Cruises in May 2027: where to go and what to expect

Where to cruise in May 2027

Best this month: Mediterranean and Europe. Each region below links to its full guide, with the lines that sail there and the ports they leave from. Ratings follow the “best time to go” advice in our destination guides.

Best this month

• Mediterranean and EuropeFrom late May, the best all-round window for the Med.
  From $592 per personChecked October 2026

Also in season

• AlaskaCheapest and quietest part of the season, long days, whale watching.
  From $284 per personChecked October 2026
• The CaribbeanShoulder season: hotter but quieter.
  Fares change daily; check current prices
• GreeceWarm days, fewer crowds; some island businesses open late.
  From $592 per personChecked October 2026
• Northern Europe, Iceland and NorwaySeason starts: quieter, snowmelt waterfalls in the fjords.
  From $1,055 per personChecked October 2026
• Panama CanalSpring repositioning, near the end of the dry season.
  From $13,738 per personChecked October 2026

Possible, with trade-offs

• BermudaWarming up, sea still cool; a quieter shoulder month.
  From $618 per personChecked October 2026
• Canada and New EnglandFewer ships and lower fares, cool days and green scenery.
  From $518 per personChecked October 2026
• HawaiiOnly Pride of America inter-island cruises, plus a few one-ways.
  Fares change daily; check current prices
• MexicoMost Pacific ships leave for Alaska; Baja and Western Caribbean trips continue.
  Fares change daily; check current prices

Holidays and school breaks

Schools are in session for most of May, which is why the month is quiet and fares are lower than in summer. The exception is the last weekend. Memorial Day is Monday, May 31, 2027, which marks the unofficial start of summer, and sailings over the long weekend are busier and priced to match. If you want a May deal, sail in the first three weeks.

Alaska cruise in May: weather and what to pack

May is the first full month of the Alaska season, and with September it has the lowest fares. Ships are quieter because schools are still in. The trade-off is temperature. Travel Alaska, the state tourism office, gives Juneau an average range of 42 to 56°F in May, five or six degrees cooler than June, and snow is still on the mountains. Days are already long, with up to 18 hours of daylight as far north as Fairbanks. Travel Alaska names May and June as the best months for whale watching.

What to wear on an Alaskan cruise in May:

• a waterproof jacket, because Southeast Alaska is rainforest and showers come in any month
• a fleece or light insulated jacket, one layer warmer than you would bring in July
• a warm hat and gloves, for the glacier day and for early mornings on deck
• shoes that can get wet
• binoculars and sunglasses

Travel Alaska’s packing advice is layers and rain gear in any month of the season. In May, expect to wear most of the layers at once at the glacier.

Travel Alaska dates the main cruise season from May to September, and some lines start earlier. Norwegian’s Seattle round trips start in late April, and Virgin Voyages starts its adults-only Brilliant Lady season in May. Our best cruise lines for Alaska ranking covers which line to pick. If warmth matters more than price, look at June instead.

Europe in May: the Mediterranean warms up

Late May and June are the best all-round window in Europe. Early May is milder and cheaper, with fewer people at the big sights, but the sea is still cool for swimming. Greece is mild, green and far less crowded than in summer, though a few island businesses open late in the spring. Orthodox Easter falls on May 2, 2027, which matters if you’re looking at a Greek sailing in the first days of the month.

Northern Europe starts its season in May: cooler and quieter, with snowmelt feeding the waterfalls in the Norwegian fjords. The midnight sun also begins this month in the far north. Visit Norway gives the first dates as May 14 at the North Cape, May 20 in Tromsø and May 28 in the Lofoten Islands.

The Caribbean, Bermuda and repositioning cruises

The Caribbean is in a shoulder season: hotter than winter, but quieter. The Atlantic hurricane season doesn’t start until June 1, so May is outside it. On the Pacific side, NOAA dates the season from May 15, and most West Coast ships leave the Mexican Riviera for Alaska.

Bermuda is warming up. Go To Bermuda gives an average of about 76°F in the air and 72°F in the water, which is pleasant for sightseeing and cool for swimming. Celebrity Silhouette starts its short 2027 Bermuda season from Cape Liberty in May.

May is also a repositioning month. Ships move from the Caribbean to Europe on transatlantic crossings, and through the Panama Canal to the West Coast for the Alaska season. These one-way trips are often good value per night, and you need a one-way flight home. In the Northeast, Holland America starts its Canada and New England season in May.

Sample May 2027 sailings

May cruise FAQ

Other months: April, June. See every month on our cruises by month page.