Best Days to Travel to the Caribbean?

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A passport is not required for entry into a US territory from the US or another US territory. You are required to show government ID which shows you are a US citizen. Of course a passport is the best way to do that but other documents work as well. St. Croix Passport Requirements - Entry Documents - Necessary ID - US Virgin Islands - USVI

Not true. When I traveled to St. John and St. Thomas I could not get through TSA, get a bording pass, nor could I board without a passport. Territories of the United States are not the United States. Don't know about Puerto Rico but I would guess a passport is required to fly there as well. I'll chack this thursday with someone that traveled there a couple weeks ago and post the answer friday.
 
If you haven't gotten a new driver's license or state ID recently, though, you'll need a passport even to fly within the U.S. soon: REAL ID
 
Interesting, everything I read says that US citizens don't need a passport to travel to/from the US territories but it appears that you need identification and it is much easier if you carry a passport. I can't remember what we did on our LOB trip to St. Croix but we probably carried our passports:

St. Croix Passport Requirements - Entry Documents - Necessary ID - US Virgin Islands - USVI

A passport is not required for entry into a US territory from the US or another US territory. You are required to show government ID which shows you are a US citizen. Of course a passport is the best way to do that but other documents work as well. St. Croix Passport Requirements - Entry Documents - Necessary ID - US Virgin Islands - USVI

We were told at TSA security by TSA security that unless we had a passport we would be turned away. Drivers license was not acceptable. Fortunately we had our passports just in case we wanted to go to BVI while on St. John. Maybe the TSA didn't know what they were talking about. I do know we would not have gotten to our flight without passports. This was 2014 so I don't know if things have become more or less strict. I do know October 1st a passport or enhanced drivers license is needed for air travel even within the US so my guess would be more strict.

Oh, and, what we saw online at that time was that we didn't need a passport. But we did. Go figure.
 
Well, Bonaire and Curacao are both below the so-called 'hurricane belt,' even in winter the water's still pretty warm (though summer vs. winter there is a little difference, at least in my Bonaire trips), and you're looking to travel in summer so there's not the issue of snow and ice at your local airport creating a risk of cancelled flights or an inaccessible airport. If you want to read up more on those 2 destinations, here are some threads that might help:

Curacao Trip Research Notes
Curacao Trip Report with SB Surge Jan. 2019
My Research Notes for Bonaire - My Research Note For Bonaire

Read some recent Curacao threads; more sandy beach there, and it's larger so VRBO/AirBnB offerings may be richer I suspect. Dive Hut in Bonaire is pretty budget.

You didn't ask about Cozumel, but a fun-loving bunch of young divers looking for trips on a budget - well, you will be asking about Cozumel sometime, so here you go -
My Research Notes from Planning Cozumel Trip - My Research Notes from Planning Cozumel Trip and Tres Pelicanos & Casa Mexicana, Cozumel Sept. 2018 Report - Tres Pelicanos/Casa Mexican Trip Report Sept. 2018

Haha right after I posted this I read up on Cozumel and Roatan. Thanks for the information, I'll use it when we meet up to talk about the trip.
 
This is very helpful but you didn't give an estimate of budget per person excluding airfare. I tend to think of college students as financially constrained but perhaps that is not the case in this situation. I just know that I was broke when I was in college but it was a long time ago.

Just in case budget is an important factor I suggest taking a look at Blackbeards liveaboard cruises in the Bahamas. It is a no-frills "eat, sleep, and dive" all-inclusive vacation. Not the finest coral reefs in the entire Atlantic/Caribbean area but nice, and lots of diverse sealife and usually plenty of sharks and some wrecks, too. The water will be warm in the summer and it is usually easy to find reasonable flights into Nassau; see the link below:

https://allstarliveaboards.com/blackbeards-liveaboard-diving/

Yeah we are on sort of a college budget, which means on a trip like this we wouldn't want to spend more thank 1500 to 2500 per person. It might seem like a lot for a standard college student to put down on a vacation, but we are also part of a club that can support us financially part of the way.
 
Yeah we are on sort of a college budget, which means on a trip like this we wouldn't want to spend more thank 1500 to 2500 per person. It might seem like a lot for a standard college student to put down on a vacation, but we are also part of a club that can support us financially part of the way.

Not a big budget but you should be able to find something during the summer months. The Blackbeard's Liveaboard cruise I mentioned is $995 per person for lodgings, diving, food, beer, and rum punch with up 19 dives over 6 days. There is also a $135 pp charge for taxes and port fees. Tips are not included and I don't think that Nitrox is available.

With a simple search I found direct, nonstop flights from ATL to NAS in July ranging from $460 to $550 roundtrip on Delta.

We did a Blackbeard's trip many years ago when we were younger and it was a good value, good diving, lots of sharks, and an overall great "no frills" experience. It is the kind of trip you should do when you are young IMO, it's sort of like "camping at sea"!

https://allstarliveaboards.com/blackbeards-liveaboard-diving/
 
On Roatan, Turquoise Bay Resort has been the destination for a number of local group organized trips in my region, so I imagine it's economical in terms of overall cost. I haven't been to Roatan.

While dive resorts often assume double occupancy (and there's an extra charge if you're alone), regular land hotels do not. By packing people 4/room, it's possible to bring average trip costs down a good deal, especially if a number of people share a rental vehicle at destinations where one is needed. Live-aboard prices generally assume you are willing to be roomed with a same sex person; if you happen to end up alone, no extra charge. Your group renting a house or condo. may bring down costs nicely.

I found diving with Rainbow Reef Dive Center using a 20-dive package over 5 days a good value. Unlike a live-aboard, vehicle rental (and likely insurance on it) is a significant expense. On a positive note, you can drive around and enjoy some topside sights.

When you price trips, pay special attention to round-trip airfare costs, and whether you need a vehicle there (and enough vehicles to transport your luggage). Big SUV rentals are way more expensive than cars from what I've priced. You can pack people into housing and cut costs land-based if you don't use 'dive resorts,' but that won't work on live-aboards.

I'm speaking in generalities, so pay attention to specific providers you book with.

Since Blackbeard's was mentioned, some threads on it:
JlcNuke’s 2017 My Blackbeard's Cruise Report - My Blackbeard's Cruise Report Includes some need-to-know discussion about bathing and bathroom concerns.
T.C.’s Report on Blackbeards May 2014 - http://www.scubaboard.com/forums/bahamas/484271-trip-report-blackbeard-s-cruises-24-30-may.html
Kimbalabala’s Blackbeards review 2013 - http://www.scubaboard.com/forums/wo...-liveaboard.html?highlight=Blackbeards+review
Craig66’s Question thread about Blackbeards - http://www.scubaboard.com/forums/li...stion-about-dives-blackbeards-liveaboard.html
 
On Roatan, Turquoise Bay Resort has been the destination for a number of local group organized trips in my region, so I imagine it's economical in terms of overall cost. I haven't been to Roatan.

While dive resorts often assume double occupancy (and there's an extra charge if you're alone), regular land hotels do not. By packing people 4/room, it's possible to bring average trip costs down a good deal, especially if a number of people share a rental vehicle at destinations where one is needed. Live-aboard prices generally assume you are willing to be roomed with a same sex person; if you happen to end up alone, no extra charge. Your group renting a house or condo. may bring down costs nicely.

I found diving with Rainbow Reef Dive Center using a 20-dive package over 5 days a good value. Unlike a live-aboard, vehicle rental (and likely insurance on it) is a significant expense. On a positive note, you can drive around and enjoy some topside sights.

When you price trips, pay special attention to round-trip airfare costs, and whether you need a vehicle there (and enough vehicles to transport your luggage). Big SUV rentals are way more expensive than cars from what I've priced. You can pack people into housing and cut costs land-based if you don't use 'dive resorts,' but that won't work on live-aboards.

I'm speaking in generalities, so pay attention to specific providers you book with.

Since Blackbeard's was mentioned, some threads on it:
JlcNuke’s 2017 My Blackbeard's Cruise Report - My Blackbeard's Cruise Report Includes some need-to-know discussion about bathing and bathroom concerns.
T.C.’s Report on Blackbeards May 2014 - http://www.scubaboard.com/forums/bahamas/484271-trip-report-blackbeard-s-cruises-24-30-may.html
Kimbalabala’s Blackbeards review 2013 - http://www.scubaboard.com/forums/wo...-liveaboard.html?highlight=Blackbeards+review
Craig66’s Question thread about Blackbeards - http://www.scubaboard.com/forums/li...stion-about-dives-blackbeards-liveaboard.html

Good information! Blackbeard's has dormitory accommodations, basically a bunk with a curtain - like I said - camping at sea!
 
Since you mentioned not having much experience with international travel and wanting general advice, don't forget to look into required or recommended immunizations for the places you visit. And you should definitely bring some Immodium and/or Pepto-Bismol, and perhaps consider taking Pepto prophylactically to prevent traveler's diarrhea. If you do a land-based trip, bring bug spray with DEET; don't mess around with dryer sheets or Avon Skin So Soft or whatever other urban legend mosquito repellant is kicking around these days. Check local laws on any medications you plan to bring; Sudafed is illegal in Mexico, for example.
 
Tips:

  1. Travel after labor day oftentimes gets dirt cheap and its after the brats go back to school.
  2. Use a site like cheaptickets, google flights or travelocity and you can use a calendar to see the cheapest days of the week/month
  3. Check the package price on cheaptickets against booking each piece independently, you’ll see you don’t always get the best deal booking it together.
  4. Make sure your passport is valid for whatever the country requires
  5. Go apply for global entry, best $100 I’ve spent traveling all over
 
https://www.shearwater.com/products/peregrine/

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