NICE PLACES TO WEAR NICE THINGS
The Social Beer Garden in Christiansted town offers beautiful indoor/outdoor dining where dressing up—heels included—is welcomed.
St. Croix has lots of amazing places to dine and fun nightlife spots for you to unwind, but it can be a literal pain in the foot to wear certain shoes to certain places.
Not to worry, ladies, Dress Better on the Weekend is making it easy for you to look good and feel great the next time you plan to step out in style!
We’ve visited every restaurant or nightspot on St. Croix—from west to east—focusing on exterior surroundings and interior flooring and have compiled our First Annual List of Heel-Friendly Spots on the Big Island.
That’s right, we did the work, so you don’t have to!
Ladies, you’ll finally be able to wear those stilettos, strappy sandals, pumps, or sling-backs with confidence, whether you’re heading to Happy Hour this evening or a night out on the town this weekend.
IMPORTANT: Not being named to this list is not a reflection of the service the business renders. This list only reflects the ease in walking to and from your transportation, as well as inside the establishment when wearing heels 3 inches or higher. We recommend wearing any variety of flats, low-cut wedges or a pair of dressy sneakers to your favorite spots not listed below.
PS: No restaurant located on the Christiansted boardwalk made our list due to the openings between the slats, which could pose a safety challenge for high-heel-wearing fashionistas.
Judging Criteria
Even Sidewalks
Good Exterior Lighting
Smooth and Even Interior Flooring
Parking Lot/On-Street Parking Free of Potholes, Gravel and Excessive Dirt
Read on for our carefully curated list of heel-friendly restaurants and hotspots on St. Croix.
FREDERIKSTED TOWN
The Fred
The vibe at The Fred is as luxe in the day as it is at night. Pull up a chair at one of the umbrellaed tables or at the expansive concrete bar at this beautiful boutique hotel located in the heart of historic Frederiksted. From the time you drive up, you’ll be greeted with a bright and modern exterior that makes strutting in your high heel of choice effortless. It’s giving Miami beach club vibes mixed with Condado-chic.
NORTH SHORE
Carambola Beach Resort
Carambola remains as classy as the last time you visited, after all, it’s part of the Marriot family of hotels known for their exclusivity. Us locals don’t take the long drive out there as often as we used to before the 2017 hurricanes, now that the popular buffet night is a thing of the past. But, the restaurants are still open and the property views are still breathtaking! So, get dressed up this weekend, put on those heels and get down there. You won’t regret it. Online reservations are required for dinner.
SION FARM
Mutiny Island Vodka
Mutiny Island Vodka is the home of the breadfruit vodka. Not only can you purchase bottles of the stuff or sip on refreshing cocktails made with the local spirit, you’ll appreciate the great parking and beautiful, welcoming interior. Like most places on St. Croix, it is casual fare, but no one’s stopping you from wearing those heels you love.
LA GRANDE PRINCESSE
The Palms at Pelican Cove
A favorite for large gatherings, meetings and celebrations—The Palms at Pelican Cove is a go-to for locals. For one, the food is chef’s-kiss good, and the live entertainment will have you on the dance floor all night long! Everyone knows it’s dress-to-impress when visiting The Palms.
CHRISTIANSTED TOWN
Ambiance Cocktail Lounge
It’s the newest and hottest nightlife spot on St. Croix, and the name says it all. Located on Strand Street in the heart of Christiansted’s downtown shopping district, Ambience invites a mature 30+ crowd to enjoy seriously delicious cocktails—some of the best on-island (mocktails are available, too) and 90s R&B in an intimate setting perfect for date night, Ladies, make sure your style game is on 100 because the dress code is strictly enforced (no flip-flops, crocs and other casual styles).

Galangal
A longtime staple in St. Croix’s high-end dining scene, the elegant Galangal on the Christiansted waterfront serves up delicious Southeast Asian and French cuisine. There’s no better place to pretend like you’re in Paris, the fashion capital of the world, than here. So, strut in wearing a fabulous outfit and the highest heels you can handle.
Jubilee by Yaadie in St. Croix
Sadly, Jubilee will be closing its doors permanently this weekend (July 31), but it has earned its spot on this list! The quaint, but well-appointed restaurant is located at 45 King Street in Christiansted and can seat fairly decent-sized groups. Plan to arrive early for the final Sunday Brunch on July 27. You can slip on some higher heels, if you choose to, because the exterior sidewalk and interior floors have been beautifully restored and maintained.
The Social Beer Garden
This was the first spot we visited when the idea came to compile this list. Needless to say, it did not disappoint. The Social Beer Garden, located at 50 AB Company St., in Christiansted, is an outdoor dining oasis with chic and earthy vibes. It’s more than safe to wear your best heels when visiting this St. Croix gem, as a paved, smooth sidewalk with ample space escorts you straight to the entrance. Sip a delicious cocktail and have a small, savory dish while you take in your surroundings in this beautiful indoor-outdoor setting.
GALLOWS BAY
No Bones Cafe
Locals and visitors have no problem with No Bones. When it comes to pulling up, parking and walking in for a delicious meal, the Chandler’s Warf restaurant is always a fan favorite. It’s a casual dining space, but if you wanted to mix things up a bit, wearing a pair of heels would be the perfect touch.
EASTEND
The Mermaid at The Buccaneer
The Mermaid offers the finest in oceanfront dining on St. Croix and everything about this venue has been planned to perfection. With its bight, open-concept dining room, clean sidewalks, and muted decor, it’s giving luxury girls’ brunch where elevated tropical style is on the menu. Leave the flip-flops and slides at home and slip on some sky-high platforms with a flowy maxi for a grand entrance.
Galleon Steaks and Seafood
It’s natural to get dressed up when dining out at a steakhouse and you can go full-glam at Galleon. We recommend sitting in the formal dining area if wearing heels, but outdoor dining on the deck is also available on casual days. It’s the place where the who’s-who on St. Croix go to enjoy exquisite cuts of steak in an exquisite atmosphere.

GOAT Soup & Whiskey Restaurant
Nestled on the grounds of the Coakley Bay Condominiums, you’ll enjoy really good food in a casual, outdoor setting at GOAT. There’s ample parking in a well-maintained lot that surrounds the property. You’ll have no problem getting to and from your car into the restaurant wearing those heels
Oceans At Carina Bay (Casino & Restaurants)
The adult-only, all-inclusive resort and casino located on St. Croix’s East end offers locals a staycation like no other. After your last meeting on Friday, pack a bag and head east to Oceans for a weekend of your dreams. Bring that little black dress, those heels, and that special someone. If you’re arriving only for dinner, lunch or brunch, a voucher is required to be purchased to access the resort’s restaurants and other amenities.
HONORABLE MENTIONS
KFC & McDonald’s (Golden Rock)
Burger One (Five Corners)
Most of us will never have the need to wear high heels to place an order of burgers and fries, but in the event such an occasion arises, these fast-food spots can accommodate your high-heel style. With well-lit, paved parking, you can quickly and confidently get in and out and on to the next.
If you believe we’ve overlooked a business that should be included on this list, send us an email at info@dressbetterontheweekend.com with your suggestion.