20 Old Money Vacation Destinations and Beautiful Getaway Ideas

Explore 20 old money vacation destinations and getaway ideas, from Capri’s sea views and New England harbors to lakeside gardens, Alpine terraces and countryside retreats.

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Looking for old money vacation destinations with pretty harbors, lakeside gardens and grand old buildings? These views give you plenty to dream about.

Think sailboats outside waterfront houses, flower-filled terraces and mountain scenery that deserves a little extra room in your itinerary.

You can plan around a seaside town or choose a countryside escape. Some pictures show recognizable landmarks, while others are inspiration for the kind of setting to look for rather than a confirmed hotel or address.

Read also: 20 Best Places to Travel for Christmas, From Festive Cities to Beach Escapes

Beautiful places and getaway inspiration to save

sailboats and waterfront gardens

We’re starting off strong with this gorgeous waterfront view. I love the white sails in front of the gray house, especially with all those hydrangeas along the lawn.

If you want a New England coastal getaway, use this as your starting point. Look for a harbor town where you can make a waterfront walk part of your day.

lakeside arches and flowers

How pretty is this garden path? The twisted columns and tall arch sit right beside the blue water, with flowers filling the slope on the other side.

For an Italian lakes trip, I’d put a lakeside garden visit near the top of the list. Leave yourself time to enjoy the steps and little terraces rather than rushing straight through.

Edgartown’s white lighthouse

If you love a classic coastal view, this one is for you. Edgartown Lighthouse on Martha’s Vineyard stands above the beach grass, with blue water and a wooded shoreline behind it.

Make a lighthouse walk part of your island plans. The white tower and black lantern are lovely all on their own.

mountains and tables on ice

Okay, this is quite a setting for a table! White tablecloths and curved chairs are arranged on the ice, with snowy mountains behind them.

People in dark suits stand nearby while others relax in the chairs.

If this is your kind of winter escape, look into organized Alpine events in places such as St. Moritz. Check the actual event details before planning around a scene like this, rather than treating a frozen lake as a picnic spot.

a grand house by the harbor

I am obsessed with the blue and white flowers around this house. The tall columns, black shutters and sailboats in the background give you so much to look at.

For a getaway with a similar feel, consider Newport and plan visits to properties that are open to the public. This image is architectural inspiration, not a confirmed place to stay.

a little tea on the water

How cute is this boat table? There are strawberries, colorful macarons and a little teapot, plus white flowers beside the place settings.

The turquoise cove behind it is just as pretty.

If you’re planning a Mediterranean boat outing, you could bring a simple picnic of your own. You don’t need this entire spread to enjoy the view.

palms and a vintage convertible

This palm-lined lane may just be one of my favorite views here. I love the pale walls, dark shutters and pink flowers around the steps.

The vintage convertible is a lovely extra detail.

Save this as inspiration for a Palm Beach-style escape, with garden walks and pretty architecture on your list.

a boat beside the villa

Don’t want your lake trip to be all about busy town squares? This is the kind of waterside view to save.

A small motorboat sits beside a white villa with arched doors and a little terrace.

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For a Lake Como itinerary, you could pair a boat excursion with a waterfront lunch. Just check access before assuming a terrace like this welcomes visitors.

Capri’s sea stacks

I am obsessed with this view of Capri’s Faraglioni. The tall rocks, tiny boats and bright pink flowers are so pretty together.

Read also: 20 Tropical Vacation Destinations and Dreamy Views to Inspire Your Next Trip

You can build part of your visit around a scenic walk rather than filling every hour with plans. I’d leave plenty of time for a stop overlooking the water.

Read also: 20 Beautiful Places to Visit in North Carolina and Views Worth Saving

a chalet terrace in the hills

If you’re looking for a mountain escape instead of a beach trip, this one is for you. The dark chalet has pink window flowers, pale chair coverings and a terrace facing green slopes.

I especially love the little dog by the steps. For a similar Alpine getaway, look for accommodation with outdoor seating and a view you actually want to linger over.

lunch above the sea

This is such a pretty lunch setting. Pale blue shutters line the villa, while a round table and white-curtained daybed face the water below.

If you’re considering the French Riviera, save this for the atmosphere rather than a specific booking. I’d choose one leisurely seaside meal over trying to squeeze in another stop.

an autumn harbor

Who says your coastal getaway has to happen in summer? The orange and red trees behind this harbor are gorgeous.

There’s a white church steeple above the houses and a boat tucked beside the docks.

Use this as inspiration for a fall trip along the New England coast. A small harbor and colorful foliage make a lovely combination.

Monaco at sunset

The sunset over Monaco is doing plenty here without any extra decoration. I love the orange light on the water and the buildings rising toward the mountain.

This picture takes in the harbor from a yacht, but you could make an evening waterfront stroll your own version of the idea.

a classic lake cruiser

Don’t want to go all out with a huge yacht? This smaller boat is beautiful too.

The dark glossy sides, cream seats and enclosed cabin look lovely against the blue lake.

For a Lake Tahoe getaway, consider looking into a sightseeing cruise. I’d make the mountain-and-water view the main reason to go.

arched windows and a garden pond

This garden may just be my favorite countryside scene on the list. I love the tall arched windows reflected in the pond, with lily pads and greenery filling the foreground.

If you’re dreaming of an English country escape, look for garden visits or country-house stays with a similar setting. Don’t assume the house pictured is bookable.

a scooter in the courtyard

How sweet is this little courtyard? A cream scooter sits between flowerpots, with tall cypress trees and hillside buildings behind it.

Save this for a Tuscany-inspired itinerary. You could spend an afternoon exploring a village on foot, then stop somewhere with a terrace rather than planning every minute around driving.

a house beneath spreading oaks

I love how the big branches frame this pale house. The dark shutters and curved driveway are so pretty in the late light.

For a Southern getaway with a similar setting, consider the Savannah area. Look for public gardens and house museums you can actually visit rather than planning around an unidentified private home.

a turret and long verandas

The turret at the Jekyll Island Club is such a lovely detail. The pale yellow exterior, white railings and rounded shrubs make this a beautiful piece of architecture to add to your travel list.

I’d leave time to enjoy the grounds as well as looking up at the building. Those spreading trees are a big part of the view.

colorful villas above a cove

If you are looking for a seaside view with lots of color, then this one is for you. There are yellow and pink buildings above the rocks, plus swimmers in that gorgeous clear water.

For an Italian Riviera trip, look into the coastline around Portofino and Paraggi. Check public beach access when planning your own swim stop.

a playful little shopping lane

Last but definitely not least, we have this colorful lane with flowerpots and a yellow taxi decoration above the restaurant entrance. I love the tiny dashed road markings down the middle!

It’s a more playful finish than the grand villas above. Leave a little room in your itinerary for side streets and unexpected storefronts too.

Just a little note - some of the links on here may be affiliate links, which means I might earn a small commission if you decide to shop through them (at no extra cost to you!). I only post content which I'm truly enthusiastic about and would suggest to others.

And as you know, I seriously love seeing your takes on the looks and ideas on here - that means the world to me! If you recreate something, please share it here in the comments or feel free to send me a pic. I'm always excited to meet y'all! ✨🤍

Xoxo Emily

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