive vacation, however, if you split that three ways and consider your food, drinks, activities, airport transfers, Wi-Fi, and other added benefits, it’s really not bad. It is definitely a luxury vacation and you feel like you are taken care of 24/7! You can see all rates here!

Sea Sickness: Did you experience it and what did you take for it?!

Fortunately, none of us experienced sea sickness, but as a preventative, we took less-drowsy Dramamine chewable tablets every day. I also took a regular Dramamine pill before bed every night because I just never wanted to risk getting sick. I will say, you aren’t sailing all that often in the grand scheme of the trip. Most of our days we only sailed a couple of hours and the rest of the time we were docked and off the boat doing things! We were also always docked at night. The first evening I noticed the boat rocking while we slept and it bothered me a little bit [I simply went out front on the boat for a little while to see the horizon and took a Dramamine] while everybody else thought the gentle rocking was super peaceful and put them right to sleep. We did encounter some [very] rough waters thanks to Tropical Storm Nicole for a day but even with that, we stayed okay the entire time! My biggest tip: take medicine as a preventative and if you’re ever feeling sick, stay outside looking at the horizon!

How much time are you on the boat?

Like I said above, the actual sail time every day was pretty short [just a couple hours] so the rest of the time we were either off the boat doing things, in the water swimming, eating yet another delicious meal on board, or just kicking back relaxing with a book and drink in hand.

Could you do this trip with kids?

Yes, you could – but I would be cautious of what ages. I believe Penny Jo recommends kids 12 or older. You would want them to be good swimmers because a lot of your time is spent in the water and you would want to make sure they have activities for on the boat to stay busy with [if they aren’t good relaxers]. There are games on board, and also wi-fi so that helps!

What should I pack? Any tips?

First of all, whatever clothes you think you’ll need, cut it in half and that should be about right 😉 We lived in swimsuits and coverups all day every day and only ate dinner off the boat twice for the week. I would recommend one sandal [I always rely on Tory Burch Millers for sandals that you can dress up or down] as you really won’t need shoes otherwise. The only other shoe I wore were water shoes [we bought these!], a waterproof phone bag if you want to be able to take your phone with you in the water, Dramamine, sunscreen [non-aeresol], sunglasses, books, and whatever else you want for your week! I did bring all of my makeup along with a hair dryer, curling iron, straightener, etc! One big tip – bring a soft duffel bag instead of hardshell luggage as you won’t have room on the boat to store the hard luggage but a duffel you can fold up and put in a drawer!

waterproof phone case

Here’s a look at a few outfits I wore during the week [we typically always showered and got ready before dinner every night]!

Romper [size up one]

Coverup [true to size]

My coverup // My sister’s coverup

My swimsuit [size up one, wearing in 6] // Coverup Shorts [true to size, wearing in small] // Shawn’s Swimsuit

Is there Wi-Fi on board and can I make calls?

Yes, and yes! They have Starlink internet on the boat so you’re able to be connected while on board! We have Verizon and had the daily travel pass [I believe for $10/day] to be able to make calls and text.

How can I book?

Easy! All you have to do is contact Penny Jo Sailing Charters and they will be in touch with you to talk about dates, pricing, etc! I can’t recommend our time with them more – they will take care of you from start to finish to ensure it is a trip of a lifetime!