Friends Who Travel Together, Stay Together: Where to Go Next

Traveling with friends is an excellent option for any vacation. You can reconnect with your friends, experience new cultures and make lasting memories. The experience can relieve stress and enhance your creativity, making it a reinvigorating opportunity for everyone in your travel group.

The hardest part is usually agreeing on where to go. What if one friend wants beaches, another wants a city, and a third wants culture and cuisine? A cruise solves that problem before it starts. With multiple destinations built into a single itinerary, everyone in the group gets their version of the perfect trip, without the group chat debate over which single place makes the cut.

“At the end of the day you’re traveling to experience a new culture, a new country, and getting out of your comfort zone,” says Zulay Labra, who’s currently planning a Tahitian cruise on Star Breeze with friends she met on another Windstar voyage. “With friends, though, you’re traveling in a comfortable way. And taking a cruise comes without the anxiety of planning everything independently.”

We’ve picked a selection of cruise regions that really do offer something for everyone to enjoy, whether it’s culinary, active exploration, big city museums or local culture. Or all of them! And at the end of the day, remember this: It’s perfectly okay to go in different directions during the day, and then reconnect for cocktails and dinner to share experiences. 

Alaska and British Columbia

Kayaking in Alaska’s Valdez./

Alaska is an unforgettable destination for your friends with diverse . The state contains a wide range of natural landmarks, from glaciers and shorelines to breathtaking mountains and crowded cities. Alaska is famous for its natural beauty and wildlife, making it an excellent option for friends who love the outdoors. Possibilities include bear trekking, kayaking, hiking, and flightseeing. This region is also well known for its fantastic microbrews; in Ketchikan, in particular, both Baleen Brewing Co. and Bawden Street are worth visiting. 

Tokyo on a mostly around-Japan voyage

Another example of the best places to go on a trip with friends is Tokyo, Japan. Asia can be a multi-faceted trip for adventurers and it’s nice to have pals along to share discoveries. Tokyo is a fast-paced and beautiful city, known for its technology, historical sites and delicious food. It has a unique blend of modernity and tradition, with new skyscrapers resting next to ancient temples.

The busy streets of Tokyo have much to offer for travelers. From endless shopping opportunities to interactive museums, you and your friends can find activities that match your interests. You could visit the Sensoji Temple, the oldest religious site in Tokyo, or explore the Tokyo Skytree. Or, you could explore Akihabara, a neighborhood dedicated to manga and electronics. No matter how you spend your time, be sure to taste Tokyo’s extraordinary food, from sushi to tempura.

Because of Japanese cabotage restrictions that require around-Japan itineraries to call in at least one foreign port, most Windstar cruises visit the fantastic “Los Angeles of Korea” city of Busan. 

Circumnavigating Iceland

Cafe hopping is a summer pastime in Reykjavik./Carolyn Spencer Brown

Iceland is a one-of-a-kind travel experience in which craggy natural scenery and cosmopolitan towns and cities. The country’s dramatic landscape features volcanoes, mountains, glaciers, hot springs and more. Its capital city, Reykjavik offers art and cultural experiences like the National Museum of Iceland and the National Gallery of Iceland. Akureyri, its second largest city, is home to the North Iceland Symphony Orchestra.

And yet, what both also offer to diverse groups of travelers is plenty of expedition-type exploring. 

What may surprise you about Iceland is how delightful are the ports that you may never have heard of. In Grundarfjordur  Snæfellsjokull National Park is magically full of regal glaciers, lava fields, waterfalls, caves, calderas, and basalt cliffs. In Seydisfjordur, spend a few hours chasing waterfalls and then attend Windstar’s exclusive Destination Discovery Event, Sagas & Songs at the Blue Church. Nested between mountains that are snowcapped even in summer and the sea, Isafjordur is a charming small town, perfect for just strolling and it’s also home to Dokkan brugghús, one of Iceland’s best breweries. 

St. Maarten/St. Martin and the Eastern Caribbean

On the French island of St. Barts, head over the mountains to the sleek village of St. Jean, where beaching it competes with shopping in chic boutiques and lavish meals./Adobe

Hankering for the Caribbean? St. Maarten, a departure port for many Windstar cruises, is part of a two-nation island. The Dutch St. Maarten is the spot for nightlife, casinos and an awesome zipline experience. The French St. Martin is better known for its culinary fusion that blends Creole and French techniques, its duty free shopping, and the lively bustle of Marigot, a market town. Both have plenty of beaches, all with different personalities and in both cases water-based sports, from kayaking to parasailing, are plentiful. And you can easily travel between the two as there’s no border control. 

Choose an itinerary that spends time in the British Virgin Islands and St. Barts for the perfect balance of sophisticated shopping and dining and just-chillin’-out. 

Costa Rica and the Panama Canal

Beach dancing in Costa Rica/

Another tropical destination for your group of friends is Costa Rica. This gorgeous location has a diverse range of nature, from rainforests to volcanoes. If you have any animal lovers in your group, Costa Rica is full of exotic wildlife you can view up close. Watch a rare bird soar through the sky or spot a shark in the blue water.

You can rest on the beautiful beaches or sample the tasty local food offerings. Costa Rica also offers various wellness activities, like immersive body wraps or hydrotherapy. It’s an ideal place for refreshing and relaxing from work or other life stressors. And once you learn new relaxation techniques, you can integrate them into your lifestyle at home. 

Athens and the Greek Isles

A pure and blissful moment in Athens: sharing a bottle of Greek rose with friends, and a view of the Acropolis — and the Mediterranean, just beyond./Carolyn Spencer Brown

Athens is a popular home port for around Greece voyages. Itineraries typically depart from Athens, so plan a pre- or post-cruise stay there before heading out to remote islands, picturesque villages and fabulous beaches. In Athens, you can immerse yourself in Greek culture and the elegant landscapes. Athens is one of the world’s oldest cities, displaying centuries of history and culture. Greece is an unforgettable vacation spot, with breathtaking landscapes and historical monuments. You and your companions can visit everything from historical temples to theatres, either on foot or on a bike. Athens has endless opportunities for dining, exploration and leisure, allowing your travel group to create an itinerary that matches your needs.

Italy’s Venice and the Adriatic Sea — in winter!

An empty gondola! One of the many appeals of a winter season cruise from Venice is there are plenty of opportunities./Carolyn Spencer Brown

There’s a lot to love about an off-season (winter) Mediterranean voyage that travels between Venice and Rome by way of the Adriatic Sea. An Adriatic cruise that departs from (or arrives at) Venice is a classic destination for world travelers.  Plan to arrange for a few days in La Serenissima before heading out to Croatia, Kotor, and Italy’s Sicily and Sorrento. Advantages to an off-season voyage? Attractions and museums are open — and uncrowded. Dining reservations are easier to secure. And discounts abound from pre- or post-cruise hotels to the voyages themselves.

In Europe, visit London, Amsterdam and Bruges on Quick Getaways 

Windstar’s small yachts allow travelers to get up close and personal with cities like London and rivers like the Thames./Windstar

New for Windstar is a series of short European sailings that are a perfect way for busy pals to commit to a trip together. Quick Getaways: Belgium: A Sweet Getaway is a four night sailing that sails down London’s Thames and visits the Belgian cities of Bruges and Antwerp before returning to London.

Other options include the four night London-based St. Malo getaway to visit Mont St. Michel, truly a bucket list destination, and Seaside Charms and Dutch Waterways, a three night trip from London to Amsterdam by way of Bruges and Harlingen. Want an onboard overnight on the Thames? The five night Timeless Maritime Powerhouses sails from Amsterdam via Antwerp and Normandy’s Honfleur, before docking in central London. 

French Polynesia’s Tahiti, Bora Bora and Huahine

In the Marquesas, a couple of friends get immersed in nature via bikes./

Tahiti is another one of the best places for travel, characterized by clear waters, thick forests, luxurious resorts and French cuisine. This remarkable island provides the ultimate relaxation experience, surrounded by warm sunshine and fresh fruit. It’s one of the best beach vacations for large groups.

One of the top ways to experience Tahiti is by cruise. You and your friends can ride through crystal-clear water to reach this paradise-like island. Once you’re there, explore the nearby waterfalls and gardens. Or, spend all day on the beach, with its pure white sands and clear blue waters.

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