6 Proposal Trip Ideas From the Experts

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Fora Author Fora Travel

The Modern Travel Agency

Fora Travel

    Catalina Island

    Many people travel for weddings and honeymoons, but popping the question – one of the most exciting parts of a couple’s journey — is an event that’s all the more special if it happens during a getaway. 

    We turned to our community of Fora Advisors for their recommendations for places to propose — including destinations, hotels and creative ideas — based on proposal trips these advisors have planned themselves. Spoiler alert: they all resulted in a ‘yes!’ 

    Interested in planning a proposal or other special event? Your Fora Advisor is there for you through all of life's big moments, from proposals to bachelorette parties to babymoons. They can matchmake you with the perfect destination and hotel, plus help with logistics and arrange special surprises along the way. Reach out to Fora to start planning today.

    1. For a warm-weather getaway… Belize or Turks & Caicos

    Wymara Resort Turks & Caicos

    Image courtesy of Wymara Resort Turks & Caicos

    It doesn’t get much better than a romantic beach vacation. We love Belize and Turks and Caicos. Both destinations offer direct flights from many U.S. cities, plus top-tier resorts with excellent accommodations and service to make planning a breeze. 

    Fora Advisor Alexandra Farrington planned a proposal trip to Belize, and pulled out all the stops to make it extra-special. 

    “I built in many opportunities for him to pop the question (private candlelit dinner at the resort, at the top of a pyramid in Caracol, sunset catamaran cruise…),” Alexandra said, sharing that she wanted to make sure he could be spontaneous. “He ended up using their scuba guide's waterproof sign during a dive at the Great Blue Hole!”

    There are plenty of great hotel options in Belize, but one particularly romantic spot is the intimate, 28-room Turtle Inn. The hotel is home to seafront cottages, two pools and a trio of restaurants, but the real standout is the white-sand beach.

    In Turks and Caicos, meanwhile, couples can create epic memories with a postcard-perfect tropical backdrop.

    “I planned a really lovely proposal at Wymara Resort Turks & Caicos,” said Fora Advisor Jennifer Schwartz.He proposed on a private sunset cruise, followed by dinner & drinks on board. It was a really easy, romantic trip.”

    Fora Perks at Turtle Inn: $100 food / beverage credit, breakfast daily, upgrade & extended check-in/out whenever possible.

    Fora Perks at Wymara Resort Turks & Caicos: $100 food / beverage credit, breakfast daily, upgrade & extended check-in/out whenever possible.

    2. For tropical vibes sans passport… Hawai'i

    sleek infinity pool surrounded by palm trees

    Image courtesy of Mauna Lani

    For a couple looking for somewhere warm and beachy, but still in the States,  Fora Advisor Ashley Vascellaro said Hawai'i is the perfect option.

    Hawai'i’s larger-than-life landscapes provide a wonderfully dramatic setting to pop the question.

    “I was able to get them on nonstop flights to Honolulu, staying at the beautiful Queen Kapiolani Hotel Waikiki Beach,” Ashley said. “I worked with the future husband to find proposal locations that wouldn’t be too crowded. I also gave him recommendations for restaurants for a celebratory dinner after the proposal.”

    Another great property in Hawai'i is Mauna Lani, an Auberge resort nestled along the dramatic Kohala Coast in the center of five mountains.

    Fora Perks at Mauna Lani: $100 food / beverage credit, breakfast daily, upgrade & extended check-in/out whenever possible.

    3. For an ultra-romantic backdrop… Santorini, Greece

    Canaves Oia

    Image courtesy of Canaves Oia Suites

    With its mind-blowing sunsets and cascading hilltops, Grecian islands like Santorini are known for their vistas — which provide captivating (and very Instagram-friendly) locations for proposals.

    “I helped plan one of my best friends’ proposals in Santorini last summer,” said Fora Advisor Candice Jankowski. “She had no clue. He proposed at the Canaves Oia Suites at their panoramic balcony, and [the hotel] could not have been better to work with!”

    Canaves Oia is one of our favorite hotel groups in Santorini (see more of our top Santorini, Greece hotels).  Canaves Oia offers several different properties, so choose the one that fits the vibe for your romantic vision. For example, Canaves Oia Suites offers the famous Santorini cliffside views, or Canaves Oia Epitome is removed from the crowds and has chic plunge pools at many of the suites. An advisor can help you choose which property fits your vision.

    Fora Perks at Canaves Oia Suites: $100 food / beverage credit (an extra $200 for stays of seven+ nights), breakfast daily, upgrade & extended check-in/out whenever possible.

    Fora Perks at Canaves Oia Epitome: $100 food / beverage credit (an extra $200 for stays of seven+ nights), breakfast daily, upgrade & extended check-in/out whenever possible.

    4. For a once-in-a-lifetime moment… a day trip surprise

    Napa Valley, California

    A day trip (complete with a spectacular experience) is a great way to punctuate a vacation and set the stage for the surprise.

    “My clients were planning to visit the Bay Area and we planned a stop in Napa,” said Fora Advisor Timadge Berkhadley. “We arranged a private balloon ride above the vineyard with a photographer, and my client proposed to his girlfriend. It was such a magical moment that they will never forget.”

    If you’re looking to extend the celebrations, opt for a stay at Carneros Resort and Spa, where guests stay in private cottages with fireplaces and private gardens.

    Fora Perks at Carneros Resort and Spa: $150 resort credit, breakfast daily, upgrade & extended check-in/out whenever possible.

    5. For a high-adrenaline adventure… a national park

    Grand Canyon national park

    For nature-lovers, a national park can act as the perfect setting for a romantic proposal and getaway.

    “Hiking is a significant way we connect as a couple, so proposing on a hike was personalized and meaningful to us,” explained Fora Advisor Anne Zdon, who planned her own proposal to her now-husband at the bottom of the Grand Canyon.

    “I wanted to be certain no one else would be around for this very private moment,” Anne said. “I popped the question on the banks of the Colorado River, halfway through the hike. He proposed right back to me.”

    A glamping experience can be the perfect complement to a national park adventure. We love Under Canvas Grand Canyon, a glamping dream just 25 minutes from the South Rim entrance.

    6. For an unexpected proposal… a staycation

    Catalina Island

    Of course, you don’t have to go far to curate the perfect proposal. A staycation offers a great setting to pop the question. 

    “I recently had clients opt for a staycation at one of the luxury hotels in town so they could elevate their [proposal] weekend without traveling far,” said Fora Advisor Alexandra Vigilante Chamberlin.

    “As travel advisors, we always make sure the hotel is looped in on the occasion. [During the staycation proposal], the bride-to-be said the service and surprises (Champagne, rose petals and sweet treats!) were above and beyond,” said Alexandra.

    Staycations add an element of luxury and novelty to the experience, and the planner — with the help of their advisor —  can organize extras (like photographers) based in the local area, making the process more seamless.  

    Katie Gooding is another Fora Advisor who organized a proposal/staycation combo, helping arrange the logistics for a fun-yet-close getaway to Catalina Island. 

    “The future bride was blissfully unaware,” Katie said. “He rented a golf cart for the afternoon to explore and we organized a photographer to capture the big moment. The future bride was surprised once again later that night with ~20 of their family & friends waiting for them at their dinner reservation!” 

    If you’re ready to plan your proposal (or special event, or staycation…), your Fora Advisor is here to help. They can plan a trip top-to-bottom or simply level-up your hotel stay with extra perks.  Reach out to Fora to learn more and start planning today.


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