An extended, adventurous date is ripe with opportunity for exploration. As one of my long-term friends explains it, these novel experiences bring out unexpected and delightful parts of ourselves that we didn’t know existed.
Below are a few bucket list date ideas I have in mind for exploring the world, and each other, together.
Dream Dates
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Let’s pretend we’re in Renaissance Italy and attend the Venice Carnivale. A mask-making workshop would be essential. After all, we’ll need it for masked ball, which, by the way, is held in a 15th century palace.
Let’s take a private helicopter tour of the Matterhorn, landing on a glacier for a champagne picnic. Continue to a luxury mountain chalet for a private fondue experience with vintage wines.
Charter a luxury yacht along the Amalfi Coast for a half or full day, stopping at hidden coves for swimming. We could also have a personal chef prepare freshly caught seafood as we watch the sunset over Positano.
The famous Neuschwanstein is the inspiration behind the famous Disney castle, and for good reason too – it looks like an absolute fairy tale! While we can’t stay in the actual castle, we can always enjoy a luxurious evening or three at Hotel Das Rübezahl, with a suite that looks out over the mountains.
Lisbon Hidden Fado
Explore the winding streets of Alfama, stopping at a tiny, family-run tasca for dinner where locals spontaneously break into fado songs. End with port wine tasting in a historic cellar.
Alpine Lake Romance
Charter a vintage steamboat on Lake Como, stopping at private villas for wine tasting, with a personal chef preparing northern Italian specialties.
Loire Valley Château Romance
Charter a private hot air balloon at dawn over the Loire Valley châteaux, landing at a private vineyard for a wine tasting of rare vintages. Continue with a personal driver to tour hidden château gardens closed to the public, ending with a candlelit dinner in a medieval castle tower prepared by a renowned local chef.
French Riviera Villa Soirée
Reserve an exclusive Belle Époque villa at the Four Season in Cap Ferrat with panoramic Mediterranean views. Begin with a private yacht cruise along the coast, stopping for swimming in secret coves. Return to the villa for a sunset cooking class with Michelin star chef Yoric Tièche, learning to make traditional Provençal dishes. Enjoy dinner on the terrace with a string quartet performing, followed by a private screening of a classic French film in the villa's garden cinema.
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Book the underwater restaurant Ithaa for a private dinner, then retire to an overwater villa with a personal butler and midnight spa treatments under the stars.
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Countryside Escape in Oxfordshire
I might be the only girl I know who’s never stayed at Estelle Manor. Appalling that I’ve never been taken here, never gone on a forestry falcon walk, haven’t enjoyed their Roman baths, haven’t blown anyone’s mind in their gorgeous suites. Please, I beseech you, let’s remedy this immediately.
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Blackberry Farms, Tennessee
Let’s reserve a vintage convertible and head to Tennessee’s countryside for a weekend of wine tasting, horse riding, hiking, paddle boarding and farm-to-table fare. I promise I look adorable in overalls and braids!
Southern Gothic in Savannah
Rich with history and culture, Savannah is top of my list to explore. Let’s check in to Perry Lane Hotel or the Mansion on Forsyth Park, take our time exploring the historic district, or join a guided ghost tour through cobble-stoned streets.
It’s important to me to understand America’s complex history, and I have a keen interest in exploring plantations ethically.
Romantic Weekend in upstate NY
Let’s head out of the city and upstate to Maker Hotel, a design lovers dreams with reportedly the best beds in NY. After breakfast at the Maker’s on-site bakery, we could wander down town for some antique shopping, explore the areas nearby waterfalls, or check out the Hudson-Athens Lighthouse.
Twin Farms, Vermont
300 acres of serene birch forest awaits us at Twin Farms, Vermont, an intimate, all-inclusive retreat at the foothills of the Green Mountains. My favourite part about the restaurant at this farm is that there is no menu, and they cook for you based on vibes and requests alone. They also have a spa onsite, featuring a honey scrub-down from local honey. Just adorable.
CITY RECOMMENDATIONS
San Francisco
Museums: de Young Museum, Legion of Honor, Book Binders Museum
Fine Dining: Atelier Crenn, Benu, Shizen, Anomaly, Acquerello, Californios
Theatre/Ballet: War Memorial Opera House (SF Ballet, SF Opera), Davies Symphony Hall (SF Symphony), Magic Theatre (experimental works), ODC Theater (contemporary dance)
Historical: Victorian architecture in Pacific Heights, walking tour of downtown SF
Day spas: Reméde Spa at The St. Regis San Francisco
Nature: Muir Woods
Seattle
Museums: Seattle Art Museum, Chihuly Garden and Glass
Fine Dining: Canlis, Altura, The Herbfarm, Willmott's Ghost, Surrell, Aerlume
Theatre/Ballet: Seattle Opera and Pacific Northwest Ballet (McCaw Hall), Seattle Symphony (Benaroya Hall), On the Boards (experimental performance), Cornish Playhouse (interdisciplinary arts)
Nature: Discovery Park
Chicago
Museums: Art Institute of Chicago, Chicago Architecture Center, International Museum of Surgical Science, Driehaus Museum (Gilded Age mansion), Chicago History Museum's diorama room
Fine Dining: Cariño, Alinea, Indienne, Oriole.
Theatre/Ballet: Lyric Opera, Chicago Symphony Orchestra (Orchestra Hall), Lookingglass Theatre (physical storytelling), Chicago Shakespeare Theater on Navy Pier
Historical: Chicago History Museum, Architecture boat tours, Graceland Cemetery (architect-designed monuments), Gangsters and Ghosts Tour
Architecture: Frank Lloyd Wright homes in Oak Park, The Richard H. Driehaus Museum
Day spas: Aire Ancient Baths, The Spa at Four Seasons, The Peninsula Spa & Wellness Center, The St. Regis Spa
NYC
Museums: Metropolitan Museum, MoMA, Guggenheim, Frick Collection, Morgan Library (medieval manuscripts), Tenement Museum basement tours, The Cloisters (medieval art in park setting), NYC historical society
Fine Dining: Eleven Madison Park, Chef's Table at Brooklyn Fare, Per Se, Daniel, Ying Tao, L’Abeille.
Theatre/Ballet: Broadway theaters, Lincoln Center (Met Opera, NYC Ballet, NY Philharmonic), Life and Trust (immersive theater), New York Transit Museum
Historical: NYC Catacombs, City Hall Station (abandoned subway stop tours)
Day spas: Aire Ancient Baths, The Spa at Mandarin Oriental, Spa de La Mer at The Baccarat Hotel
Boston
Museums: Museum of Fine Arts, Isabella Stewart Gardner Museum, Harvard Museum of Natural History (glass flowers), MIT Museum, Boston Tea Party Ships, historical tour of Boston Public Library
Fine Dining: Deuxave, Amar, La Padrona
Theatre/Ballet: Emerson Colonial Theatre, Boston Symphony Orchestra (Symphony Hall), Boston Ballet, American Repertory Theater (experimental productions), Boston Lyric Opera (smaller opera company)
Historical: Forest Hills Cemetery (sculpture garden cemetery), Boston Athenaeum (private library tours), Charles River Esplanade
Day spas: Mandarin Oriental Spa, Four Seasons Spa
Other: Boston Market District, Brattle Book Shop, Boston Public Garden