A Romantic 7-Day Clearwater Beach Getaway: Sunsets, Seafood, and Local Breweries
Clearwater, Florida blends powdery white sand, calm Gulf waters, and a laid-back beach town energy that’s tailor-made for romance. The barrier islands here lead to legendary sunsets, while nearby towns like Dunedin and Tarpon Springs add artisan shops, breweries, and Greek cuisine to your seaside escape. December brings mild weather, festive lights, and smaller crowds—an ideal window for couples.
History buffs will appreciate that Clearwater’s name comes from the area’s freshwater springs—long gone, but the crystal Gulf still shines. Today, Clearwater Beach routinely ranks among America’s best beaches, and the nightly Sunset Festival at Pier 60 turns dusk into a ritual. The region’s marine icon is the rescue-focused Clearwater Marine Aquarium, which continues to rehabilitate sea turtles, dolphins, and seabirds.
Practical notes for December (your dates: Dec 8–13, 2025): expect highs around 68–73°F and cool evenings—pack layers for sunset cruises. Parking runs about $3–5/hr on the beach; the Suncoast Beach Trolley is an easy, budget-friendly option. Seafood dominates menus (don’t miss local grouper), but you’ll also find refined waterfront dining, vibrant Latin spots, and a tight-knit brewery scene.
Clearwater
Clearwater Beach is the postcard: sugar-fine sand, a long, inviting shoreline, and the nightly glow of Pier 60. North Beach feels quieter and more local; Sand Key Park is a peaceful escape just over the bridge. Inland, the Cleveland Street District sprinkles boutiques and cafes along a bluff with views across the bay.
Top reasons to go: sunrise strolls and technicolor sunsets, dolphin spotting in the pass, ferry rides to shell-studded islands, and a brewery hop in adjacent Dunedin. Foodie highlights range from just-caught grouper sandwiches to chef-driven tasting menus overlooking the Gulf.
Getting there (flights): Fly into Tampa International (TPA, ~35–45 minutes to Clearwater Beach) or St. Pete–Clearwater (PIE, ~25–30 minutes). Search fares on Trip.com Flights or Kiwi.com. December roundtrips from major U.S. cities often run ~$150–$350 if booked early. Rideshare from TPA to the beach is typically $40–$70 depending on traffic.
Where to stay: For a romantic vibe and easy beach time, base on Clearwater Beach (north end for quieter nights). Sand Key suits sunset seekers; downtown Clearwater offers value and quick ferry/trolley access.
- Browse beachfront condos and cozy cottages on VRBO Clearwater.
- Compare resorts and boutique hotels on Hotels.com Clearwater. Look for stays near Pier 60 for sunset walks.
Getting around: The Suncoast Beach Trolley connects Clearwater Beach, Sand Key, and down-island communities. Day passes are budget-friendly (~$5). Parking is plentiful but can fill near sunset; arrive early or consider the Clearwater Ferry (seasonal) to avoid traffic.
Day 1: Arrival, Beach Strolls, and a Pink-Sky Welcome
Afternoon: Arrive, check in, and shake off the flight with a barefoot walk along North Clearwater Beach. Stop for an iced latte at Restoration Cafe (island estates) or a cappuccino at Another Broken Egg Cafe if you’re peckish.
Evening: Time your first sunset at Pier 60’s Sunset Festival—buskers, local crafts, and that famed orange-pink horizon. For dinner, choose from these local staples:
- Frenchy’s Rockaway Grill – iconic grouper sandwiches and live music right on the sand; casual and fun.
- Island Way Grill – sushi and wood-fired seafood; book a window table for twinkling harbor views.
- Palm Pavilion – open since 1926, a toes-in-the-sand classic with beachside cocktails.
Day 2: Beach Bliss, Clearwater Marine Aquarium, and Dolphins
Morning: Breakfast at Clear Sky Cafe (crab cake benedict, stuffed French toast), then claim a cabana near the lifeguard towers. Swim or stroll to the jetty; the Gulf is calmer in the morning, perfect for a couples’ dip.
Afternoon: Visit the Clearwater Marine Aquarium to learn about rescue and rehab efforts; exhibits are intimate and moving. Then head to the marina for a classic dolphin outing:
Little Toot Dolphin Adventure at Clearwater Beach
Evening: Rooftop dinner at Marina Cantina (Yucatecan shrimp, street corn, and smoky mezcal cocktails) with a rooftop firepit vibe. Cap the night with gelato at Gelato-go or a moonlit walk along the surf line.
Day 3: Dunedin Day—Artful Shops and a Brewery Trail
Morning: Uber 15 minutes to Dunedin, a walkable, artsy town. Grab a flat white at 9th Bar Espresso and browse Main Street boutiques like Kelly’s Chic-a-Boom courtyard shops and local galleries. Stroll a scenic slice of the Pinellas Trail.
Afternoon: Brewery-hop:
- Dunedin Brewery – Florida’s oldest microbrewery; order the Apricot Peach Ale or a seasonal stout.
- Woodwright Brewing Co. – set in a historic woodshop; live music and German-style lagers.
- 7venth Sun – creative sours and IPAs; small-batch gems.
- Clearwater Brewing Company – just south in Clearwater; neighborhood feel and rotating taps.
Evening: Go dressy for a romantic dinner: The Black Pearl (intimate, French-leaning tasting menus) or waterfront Bon Appétit at the marina. Watch the sunset over St. Joseph Sound, then grab a cone at Strachan’s before heading back.
Day 4: Caladesi Island—Shelling, Sea Oats, and Sunset at Sea
Morning: Drive ~25 minutes to Honeymoon Island State Park and catch the ferry to Caladesi Island (~$18–$20 RT; weather-dependent). Wander the nature trail through slash pine and sea grapes, and comb for lightning whelks and olives along the quiet shoreline.
Afternoon: Picnic under a dune pavilion (pick up provisions from Nature’s Food Patch in Clearwater). Rent a tandem kayak or simply laze beneath the sea oats—this is one of Florida’s last undeveloped barrier islands, perfect for couples.
Evening: Return for your romantic golden-hour sail:
Sunset Celebration Cruise on Tropics Boat Tours
Day 5: Tarpon Springs Traditions and Clearwater Date Night
Morning: Drive ~30 minutes to the Tarpon Springs Sponge Docks, founded by Greek sponge divers in the early 1900s. Sip a strong Greek coffee and split a honey-soaked baklava at Hellas Bakery.
Afternoon: Browse sponge shops and maritime curios; if weather’s calm, consider a short boat ride to Anclote Key (check schedules on-site). Lunch on the water at Dimitri’s (whole grilled fish, lemon potatoes) or Mr. Souvlaki (classic gyros).
Evening: Back in Clearwater Beach, reserve a table at Caretta on the Gulf (Sandpearl). Think coastal tasting menus, an excellent wine list, and candlelit Gulf views—an elegant splurge night. Nightcap with a stroll past the dunes at Sand Key Park.
Day 6: Paddle-Clear Waters and a Yacht Night Out
Morning: Start with acai bowls at Basimo Beach Cafe, then join a unique paddle:
Kayaking Clear through Clearwater
Afternoon: Relax by the pool or book a couples’ massage. For a casual bite, try Tate Island Grill (beachy burgers and mahi tacos) or Backwaters on Sand Key (grouper sandwiches, intercoastal views).
Evening: Dress up for a night on the water:
Clearwater Evening Yacht Cruise with Optional Dining
Day 7: Slow Morning, Last-Call Shopping, and Departure
Morning: Brunch near the pier—Speggtacular (from-scratch pancakes) or the old-school Tin Can Cafe in town. Pick up locally made soaps, shells, and sea-glass jewelry at the Pier 60 huts or Cleveland Street boutiques.
Afternoon: One last shoreline stroll before checkout. Drive to TPA/PIE for your flight home—search or check-in via Trip.com Flights or Kiwi.com. If your trip is Dec 8–13 (6 days), use Days 1–6 and save any favorite for your next visit.
Optional/Weather Flex Ideas
- Pier 60 movie night or holiday lighted boat parades (mid-December dates vary; ask your concierge).
- Columbia Restaurant Sand Key – Cuban-Spanish classics (1905 Salad, paella) with bay views.
- Sea-Guini – coastal Italian at Opal Sands; book around sunset for a painterly sky.
Handpicked Tours You Might Swap In
Prefer a sailing vibe or party beats? Consider one of these in place of a day’s activity:
Calypso Queen Tropical Party Buffet Cruise
Summary: Across seven days, you’ll savor Clearwater’s best: languid beach mornings, shelling on wild islands, brewery nibbles and pints, and romance-filled sunsets from the water. It’s a December beach escape with heart—equal parts laid-back Gulf Coast and unforgettable date nights.