Celebrating Drew’s 60th Birthday at The Sip, Savor and Sound Experience

Arrr You Ready to Party?!

The Gasparilla Inn • Boca Grande, Fl
Thursday, January 7 – Sunday, January 10, 2027

For over 112 years, The Gasparilla Inn has been the crown jewel of Old Florida. A storied seaside retreat where pastel cottages, palm-lined lanes, and golf carts set the pace of island life. We’ve planned a weekend that blends celebration, relaxation, and the Inn’s signature Sip, Savor and Sound Experience: three days of curated cocktails, extraordinary cuisine, and live music under the stars. Pack your sunniest spirit. Here’s what awaits to celebrate Drew’s 60th!

Transportation

In order to arrange ground transportation for the group, we will be reaching out to collect your flight information. Fort Meyers is the preferred airport. However, there are two airports in close proximity.

Fort Myers International Airport (RSW)

Nonstop options available from Houston on United, Delta, and Southwest.
One stop option available on American.
Nonstop options available from Dallas Love on Southwest and from DFW on American.

Sarasota Bradenton International Airport (SRQ)

Nonstop options available from Houston on United, Delta, and Southwest.
One stop option available on American.
Nonstop options available from Dallas Love on Southwest and from DFW on American.

Both of these airports are about an hour’s drive to Boca Grande Island.

If you prefer to make your way there on your own and rent a car, please note that there is a $6.00 toll fee associated with crossing the Boca Grande Island Bridge. Forms of payment accepted include cash, credit card, Apple Pay and GIBA toll pass.

Itinerary

  • ARRIVALS
    The Gasparilla Inn

    Make your way to Boca Grande and settle into the Inn. Take the afternoon to roam the resort in the Florida sunshine, cruise the coast in a golf cart, or stroll along the palm trees into island time.

    DREW’S BIRTHDAY DINNER
    The Pink Elephant • 7:00 PM

    Kick off the weekend at the iconic Pink Elephant. This beloved spot on the Boca Grande Bayou has been serving fresh Florida flavors and signature cocktails for over 60 years. Join us for a festive evening of great food, waterfront views, and a Spicy Pink toast (or several) to the birthday boy.

    ATTIRE
    Island Festive Pinks — sundresses or chic separates for ladies; collared shirts with slacks or chinos for gentlemen. It’s a celebration, so don’t be afraid to Think Pink!

  • GUYS’ GOLF
    The Gasparilla Golf Club • Morning

    Hit the links on the Inn’s Pete Dye designed championship course, a par 72 masterpiece surrounded by the sparkling waters of Charlotte Harbor. Exclusive to Inn guests and members. Clubs and Gasparilla-branded gear are available at the pro shop.

    ATTIRE
    Proper Golf Attire — collared shirt and golf slacks or shorts.

    LADIES’ LOUNGE
    The Beach Club • Morning

    While the guys chase birdies, the ladies claim the beach. Sink your toes in the sand, soak up the Gulf sunshine, or be treated to an optional morning spa service at The Gasparilla Inn Spa.

    ATTIRE
    Beach Attire — swimsuit with a cover-up, sun hat, and sandals.

    HOSTED LUNCH AT YOUR LEISURE
    The Beach Club • 11:30 AM - 2:30 PM

    As the golfers finish their final holes and the beach crew works up an appetite, wander over to The Beach Club — the Inn’s breezy, oceanside spot for casual Gulf-front dining.

    SIP, SAVOR AND SOUND
    WELCOME FESTIVITIES
    Afternoon & Evening

    The Inn’s signature weekend officially begins! The afternoon opens with a warm welcome gathering, followed by an evening elebrating the flavors of the south, an interactive dining experience by the Inn’s culinary team. Exact timing and details will be shared as we get closer to the weekend.

    ATTIRE
    Elevated Island Casual — breezy dresses or summery separates for the ladies; collared shirts and slacks (a sport coat never hurts) for gentlemen. Evenings by the gulf can be cool in January, so pack a light layer or wrap.

  • SIP, SAVOR AND SOUND
    BREAKFAST & MORNING AT YOUR LEISURE
    Morning

    Ease into the day with a relaxed breakfast buffet and cocktail bar at the Inn. Then make the morning your own — shopping in the village, a bike ride to the lighthouse, or simply enjoy coffee on the veranda. We would love to meet you on the Inn’s world-renowned croquet lawns for a friendly match – stay tuned!

    LUNCH
    Details to come!

    HOSTED AFTERNOON ACTIVITY
    Afternoon

    The Sip, Savor and Sound team has something special planned for the afternoon. In past years, guests have headed out on the water with inspired bites and cocktail demonstrations along the way.

    More to follow; be ready for a little adventure.

    ATTIRE
    Resort Casual – comfortable flat shoes, sunglasses and a hat.

    SIP, SAVOR AND SOUND
    AN EVENING TO REMEMBER
    Evening

    The crown jewel of the weekend. The evening unfolds with cocktails and canapés during golden hour, followed by a multi-course tasting dinner crafted by an acclaimed guest chef with thoughtfully paired wines. Then, as the stars come out, settle in for an intimate live musical performance, the “Sound” that gives the weekend its name.

    ATTIRE
    Coastal Cocktail — jackets (no tie needed) for gentlemen; colorful dresses or elegant separates for ladies. The evening is held on the lawn, so wedges or block heels are your friend, and a shawl or light jacket is a must for the January night air.

  • FAREWELL BRUNCH
    Morning

    One last gathering over traditional southern fare and Old Florida charm before we say our goodbyes. Safe travels home!

    ATTIRE
    Travel Casual

IN YOUR DOWNTIME

Between events, the island is yours. A few Gasparilla favorites:

  • THE INN BAKERY — grab-and-go breakfast; do NOT miss the homemade donuts.

  • CROQUET — a Gasparilla staple, played on three world-class championship lawns (whites required on the courts).

  • THE SPA — massages, facials, and salon services; book ahead.
    Call 941-964-4555 to make a reservation.

  • SHOPPING — charming boutiques in the village of Boca Grande.

  • THE BOCA GRANDE LIGHTHOUSE — a picture-perfect piece of local history at the island’s southern tip.

  • TENNIS, POOL, FITNESS, BIKES, AND BEACH — all just steps away.

GOOD TO KNOW

  • January days on the island are typically sunny and mid-70s, with evenings dipping into the 50s–60s — pack layers for nights outdoors.

  • The Inn keeps a classic dress code: no jeans, shorts, or tank tops at dinner venues; gentlemen wear jackets in the Main Dining Room during the winter season.

  • Golf carts and bicycles are the island’s favorite way to get around. Your reservation at the hotel includes a golf cart!

  • Sip, Savor and Sound event timing may be fine-tuned by the Inn; a final schedule will be provided.