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Sailing Destinations

Cruising Guides | Bareboat Charter Trip Reports | Sailing Itineraries

Top Destination Guides

Our favorite bareboat charter sailing trip destinations include the British Virgin Islands, Exumas Bahamas, and Spanish Virgin Islands. These are some of our essential posts.

Tunnels beach and the Makua Reef anchorage in Kaui
August 9, 2022 . Matt

Sailing in Hawaii: Is a Bareboat Charter Possible?

Ladies at Flamenco Beach
July 6, 2022 . Matt

Top 5 Culebra Anchorages in the Spanish Virgin Islands

Fowl Cay anchorage
June 29, 2022 . Matt

Top Exuma Anchorages to Drop the Hook

Sailing to the Dry Tortugas
June 21, 2022 . Matt

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

Brewers Bay in the British Virgin Islands
June 14, 2022 . Matt

BVI Redlined: What Areas are Off-Limits?

filleting a wahoo in the Exumas
May 31, 2022 . Matt

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

Anchorage in Anegada at Setting Point
May 16, 2022 . Matt

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

East End on St Croix USVI
April 28, 2022 . Matt

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

painkillers at the soggy dollar bar in white bay jost van dyke
April 14, 2022 . Matt

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

March 11, 2022 . Matt

The Tobago Cays: An Essential Guide to the Grenadines Gem

Virgin Gorda Sound BVI
January 28, 2022 . Matt

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

Wahoo caught on the drop in the Exumas sound
January 8, 2022 . Matt

Sailing the Exumas: Bareboat Charter in December

Fowl Cay anchorage
November 16, 2021 . Matt

Exumas Cruising Guide: Our Favorite Bahamas Sailing Destination

Sunset at Green Beach Vieques
October 1, 2021 . Matt

Sailing in Puerto Rico: Spanish Virgin Islands Cruising Guide

Benures Bay Sunset
September 1, 2021 . Matt

Our Favorite Secret BVI Anchorages: Escape from the Crowds

Drone shot of Garden Key and Fort Jefferson at sunset
August 19, 2021 . Matt

Bareboat Charter Key West | Sailing Trip Adventure to the Dry Tortugas

Virgin Gorda Sound sunset with Saba Rock in the background (Pre-Irma)
July 27, 2021 . Matt

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