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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
September 7, 2023 . Matt Weidert

Cheeseburger in Paradise’s True Origins

Fowl Cay anchorage
August 1, 2023 . Matt Weidert

Top Exuma Anchorages to Drop the Hook

Sailing the Virgin Islands
July 21, 2023 . Matt Weidert

Sailing the Virgin Islands: What We’ve Learned

Antigua bareboat charter at Dickenson Bay
July 11, 2023 . Matt Weidert

Antigua Bareboat Charter: A Week in Paradise

how to get to the british virgin islands
June 16, 2023 . Matt Weidert

How to get to the British Virgin Islands?

Fowl Cay anchorage Exuma Bahamas
June 12, 2023 . Matt Weidert

Exumas Cruising Guide: Our Favorite Bahamas Sailing Destination

The Baths BVI
April 17, 2023 . Matt Weidert

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
March 9, 2023 . Matt Weidert

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

Yacht Charter destination bucket list
February 15, 2023 . Matt Weidert

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

Benures-Bay-Sunset
February 1, 2023 . Matt Weidert

Our Favorite Secret BVI Anchorages: Escape from the Crowds

Best Caribbean Bareboat Charter Destinations
January 28, 2023 . Matt Weidert

The Best Caribbean Bareboat Charter Destinations

swimming at white bay jost van dyke
January 17, 2023 . Matt Weidert

BVI Catamaran Charter: 10 Day Sailing Plan

10-day Exuma Sailing Itinerary
January 13, 2023 . Matt Weidert

Exuma Sailing Itinerary: 10 Days to See it All

BVI Beach Top 10 list in the British Virgin Islands
January 12, 2023 . Matt Weidert

The BVI Beach Top 10 List

USVI Sailing Itinerary, an epic week sailing the US Virgin Islands
December 30, 2022 . Matt Weidert

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

Antigua yacht charter
December 6, 2022 . Matt Weidert

Antigua Yacht Charter: Beaches, History & Adventure

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?

Sunset at Green Beach Vieques
November 3, 2022 . Matt Weidert

Sailing in Puerto Rico: Spanish Virgin Islands Cruising Guide

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

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

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

5 Ways to Experience Norman Island, British Virgin Islands

October 3, 2022 . Matt Weidert

Top 7 BVI Webcams to Check in on the Action

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

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?

Lagoon 46 in the Spanish Virgin Islands, Culebra at sunset; culebra anchorage
July 6, 2022 . Matt Weidert

Top 5 Culebra Anchorages in the Spanish Virgin Islands

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: Bahamas Bareboat Charter

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

Bareboat Charter Key West | Sailing Adventure to the Dry Tortugas