
Get swept away to Santorini for a 6-night escape that’s all about those postcard-perfect views and dreamy Greek vibes. We’ve locked in a 4-star cliffside hotel with caldera views that’ll make your heart skip, all without the wallet-busting price tag. Picture a private boat tour around volcanic islands, wine tastings that hit all the right spots, and romantic dinners in Oia as the sun dips into the Aegean. Thanks to our deal-hunting, this trip feels like a splurge but costs way less than you’d think. It’s perfect for lovebirds, solo wanderers, or anyone craving Mediterranean magic with a side of luxury.
What’s Included
Your Stay
You’re staying in a 4-star cliffside hotel in Santorini, perched high above the caldera with views that scream Instagram. Think whitewashed walls, blue-domed vibes, and a room with a private balcony or terrace to watch ships glide by. Beds are plush, bathrooms have those fancy rain showers, and some rooms might even have a hot tub. Breakfast’s included daily—Greek yogurt with honey, fresh figs, pastries, and coffee strong enough to wake you for sunrise. The hotel’s close to Fira or Oia but quiet enough to feel like your own slice of paradise.
Private Boat Tour
Hop on a private 4-hour boat tour around Santorini’s volcanic islands. You’ll sail past red and black sand beaches, stop at hot springs for a warm dip, and maybe anchor near a tiny islet for snorkeling. The captain shares island secrets, and you’ll get drinks—think chilled ouzo or juice—plus snacks like olives and pita with tzatziki. It’s just your crew, making it intimate and unforgettable, with the caldera sparkling all around.
Wine Tasting
One afternoon, you’re off for a guided wine tasting at a local vineyard. Santorini’s volcanic soil makes its wines unique—crisp Assyrtiko, bold reds. You’ll sample 4-5 wines, paired with cheeses and local nibbles, while learning about the island’s winemaking tricks. The setting’s gorgeous—think vine-covered terraces with sea views. It’s relaxed, a little tipsy, and perfect for soaking up the island’s soul.
Oia Sunset Dinners
Two dinners in Oia are included, timed to catch those famous Santorini sunsets. Picture candlelit tables at cliffside tavernas, with plates of grilled octopus, fava beans, or lamb kleftiko, plus a glass of local wine. The sky turns pink and gold as you eat, and the vibe’s pure romance, whether you’re with someone special or just vibing solo. These spots are handpicked for killer views and food that’s as good as the scenery.
Extras
We’ve slipped in a guide to Santorini’s hidden gems—think secret beaches or a quiet café for baklava. Our airline deals (flights not included) keep your travel budget tight, and we’ll scout the best fares. Want to add a cooking class or a hike to an ancient ruin? Just let us know, we’ll make it happen without a hitch.
Sample Itinerary
Day 1: Arrive & Soak It In
Land in Santorini, transfer to your cliffside hotel, and let the caldera views hit you. Unwind on your balcony or dip in the pool. Dinner’s on you—try a local spot we recommend for souvlaki.
Day 2: Boat Tour Bliss
Morning’s free—sleep in or wander Fira. Afternoon’s your private boat tour, sailing and splashing. Evening’s chill, maybe grab a gyro nearby.
Day 3: Wine & Sunset
Morning’s for exploring—maybe a beach or village. Afternoon wine tasting at a vineyard, sipping with a view. First Oia sunset dinner caps the day—pure magic.
Day 4: Free Day Vibes
All yours—laze by the pool, hike to a ruin, or shop for ceramics. Evening’s open; our guide’s got recs for a lively taverna or quiet bar.
Day 5: Second Sunset Dinner
Day’s free—maybe hit a black sand beach or nap. Second Oia sunset dinner steals the show, with food and views to die for. Sleep happy.
Day 6: Last Hurrah
Free morning to revisit a fave spot or just chill with caldera views. Check out by noon, head to the airport, unless Santorini’s got you hooked.
Why This Trip?
Santorini’s a bucket-list dream, and this escape delivers its iconic beauty with a luxe twist that won’t break you. The 4-star hotel’s your cliffside haven, boat tours and wine tastings add adventure, and Oia dinners are pure romance. We’ve slashed costs so you get that high-end feel for less. You’ll leave with sun-kissed skin and memories of sunsets that feel like they were painted just for you.

Price Details
$1,650 covers 6 nights for two in a 4-star cliffside hotel, daily breakfast, a private boat tour, a wine tasting, and two Oia sunset dinners. Flights and transfers extra, but we’ll snag you deals. Taxes and fees? All wrapped in, no surprises.
Note
Cliffside hotels book up quick, especially in summer, so don’t wait. Got dietary needs or want a room with a hot tub? Tell us, we’ll sort it. Solo, couple, or small crew—this trip’s got the vibe for everyone.