Santorini caldera view with whitewashed buildings and blue domes
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A Romantic Greek Escape

Santorini, Greece

Breathtaking caldera views, world-class cuisine, and unforgettable sunsets await you and your partner.

5-7 Days
Santorini, Greece
2 Travelers
Flexible Dates

What to Expect

The Ultimate Romantic Getaway in the Heart of the Aegean

Santorini is more than a destination. This iconic Greek island, shaped by ancient volcanic eruptions, offers dramatic cliffs, whitewashed villages cascading down to the sea, and sunsets so breathtaking they've inspired poets and artists for centuries.

Your resort experience means every moment is designed for relaxation and romance. Wake up to breakfast served on your private terrace with caldera views, spend lazy afternoons by infinity pools that seem to merge with the Aegean Sea, and end each day watching the famous Santorini sunset paint the sky in shades of gold and crimson.

Whether you choose the vibrant energy of Oia with its iconic blue domes, the sophisticated charm of Fira, or the quieter luxury of Imerovigli (the "Balcony to the Aegean"), you'll discover why Santorini is consistently ranked among the world's most romantic destinations.

Trip Highlights

Unforgettable Experiences Await

Santorini - Iconic blue dome churches in Oia
Santorini - Caldera sunset views
Santorini - Infinity pool with caldera views
Santorini - Romantic cliffside dining
Santorini - Whitewashed village architecture
Santorini - Wine tasting with sea views

Experience one of the world's most romantic destinations with stunning caldera views and legendary sunsets over the Aegean Sea

Relax by infinity pools perched on volcanic cliffs, with the sparkling blue waters of the caldera as your backdrop

Savor world-class Greek wines and Mediterranean cuisine at award-winning restaurants with panoramic views

Wake up to in-suite breakfast served on your private terrace overlooking the iconic whitewashed villages and blue domes

Indulge in gourmet dining experiences featuring fresh Aegean seafood and traditional Greek flavors

Unwind with spa treatments, heated jacuzzis, and plunge pools at award-winning boutique hotels

Where You'll Stay

Recommended Accommodations

We've curated options for both peak season (July) and off-season (October) to match your travel style of smart spending with strategic splurges.

Peak Season

Peak Experience

July: Avg. High 84°F / Low 75°F. Prime summer weather, vibrant atmosphere

6 Nights

Astra Suites - Exterior Photo
Astra Suites - Room Photo
Astra Suites - Bathroom Photo

Astra Suites

★★★★

Imerovigli

Senior Suite (Higher floor, more privacy)

Award-winning all-suite boutique hotel on the cliffs of Imerovigli, the highest point on the caldera. The 20 suites and villas have high ceilings, four-poster beds, and oversized private balconies with heated jacuzzis or plunge pools. Cliff-side infinity pool with caldera and Aegean views, pool bar, gourmet restaurant (V Senses), hot tub, steam room, and massage area. Breakfast served in-suite each morning. Listed in TripAdvisor's Top 25 Hotels of the World, 3x World Travel Awards winner for Greece's Leading All-Suite Hotel, and Conde Nast Johansens Most Romantic Hotel. No elevator (cliff-side stairs). 20-min drive from airport, 2 km from Fira.

TripAdvisor Top 25 WorldConde Nast Most RomanticCliff-side infinity poolIn-suite breakfastHeated jacuzzis

Per Night

$789

Total (6 nights)

$4,733

Santorini Secret Suites & Spa - Exterior Photo
Santorini Secret Suites & Spa - Room Photo
Santorini Secret Suites & Spa - Bathroom Photo

Santorini Secret Suites & Spa

★★★★★

Oia

Premium Suite, Hot Tub, Caldera View

Chic 5-star boutique hotel carved into the volcanic cliffs of Oia, a member of Small Luxury Hotels of the World. The 17 suites and villas feature whitewashed Cycladic design, private pools or hot tubs on spacious terraces, and unobstructed caldera and volcano views. Black Rock Restaurant serves acclaimed Greek-international fusion cuisine. Harmonia Spa offers massages, facials, and body treatments (in-suite available). Infinity pool, poolside bar, daily breakfast on your private terrace. Steps from Oia Castle and the famous Blue Dome Church viewpoint. Staff remember guests by name. 18 km from airport.

SLH memberPrivate pool or hot tub per suiteBlack Rock RestaurantOia caldera viewsBreakfast on terrace

Per Night

$944

Total (6 nights)

$5,661

Astro Palace Hotel & Spa - Exterior Photo
Astro Palace Hotel & Spa - Room Photo
Astro Palace Hotel & Spa - Bathroom Photo

Astro Palace Hotel & Spa

★★★★★

Fira

Pool Suite, Sea View

Elegant 5-star hotel built in 2010 in Fira, blending contemporary design with traditional Cycladic architecture. The 28 rooms and suites have unobstructed Aegean Sea views, large balconies or patios, some with private pools or jacuzzi tubs. Pleiades Pool Restaurant by award-winning chef Michalis Ntounetas serves Greek-Mediterranean cuisine with wine tastings. Cassiopeia Spa with private pool, steam room, massages, facials, and yoga classes. Indoor and seasonal outdoor pools, hot tub, poolside bar, gym. Free buffet breakfast included. 4-minute walk to Fira town center with shopping, bars, and restaurants. 5 km from airport, bus station nearby for island access (2 euro rides).

5-star in Fira centerAward-winning chef restaurantCassiopeia Spa + private poolIndoor + outdoor poolsFree breakfast

Per Night

$1,091

Total (6 nights)

$6,543

Off-Season

Best Value

October: Avg. High 72°F / Low 63°F. Lower prices, fewer crowds, pleasant weather

6 Nights

Astra Suites - Exterior Photo
Astra Suites - Room Photo
Astra Suites - Bathroom Photo

Astra Suites

★★★★

Imerovigli

Classic Junior Suite

Award-winning all-suite boutique hotel on the cliffs of Imerovigli, the highest point on the caldera. The 20 suites and villas have high ceilings, four-poster beds, and oversized private balconies with heated jacuzzis or plunge pools. Cliff-side infinity pool with caldera and Aegean views, pool bar, gourmet restaurant (V Senses), hot tub, steam room, and massage area. Breakfast served in-suite each morning. Listed in TripAdvisor's Top 25 Hotels of the World, 3x World Travel Awards winner for Greece's Leading All-Suite Hotel, and Conde Nast Johansens Most Romantic Hotel. No elevator (cliff-side stairs). 20-min drive from airport, 2 km from Fira.

TripAdvisor Top 25 WorldConde Nast Most RomanticCliff-side infinity poolIn-suite breakfastHeated jacuzzis

Per Night

$417

Total (6 nights)

$2,503

Santorini Secret Suites & Spa - Exterior Photo
Santorini Secret Suites & Spa - Room Photo
Santorini Secret Suites & Spa - Bathroom Photo

Santorini Secret Suites & Spa

★★★★★

Oia

Premium Suite, Hot Tub, Caldera View

Chic 5-star boutique hotel carved into the volcanic cliffs of Oia, a member of Small Luxury Hotels of the World. The 17 suites and villas feature whitewashed Cycladic design, private pools or hot tubs on spacious terraces, and unobstructed caldera and volcano views. Black Rock Restaurant serves acclaimed Greek-international fusion cuisine. Harmonia Spa offers massages, facials, and body treatments (in-suite available). Infinity pool, poolside bar, daily breakfast on your private terrace. Steps from Oia Castle and the famous Blue Dome Church viewpoint. Staff remember guests by name. 18 km from airport.

SLH memberPrivate pool or hot tub per suiteBlack Rock RestaurantOia caldera viewsBreakfast on terrace

Per Night

$697

Total (6 nights)

$4,184

Rocabella Santorini Hotel & Spa - Exterior Photo
Rocabella Santorini Hotel & Spa - Room Photo
Rocabella Santorini Hotel & Spa - Bathroom Photo

Rocabella Santorini Hotel & Spa

★★★★

Imerovigli

Premium Room, Caldera View, Plunge Pool

Stylish 42-room resort in Imerovigli combining traditional Cycladic whitewash architecture with modern design and splashes of color. Rooms and suites have private balconies with caldera views, some with outdoor heated plunge pools. Buffet and a la carte breakfast through the Greek Breakfast Initiative. Axinos Restaurant serves Mediterranean cuisine poolside with panoramic caldera views. Night bar and pool bar lounge for sunset cocktails. Anedosa Spa with hammam, sauna, and body treatments. Fitness center and yoga classes available. Free parking on site. Part of the Rocabella group (also in Mykonos with loyalty discount). 15-min walk to Imerovigli center, easy reach of Fira and Oia.

42 roomsPlunge pools (heated)Axinos Restaurant poolsideHammam + saunaGreek Breakfast Initiative

Per Night

$589

Total (6 nights)

$3,533

Brenden's Note:

October offers significant savings (often 40-50% less than peak season) while still enjoying warm weather, fewer crowds, and beautiful sunsets. July is ideal if you want the full summer experience with vibrant nightlife and beach clubs. Let me know which season appeals to you!

Hotel Rates Summary

6 nights accommodation - Peak Season (July) vs Off-Season (October)

Astra Suites

Location:Imerovigli
Room Type:Senior Suite (Higher floor, more privacy)
Peak Season (July):$4,733
Off-Season (October):$2,503

Santorini Secret Suites & Spa

Location:Oia
Room Type:Premium Suite, Hot Tub, Caldera View
Peak Season (July):$5,661
Off-Season (October):$4,184

Astro Palace Hotel & Spa

Location:Fira
Room Type:Pool Suite, Sea View
Peak Season (July):$6,543
Off-Season (October):-

Rocabella Santorini Hotel & Spa

Location:Imerovigli
Room Type:Premium Room, Caldera View, Plunge Pool
Peak Season (July):-
Off-Season (October):$3,533

All rates shown are for 6 nights accommodation. Contact Brenden to discuss which option works best for your travel dates and budget.

Brenden Huey - WayFy Travel Consultant

Ready to Make This Trip a Reality?

Whether you prefer the value of October or the vibrant summer of July, I'll help you create the perfect romantic Santorini escape.

Contact Brenden