Travel Trending with Kathy Witt: It's Margaritaville at Sea Islander and Tradewinds Resort for the family win

Sunbathers who wish to bask poolside and shade seekers in pursuit of a good read, interactive game show lovers and arts and crafts fans, night owls and early risers, picky eaters and one self-professed gourmand; it can be a challenge to find a vacation that pleases everyone. But when the destination is a cruise, and the cruise line is one that takes its cues from the iconic Jimmy Buffett brand, the search is quickly over. With its laid-back, family-friendly, on-island-time vibe, it's Margaritaville at Sea for the win.

In early June, our group of nine-a mix of tweens, teens and adults, half cruise ship newbies, the other half seasoned cruisers-embarked on a five-day cruise aboard the 2,210-passenger Islander, which departs from Tampa, Florida, and featured stops in Progreso and Cozumel in Mexico.

The Islander offers plenty of choice, from onboard activities that include everything from morning trivia, poolside fun and splashy production shows to an excellent mix of restaurants, quick bites and sweet treats. Additionally, the ship has no fewer than 11 stateroom categories. We chose four different types for our group: a cozy inside cabin, a "picturesque" ocean view cabin with large window, a breezy balcony cabin and a Grand Terrace suite. (Three of us shared the suite, while the other cabins held two each.)

Everyone agreed their individual cabins perfectly suited their needs. They were clean and comfortable and 100% on brand with Margaritaville at Sea's bright island palette accented with vivid parrot artwork and, in the case of the suite, a glowing panel of dolphins illuminated with pinpoints of light. The décor, including pillows stitched with lyric-inspired sayings drawn from Buffett's easy-breezy trop-rock songs, was playful without being kitschy and set the tone for the rest of the ship.

Our group appreciated the variety of food offered in the Port of Indecision Buffet, with everything from soup and salad, cheeses and focaccia breads to multiple hot entrées. For our picky eaters, the Cheeseburger in Paradise Burger Bar was-hands down-the lunchtime favorite. A close second (but not just for lunch), was Frank & Lola's Pizzeria. The crispy thin-crust pizza disappeared fast: blistered edges, bright sauce, the whole deal. At the Mexican Cutie Cantina, the tacos and bowls with choice of meat and beans were also a hit, especially because of the Salsa Bar mix-ins: tomato, cheese, crunchy lettuce, crema, salsas, diced watermelon.

We all enjoyed gathering for the evening in Fins, the Islander's main dining room. Daily entrées, such as crusted salmon, ranchero flat iron steak, chicken marsala and deviled shrimp, were tasty, but where the restaurant really shines is with its "Opening Acts." Cuban croquettes, Florida hushpuppies, carnitas, cheese ravioli, Jamaican pumpkin soup and more-the selections were plentiful and absolutely delicious.

The serious carnivores in our group visited JWB Prime Steakhouse. Wagyu meatballs, onion soup, prime ribeye, banana cream pie. Rich and indulgent, the dishes arrived in an unhurried, unstuffy setting-an experience worth every penny of the upcharge. Several tried the à la carte sushi rolls, sashimi and poke bowls at Far Side Sushi. And all of us kept the Margaritaville Coffee Shop busy with orders of lattes, iced macchiatos and hot chocolate-but the No. 1 beverage of choice for the kids: frosty virgin pina coladas.

The Islander offers a Parrots, Pirates and Pancakes character breakfast hosted by Salty the Pirate, but our kids opted instead for breakfast in bed one morning with room service. The menu is à la carte, but I felt the food was well worth the minimal charges, especially the breakfast sandwich: a toasted English muffin with scrambled eggs, caramelized onions, cheddar cheese and avocado served with roasted potatoes.

Some Islander standouts for our group:

• Mornings: The sunworshippers staked our loungers at the 5 O' Clock Somewhere Pool while others preferred slipping off to the morning trivia games or hitting the treadmills in the gym. There aren't many treadmills, but the gym was never overly crowded and at least one was always available.
• St.Somewhere Spa: We had originally booked the Mom and Me mani/pedi session, but the nail technician was on sick leave, so we switched to a massage: hot stones for me, gentle light-touch for the teen and tween-leaving the three of us feeling delightfully pampered.
• The Hangout: Our tweens enjoyed the activities in the kids' club on the two occasions they attended but ultimately preferred participating in games like Pictionary, Name That Tune: Pop Stars! and Celebrity Heads hosted by the Fins Up Crew, playing mini golf and pickleball, or hanging at the pool.
• Evenings: While the kids attended evening movies on deck ("Captain America," "Five Nights at Freddy's 2"), a couple of us adults settled into the quieter atmosphere of Hemisphere Dancer for the violin music.
• Showtime: The Islander's big production show, "Conky Tonkin' at Sea," is a standing-room-only hit. Ventriloquist Taylor Mason, famous for his signature blend of piano music, magic, stand-up and ventriloquism, brought down the house. Comedian Rob Little, named Happiest Comic in America by NBC's "Last Comic Standing," had everyone roaring with laughter during his family-friendly PG show, which we all attended, and his R-rated adults-only show that two of the group sat in for-and loved.

For a group vacation with a mix of ages and interests, the ship and itinerary offered plenty of freedom to explore independently and no shortage of shared moments and memories. All in all, the Margaritaville at Sea Islander is a great choice for groups seeking some relaxed and meaningful family time at sea.

Paradise prolonged: Pre- and post-cruise resort fun

If the Margaritaville at Sea Islander is all about easygoing island energy, then TradeWinds Resort on St. Pete Beach is its ideal shoreside companion, a tropical playground where effortless family fun sets the tone before you ever step onboard or keeps the island glow going afterward.

With two distinct hotels, Island Grand and RumFish Beach, TradeWinds is all about sun, sand, color and motion: the splashy oasis of five swimming pools, the whoosh of the three-story High Tide slide, the ping and clang of the Shipwreck Arcade games; the thwack of clubs smacking balls along the mini golf course.

Restaurants are plentiful across the resort. At the newly opened Playa Taco Cocina y Tequilería, it was fun sharing Macho Nachos, chicken tinga and the Three Amigo quesadillas. The double smashburgers on soft brioche buns suited the mood and mindset for al fresco lunchtime dining at Pete's Gulf Bistro. And the Underboss, a meaty and mozzarella-heavy pie drizzled with hot honey from Coastal Pizza was perfect for poolside munching.

We spent most of our time doing exactly what a pre-cruise weekend stay calls for: lounging on the beach, zipping down the water slide, playing mini golf and (sadly) losing money in the arcade. (We all agreed the claw machine had to be rigged!) Evenings meant shoreline walks, s'mores at the campfire and splashing about in the illuminated pool.

On Sunday, we ventured into downtown St. Pete for an afternoon of digging into clay at the Morean Center for Clay. The center offers a free, family-friendly studio session on Sundays, and it's creative good fun for all ages. Afterward, we visited FloridaRAMA, a wonderfully wacky, immersive world created in collaboration with more than 75 artists, filled with playful exhibits that celebrate old-school Florida.

With its colorful, casual, family-centric spirit, we thought TradeWinds Resort was a natural match for our Margaritaville at Sea sailing. It's an idyll where kids can burn off energy, adults unwind and everyone reconnect before or after a cruise.

Plan your travels

The Margaritaville at Sea Islander is an excellent choice for first-time cruisers, especially families-the ship's target audience. Families find so many activities, from pools, hot tubs, water slide and kids' clubs to pickleball, mini golf, interactive games, music, movies and outstanding shows. Islander sails from Port Tampa Bay on four- to 10-night cruises to Key West, Mexico and the Caribbean. For more information, visit www.margaritavilleatsea.com or call 800-814-7100.

TradeWinds Resort is 40 lush and tropical acres set along 1,600 feet of award-winning shoreline on St. Pete Beach with amenities galore: restaurants and bars, swimming pools, High Tide Water Slide, Dive-In Movies, paddleboats, kids poolside crafts and activities, pickleball courts, gift shop and more. For more information, visit www.tradewindsresort.com or call 888-598-4304.

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This story was originally published June 30, 2026 at 12:05 PM.