A Luxurious Weekend Itinerary in Downtown Sarasota & Her Islands

Photo courtesy of Pat Phillips

Arrival & Lunch: Begin your weekend by first stopping on Lido Key on your way up to Sarasota's most northern barrier island, Longboat Key, Grab an early lunch at Crab & Fin restaurant on St. Armands Circle, a glamorous outdoor retail destination. Fresh-caught Gulf Coast seafood meets elevated alfresco ambiance. White table-cloth tables line the sidewalk as piano playing sets the tone for a romantic meal. Indulge in some decadent gelato from one of the charming ice cream shops for dessert while browsing high-end boutiques and well-known brands. This is a great chance to secure some unique treasures, keepsakes or contemporary artwork on your trip.

Check-In & Drop Bags: Enjoy the scenic cruise up Gulf of Mexico Drive to your home away home. Settle into your five-star suite at the opulent St. Regis Longboat Key Resort – this newly opened jewel offers breathtaking views, top-shelf amenities and the pinnacle of luxury hospitality. After dropping bags and freshening up, enjoy a leisurely stroll around the property to get a lay of the land.

Afternoon: Depending on your interests and company, stay close and choose between the many resort offerings. If you're a solo traveler or couple looking for a relaxing retreat, book an afternoon at the world-class Spa and Relaxation Lounge for champagne and wellness shots paired with a massage, facial, pedicure and more. For families with kids, or adults who are kids at heart, head outside for a float down the Winding River, a snorkel in the Under The Sea Lagoon or a swim in the Resort Pool.

Dinner: Get dressed in your best resort wear to head to Euphemia Haye Restaurant, just a few minutes' drive up the Key. Euphemia is a locally renowned fine-dining institution known for its impeccable service and globally inspired cuisine. It's the perfect spot close by to toast the start of your weekend before trying the scratch-made fare with a French touch. If you're up for it, head to the restaurant's Haye Loft afterward for a signature cocktail and decadent desserts. 

Late Evening: Return to the St. Regis and unwind with a nightcap at The Monkey Bar, infusing mid-century Hollywood glamor with tiki cocktail culture. Or throw on your robes and take a moonlit walk along Longboat Key’s serene shoreline under the stars.

Photo courtesy of Visit Florida

Morning: Wake up early and venture off the Key to Marie Selby Botanical Gardens' Downtown Sarasota campus. There, you can indulge in a slow yoga flow to get your morning on the right foot. Enjoy a restorative vinyasa under the billowing trees, listening to the sounds of seabirds before exploring the gardens' gorgeous grounds and exhibitions (a ticket for yoga means free museum entry for after). Grab a coffee or a bite for breakfast at The Green Orchid onsite before heading to your next adventure.

Midday: Just down the road, pull into Sarasota Bayfront Park to embark on a private yacht charter for the day with Kokomo Charters or a luxurious sailing expedition with Key Sailing Charters. Whatever your vessel, you'll embark through Sarasota Bay and the Gulf soaking up the sun, savoring champagne and marveling at the stunning coastal scenery. Keep an eye out for playful dolphins as you glide through turquoise waters. 

Lunch or Afternoon Drinks: For a late lunch or happy hour for you and your charter companions, Jack Dusty at The Ritz-Carlton Sarasota is about a two-minute drive once you deboard from Bayfront Park. Grab seats at the opulent bar to chat with the knowledgeable bartenders, enjoy ceviche and oysters in the coastal-chic dining room or relax on the outdoor lounges to enjoy water views with a famous Siren cocktail. 

Early Evening: From The Ritz-Carlton, take another two-minute drive towards Downtown Sarasota to stroll the quaint, pedestrian-friendly streets and walkways. Window shop (or in-store shop) the high-end art galleries, bookstores, antique shops and fashion boutiques that line the strip. Walking distance is the historic Sarasota Opera House to catch an musical performance on stage. Depending on the day, you can book tickets to see esteemed performing arts organizations like the Sarasota Opera, The Sarasota Ballet, Key Chorale, Sarasota Orchestra and more.

Dinner: After the show, walk up Main Street about two blocks to Selva Grill, an upscale Peruvian restaurant known for its Latin-fusion dishes, moody ambiance and craft cocktails. Head to the very back of the restaurant to the darkened lounge and intimate bar area for digestifs and dessert. 

Morning: Start the day with coffee and a gourmet breakfast at the St. Regis' Italian-chic restaurant, Riva, followed by a leisurely walk along Longboat Key Beach or a refreshing morning dip in the Gulf of Mexico to set the tone for your final day.

Check-Out & Lunch: After checking out of the resort, wrap your weekend with a fancy lunch on the Key at either Shore LBK or Chart House. The Chart House is located on the south end of Longboat with an exquisite dining room overlooking the water, while Shore is located on the north end of the key with contemporary-chic patio seating. Both restaurants include boat slips to dock up and dine.

Afternoon: Make your way off Longboat and back to the mainland to sneak in a visit at The Ringling. For a cultural adventure delving into Sarasota's circus legacy and magnate, John Ringling, explore the glorious museum architecture and grounds – including a sculptural courtyard, art galleries and historical exhibitions, the majestic Ca' d'Zan mansion, Mable's bayfront rose garden, The Ringling Grillroom for an early dinner and a beautiful gift shop for last-minute souvenirs. 

Departure: As your luxurious weekend comes to an end, take a moment to soak in the serene beauty of Sarasota’s coastline and city skyline as you make your way back home. Safe travels until we meet again. 

Consider looking into The Coastal Concierge to book additional bespoke experiences while in Sarasota such as sunset beach picnics, private events, upgrades and more to elevate your Sarasota getaway.

You can also take advantage of concierge services at the St. Regis to arrange transportation, restaurant reservations and exclusive experiences around the area.