The Cruising Insider

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

May is when the big summer regions get going: Alaska's main season and Northern Europe's both start, the Mediterranean warms up, and late May is one of the best all-round weeks in Europe. The Caribbean enters a quieter shoulder season.

A cruise ship docked at Ketchikan, Alaska, below the mountains
Photo: Sunnya343, CC BY-SA 4.0, via Wikimedia Commons

Book it if

  • You want a cheaper, quieter Alaska cruise.
  • Late-May Mediterranean weather is your sweet spot.
  • You're after a quiet Caribbean week.

Skip it if

  • You need warm Alaska days.
  • Memorial Day week is your only option and you want a deal.
  • You want Hawaii round trips: only Pride of America sails there in summer.

Where you can cruise in May 2027

Regions with the most departures in May 2027, from the sailings we track. Each button opens Cruisebound with that region and month already filtered.

Prices checked October 2026; fares change daily. See every cruise departing in May 2027

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

Also in season

  • AlaskaCheapest and quietest part of the season, long days, whale watching.
    From $599 per personChecked October 2026
  • The CaribbeanShoulder season: hotter but quieter.
    From $333 per personChecked October 2026
  • GreeceWarm days, fewer crowds; some island businesses open late.
    From $866 per personChecked October 2026
  • Northern Europe, Iceland and NorwaySeason starts: quieter, snowmelt waterfalls in the fjords.
    From $379 per personChecked October 2026
  • Panama CanalSpring repositioning, near the end of the dry season.
    From $9,949 per personChecked October 2026

Possible, with trade-offs

  • BermudaWarming up, sea still cool; a quieter shoulder month.
    From $599 per personChecked October 2026
  • Canada and New EnglandFewer ships and lower fares, cool days and green scenery.
    From $687 per personChecked October 2026
  • HawaiiOnly Pride of America inter-island cruises, plus a few one-ways.
    From $876 per personChecked October 2026
  • MexicoMost Pacific ships leave for Alaska; Baja and Western Caribbean trips continue.
    From $316 per personChecked October 2026

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

Sample sailings departing in May 2027. From-prices per person, checked October 2026.
DepartsLine and shipNightsItineraryFromLink
May 1, 2027AmaWaterways, AmaDante77 Night Impressions Of The Seine & Paris (from Le Havre (Paris) France)$5,179Check price
May 1, 2027AmaWaterways, AmaLea1414 Night Magnificent Europe (from Budapest Hungary)$8,159Check price
May 1, 2027AmaWaterways, AmaMora77 Night Romantic Danube (Modified) (from Vilshofen Germany)$4,429Check price
May 1, 2027AmaWaterways, AmaNubia1111 Night Secrets Of Egypt & The Nile (from Luxor/Karnak (Safaga) Egypt)$6,689Check price
May 1, 2027AmaWaterways, AmaSofia1414 Night Magnificent Europe (from Amsterdam The Netherlands)$8,559Check price
May 1, 2027AmaWaterways, AmaVida77 Night Flavors Of Portugal & Spain (from Porto Portugal)$5,179Check price
May 1, 2027Avalon Waterways, Avalon Panorama77 Night Tulip Time Cruise (from Amsterdam The Netherlands)$4,951Check price
May 1, 2027Avalon Waterways, Avalon Visionary77 Night Danube Dreams (Westbound) (from Budapest Hungary)$4,076Check price
May 1, 2027Carnival Cruise Line, Carnival Dream67 Day Western Caribbean (from Galveston Texas)$638Check price
May 1, 2027Carnival Cruise Line, Carnival Elation45 Day Bahamas (from Jacksonville Florida)$463Check price
May 1, 2027Carnival Cruise Line, Carnival Jubilee78 Day Bahamas (from Galveston Texas)$861Check price
May 1, 2027Carnival Cruise Line, Carnival Magic78 Day Southern Caribbean (from Miami Florida)$658Check price

May cruise FAQ

What are the best cruises in May?

The Mediterranean from late May is our first pick. Alaska, Greece, Northern Europe and the Caribbean are all in season and quieter than in summer.

Is May a good time to cruise Alaska?

Yes, for price and whales. It’s among the cheapest and quietest parts of the season, with long days, though still cool.

What is the weather like on an Alaska cruise in May?

Cool. Juneau averages 42 to 56°F in May, with snow still on the mountains and long daylight. Expect showers and a cold wind at the glaciers.

What should I pack for an Alaska cruise in May?

Layers: a waterproof jacket, a fleece or light insulated jacket, a warm hat and gloves, shoes that can get wet, binoculars and sunglasses.

Is May a good time for a Mediterranean cruise?

Late May is one of the best windows: warm, long days and fewer crowds than July and August. Early May is cheaper, with a cooler sea.

Is May hurricane season in the Caribbean?

No. The Atlantic season runs from June 1 to November 30. The Eastern Pacific season starts earlier, on May 15.

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

Sources

  1. NOAA National Hurricane Center: tropical cyclone climatology (Atlantic season June 1 to November 30; Eastern Pacific May 15 to November 30)
  2. Travel Alaska (State of Alaska tourism): Alaska weather by month (May temperatures and daylight)
  3. Travel Alaska: Alaska cruises (season, whale watching months, what to pack)
  4. Visit Norway: midnight sun dates by place
  5. Go To Bermuda: Bermuda's monthly weather (May air and water temperatures)