One of the most appealing things about taking a cruise is getting to visit several new islands or cities during a single vacation. Cruise often enough, however, and you’ll likely double back on ports you’ve already seen. But is that always a bad thing?
Not if the port is a place with lots of sights and activities that can’t all be enjoyed during a single visit. That means certain places are definitely worth going back to on another cruise. Here’s a helpful guide to the nine best cruise ports for repeat visits — and yes, I’ve been to all of them multiple times.
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Barcelona
If you’ve cruised the Mediterranean, chances are good you’ve already been to Barcelona since many ships use it as a home port for the season. I’ve visited six times — including several precruise overnight stays — and I’ve yet to experience everything in this sprawling city filled with architectural landmarks, lush parks, world-class museums, inviting tapas bars and even a beachfront boardwalk.
Perhaps the biggest attraction in Barcelona is architect Antoni Gaudí’s soaring La Sagrada Familia, still a work in progress almost 100 years after his death. (It’s scheduled for completion in 2026.) I’ve visited this landmark each time I’ve been in Barcelona, first in 2005 and most recently in 2022, and I always find something new to appreciate in its towering, whimsical interior.
If you like Gaudí’s style, take advantage of a repeat visit to Barcelona to explore his other creations. You can admire the art nouveau flourishes and alien-looking rooftop chimneys of La Pedrera (aka Casa Mila), an apartment building on the Passeig de Gracia, and the colorful mosaics and sculptures of the whimsical Park Guell.
Many folks walk up and down Las Ramblas on their first visit, but take time on a return trip to further explore The Gothic Quarter, home to Barcelona’s 15th-century cathedral (La Seu), edgy art galleries and bustling tapas bars. Also within walking distance of the port are the Barcelona Aquarium and Barceloneta Beach.
If you’ve seen the city and prefer green spaces, check out Montjuic. This mountaintop park with sweeping city views is home to the Joan Maragall Gardens and the Barcelona Botanical Garden, plus a half-dozen museums, including the Fundacio Joan Miró and the National Art Museum of Catalonia.
Boston
I’ve visited Boston just once on a cruise, in September 2023 during a Canada and New England sailing, but it was my sixth or seventh time in the city. I approached the day without any been-there, done-that frustration because Boston — a city that buzzes with both historic charm and modern-day energy — always has something new to discover.
Boston’s top sights — including Fenway Park, the Isabella Stewart Gardner Museum, the 18th-century USS Constitution, the kid-approved Museum of Science and the John F. Kennedy Presidential Library and Museum — are scattered around the city, so you might not get to all of them in one port stop. If you’ve managed to see them all, a DIY walking tour is a great way to spend a return visit if the weather is nice.
Most cruise lines offer free shuttles from the Flynn Cruiseport to a central location, typically near Faneuil Hall and Quincy Market. That’s perfect if you’re looking to explore a few neighborhoods or take a walk back in time along the 2.5-mile Freedom Trail.
I suggest you start at the Boston Common, America’s oldest park, created in 1634. Look for its newest artistic landmark, The Embrace, a massive 65,000-pound abstract bronze sculpture modeled after a 1964 photo of Rev. Martin Luther King Jr. and his wife, Coretta Scott King.
At the nearby Granary Burying Ground, you can pay your respects to Paul Revere and several signers of the Declaration of Independence, including John Hancock and Samuel Adams. Across the footbridge, you can wander through the neighboring Public Garden and ride the whimsical pedal-powered Swan Boats that have been in operation since 1877.
Don’t miss the charming Beacon Hill and Back Bay neighborhoods, especially the lavish late-19th-century townhouses along Commonwealth Avenue. Trudge to the Old North Church for a refresher on Paul Revere’s 1775 midnight ride.
Reward yourself for getting your steps in with a bowl of creamy New England clam chowder at the Union Oyster House, established in 1826. Across the street in Union Street Park, you’ll discover the New England Holocaust Memorial. This free outdoor installation features six glass towers etched with numbers representing the tattoos of millions of Holocaust victims, as well as quotes from survivors.
Cabo San Lucas, Mexico
Quite a few sun-and-fun cruise ports offer the same-old options — the beach, a snorkel tour or duty-free shopping — but Cabo San Lucas on Mexico’s Baja Peninsula features so many activities it’s possible to visit multiple times and not do the same thing twice. Since Cabo is a premier port on both Mexican Riviera cruises and Panama Canal transits, it’s a safe bet frequent cruisers might find themselves here more than once.
What can you do in Cabo? On my first visit, I enjoyed a catamaran sail to see the destination’s best-known landmark: the photogenic El Arco natural stone arch and adjacent Lovers Beach. Both are located where the Pacific Ocean meets the Sea of Cortez — a spot where barking sea lions also love to gather. If you visit from December to March, you also might see the humpback and gray whales that winter here; alternately, you can book a whale watching tour to get a closer look.
Other popular water-based activities include glass-bottom boat tours and sport fishing. While the Pacific isn’t as snorkel-friendly as the Caribbean, it is possible to snorkel in the calm waters of Chileno Bay.
If you’ve crossed sightseeing from the water off your must-do list, you can dive into Mexico’s food and beverage culture on a repeat visit to Cabo. A tequila tasting is a must for anyone who craves authentic local flavors and can be enjoyed on its own or in combination with a cooking class or a salsa-making (and salsa dancing) class. Or, skip the tour and visit one of the many bars and eateries near the Cabo San Lucas Marina, where you can pair a salt-rimmed margarita with fresh Baja-style fish tacos.
For something more active, spike your adrenaline during an off-roading adventure, or go old-school with a horseback or camel ride along the beach. Have an artsy side? Options include excursions to San Jose del Cabo, known for its historic Mission (one of Baja’s oldest) and Arts District with eclectic galleries, or to Todo Santos, a quaint Baja village filled with shops and galleries.
Charlotte Amalie, St. Thomas
It’s hardly a secret that Eastern Caribbean cruises can get repetitive, especially the itineraries on the newest megaships, which due to their size can call on only a limited number of ports. One of them is Charlotte Amalie on St. Thomas in the U.S. Virgin Islands, which welcomes 1.5 million cruise passengers a year and can accommodate up to six cruise ships in port daily.
I’ve been to St. Thomas five times, most recently on a cruise in 2019, and have yet to try all the activities on offer. The island offers both thrills (including zip lining, snorkeling and helmet diving) and chills (such as beach time, daiquiri-sipping and duty-free shopping). Plus, you can tick another island off of your bucket list by visiting neighboring St. John for an island tour or snorkel excursion to stunning Trunk Bay.
If spotting sea creatures is your thing, you can snorkel off of Sapphire Beach or in Christmas Cove or sail on a catamaran to a reef teeming with fish and coral. You can also bump up the adventure with a Sea Trek helmet dive at Coral World Ocean Park (the full-head apparatus allows you to walk along the ocean floor on a guided tour) or book a scuba dive to offshore reefs.
Prefer to stay atop the water? St. Thomas offers sea kayaking tours or, for a bigger adrenaline kick, flyboarding (where you strap your feet onto a water-powered hoverboard and blast out of the water to seemingly fly above it).
Crescent-shaped Magens Bay Beach on the island’s north coast is St. Thomas’ premier sunbathing spot; the panoramic view from Drake’s Seat on the ride there is awesome, too. For a repeat visit, consider taking a 15-minute ferry ride from the Crown Bay cruise port to Water Island, where you can walk to Honeymoon Beach with its shaded palapas and beach bar or head to the island’s east side to enjoy a swim from white sand Sapphire Beach.
If you’re not afraid of heights, you can board a gondola for a ride to Paradise Point for panoramic harbor views from an elevation of 700 feet. Another thrilling option is a zoom above the treetops in a harness during a zip line adventure.
Copenhagen
The major ports of Northern Europe are all ideal for fans of art, culture and architecture, but Copenhagen tops my list for a repeat visit because it also adds culinary creativity and contemporary design to the mix. I’ve visited the canal-laced capital of Denmark three times on cruises, spending a total of seven days — and I’ve yet to see everything.
Perhaps that’s because I’m always drawn to three places. The world’s longest pedestrian street, Stroget, is lined with shops and casual eateries and cuts through the city’s historic center. The much-photographed Nyhavn harbor, where buildings date to the 17th century, offers outdoor cafes that are a magnet for both locals and visitors. The delightful Tivoli Gardens, a nearly 200-year-old amusement park, entices with its extraordinary landscaping, twinkling lights and wonderful dining options (from traditional Danish specialties to international favorites).
I’ve also enjoyed a canal cruise on each visit because it’s both inexpensive (about $15) and offers a terrific overview of the city’s architecture. Sights include the colorful facades of Nyhavn, the unique spire of the Church of Our Savior, the strikingly modern Royal Danish Opera House and the tiny Little Mermaid statue honoring native son Hans Christian Andersen.
Copenhagen also has a regal side, since Denmark is home to one of the world’s oldest monarchies. Experience the pomp firsthand at Amalienborg Palace, the official residence of the royal family; visit at noon for the ceremonial changing of the guard. Rosenborg Castle, meanwhile, is home to 400 years of Danish treasures, including the crown jewels.
Museums are another way to absorb Denmark’s rich artistic and cultural heritage. Statens Museum for Kunst — National Gallery of Denmark houses a collection of Danish and international art, while Copenhagen Contemporary showcases installations from well-known artists and emerging talent. The Designmuseum Danmark features centuries of fascinating objects and special exhibits dedicated to Danish Modern furniture and home design.
Foodies, meanwhile, can follow their noses to an eclectic array of eateries, including street carts selling polser (the Danish version of the hot dog), cafes serving smorrebrod open-faced sandwiches and fresh herring, and 17 Michelin-starred restaurants.
Kahului, Maui
Of all the Hawaiian Islands, Maui offers visitors the most versatility. Not only does its coastline change from golden sand to black lava, but its interior varies from lush valleys to volcanic craters. I’ve been to Maui five times — twice on a cruise — and have spent 16 days enjoying its beaches and top tourist sights. Maybe I’m beginning to sound like a broken record, but, again, I still haven’t done everything.
If you haven’t yet been to the top of Haleakala, the 10,023-foot dormant volcano that dominates Maui’s landscape, book a tour that offers panoramic views from its summit or lets you bike down its slopes. A whale watching excursion to spot humpbacks is an ideal choice from December through April; if the whales are off to their summer home, you can book a dolphin-watching tour instead. You can also enjoy a snorkel excursion to Molokini Crater or the nearby island of Lanai, where spinner dolphins and sea turtles are common sights.
Another Maui highlight is the Road to Hana, the infamously narrow and curved route that leads to the bucolic east Maui town of Hana with its dramatic black-lava beaches. If you’re prone to motion sickness, you’ll want to skip the road’s 59 one-lane bridges and 620 hairpin turns.
If you’re an independent type, you can rent a car near the port in Kahului and see a lot in one day. Visit scenic Iao Valley before heading to Upcountry on the lower volcanic slopes of Haleakala. There, you’ll find the historic cowboy town of Makawao, home to craft shops and the T Komodo Store and Bakery (get there early before the cream puffs sell out), as well as Ali’i Kula Lavender and Surfing Goat Dairy.
Back at sea level, especially if cruising with younger kids, a fun alternative is the Maui Ocean Center, The Aquarium of Hawaii. It features an array of native and endemic marine species. And did I mention Maui’s incredible beaches? You can visit them over and over again and never tire of their white sand beauty.
Naples, Italy
Discovering the complex beauty of Naples during a 2023 Mediterranean cruise was a revelation. I’d been “through” Naples three or four times before — on my way to Capri and the Amalfi Coast — but I’d never actually explored the city. What I learned is that Napoli, Italy’s third-largest city, is more than just the birthplace of pizza and the gateway to Pompeii. Its superb architecture, fascinating history and cache of archaeological treasures have all helped to inspire a recent tourism renaissance.
Naples has something for everyone. History buffs, shoppers and foodies will all enjoy a stroll along the narrow pedestrian street called Spaccanapoli in the city’s historical center. Walking here, you’ll feast your eyes on everything from intricate architectural details and bakery windows lined with cream-filled pastries to two landmark churches: the 15th-century Chiesa del Gesù Nuovo, with its fortresslike facade, and the Cappella Sansevero, a Baroque church known for its sculptures.
More monumental architecture from the 16th to 19th centuries awaits across town, including the ornate Teatro di San Carlo opera house and the elaborately domed Galleria Umberto I shopping arcade. The lavish Royal Palace of Naples was once home to the kings and queens who ruled the kingdom of Naples until the 19th century.
Naples has terrific museums and castles, too. Topping your list should be the National Archaeological Museum of Naples, which counts among its treasures the Roman artifacts from Pompeii. In the medieval Renaissance fortress of Castel Nuovo, you can find a collection of Italian frescos and paintings.
Beyond navigating Naples’ fascinating urban mosaic, you can hop a fast ferry from the cruise port to the isle of Capri. There, take the funicular to chic shop-lined Capri Town, where scenic walkways fan out to stellar viewpoints. You can also take ferries to Amalfi Coast towns, including Sorrento and Positano, or book a tour to see the ruins of Pompeii.
Just remember: Before leaving Naples, enjoy one of the city’s crispy thin-crust pizzas — or make that the reason for your return visit.
San Juan, Puerto Rico
My second Caribbean cruise in 1998 embarked in San Juan, and I’ve been back eight times since — with Old San Juan being my default setting for a day in port. Why? This colorful 500-year-old neighborhood is the perfect spot to explore on foot, has a lively vibe and offers something for history buffs, foodies and souvenir-hunters alike.
On the history front, there’s no missing El Morro (officially Castillo San Felipe del Morro), the hulking fortress set on a promontory overlooking Old San Juan. Other centuries-old sights include the Cathedral of St. John the Baptist, constructed in 1540, and Casa Blanca, San Juan’s oldest residence. The latter was built in 1521 for then-governor Juan Ponce de León and is now a museum.
Whenever I’m in Old San Juan, I always stroll the shaded Paseo de la Princesa to the walkway between the sea and the city’s old stone walls that passes beneath the Tiffany-blue La Fortaleza. Completed in 1540, it was originally a fort and prison but was converted to a palace that serves as the governor’s official residence. I reenter through the Puerta de San Juan, a massive red gate, and make my way to vibrant Calle de la Fortaleza (famous for its overhead art installations) to snap a few photos.
If you’ve already seen Old San Juan, try a foodie walking tour to sample local specialties, such as garlicky mofongo (mashed plantains) and a creamy pina colada (which was invented here), or a bike tour from Old San Juan to Condado. This lively beachfront neighborhood is lined with resorts, bars and restaurants.
Beyond San Juan itself, a port call in Puerto Rico offers snorkeling at Escambron Marine Park, a surf lesson at Isla Verde beach and exhilarating all-terrain-vehicle or zip line adventures. Nature lovers can also book a tour of El Yunque National Forest, the only tropical rainforest in the U.S. forest system.
Vancouver, British Columbia
Just because you’ve visited Vancouver before on an Inside Passage sailing to Alaska doesn’t mean you shouldn’t return on a Pacific coast cruise or even another Alaska itinerary. My three visits to this sophisticated city that’s surrounded by the beauty of British Columbia’s mountains-meet-sea wilderness have each been filled with remarkably different experiences — from totem poles and Chinese gardens to whale watching and sky-high gondola rides.
One option for a return visit is a stroll through Vancouver’s downtown neighborhoods. Gastown, the city’s historic core, offers heritage architecture, avant-garde galleries, fashion boutiques and trendy bars, restaurants and music venues. Don’t miss the Gastown Steam Clock, which looks like an antique and sounds and steams every 15 minutes. In Chinatown, you can visit the Dr. Sun Yat-Sen Classical Chinese Garden, which replicates Ming Dynasty-era traditions and is the first of its kind outside of China.
For a more nature-based wander, follow the shoreline all the way to Stanley Park on the Seawall Water Walk. (It’s a bit of a hike — bike rentals are an option.) Once in the 1,000-acre park, check out its First Nations totem poles, pretty gardens and city skyline views. Families especially might wish to visit the park’s Vancouver Aquarium to spy on sea creatures large and small or head to Second Beach to take a dip or splash in the fountains.
Take your sightseeing to greater heights with a seaplane tour — or stay grounded and simply watch the planes take off and land in the harbor. Flyover Canada (in Canada Place) only requires you to strap into a flight motion seat to virtually soar above the stunning landscapes of the Canadian Rockies.
Whether you’re hungry for a taste of Vancouver or a souvenir, head to the Granville Island Public Market, which features local food outlets, farmers market stalls and artisans selling handcrafted items. Vancouver is also known for its inventive food trucks, serving everything from hot dogs infused with Japanese flavors to tasty tacos.
And then there’s the great outdoors. On my last visit in April 2019, I finally got around to doing two Vancouver activities I hadn’t done before. I took the Skyride to the summit of 4,039-foot Grouse Mountain to enjoy lunch with a panoramic view (if you’re lucky, you’ll glimpse one of two resident grizzly bears), and I explored the trails and dizzying elevated walkways at Capilano Suspension Bridge Park. The fresh mountain air sealed the deal. I’ll definitely head back to Vancouver for more.
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