Wine Tastings for Two: the 15 Best Worldwide

1.Romantic Sunset Champagne -Private- Maui Air Tour: Intimate & Spectacular!

★★★★★★★★★★5.0 · 264 reviews · 1 hour (approx.) · from $420Our pick

You’ll take a private one-hour flight for up to three people from Kahului, with a headset, live commentary, and wide views of Maui’s beaches, resorts, Molokini Crater, Kahoʻolawe, and Lahaina. Pilots including Steve and Eric have been praised for clear explanations and smooth, friendly service. A champagne toast follows the flight.

“This was as a gift for my husband, we had a blast and a Perfect view of the sunset. Steve our guide was great! 100% recommend!”

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2.Romantic Wine Tasting Experience at Koccio Valletta

★★★★★★★★★★4.5 · 259 reviews · 1.5 hours · from $57Best value

Settle into Koccio Valletta at the foot of Valletta’s photogenic steps for 90 minutes of wine, local bites, and easy conversation. You’ll taste three glasses of wine, champagne, or prosecco, with food matched to each pour. English and Italian hosts explain the drinks, and the small group is limited to eight people.

“We thoroughly enjoyed our wine tasting experience! We were visiting as a family for my mum's 60th birthday and this was one of the highlights of our trip! Our host did an excellent job of getting us seated and comfortable, before giving us a fascinating introduction to wine making in Malta and the wines we were going to be tasting. The three wines had a great variety and we really enjoyed all of them (even ordering an extra bottle!) We weren't expecting so much food! We thought we were just getting nibbles but the portions were super generous and absolutely delicious. This is a really thoughtful experience with careful wine…”

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3.Heraklion: Dia Island Romantic Sunset Cruise with Wine

★★★★★★★★★★4.8 · 144 reviews · from $86

Set sail from Heraklion on a semi-private catamaran to Dia Island. You’ll get a Prosecco welcome, cheese and cold-cut platters, fruit, unlimited wine, beer, and soft drinks, plus time to swim, snorkel, paddleboard, and watch the sunset. The crew speaks English and Greek, and private groups are available.

“everything was beautiful, the crew was friendly, and the captain was very Amazing”

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4.Private 60 Minute Romantic Air Tour with Champagne in Miami

★★★★★★★★★★4.5 · 84 reviews · 1 hour (approx.) · from $115

Fly privately from Miami Executive Airport in a Cessna 172 over Coral Gables, Coconut Grove, Miami Beach, Sunny Isles, Biscayne Bay, and Miami’s island mansions. Your pilot narrates the route through a headset, and you can toast with nonalcoholic champagne. Choose English or Spanish and a morning, afternoon, or evening departure.

“Great experience!! Safe flight, the pilot was wonderful. The flight was long enough to take lots of pictures.”

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5.Miami Beach: Private Romantic Luxury Airplane Tour With Champagne

★★★★★★★★★★5.0 · 64 reviews · 50 minutes to 1 hour (approx.) · from $138

Share a private Cessna 177 Cardinal flight for two or three people, departing Miami Executive Airport. Your pilot points out Pinecrest, Coral Gables, South Beach, Miami’s skyline, and Biscayne Bay while you enjoy Italian Champagne. Daytime and evening departures are available, with pilots such as Leo, Luca, and Valentina praised for smooth flying and clear commentary.

“Probably would’ve been great if my date didn’t dump me two hours before the flight lol 😭😭😭 Looks like it was a great time I probably would’ve been a great time but I wasn’t able to reschedule or get a credit so I may never know but I’m sure it would’ve been amazing”

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6.Romantic 1-Hour Private Flight Tour with Champagne

★★★★★★★★★★4.6 · 54 reviews · 1 hour · from $115

Fly privately over Miami in a Cessna 172 with an FAA-certified English- or Spanish-speaking pilot. You’ll see South Beach, Key Biscayne, Star Island, Palm Islands, the Venetian Causeway, and Downtown Miami, then toast with non-alcoholic Champagne. The flight lasts one hour and includes headsets, narration, and free parking.

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7.Private Romantic cruise with sparkling wine- 2-Hour- Lisbon

★★★★★★★★★★4.9 · 52 reviews · 2 hours

You and your partner sail the Tagus River for two hours aboard a yacht, with a bottle of sparkling wine included. A discreet skipper handles the boat while you take in Lisbon’s coastline. Rui and Ricardo can help time a marriage proposal, while Spanish, English, and Portuguese are available.

“Antonio et Vanda ont été fantastiques du début à la fin de notre croisière !”

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8.ROMANTIC WINE TOUR FOR 2 – Wine Tour in Chianti (Tuscany)

★★★★★★★★★★5.0 · 27 reviews · 99 days

Spend about eight hours with a private driver-guide visiting two Chianti wineries, tasting more than 10 wines, enjoying a Tuscan meal, and exploring San Gimignano. Guides including Andrea, Andrew, and Florian are praised for warm, informed service. The day includes Florence pickup, Michelangelo Square, olive oil and balsamic tastings, and free time in the medieval town.

“We had a wonderful time and Andrea was a fantastic guide! He was so knowledgeable about the area and he made us feel so welcome in Italy. The wineries he took us to were incredible and we appreciated the free time we had in San Gimignano. The wine tour was our favorite part of our trip so far.”

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9.Private 60 Minute Romantic Excursion Air Tour with Champagne

★★★★★★★★★★4.5 · 27 reviews · 1 hour (approx.) · from $115

Take a private 60-minute flight over Miami with a certified flight instructor. The route includes South Miami, Coconut Grove, Fisher Island, Key Biscayne, Miami Beach, Brickell, Bayfront Park, and the Port of Miami. Sergio is one pilot named in guest feedback. Champagne is non-alcoholic, and the flight returns to its Miami meeting point.

“We had a really wonderful experience with our pilot, Sergio! Will definitely come back again! We had a beautiful view of the Miami Beach and skyline. He made sure everyone was having a great time, and it was such a memorable experience for me and my children!”

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10.Wine tasting in a romantic castle with archaeologist guide

★★★★★★★★★★4.7 · 25 reviews · 2 hours · from $73

Meet archaeologist Fabio in Bibbona, then drive your own car along a scenic road to a romantic medieval castle near Bolgheri. Explore the private church, courtyard, and old barrel cellar before tasting four reds, one white, and olive oil. A cold cuts and cheese platter is available on request.

“Fabio is a great guide and the whole trip was very interesting and unique. We were very satisfied.”

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11.Lisbon Private Romantic 2h Cruise with sparkling wine-Day/Sunset

★★★★★★★★★★5.0 · 24 reviews · 2 hours (approx.)

Set out from Belém on a private two-hour sailing cruise for two. You’ll pass the Discoveries Monument, Belém Tower, 25 de Abril Bridge, Christ the King, and Praça do Comércio while sharing sparkling wine and water. Sunset departures offer the prettiest light, and crew members including Antonio, Mario, Carlos, and Pedro are praised for warm service.

“Wonderful & engaging crew made the incredible views of late afternoon Lisbon & a perfect sunset a memory we will always cherish. So glad we chose the private cruise.”

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12.Private day trip to the Romantic Rhine Valley with river cruise and wine tasting

★★★★★★★★★★5.0 · 22 reviews · 7 to 10 hours (approx.) · from $838

Join Florian Härtl for a private 7 to 10-hour Rhine Valley outing from Frankfurt. Visit Kloster Eberbach, Schloss Johannisberg, Rüdesheim, Rheinfels, Oberwesel, and Bacharach, then taste local wine in a cellar and cruise the Rhine for two hours. Pickup is available from your hotel, train station, or airport.

“Had an absolutely wonderful day with Florian. He was an amazing guide, very knowledgeable and he had a great day planned out for us. He had all our reservations for the day made, which made things much easier for us especially with a baby. He was great with our 5 month old, very patient and considerate of her needs. He was extremely helpful with recommendations of what wines and foods to try, and we loved everything he recommended to us!”

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13.Romantic Dinner and Wine Tasting in San Gimignano Winery

★★★★★★★★★★4.5 · 21 reviews · 2 hours 30 minutes (approx.) · from $90

Meet at Tenuta Torciano Winery near San Gimignano for a 2.5-hour Italian dinner built around Tuscan products, local wines, olive oils, and dessert. You’ll taste Chianti, Vernaccia, Super Tuscan wines, and more while enjoying truffle lasagna or ribollita, roast meat, vegetables, and cantuccini.

“An awesome experience, staff, food and wine were all exceptional. Would definetly reccomend and return”

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14.Santorini Private Romantic Tour with Dinner & Wine Tasting

★★★★★★★★★★5.0 · 21 reviews · 6 hours (approx.) · from $330

Spend about six hours exploring Santorini with a private driver-guide such as Mike, Evans, Fon, or Xenofon. Visit Oia, Firostefani, Santo Wines, Red Beach, Akrotiri, and Megalochori, with a four-wine tasting, seaside dinner, and local wine at sunset. Pickup and drop-off are included.

“I’m am very, very pleased with my excursion. Evans was absolutely the best host during our 9 hour port stop in Santorini. We were able to hit all the hot tourist spots and even some hidden gems. The wine tasting that was included was awesome. Dinner at the restaurant was awesome and the breath taking views of the island were awesome. This experience was just what we were looking for! A+ across the board!”

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15.Valle de Guadalupe Couples Wine Tour

★★★★★★★★★★5.0 · 20 reviews · 6 hours (approx.)

Spend about six hours exploring Valle de Guadalupe with a private guide and air-conditioned vehicle. Visit Villa Montefiori, Adobe Guadalupe, and Vinos Pijoan, with pickup in Ensenada or the valley. Andrea may guide your day, sharing local history and adjusting the plan for your group. Wine tastings and lunch cost extra.

“We had a blast with Andrea! We wanted to tequila taste and wine taste and she selected 2 outstanding places to visit. She has a wealth of knowledge about the Valle de Guadalupe wine region as well as the city of Ensenada. We plan to bring friends and hire Andrea as our tour guide. She was outstanding. She also is very well respected in the area and it shows as we were treated like VIP guest.”

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