December is peak season for warm-water boating. Most of the US is cold, while the Caribbean, Mexico and Hawaii offer air temperatures around 80°F. Safety matters more than the view. According to the U.S. Coast Guard’s 2023 Recreational Boating Statistics, 75% of fatal boating victims drowned, and 87% of those drowning victims were not wearing a life jacket.
This guide ranks family-friendly December destinations by what actually matters on board.
How We Rank the Best Places to Travel in December for Boating Families
A good family destination is not just a pretty beach. We score each place on four criteria, from 1 to 5:
- Calm water: protected anchorages and manageable wind for young crew.
- Paperwork: passports, cruising permits and customs complexity.
- Kid comfort: water temperature, short hops between stops, easy beaches.
- Connectivity: cell coverage for weather updates and family location sharing.
| Destination | Calm water | Paperwork | Kid comfort | Connectivity | Total |
| US Virgin Islands | 4 | 5 | 5 | 5 | 19 |
| Florida Keys | 4 | 5 | 3 | 5 | 17 |
| Maui, Hawaii | 3 | 5 | 4 | 4 | 16 |
| British Virgin Islands | 4 | 3 | 5 | 3 | 15 |
| Exumas, Bahamas | 4 | 3 | 5 | 2 | 14 |
| Los Cabos, Mexico | 3 | 3 | 4 | 3 | 13 |
The Best Places to Travel in December: Our Top 6 Destinations
1. US Virgin Islands: Best Overall
The USVI is our top pick for American families. US citizens do not need a passport to arrive from the US mainland, and the US dollar is the local currency. St. John offers sheltered bays and short sailing distances. Expect the “Christmas winds,” stronger trade winds that often blow 15 to 25 knots in December and January. Plan shorter legs on windy days.
2. Florida Keys: Best Without Flying
The Keys are drivable from most of the East Coast. December is the start of the dry season, with highs around 75°F in Key West. Water can feel cool for small children, so pack rash guards. Florida requires boater education for anyone born on or after January 1, 1988 who operates a vessel of 10 horsepower or more.
3. Maui, Hawaii: Best for Wildlife
Humpback whale season in Hawaii runs from December to April. Family whale-watching charters leave from Lahaina and Maalaea harbors. Seas are rougher in winter on north-facing shores, so stick to the protected southwest side.
4. British Virgin Islands: Best Bareboat Charter
The BVI is the world’s classic charter ground. Islands sit close together, so kids rarely spend more than two hours underway. A passport is required. The BVI also uses the US dollar.
5. Exumas, Bahamas: Best Water Color
The Exumas offer shallow, clear water and endless sandbars. Private vessels need a Bahamas cruising permit on arrival. Cell coverage can be patchy between cays, so download everything before you leave.
6. Los Cabos, Mexico: Best for Older Kids
Humpback whales arrive in Los Cabos from around mid-December. Pacific swells make this a better fit for teens than toddlers.
Safety Gear Checklist for the Best Places to Travel in December
US federal rules require a USCG-approved wearable life jacket for every person on board. Children under 13 must wear one on a moving recreational vessel unless they are below deck or in an enclosed cabin, unless a state sets its own rule. Abroad, local rules apply, so bring your own properly sized jackets.
Our family checklist:
- Life jackets sized by weight: infant (under 30 lb), child (30 to 50 lb), youth (50 to 90 lb).
- Personal locator beacon (PLB) or a vessel EPIRB.
- Handheld VHF radio. It remains your primary emergency tool at sea.
- Reef-safe sunscreen, hats and rash guards.
- Seasickness remedies approved for children, checked with your pediatrician.
- Waterproof dry bags for phones and documents.
Staying Connected at the Best Places to Travel in December
A phone is never a replacement for a VHF radio. But it is essential for weather checks, offline charts and keeping track of family members ashore.
Before departure:
- Download offline nautical charts in apps such as Navionics.
- Save offline maps of each island in Google Maps.
- Set up live location sharing with family members (WhatsApp or Find My).
- Install a weather app such as Windy for wind and swell forecasts.
Avoiding Roaming Fees on the Water
Roaming is the hidden cost of island-hopping. The USVI usually counts as domestic for major US carriers. But in the BVI, the Bahamas or Mexico, daily roaming passes add up fast for a family of four. Phones near the USVI and BVI border can also switch to foreign towers without warning.
An eSIM is a digital SIM card you install by scanning a QR code. Many traveling families use Holafly to buy a local data plan before leaving home. Check that your phone is unlocked and eSIM-compatible first.
FAQ: Best Places to Travel in December by Boat
What is the warmest family boating destination in December?
The US Virgin Islands, with highs in the mid-80s°F and warm water year-round.
Do I need a passport for the USVI?
No. US citizens arriving from the US mainland do not need one. Bring a government-issued photo ID.
Is December hurricane season in the Caribbean?
No. The Atlantic hurricane season officially ends on November 30.
Can toddlers go on a sailing charter?
Yes, with a properly fitted infant life jacket, safety netting on the lifelines and short daily leg
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