Explore the world with Tipsy Travel
At Tipsy Travel, we believe the best journeys are the ones you never stop talking about. We help travelers see the world in a way that feels personal.
A few times each year, we host group adventures for travelers who crave something far beyond the ordinary. Our hosted experiences are thoughtfully designed to be unique, personal, and tailored to the group. These are not cookie-cutter vacations or everyday getaways.
With Tipsy Travel, there is always a little element of surprise that creates a big wow moment you will be talking about long after you return home.
Are you ready to island-hop through paradise, sip your way through wine country, explore iconic cities, or sail somewhere spectacular? Our upcoming group trips are where the adventure begins. Explore our current travel opportunities, find the trip that speaks to you, and get ready to pack your bags.
And for even more inspiration, visit our blog, The Travel Wino, where we share travel tips, insider secrets, destination ideas, and plenty of inspiration.
Croatia by Private Yacht
SEPTEMBER 26 to OCTOBER 3, 2026
Step aboard a private yacht and experience Croatia the way it was meant to be seen: by sea. From sparkling Adriatic waters to charming coastal towns, this is a relaxed, luxurious escape filled with beautiful scenery, effortless comfort, and unforgettable moments.
Luxury without the stress
Unpack once, settle into your air-conditioned cabin, and enjoy complimentary WiFi and the sun deck as you sail from one stunning destination to the next.
Exceptional dining at sea
Enjoy breakfast and multi-course lunches onboard daily. And a Captain’s Dinner that brings the group together for an unforgettable evening.
Relaxation at every turn
Swim in crystal-clear coves, soak in the hot tub, lounge on the sun deck, and take in the beauty of Croatia’s coastline. This is easy relaxation with just the right touch of adventure.
Windstar Cruise: Iceland
AUGUST 3 to SEPTEMBER 13, 2026
Iceland by Sea, Solar Eclipse by Land. Join us for an unforgettable cruise around Iceland, where dramatic landscapes, charming coastal towns, and once-in-a-lifetime moments come together in one extraordinary journey. After the cruise, guests may choose to extend their adventure with an optional post-cruise land package centered on the awe-inspiring solar eclipse.
A Front-Row Seat to Iceland’s Natural Wonders
Sail past glaciers, fjords, volcanic coastlines, waterfalls, and rugged scenery that feels almost otherworldly.
An Optional Solar Eclipse Experience
Extend your trip with a curated land package designed for travelers seeking to witness one of nature’s rarest and most breathtaking events.
Limited Space, Exclusive Details
Space is limited, and interest is high. Secure your spot now to receive exclusive trip details, pricing, and next-step information before availability disappears.
Croatia by Private Yacht
SEPTEMBER 2 to OCTOBER 2, 2027 & OCTOBER 3 to 9, 2027
Step aboard a private yacht and experience Croatia the way it was meant to be seen: by sea. From sparkling Adriatic waters to charming coastal towns, this is a relaxed, luxurious escape filled with beautiful scenery, effortless comfort, and unforgettable moments.
Luxury without the stress
Unpack once, settle into your air-conditioned cabin, and enjoy complimentary WiFi and the sun deck as you sail from one stunning destination to the next.
Exceptional dining at sea
Enjoy breakfast and multi-course lunches onboard daily. And a Captain’s Dinner that brings the group together for an unforgettable evening.
Relaxation at every turn
Swim in crystal-clear coves, soak in the hot tub, lounge on the sun deck, and take in the beauty of Croatia’s coastline. This is easy relaxation with just the right touch of adventure.
Summer Solstice: Alaska
June 14 to 24, 2027
Experience Alaska in a way few travelers ever do, sailing with Oceania through towering glaciers, misty fjords, charming frontier towns, and wildlife-rich waters. This hosted journey pairs Oceania’s elevated, adult-only cruise experience with the magic of the summer solstice, when Alaska comes alive under nearly 24 hours of daylight.
ONLY A FEW CABINS REMAINING
A More Refined Way to See Alaska
Sail with Oceania and enjoy an elegant, adult-focused atmosphere, exceptional cuisine, thoughtful service, and a more relaxed style of cruising.
The Magic of the Summer Solstice
Experience Alaska during one of its most extraordinary times of year, when the longest days bring extended daylight, glowing scenery, and more time to take it all in.
VIP Pricing and Exclusive Perks
Secure your spot now to receive special group pricing, valuable perks, and insider details for this unforgettable journey through America’s Last Frontier.
Christmas Market Cruise
Step into the magic of the season on a festive Christmas market river cruise, where twinkling lights, charming villages, historic cities, and cozy holiday traditions come together in one unforgettable journey.
Do Not Wait to Book. This sailing will sell out.
Holiday Magic Along the River
Explore storybook towns and iconic European cities dressed in their Christmas best, with festive markets, handcrafted gifts, warm drinks, and sparkling holiday décor around every corner.
A Cozy, Effortless Way to Travel
Unpack once and enjoy the ease of river cruising as you glide from one magical destination to the next, with beautiful scenery, comfortable accommodations, and thoughtful service along the way.
Details Coming Soon
Space will be limited, and interest is already building. Stay tuned for dates, itinerary, pricing, and exclusive perks for this festive hosted journey. Join the waitlist for early details and first access to booking.
Tahiti: Windstar Style
Set your sights on paradise as we prepare for an unforgettable sailing through Tahiti and French Polynesia aboard the Wind Star, one of Windstar’s most intimate sailing ships. Details are coming soon. This journey is designed for travelers who dream of turquoise lagoons, iconic islands, warm ocean breezes, and a relaxed, effortless luxury from start to finish.
This experience will also include optional pre- and post-add-on packages, giving you the opportunity to extend your time in paradise before or after the sailing.
An Intimate Sailing Experience
Board the beautiful Wind Star and experience Tahiti from the water, with the charm of a smaller sailing ship (only 74 cabins) and the relaxed elegance Windstar is known for.
More Time in Paradise
Optional pre- and post-add-on packages will allow guests to extend the experience, explore more of French Polynesia, and make the most of this once-in-a-lifetime destination.
Details Coming Soon
Space will be limited, and interest is already building. Stay tuned for dates, itinerary, pricing, and exclusive perks for this festive hosted journey. Join the waitlist for early details and first access to booking.
Paris & Normandy with Uniworld
Sail through the heart of northern France on an elegant Uniworld river cruise that brings Normandy’s history, beauty, and culture to life. From charming riverside towns and storybook landscapes to moving World War II sites and unforgettable French cuisine, this journey is designed for travelers who love meaningful experiences wrapped in comfort, style, and exceptional service.
History That Stays With You
Walk through some of the most powerful and important places in modern history, including Normandy’s legendary D-Day sites and memorials.
French Charm Along the Seine
Enjoy picturesque villages, scenic river views, local flavors, beautiful architecture, and the effortless elegance of sailing through France by river.
Details Coming Soon
Space will be limited, and interest is already building. Stay tuned for dates, itinerary, pricing, and exclusive perks for this festive hosted journey. Join the waitlist for early details and first access to booking.
South Africa Wine & Safari
Experience the best of South Africa on an unforgettable journey that blends world-class wine country with the thrill of safari. From rolling vineyards, exceptional cuisine, and breathtaking landscapes to exhilarating game drives in search of the Big Five, this hosted experience is being designed for travelers who want something extraordinary, immersive, and truly unforgettable.
Wine Country Worth the Travel
Sip, savor, and explore South Africa’s celebrated wine regions, where beautiful estates, rich history, and stunning scenery create the perfect start to the journey.
The Magic of Safari
Head to the wide-open wilderness as you experience the excitement of safari, incredible wildlife, and unforgettable moments in one of the world’s most iconic destinations.
Very Limited Availability
There will be extremely limited space, and it is expected to sell out quickly. Join the waitlist now for early access to trip details, pricing, and booking before they are released.
Travel Tips, Inspirations & Deals
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