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Sailing Destinations

Cruising Guides | Yacht Charter Trip Reports | Bareboat Sailing Itineraries

Sunset at Setting Point in Anegada

British Virgin Islands

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Sunset at Green Beach Vieques

Spanish Virgin Islands

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Magens Bay USVI in St Thomas

US Virgin Islands

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Fowl Cay anchorage Exuma Bahamas

Exuma Bahamas

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Fort Jefferson Dry Tortugas

Florida Keys & Key West

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Top Destination Guides

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

USVI Bareboat Charter
November 28, 2022 . Matt Weidert

USVI Bareboat Charter: November Sailing Yacht Adventure

Christmas Cove anchorage on our USVI bareboat charter in the US Virgin Islands
November 17, 2022 . Matt Weidert

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

Sailing from Key West to the Dry Tortugas
October 18, 2022 . Matt Weidert

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

Virgin Gorda Sound sunset with Saba Rock in the background (Pre-Irma)
October 12, 2022 . Matt Weidert

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

Norman Island British Virgin Islands | 5 Ways to Experience
October 11, 2022 . Matt Weidert

5 Ways to Experience Norman Island, British Virgin Islands

Sunset at Green Beach Vieques
October 10, 2022 . Matt Weidert

Sailing in Puerto Rico: Spanish Virgin Islands Cruising Guide

October 3, 2022 . Matt Weidert

Top 7 BVI Webcams to Check in on the Action

September 27, 2022 . Matt Weidert

The BVI Beach Top 10 List

Sailing Southern California - San Diego Bareboat Charter
September 21, 2022 . Matt Weidert

Sailing in Southern California on a San Diego Bareboat Charter

san diego sailing conditions
September 7, 2022 . Matt Weidert

San Diego Sailing Conditions

September 2, 2022 . Matt Weidert

Where to go Sailing During Hurricane Season

Best Caribbean Bareboat Charter Destinations
August 29, 2022 . Matt Weidert

The Best Caribbean Bareboat Charter Destinations

A typical day representing the best time to visit the British Virgin Islands
August 26, 2022 . Matt Weidert

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

Lounging on the trampoline in the British Virgin Islands
August 26, 2022 . Matt Weidert

5 Ways the British Virgin Islands’ Vibe is Changing

Sailing in Hawaii on a bareboat charter
August 9, 2022 . Matt Weidert

Sailing in Hawaii: Is a Bareboat Charter Possible?

Ladies at Flamenco Beach
July 6, 2022 . Matt Weidert

Top 5 Culebra Anchorages in the Spanish Virgin Islands

Fowl Cay anchorage
June 29, 2022 . Matt Weidert

Top Exuma Anchorages to Drop the Hook

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

BVI Redlined: What Areas are Off-Limits?

Exuma fishing tips: filleting a wahoo in the Exumas
May 31, 2022 . Matt Weidert

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

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

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

Sailing to St Croix: East End on St Croix USVI
April 28, 2022 . Matt Weidert

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 Weidert

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

March 11, 2022 . Matt Weidert

The Tobago Cays: An Essential Guide to the Grenadines Gem

Virgin Gorda Sound BVI
January 28, 2022 . Matt Weidert

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

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

Sailing the Exumas: Bareboat Charter in December

Fowl Cay anchorage Exuma Bahamas
November 16, 2021 . Matt Weidert

Exumas Cruising Guide: Our Favorite Bahamas Sailing Destination

Benures-Bay-Sunset
September 1, 2021 . Matt Weidert

Our Favorite Secret BVI Anchorages: Escape from the Crowds

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

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