I was just there Feb 15 - 24 and have been there many times....Here are a few ideas...I've been to all that I listed (or noted that it was a suggestion by others to go there)

There are a couple of restaurants/bars in that area that I would suggest:

1. La Rosa (highly suggested - italian in Maho)
2 La Gondola - Loved it, Rare, Temptation (highly suggested) - Cupecoy (near Atlantis Casino) - fine dining - in Cupecoy
3. There is a bar on the 2nd level of the plaza in Maho - where the asian food restaurant is - it's roof top - the views are great and the bar is cool - good drinks and there are areas with sand..like you are at a beachside -roof top bar! In Maho
4. Good Piano bar at Soprano's - In Maho (Suggested)
5. Sunset Beach bar during the day - can listen to the tower talk to the airplanes - other side of Maho - at traffic circle - head towards the other side of the runway.

Beaches - Simpson Bay Beach on the dutch side is lovely and long - with lots of condos and a few small boutique hotels/guest houses - there is a bar called Karacters - GREAT food and beverages - Dutch Side by airport

Friars Bay is very nice and has 2 restaurants - French Side - other side of Marigot

Orient Beach - very popular beach lined with beach bars - French side - on the way you could stop at Paradise View for lunch....view is spectacular - Also - Bikini Beach Bar or Kakao's on Orient are good!

Mullet Bay Beach - great for a burger (closes at 4pm) - not far from Maho - has giant waves - nice to see at sunset - faces west - get there from the golf course.

Dawn Beach - on the east side -bigger waves - but great bar/restaurant (also has great breakfasts) called Mr. Busby's Beach Bar - Also, there is a pizza place by Oyster Pond called Mama's Pizza.

Pinel Island - french side - get ferry (like $10.00 rt) and take 5 minute ride to this island - beautiful calm water, restaurants, and a view of orient beach.

French side restaurants - highly recommend - but just watch out for the Euro to Dollar conversion.

Le Tavisten, Mario's, La Cigale are highly rated....Went to Mario's on this last trip and loved it... Le Tavisten and La Cigale were top rated in a recent magazine I read.

Also, the Lolo's on the french side in Grand Case are greta - Taste Of The Town - and they are cheap.....

Duty Free shopping in Phillipsburg is GREAT! There are also great restaurants/bars....Greenhouse, Taloua Mangos, Ocean Lounge at the Holland House (even if you just want to have a drink...Antoines (Lobster Thermidor), and Le Escargot....Also - if you want to pray for good luck (smile) - the church on front street in Phillipsburg is a great experience....(really)....it's jammed packed - everyone participates...and it's fun and meaningful!

Shopping in Marigot...higher end - market is nice

Simpson Bay restaurants (I do not suggest Pineapple Petes - been there 2x now and did not like it - service or food

Lee's roadshouse is great and inexpensive.

The Yacht Club right by the bridge - go at 11 or 5 and watch the boat parade...boats pass through from the sea to the bay - it's really a cool sight to see! And they make GREAT bloody Mary's - not far from Maho....

Toppers - great for drinks

Carousel -great for ice cream (highly suggested)

Le Sucriere -french bakery goods!

Pelican Bay - The Red Piano Bar is fun and The Buccaneer is good for burgers/pizza

Day Trips - could take Ferry to Anguilla and go to Shoal Bay East.....could take catamaran to Prickley Pear or Sandy Island - both owned by Anguilla - could also take ferry to Saba - beautiful volcanic island - great hiking...St. Barts...island of beautiful people....pretty island as well.