A small ship Caribbean cruise in June or July takes a couple to anchorages the big ships can't reach, like Jost Van Dyke, The Baths on Virgin Gorda and the Tobago Cays, with swimming by day and dark skies at night. Go if you want quiet over casinos and you're comfortable with heat, some motion at sea, and travel insurance for early hurricane season.
The big cruise ships are floating towns. That's fine if you want a water slide and eleven restaurants. A small ship is a different animal: a few dozen to a couple hundred passengers, no lines at the gangway, and a captain who can drop anchor in a bay with one beach bar and a goat on the hill.
For couples who have done the resort thing and want something quieter, this is the idea we suggest. You wake up somewhere new most mornings, swim off the back of the boat, and eat dinner on deck while the stars come out.
Why a small ship suits a marriage
There's less to do on a small ship, and that's the point. No shows to catch, no schedule stapled to your door. The days fall into an easy rhythm of swim, lunch, nap, read, and you find yourselves talking the way you did before kids and mortgages filled every hour.
It's also easier to feel like a couple rather than a cabin number. The crew learns your names. You'll probably make friends at dinner, but you can just as easily take your plates to the rail and be alone. Nobody minds. On a boat this size, couples slipping off to the bow at sunset is part of the scenery.
June and July: the honest trade-offs
Atlantic hurricane season officially starts June 1 and runs through November. The busiest stretch is usually August through October, and June and July tend to be quieter, but storms can and do form early. Buy travel insurance when you book, read how it handles named storms, and choose a line with a clear policy for rerouting. The Grenadines sit farther south than the Virgin Islands and have historically seen fewer direct hits, which is one reason we lean toward them for summer.
It's hot. Expect highs in the upper 80s, real humidity, and warm sea water. It's also low season, so fares are often softer and the anchorages emptier than in winter. One more thing: many small ships spend summer in the Mediterranean, so there are fewer Caribbean sailings to choose from. A crewed yacht charter is another way to do it.
Where you'll anchor
In the British Virgin Islands, a week often includes Jost Van Dyke, where you wade ashore at White Bay, and Norman Island, where you can snorkel The Caves. Virgin Gorda has The Baths, a jumble of house-sized granite boulders with tide pools and grottoes you squeeze through to reach Devil's Bay. Go early, before the day boats arrive. Some routes add flat, quiet Anegada, known for its lobster.
Farther south, the Grenadines feel even more remote. Bequia's Admiralty Bay is a lovely harbor to walk around. The Tobago Cays are a marine park of small uninhabited islands and reef where sea turtles graze in the shallows. Mayreau's Salt Whistle Bay is a curve of sand about as close to a postcard as the Caribbean gets. St. Barts shows up on some itineraries too, for a very different, very polished afternoon in Gustavia.
A sample week in the Virgin Islands
Every ship runs its own route and the captain changes plans for weather, so treat this as a feel for the pace, not a promise. Many summer weeks start and end in Tortola. We'd add a hotel night before boarding, because a missed connection in Puerto Rico or Antigua shouldn't cost you the first day at sea.
- Day 1: Board in Tortola and settle in. Dinner on deck as you leave the harbor.
- Day 2: Virgin Gorda. The Baths in the morning, a lazy afternoon on board.
- Day 3: Anegada, if the route includes it. Lobster on the beach.
- Day 4: Jost Van Dyke and White Bay. Swim ashore, then a sunset back on the ship.
- Day 5: Norman Island. Snorkel The Caves and kayak around the Bight.
- Day 6: A quieter anchorage like Cooper Island. Paddleboards off the stern.
- Day 7: Last swim, last dinner, and an evening on the top deck with the lights off.
- Day 8: Off the ship in Tortola and a flight home.
Choosing the ship and the cabin
Small ships range from motor yachts to tall sailing ships with real canvas. Ask about the watersports platform: the best ones lower a deck at the stern for kayaks, paddleboards and snorkel gear, and that's where you'll spend your afternoons. Ask how many tender stops are wet landings, too, since wading ashore can be tricky on bad knees.
For the cabin, go midship and as low as you can. There's less motion there. A window is nice but not essential, since you'll live on deck. On a smaller ship, pay for the better location before you pay for the bigger room.
Stars, Sundays and quiet time with God
At anchor, far from towns, the night sky opens up. In June and July the Milky Way stretches overhead and Scorpius hangs low in the south. If you can, book a week near the new moon. Ask the crew whether they'll dim the deck lights. Lie on a lounger and look up for a long time.
Mornings are the easy time for a devotional, before the heat and the snorkel boats. Coffee, a psalm, a prayer for each other. If your ship is in port on a Sunday, the islands have old churches, often Anglican or Methodist, where visitors are welcome. If you're at sea, hold your own short service on deck.
Practical tips
Small ships move more than big ones. Even calm water between islands can bring a roll on the open passages, so talk to your doctor before you go about seasickness remedies and bring them along. The first day or two is usually the hardest. After that most people find their sea legs and stop noticing.
- Reef-safe sunscreen, a rash guard and a wide hat.
- Water shoes for rocky landings and The Baths.
- A dry bag for phones on tender rides.
- Light, loose clothes. Nobody dresses up much.
- Check current passport and entry requirements for every island on the route.
- Drink more water than you think you need.
Questions couples ask
Is June a good time for a Caribbean cruise?
It can be. June is the start of hurricane season, but early summer is usually quieter than August through October. Expect heat and humidity, fewer crowds and often lower fares. Buy travel insurance when you book and read how it covers named storms.
What is a small ship Caribbean cruise like?
It's quiet and casual. Ships carry anywhere from a few dozen to a couple hundred guests, anchor in bays big ships can't enter, and often have a platform at the stern for swimming, kayaks and paddleboards. Evenings are dinner on deck and conversation, not shows.
Do you get seasick on a small cruise ship?
Some people do. Small ships move more than big ones, especially on open passages between islands. Choose a cabin midship on a low deck, keep your eyes on the horizon, and ask your doctor about remedies well before you leave home.
Which Caribbean islands can small ships visit that big ships can't?
Places like Jost Van Dyke, Norman Island and Anegada in the British Virgin Islands, and the Tobago Cays, Mayreau and Bequia in the Grenadines. Most of these anchorages are too shallow, small or remote for large cruise ships, which is why they feel so peaceful.
How long should a small ship Caribbean cruise be?
Seven nights is the sweet spot. It gives you five or six anchorages without rushing, and enough days to settle into the slower pace. Shorter trips tend to feel like you just arrived when it's time to pack. Ten nights works too if you can combine two island groups.
Can Covenant Retreats plan a small ship Caribbean cruise for us?
Yes. We plan this as a private trip for two: choosing the ship and cabin, flights, a hotel night before boarding, and insurance advice. It's also a trip we'd love to host as a small group retreat. Tell us what you want on our Plan With Us page and we'll plan it.
This is one of our ten romantic getaway ideas for married couples, arranged by season. Before this one on the calendar: California Coast by Train.