Destinations Without Borders

Destinations Without Borders, the WedStay newsletter for May 19, 2026

A Tuscan vineyard villa, a Colombian chapel estate, a 26-villa Key West village, and a glacier-view Montana lodge, four new destinations now on WedStay.

This issue went to our couples list on May 19, 2026. Prices and offers were current on that date; each estate page shows today’s pricing.

Olive trees casting long shadows over a centuries-old Tuscan farmhouse. A private chapel tucked between Colombian mountain ridges. Twenty-six oceanfront villas strung along Key West, lit by tiki torches at dusk. A Montana lodge with glacier views from the wraparound deck.

Four newly listed estates this week, all built for wedding weekends where the destination is half the story. A historic villa in the Tuscan countryside, a villa-and-chapel compound in Antioquia, a 26-villa waterfront village in Key West, and a glacier-view lodge near Whitefish.

Browse, save, and book from your pocket — the WedStay app puts every property in this email on your home screen.

Featured Estate

Palaia, Tuscany • Italy

Tuscany Wedding Farm Estate

Guests 100 • Sleeps 16 • Vineyard Views

From $13,500+ per night

Tuscany Wedding Farm Estate — historic villa with vineyard views and olive groves in Palaia, Italy

A working farm estate tucked into the hills outside Pisa, with a centuries-old villa, working vineyards, and olive groves that stretch toward the horizon. Sleeps 16, hosts 100 for the ceremony under the cypress trees, and the rehearsal dinner pours from your hosts' own wine cellar.

View Estate →

Also New This Week

Colombian Private Estate with villas, suites, and intimate chapel setting in Peñol, Antioquia

Colombian Estate with Private Chapel

Peñol, Antioquia • Colombia

Guests

30

Sleeps

20

Chapel

Yes

From

$6,200+

A private compound of villas and guest suites built around an intimate stone chapel — the kind of small-ceremony setting you can't replicate stateside. Ninety minutes from Medellín, in the green folds of Antioquia, with mountain views from every patio.

View Details →
Florida Keys 4-Villa Waterfront Wedding Estate with 22 additional villas in Key West, Florida

Florida Keys 26-Villa Wedding Village

Key West, Florida

Guests

500

Sleeps

350

Villas

26

From

$39,100+

Four waterfront villas plus 22 additional villas across the property — sleeps 350, hosts 500 for the reception, and every guest has direct ocean access. The kind of wedding where the entire family books a flight to Key West and stays the whole week.

View Details →
Whitefish Wedding Lodge with glacier views, theater, and saunas in Whitefish, Montana

Whitefish Wedding Lodge with Glacier Views

Whitefish, Montana

Guests

150

Sleeps

10

Theater

Yes

From

$12,800+

A Montana lodge built for the wedding weekend where everyone wants to slow down. Glacier National Park is a short drive, the property has a private theater and two saunas, and the great room hosts 150 for the reception with windows pointed at the peaks.

View Details →
From the Newsroom

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The WedStay Collective

A curated vendor network for every WedStay couple.

Photographers, planners, florists, DJs, and more — vetted by our team and ready to travel. Browse vendors who already know our estates, with built-in pricing calculators and direct inquiries.

Browse the Collective →

From Our Blog

Florida Keys Wedding Village: 26 Villas, Sleeps 260, in Key West

How an entire wedding party flies into Key West, settles into 26 oceanfront villas, and turns a single weekend into a week-long celebration. A behind-the-scenes look at the most ambitious property in this week's lineup.

Read More →

Have a specific destination in mind? We're constantly expanding our curated international collection. Let us know where you'd love to celebrate.

Explore costs with our budget planner or submit your property for consideration.

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