Start the day at Cafe Americano on Collins Ave — a highly-rated breakfast and brunch spot. Enjoy a relaxed morning meal with American-style breakfast fare. Outdoor seating may be available for a breezy Miami Beach morning.

Kick off boutique shopping at Trendz Global on Washington Ave — a well-loved clothing store just steps from the beach. Browse the latest styles in a relaxed setting. Opens at 10:00 AM, giving you first pick of the day.

Free time to wander Washington Ave — pop into Trendy Couture next door (opens 11:00 AM) for a browse through their clothing selection, or simply stroll the Art Deco neighbourhood, window-shop, and soak in the Miami Beach atmosphere at your own pace.

Lunch at Ole Ole Steak House on Lincoln Rd — a vibrant eatery on one of Miami Beach's most famous pedestrian strips. Dig into grilled meats, paella, pizza, or a burger. The lively atmosphere and eclectic menu make this a great midday stop for two.

Afternoon boutique shopping at Akira on Lincoln Rd — a well-known women's fashion chain featuring designer dresses, knitwear, denim, shoes, and accessories. A great stop to find something special for a Miami evening out.

Tonight's splurge dinner at IL Giardino on Ocean Drive — an Italian restaurant set along the iconic, palm-lined boulevard. This is your one indulgent highlight of the trip ($$$$), perfect for a special first-night dinner in Miami Beach. Enjoy the al fresco atmosphere and Italian cuisine as the Ocean Drive evening scene comes alive.

Kick off Day 2 at Cafe Americano on Ocean Drive — a cool, Latin-inflected all-day diner set in Hotel Victor South Beach. Grab a table on their lively patio and enjoy a relaxed breakfast in the morning South Beach sunshine.

Wander down Lenox Ave for some relaxed boutique browsing. Jessie Boutique is a sleek women's boutique showcasing trendy designer clothing and accessories — perfect for leisurely free-time shopping at your own pace.

Head to Osteria Positano on Collins Ave for a laid-back Italian lunch. This highly rated $$ spot offers Italian and Mediterranean fare — ideal for a relaxed midday meal. Dine al fresco if available and recharge for the afternoon.

Stroll up Collins Ave to Violet & Grace at The 1 Hotel — a boutique blending clothing and jewelry in a beautifully designed space. The 1 Hotel itself is a stunning eco-chic property worth exploring, and the boutique is open until 9 PM so there's no rush.

Dinner at Kanoli on Ocean Drive — a top-rated Italian restaurant and diner open late. Enjoy a relaxed dinner as the evening energy of Ocean Drive comes alive around you. Great for a leisurely meal for two.

OPTIONAL: End the evening at URock Couture Miami Beach — a glam boutique with late hours (open until 1 AM) on Ocean Drive, stocking name-brand fashion for men and women. Browse at leisure, or use this window to stroll Ocean Drive and soak up the jazz and live music drifting from the nearby bars and clubs that line the strip — South Beach's Ocean Drive is famously alive with jazz and Latin rhythms on weekend nights.

Start the morning at Orange Blossom, a rustic-chic diner serving New American cuisine made from local ingredients. Enjoy a relaxed breakfast and perhaps a handcrafted cocktail if you're feeling festive — a great way to ease into Day 3.

Browse Jessie Boutique, a sleek women's boutique on Lenox Ave featuring trendy designer clothing and accessories. A perfect boutique shopping stop to kick off the morning — intimate, stylish, and curated.

Wander over to Frankie. on Purdy Ave for some free-form browsing and strolling in the Sunset Harbour neighbourhood. This charming boutique clothing store makes a great anchor for a relaxed wander — pop in, explore the surrounding streets, and soak up the local vibe.

Head to Wilde on the Porch at the historic Betsy Hotel on Collins Ave. This beloved porch-side restaurant offers outdoor dining in a beautiful setting — perfectly aligned with your love of al fresco meals. A relaxed, $$ lunch with great ambiance in the heart of South Beach.

Pop into Beach Boutique at Sunset Harbour Drive — a tropical-minded shop with curated jewelry, beachwear, and gifts in chic pastel surrounds. A lovely afternoon browse that blends boutique shopping with a breezy coastal feel.

Tonight's splurge highlight: MILA on Meridian Ave Rooftop — a flamboyant, high-end venue fusing Mediterranean and Japanese cuisine in a stunning rooftop setting with a stylish cocktail bar. As the one $$$$-tier splurge of the trip, this is a truly special dinner experience. Note: opens at 5:30 PM; booking ahead strongly recommended.

Cap the evening with a stroll to URock Couture on Ocean Drive — this glam boutique with late hours is a great spot to browse name-brand styles under the Art Deco lights of South Beach. Ocean Drive at night has its own buzz with live jazz and street music frequently drifting from nearby venues, making this a fitting jazz-flavoured end to the evening. Open until 1:00 AM so there's no rush.

Start the morning at maman, a charming café and breakfast spot on Bay Rd. Order from their coffee shop and brunch menu in a cozy, welcoming setting. The 7:30 AM opening means no wait for a leisurely table for two.

Head to Trendy Couture on Washington Ave — just 0.2 km from the heart of Miami Beach. Browse their clothing boutique for fashion finds. Opens at 10:30 AM and stays open late, so no rush. A great first boutique stop of the day.

Wander over to Frankie. on Purdy Ave, a stylish clothing boutique in the Sunset Harbour neighbourhood. Browse at your own pace — no agenda, just relaxed window shopping and exploring this charming side of Miami Beach.

Lunch at San Ginés Café on Collins Ave, right in the heart of Miami Beach. This well-rated café and sandwich spot is perfect for a relaxed midday meal — coffee, sandwiches, and brunch fare in a casual, convivial atmosphere.

Stroll to Beach Boutique at Sunset Harbour — a tropical-minded boutique offering curated jewelry, beachwear, and gifts in chic pastel surroundings. Perfect for picking up a unique souvenir or accessory. Open until 6 PM.

Dinner at Españolita Miami Beach on the beloved Española Way — a top-rated Spanish restaurant and steakhouse with seafood. The pedestrian street setting offers a relaxed outdoor dining vibe that's quintessentially Miami Beach. Opens at noon; reserve ahead for the evening.

Optional evening jazz outing: High Note Jazz Club at Cuba Ocho in Miami (~9.4 km away, roughly 20-25 min drive). This live music venue is the jazz highlight of the trip — catch live jazz performances in an intimate, cultural setting. Check their schedule ahead of time as hours vary. A special splurge evening experience to cap Day 4.

Start Day 5 at this beloved local gem on Española Way — a charming, laid-back brunch and breakfast café rated an impressive 4.9. Enjoy morning coffee and breakfast dishes on this iconic, art-filled pedestrian street. A perfect, unhurried send-off breakfast.

Head to Washington Ave for some boutique shopping at Trendz Global. This well-rated clothing store opens at 10:00 AM — browse the latest styles with a relaxed pace. Washington Ave is walkable and great for strolling between shops.

Just steps away on Washington Ave, pop into Trendy Couture for some free browsing and window shopping. This is your relaxed free time — wander, try things on, and soak up the Miami Beach boutique vibe at your own pace. No agenda, just fun.

Settle in for a leisurely lunch at FL Cafe, a contemporary bistro on Collins Ave offering elevated American, French, Italian, and Latin-style dishes. Their roomy patio is ideal for outdoor dining — a key preference for your group. A solid $$ choice to close out your Miami Beach culinary experience.

Make your way to Lincoln Road to visit Akira, a well-known women's fashion retail chain carrying designer dresses, knitwear, denim, shoes, and accessories. Lincoln Road itself is a lively open-air pedestrian mall — great for a final afternoon stroll. Open until 8:00 PM.

End your 5-day Miami Beach adventure with dinner at Salt Cafe Miami Beach on Collins Ave — a laid-back restaurant with a leafy terrace perfect for outdoor dining. The menu spans steak, pasta, and breakfast plates in a relaxed atmosphere. Dine al fresco and toast to a great trip. Open until 11:00 PM.

OPTIONAL — If you're up for one last evening out, High Note Jazz Club at Cuba Ocho in Miami's Little Havana (~9.4 km away, ~20 min drive) is a live music venue with a jazz focus — a perfect match for your jazz preference. Hours were not confirmed, so call ahead to verify tonight's programming before making the trip. A memorable final night cap.