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Sailing Destinations

Cruising Guides | Yacht Charter Trip Reports | Bareboat Sailing Itineraries

Top Destination Guides

Our favorite bareboat charter sailing trip destinations include the British Virgin Islands, Exumas Bahamas, and Spanish Virgin Islands.

The true origin of Jimmy Buffett's Cheeseburger in Paradise is actually Stanley's Welcome Bar in Cane Garden Bay

Cheeseburger in Paradise’s True Origins

Fowl Cay anchorage

Top Exuma Anchorages to Drop the Hook

Sailing the Virgin Islands

Sailing the Virgin Islands: What We’ve Learned

Antigua bareboat charter at Dickenson Bay

Antigua Bareboat Charter: A Week in Paradise

how to get to the british virgin islands

How to get to the British Virgin Islands?

Fowl Cay anchorage Exuma Bahamas

Exumas Cruising Guide: Our Favorite Bahamas Sailing Destination

The Baths BVI

Rule Change at The Baths, BVI: What You Need to Know

Virgin Gorda Sound sunset with Saba Rock in the background (Pre-Irma) on a bvi catamaran charter

Bareboat Charter Guide for Beginners: How to Take Your First Sailing Vacation

Yacht Charter destination bucket list

Yacht Charter Bucket List: Here’s Where I’m Sailing


Our Favorite Secret BVI Anchorages: Escape from the Crowds

Best Caribbean Bareboat Charter Destinations

The Best Caribbean Bareboat Charter Destinations

swimming at white bay jost van dyke

BVI Catamaran Charter: 10 Day Sailing Plan

10-day Exuma Sailing Itinerary

Exuma Sailing Itinerary: 10 Days to See it All

BVI Beach Top 10 list in the British Virgin Islands

The BVI Beach Top 10 List

USVI Sailing Itinerary, an epic week sailing the US Virgin Islands

USVI Sailing Itinerary: An Epic Week in the US Virgin Islands

Antigua yacht charter

Antigua Yacht Charter: Beaches, History & Adventure

USVI Bareboat Charter

USVI Bareboat Charter: November Sailing Yacht Adventure

Christmas Cove anchorage on our USVI bareboat charter in the US Virgin Islands

When is the Best Time to Visit the US Virgin Islands?

Sunset at Green Beach Vieques

Sailing in Puerto Rico: Spanish Virgin Islands Cruising Guide

Sailing from Key West to the Dry Tortugas

Sailing from Key West to Dry Tortugas: What to Expect?

Norman Island British Virgin Islands | 5 Ways to Experience

5 Ways to Experience Norman Island, British Virgin Islands

Top 7 BVI Webcams to Check in on the Action

Sailing Southern California - San Diego Bareboat Charter

Sailing in Southern California on a San Diego Bareboat Charter

san diego sailing conditions

San Diego Sailing Conditions

Where to go Sailing During Hurricane Season

A typical day representing the best time to visit the British Virgin Islands

When is the Best Time to Visit the British Virgin Islands?

Lounging on the trampoline in the British Virgin Islands

5 Ways the British Virgin Islands’ Vibe is Changing

Sailing in Hawaii on a bareboat charter

Sailing in Hawaii: Is a Bareboat Charter Possible?

Lagoon 46 in the Spanish Virgin Islands, Culebra at sunset; culebra anchorage

Top 5 Culebra Anchorages in the Spanish Virgin Islands

Brewers Bay in the British Virgin Islands

BVI Redlined: What Areas are Off-Limits?

Exuma fishing tips: filleting a wahoo in the Exumas

Exuma Fishing Tips: How to Catch More Fish in the Bahamas

Anchorage in Anegada at Setting Point

Sailing to Anegada: How to Navigate to and Visit the Sunken Island

Sailing to St Croix: East End on St Croix USVI

Sailing to St. Croix: A Fresh USVI and SVI Sailing Itinerary

painkillers at the soggy dollar bar in white bay jost van dyke

Is White Bay in Jost Van Dyke too Dangerous to Anchor?

The Tobago Cays: An Essential Guide to the Grenadines Gem

Virgin Gorda Sound BVI

BVI Sailing Itinerary: The Perfect Week in the British Virgin Islands

Wahoo caught on the drop in the Exumas sound

Sailing the Exumas: Bahamas Bareboat Charter

Drone shot of Garden Key and Fort Jefferson at sunset

Bareboat Charter Key West | Sailing Adventure to the Dry Tortugas