Ocean Cruises: Explore the World by Sea

Best for: repeat premium cruisers, multi-generational families, couples who want one trip that handles five ports without a five-airport itinerary.

This is what most people picture when they hear “cruise” — large premium ships from Princess, Holland America, Celebrity, Royal Caribbean, Disney, Norwegian, and Virgin Voyages. They earn their keep on three things: cabin variety (an inside cabin for the teenager, a Sky Suite for the grandparents, a balcony for you), ports per dollar, and the practicality of unpacking once.

Where Trey adds value: matching the right line to the trip — Princess and Holland America for Alaska, Celebrity for Mediterranean food and design, Royal for multi-gen families, Virgin Voyages for adults-only — and then sitting on hold with the cruise line so you don’t have to. Promotions, pre-cruise hotel blocks, dining reservations, and onboard credit get handled without the back-and-forth.

What these ships do well:

• Three or more ports across one fare, with a single unpack.
• Cabin range from interior to multi-bedroom suite — useful for families booking three generations on one deck.
• Full-day kids’ and teens’ programming on Royal, Disney, and Princess so adults get adult time.
• Specialty dining, named-chef restaurants, and quiet adults-only spaces on Celebrity, Princess Premier, and Virgin Voyages.
• Itineraries that pair beach and city — Med, Caribbean, Mexico, Alaska — without flying between each one. 

Best for: experienced cruisers ready to step up from premium; 60+ travelers with the time for longer itineraries; couples celebrating a milestone; and discerning first-timers who’d rather start at the top.

Small-ship and luxury ocean cruising is a different animal. Fewer than 800 guests, suite-only or near-suite-only accommodations, and fares that include the things premium lines charge for — specialty restaurants, beverages, gratuities, and on most lines, shore excursions.

The differences between the lines matter:

• Oceania — best food at sea in this tier, classic country-club ambiance, longer itineraries, smart for the experienced premium cruiser stepping up.
• Regent Seven Seas — all-suite, all-balcony, truly all-inclusive (excursions, business-class air, pre-cruise hotel). The choice when a guest wants nothing on the bill at the end.
• Silversea — quietly elegant, strong on smaller ports, particularly good in the Mediterranean and Asia.
• Seabourn — yacht-like ambiance, excellent service ratio, strongest for couples who want a more social ship without it feeling like a resort.
• Crystal — relaunched, classic-luxury feel, longer voyages, returning Crystal loyalists and World Cruise–curious clients.

Trey will tell you which one of these you’ll actually enjoy — based on whether you want assigned seating or open dining, whether you fly business class on points or want it included, and whether your travel companion would rather hike a glacier or settle in for a wine pairing.

Best for: travelers who’d rather be on a Zodiac than at a martini bar; experienced travelers crossing one of the polar regions or the Galápagos off a long-held list; couples and solo travelers comfortable on a 200-guest ship for two weeks.

Expedition is the trip where booking through an advisor pays for itself. The window for Antarctica is November through March, the Arctic and Svalbard runs roughly June through August, and the Galápagos sails year-round but reads very differently in green season versus dry. Cabin categories matter more here than anywhere else — a forward-facing suite for ice cruising, a lower deck for the rough Drake Passage, a yacht-class category for the Galápagos.

The lines we book most often:

• Lindblad Expeditions–National Geographic — strongest naturalist team and photographic program.
• HX (formerly Hurtigruten Expeditions) — strong in polar regions, hybrid-powered ships, more relaxed price ceiling.
• Viking Expeditions — newest fleet, design-led, well-suited to first-time expedition cruisers.
• Silversea, Seabourn, and Ponant — for clients who want expedition itineraries with luxury-cruise hotel standards onboard.

Most clients do this trip once. Trey plans them as if it’s the only chance you’ll have to get it right — including the air, the pre-cruise night in Buenos Aires or Quito, and the parka that arrives at your stateroom.

The best cruises don’t end at the gangway. A few extra nights on either end is the difference between watching Rome from a coach window and actually having dinner at a Roman trattoria the night before you board.

Trey will plan the land days as carefully as the sailing — a private guided morning at the Vatican before a Civitavecchia embarkation, two nights in Bordeaux’s wine country before a river-meets-ocean repositioning, an Iceland Ring Road drive after a Reykjavik turnaround, or a long weekend in Vancouver before sailing for Alaska.

1. Flight delays. A same-day arrival into Barcelona or Vancouver puts your cruise at the airline’s mercy. One pre-cruise night solves it.
2. Jet lag. Boarding a transatlantic ship at 3 p.m. after an overnight flight is the wrong way to start two weeks. One night ashore changes the whole trip.

Shore excursions, planned the way you’d want them

Cruise-line excursions are built for the lowest common denominator: 50-person coaches, the same lunch spot, and a guide who is not the one you’d hire if you were planning the day yourself. They have their place — sometimes the cruise line really does have the best Skagway helicopter slot — but on most ports, you can do better.

Trey works with private and small-group operators in cruise ports across Europe, Alaska, the Caribbean, the Mediterranean, and beyond — the same operators a luxury independent traveler would book in the same city. A few of the moments that come up often: a sunrise visit to the Acropolis before the Athens crowds, a private guide for the day in Florence, a chartered RIB to a quiet beach in St. Barth’s, a glacier helicopter and dog-sled day in Juneau, and a wine country drive out of Auckland with a producer Trey knows by name.

All of it stays coordinated with your sailing — pickup at the pier, return well before all-aboard, and a backup if a tender day goes sideways.