A short sailing from Miami that fits a long weekend: Key West's sunsets and Hemingway's house, then a beach day in Nassau, with a day at sea to try the ship. Ideal for a first cruise or a quick escape from winter.
Cruise route for your dates
5 days from Sat, Dec 5.
- Day 1 Miami · board the ship
- Day 2 Key West · a day ashore
- Day 3 Nassau · a day ashore
- Day 4 At sea
- Day 5 Miami · leave the ship
Good to know
- US citizens can sail this closed loop with a birth certificate and government photo ID; a passport is safer if you might need to fly home.
- Key West is walkable from the pier; Nassau's best beaches need a short water taxi or cab.
- Hurricane season (June to November) brings lower fares and the occasional swapped port.
Eat this
Places the planner can use
Mark places as a must or something to skip. The itinerary is built only from this list; ★ marks the destination’s highlights.
Wide white-sand beach backed by neon Art Deco hotels — busiest, and best for people-watching, between 5th and 15th Streets.
Pastel 1930s hotels with porthole windows and neon trim, packed into a few square blocks — worth a guided walk for the history.
Cuban coffee windows, cigar rollers and domino players at Máximo Gómez Park — go for a cortadito and stay for the music.
The unofficial city hall of Cuban Miami — go for a ropa vieja plate or just a window cortadito and pastelito.
Nightly celebration with street performers, vendors and a Gulf sunset.
Bars, live music and the famous Sloppy Joe's.
Writer's former home with six-toed cats and a lush garden.
Photo stop at the buoy marking the southern tip of the continental US.
Half-day boat trips to the only living coral barrier reef in the continental US.
Climb 88 steps to the top of the lighthouse for sweeping views over the island and the Gulf and Atlantic.
Compare slices at Kermit's or Blue Heaven; the best are tart and on graham crust.
Long white-sand beach on Paradise Island with calm water, loungers and water-sports rentals.
Colorful seafood shacks serving cracked conch and conch fritters, with local beer and music.
Largest of Nassau's forts, with dungeons and ramparts overlooking the harbor and a short tour.
66 steps carved by hand into limestone by enslaved people, with a waterfall and tropical garden at the top.
Handwoven baskets, hats and crafts in a covered market near the harbor; bargaining is expected.
Interactive museum with life-size ships and exhibits on the pirates who made Nassau their base.
Street art and a long brunch in Miami's mural district before your flight home.
Open-air museum of large-scale murals by international street artists, anchoring a neighbourhood of galleries and breweries.
An Italian Renaissance-style villa built in 1916 on Biscayne Bay, with formal gardens and a stone barge just offshore.
A causeway ride to a quieter island beach with a 19th-century lighthouse and views back at the Miami skyline.