A Glamorous 5-Day Itinerary in St. Bart's

First things first, I recommend flying in midweek if you don’t plan on coming for a full week to get a lay of the land before the “buzziness” of the weekend starts. For Day 1, I recommend St. Jean Beach! This is a great spot to start as there are various beach clubs/hotels perched on the beach here. Start at Eden Rock so you can do some people-watching, I also highly recommend swimming out to the famous ER raft. If you aren't a guest at the hotel or staying at an affiliated villa, you can't reserve their daybeds unfortunately, but bring a towel and you can still order drinks at the bar. The staff is extremely friendly!

Next, make your way over to Gyp Sea Beach Club or Nao Beach for lunch - it's just a quick walk to both of them. Both provide fun experiences with incredible menus, often times turning into a dance party with a DJ later in the day. This will be a great way to get your vacation mood in full swing.

For dinner, I would recommend somewhere more low-key in the town of Gustavia. Bonito or L’Isola are fabulous options. Bonito is a beautiful open-air restaurant on a hill providing gorgeous 360 views of the island and is known for their fancy cocktails (order the famous Sex in the Bath drink!). L’Isola is known for their delicious Italian food but set in a more moody, dim-light environment in an old Creole-style building.

If you are looking for a more “party” vibe, I suggest eating at dinner at La Guerite, which is the infamous Wednesday night party spot.

I would drive to Gouverneur Beach, which is on another side of the island away from most of the hotels. It’s a beautiful beach away from the crowds with no restaurants, but worth seeing for half a day. Make sure to bring snacks!

Next, I would drive to Shellona for lunch, grab a lounge chair, order some rosé, and walk around the shops in Gustavia after.

In the evening, I suggest dinner at Tamarin. Tamarin is a unique restaurant that is tucked away in a jungle-like setting and is a MUST see when you’re on the island. It’s also about a 5-10 minute drive back to Gustavia if you want to bop around to another restaurant later for some post-dinner drinks and dancing!

If you're interested in a more “sceney” option, I would recommend dinner at La Petite Plage which is known for being the Thursday night party spot. Come prepared for the sand filled floors!

You could also check out Le Ti, another fun dinner or post-dinner option. It just reopened and is a unique nightlife experience! It’s a cabaret club set in the hills near Marigot Bay with costumes to dress up in and entertaining dancers.

For Day 3, I would advise you to embark on a hike to Columbier Beach. Bring bathing suits and spend some time there as it’s the best beach on the island, but you can only get there by boat or hike!

If you want something fancier on the beach for lunch, I would again recommend Noa Beach, Gyp Sea, or Le Kala. If you’re looking for something more casual after a hike, Jojo Burger or Le Select have great burger/sandwich options.

For dinner, I strongly encourage Bagatelle. This is THE Friday night party spot you don’t want to miss! Think VIP bottle sparklers, shots being passed around and dancing on tables. However, if you are NOT up for the party, I suggest trying a hotel restaurant. The Rosewood, Eden Rock and Le Toiny all have great options, and if you love checking out new properties, this could be a fun night to do just that.

I highly recommend a boat day! This is hands down the best way to see the island and experience water activities. I suggest St. Bart’s Yacht Charters to help you schedule your excursion.

If possible, you can have the boat drop you off at a lunch spot! Nikki Beach is the most sought-after lunch spot on the island and the best day to go is on a Sunday, shockingly! Get the later table seating as that’s when the party starts.

After a long day at sea and drinking on the beach, I recommend getting takeout from La Quintessence Chef Pizzaiolo. This might be the chicest fast-food place I have ever seen. You can either call ahead and pick up your order or order it on the spot and watch them make the pizza in the oven. It’s delicious. You can always walk around town after and choose a place to grab a cocktail! There is no lack of options here!

The best way to end any St. Bart’s trip is by reserving lounge chairs at Le Toiny. This hotel is so special and far away from anything else, but might be one of the most scenic, bougiest hotels on the island. They have a private beach that you can only get to on their chic Toiny-branded landrovers. The beach is a bit rocky, FYI, so bring some water shoes if you plan to swim or surf! This is the top surfing destination on the island, so it’s a fun place to watch or even take lessons!

I suggest spending all day here. They have a wonderful restaurant on the beach, Maya’s, a cute shop, and a long stretch of beach to explore. On your way out, you have to check out the lobby and restaurant area - the chic decor and art will make you feel like you are in a Slim Aarons photograph.

On your last night, I would recommend dining at a hotel. Check out the Rosewood, Eden Rock, Cheval Blanc, The Hotel Christopher, Le Sereno... the list goes on. All are stunning and provide different views, cocktails and dining experiences.