5 Romantic Vacations From Westchester That Are Perfect for Proposals

These stunning destinations take all the planning out of your hands…so your significant other can have something much more important on theirs.

If you often play the fun game with your significant other called, “Are They Proposing or Did They Book an Insane Vacation for Fun,” these locations could be the instance you finally win. Compound a day in paradise by having an illustrious proposal just moments later. And the best part about it all? These packages take all of the planning, guess work, and flower arranging out of what should be a stress-free and joyful time. It’s a win-win across the board.

Baoase Luxury Resort

Wellenstad, Curaçao


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This is truly a proposal that is stranger than fiction, in a perfect, fairytale way that will make lasting memories and an even better story. Nestled into the Dutch Caribbean Island of Curaçao, Baoase Luxury Resort is already dreamy (without the promise of any extra hardware). The five-star resort runs the gambit of tear-inducing, fantastically unique proposal packages (fireworks on the beach, anyone?), but none such compared to the wonder and whimsy of the “Local Fisherman” package. As the sun dips below the horizon, you and your soon-to-be-fiancé will find a quiet moment of respite in a secluded section of the beach. Moments later, a fishing boat will dock closely to you, and the local fisherman will step out, revealing the unbelievable box he found in the ocean. Inviting you to open up the box, the engagement ring is unveiled. The true magic begins when the fisherman slips away, leaving you and your partner to enjoy the intimate moment of joy in a tropical oasis. Baoase provides fresh garden flowers, torches, and glasses of bubbly to toast to the next chapter of your love story. Additionally, if the fisherman scenario just isn’t for you, the resort offers a proposal planner who will be available to coordinate and adjust to your every individual need.

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Baoase Luxury Resort
Photo courtesy of Baoase Luxury Resort

Hotel Ranga

Hella, Iceland


Hotel Ranga
Courtesy Hotel Ranga
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Do you want engagement photos that will shake Instagram to its core, leaving your friends, family, and vague high school acquaintances grasping for words? Jet set over to Hotel Ranga on the South Coast of Iceland for not only a remarkable vacation but a proposal package that no soul could possibly turn down. The package, monikered “Say Hell(a) Yes!” poses the cozy countryside hotel as the most chic (and unassuming) place to pop the question. Known for being one of the best places to see the Northern Lights, this land of fire and ice gives adventurous couples a stacked itinerary before the big moment. The proposal package includes a stay in a Master Suite with a welcome amenity, a helicopter tour, a romantic dinner at Restaurant Ranga, topped off with breakfast in bed. Guests also have the option to add on a photographer to capture the moment—because why wouldn’t you? In the case of those looking to add more extravagance to the trip, hotel staff are willing to go all hands on deck to help work out a perfectly planned proposal under a waterfall, at the hotel’s own stargazing observatory, or even in a candlelit cave. Seriously, who is saying no?

Activities at Hotel Ranga
Courtesy Hotel Ranga

Grand Universe Hotel

Lucca, Italy


Grand Universe Hotel
Courtesy Grand Universe Hotel
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Picture it now: a horse-drawn carriage, local Italian appetizers and aperitif, all while breezing through the quaint streets of a Tuscan village…What romance novel did you just stumble into? Those looking for that extravagant, decadent moment to finally pop the question to love of their life should head to Grand Universe Lucca in Italy’s charming and quaint city of Lucca. Far from the maddening crowd (read: tourists) guests can book the Lucca by Horse Carriage experience to set the mood, which includes a selection of canapés made with combinations like robiola cheese and smoked salmon, swordfish, tuna and tomato, basil bruschetta with garlic and olive oil, and more. Not to mention, a bottle of Franciacorta Saten “Carpe Diem” Bonfadini is brought along ready to be opened in celebration of that soon-to-be, emphatic, “Yes!” Finish the day with the hotel’s “Prelude of Existence” experience — a personalized theme song written by a local Italian composer, which can be played again when you walk by the aisle. Lovebirds can not only return home with the most romantic souvenir specially packaged inside a ‘time capsule’ to forever remember their love-filled time in Lucca, but with some new bling in tow.

Moon from hotel
Courtesy Grand Universe Hotel

W Hotel

Fort Lauderdale, FL


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W Hotel
Courtesy W Hotel

Stun and style with the W Fort Lauderdale’s “Marry Me Proposal Package,” a surprise they will never see coming. The award-winning oceanfront hotel is rolling out the hot pink carpet — scattered with rose petals, of course — for the big question. Upon booking your package, the beachfront WOW suite is transformed into an Insta-worthy backdrop to ask someone to spend the rest of forever with you. The hot pink carpet leads the “proposee” to an oversized Love Wall, decked out with hundreds of lush white, purple, pink, and peach silky roses and a hot pink neon sign shining, “Let’s Do This.” After popping the question, the couple can pop the bubbly with a perfectly chilled bottle of Champagne to celebrate with up to eight friends and family members (who up until that point, will be kept a surprise and anxiously waiting in the suite’s living room). The proposer also has the option of adding a preferred photographer to capture the moment (who wouldn’t want to snag that smile?) and post-yes celebration with friends and family. If the romance factor wasn’t already at an all-time high, there is an additional option of having a love song serenade from local artist Kerst Lehmann for an unforgettable moment.

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Luxe & Local

If you’re airline averse, consider a magic experience in the Empire State.

The Harold S. Vanderbilt Penthouse
Courtesy The Harold S. Vanderbilt Penthouse

No need to hop an ocean to experience a luxurious historic hotel. The InterContinental New York Barclay offers a bespoke experience in Park Avenue’s most majestic suite: The Harold S. Vanderbilt Penthouse. Offering a 1,300-square-foot private terrace with breathtaking views directly overlooking the Chrysler Building and living room space boasting floor-to-ceiling windows, the suite’s romance factor is unparalleled. Coupled with a proposal experience that includes day use of the terrace, a professional photographer to capture the moment, and a Champagne toast for two, there is no shortage or romanticism, and being so close to home there’s ample time to celebrate the occasion with friends and family.

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