Plan Your Caribbean Cruise with Simply Travel by Ashley
A Caribbean cruise lets you unpack once, wake up somewhere new and see several islands on one trip. At Simply Travel by Ashley, Ashley Muhlenkamp helps couples, families and groups compare Caribbean itineraries and find the cruise that fits. She's based in Bellbrook, Ohio, and plans trips for clients anywhere in the United States, plus select international clients. Her planning services are completely free to you, with no hidden fees.
Plan My CruiseWhy Choose a Caribbean Cruise?
Eastern, Western or Southern Caribbean?
Caribbean itineraries are usually grouped into three broad regions. Ports vary by ship and sailing, so think of these as typical examples.
Eastern Caribbean. These itineraries often center on Puerto Rico, the US Virgin Islands and nearby islands. Typical ports include St. Thomas, US Virgin Islands, near Charlotte Amalie; San Juan, Puerto Rico, steps from historic Old San Juan and its fortresses; and Philipsburg, St. Maarten, a walkable port close to beaches and shops.
Western Caribbean. These itineraries usually head toward Mexico's Caribbean coast, the Cayman Islands and Central America. Typical ports include Cozumel, Mexico, famous for snorkeling and diving; George Town, Grand Cayman, where small boats called tenders carry passengers from the ship to shore; and Roatán, Honduras, on the Mesoamerican Reef, the largest barrier reef in the Western Hemisphere.
Southern Caribbean. These itineraries reach farther south, toward South America. Typical ports include Aruba, south of the main hurricane belt; Willemstad, Curaçao; and Bridgetown, Barbados. Because these islands are farther from the mainland, Southern Caribbean sailings are often longer, and some begin in San Juan or Barbados, which means flying to your ship.
Not sure which region suits you? Ashley can compare itineraries side by side so you can see which ports and sea days fit your group.
Where Caribbean Cruises Depart From
Common US departure ports for Caribbean cruises include:
- Miami, Florida (PortMiami)
- Fort Lauderdale, Florida (Port Everglades), next to Fort Lauderdale-Hollywood International Airport
- Port Canaveral, Florida
- Tampa, Florida (Port Tampa Bay)
- Galveston, Texas (Port of Galveston)
- New Orleans, Louisiana (Port of New Orleans)
- Baltimore, Maryland (Cruise Maryland)
Gulf Coast ports like Galveston and New Orleans commonly offer Western Caribbean sailings. Ashley can help you weigh driving to a port against flying to one.
Cruise or All-Inclusive?
Both are wonderful ways to see the Caribbean.
Choose a cruise if you'd love variety: a new port many mornings, with dining and entertainment on board. Port days are set by the ship's schedule, so time on each island is limited.
Choose an all-inclusive resort if you'd rather settle into one beach and relax on your own schedule.
Travel Documents for Closed-Loop Cruises
A closed-loop cruise begins and ends at the same US port. According to US Customs and Border Protection, US citizens on a closed-loop cruise can re-enter the United States with a birth certificate and a government-issued photo ID. US citizen children under 16 need only a birth certificate or other proof of citizenship.
A few important cautions:
- The countries your ship visits may still require a passport, and the cruise line may require one too.
- The US State Department strongly recommends that every cruise passenger travel with a passport book. If illness, injury or a ship problem means you have to leave the cruise and fly home, you'll need one.
- A passport card works for re-entering the US by sea from the Caribbean, but not for international flights.
- If your cruise starts and ends at different ports, the closed-loop rule doesn't apply, so check the requirements before you book.
- Flying to your port? You'll need a REAL ID-compliant or other TSA-accepted ID, and your booking name should match it.
Hurricane Season and Cruising
Caribbean cruises sail year-round. The official Atlantic hurricane season runs from June 1 to November 30, according to NOAA's National Hurricane Center, with the peak around September 10 and most activity from mid-August to mid-October. During storms, ships may change course or dock at a different port than planned. If you're sailing in late summer or fall, a Southern Caribbean itinerary can be a good option, and it's smart to keep an eye on official forecasts as your trip gets close.
How It Works: 3 Simple Steps
Tell us about your cruise. Fill out the "Let's Plan Your Vacation!" form on our homepage or call Ashley at (419) 852-4445. Share who's sailing, your dates and the islands you're curious about.
Compare your options. Ashley puts together itineraries that fit, explains the differences and answers your questions.
Book and get ready to sail. Once you choose, Ashley takes care of the booking details.
Caribbean Cruise FAQ
Does it cost more to book a cruise through a travel advisor?
No. Ashley's planning services are completely free to you, with no hidden fees. You get personal help comparing itineraries and booking your cruise.
Do I need a passport for a Caribbean cruise?
On a closed-loop cruise that starts and ends at the same US port, US citizens can re-enter the US with a birth certificate and government-issued photo ID. Ports you visit or the cruise line may still require a passport, and the State Department strongly recommends a passport book in case you need to fly home.
Which is better: an Eastern, Western or Southern Caribbean cruise?
It depends on what you want. Eastern itineraries often visit St. Thomas, San Juan and St. Maarten. Western itineraries often visit Cozumel, Grand Cayman and Roatán. Southern itineraries reach islands like Aruba, Curaçao and Barbados and are often longer.
When is the best time for a Caribbean cruise?
Caribbean cruises sail year-round. Hurricane season runs June 1 to November 30, with most activity from mid-August to mid-October, so Ashley can help you choose an itinerary that suits your dates.
We don't live near a cruise port. Can Ashley still help?
Yes. Ashley is based in Bellbrook, Ohio, and plans trips for clients anywhere in the United States, plus select international clients. She can help you compare departure ports and plan how to get there.
Let's Plan Your Caribbean Cruise
Ready to set sail? Fill out the "Let's Plan Your Vacation!" form on our homepage, call (419) 852-4445, or email simplytravelbyashley@gmail.com. Ashley is available Monday through Friday, 9:00 AM to 4:00 PM Eastern.
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